Home Vacation Home Rentals By Owner In Holmes Beach, FL

Showing 600 Of 800 Vacation Rentals
Slider Thumb
Exceptional(23)

$285.35

/ Nightly
Private Vacation Home

Under the Tuscan Sun: *Heated Pool *Close to Beach *Perfect Central Location

Holmes Beach, Florida, United States

Pack your bags for a luxurious island getaway at Under the Tuscan Sun, a Mediterranean-inspired home with a beautiful backyard, private pool, lounge area, and propane grill. This three-bedroom and three-bathroom retreat is located on a quiet cul-de-sac and is just a few blocks from the dreamy Gulf of Mexico beaches, and shopping and dining are easily accessible via a short walk or the Island's free trolley.brbrOn the main living floor, you will find a fully equipped kitchen with Tuscan-inspired tile backsplash, stainless steel appliances, and a breakfast bar for two. Enjoy formal meals at the indoor or outdoor dining tables on the balcony and take advantage of the Florida weather. There is a sunken living room with two large sofas and a TV.brbrWalk up the stairs to the primary bedroom, with a lovely coastal flare and a fabulous private balcony with wicker seating and great views. The primary bedroom has a claw foot tub, a step-in shower stall, a bidet, and two pedestal sinks. The second bedroom is light and airy with a TV and ensuite bathroom with a walk-in shower. The third bedroom is perfect for younger guests, with two sets of bunk beds, and shares the hall bath with two pedestal sinks and a tub. A laundry room with a washer and dryer is available, and the living room sofa turns into a sleeper sofa.brbrThe Island is meant for getting out and exploring, whether by bike, golf cart, or even the complimentary AMI Trolley that will pick you up at various spots around the 7-mile Island. Fish with locals at the Rod-n-Reel, kayak, or paddle board the turquoise waters, eat fresh seafood from the neighboring gourmet restaurants, and soak up the Florida Sunshine. For more shopping, visit the one-of-a-kind boutiques that dot along Pine Ave.brbrFloor 1 (ground)brHeated pool, grill, paver patio with seatingbrBeach cart, 1 beach umbrella, and 4 beach chairs provided for guest use. Stored in garage.brbrFloor 2 (main living level)brBedroom 1: Queen with TV and ensuite bathroom with walk-in showerbrQueen sleeper sofa in living roombrbrFloor 3brBedroom 2: King master with TV and ensuite bathroom with claw foot tub and walk-in showerbrBedroom 3: Twin-over-twin bunk bed and twin-over-full bunk bed with TV (3 twins, 1 full total)brJack & Jill bathroom with a tub, shared between hall and bedroom 3.brbrPETS: Dogs are allowed with prior approval. Must be well trained and less than 40lbs. 2 dogs max. A $150 non-refundable pet fee applies per pet.brbrPARKING: 3 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. *1 parking space available in garage.brbr***OVERCROWDING CONSEQUENCES***brMaximum occupancy of rental homes on Anna Maria Island are set by the Cities and are strictly enforced. An occupant is any person staying overnight, regardless of the number of nights. Due to recent issues of overcrowding in the area, if maximum occupancy is exceeded during your stay, a $1000 (one thousand dollar) overcrowding fee will be charged to the payment method on file and your party will be immediately evicted. We appreciate your understanding and cooperation to keep Anna Maria Island enjoyable for everyone.brbrYou are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property.brbr*Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.brbrVRC19-000124
Bed 3

Bed

Bath 3

Bath

Sleep 10

Sleeps
Slider Thumb
Exceptional(105)

$326.45

/ Nightly
Private Vacation Home

Island Vibe 1: Close to Beach with Private Heated Pool

Holmes Beach, Florida, United States

p dir=ltrWelcome to Island Vibe 1, a renovated 3-bedroom, 2-bathroom home with private, heated and cooled pool plus lots of lush tropical landscaping!/pbrbrp dir=ltrLocated on 62nd Street in Holmes Beach, this lovely property is convenient to the beach and in a very quiet Holmes Beach residential neighborhood.It has one shared wall with the unit next door. From here, it's just a short walk to the many shops and restaurants of downtown Holmes Beach, as well as the Island’s only dog park.br/pbrbrbrbrbrbrbrbrp dir=ltrThis beautiful property will sleep 6 people with 1 King bed,1 Queen bed, and 2 Twin beds. Plus, there is a pullout couch in the living room!You can park up to 3 cars here: 1 in the garage, and 2 in the driveway.br/pbrbrbrbrp dir=ltrIn the backyard, you'll find a large open deck and a covered, shaded area overlooking the pool. You can even enjoy drinks at the swim-up tiki table in the pool! We've added solar string lights on the upper and lower patio for enjoying the outdoors during those great Florida evenings.br/pbrbrbrbrp dir=ltrYou'll never miss a moment of your favorite sporting event!We have a 55 television in the living room with a DVD player, a 49 television in the master bedroom, a 49 television in the second bedroom, a 49 television in the third bedroom, ANDeven a 42 television on the outdoor, covered patio!br/pbrbrbrbrp dir=ltrConvenience for our guests is a priority for us! All of the TVs are smart TVs and have streaming television with the Spectrum App. A washer and dryer, wireless internet, cable television and free domestic long distance calling are all included! Additionally, if you're traveling with little ones or pets, we gladly provide an array of convenient items upon request. We have high-chairs, pack 'n plays, baby gates, fans, and dog crates so you can pack less and enjoy a worry-free family getaway. Just let us know what you need in advance so we can make sure it is ready for you at the property upon your arrival.br/pbrbrbrbrp dir=ltrThere is plenty of opportunity for fun and games at Island Vibe 1. Inside the garage is a ping pong table, a beach cart, beach toys and lots of beach equipment. Additionally, there is a propane grill and outdoor propane fire pit.br/pbrbrbrbrp dir=ltrWe are pet-friendly!Two pets are permitted with prior approval, signed Pet Addendum, and a $150.00 non-refundable pet fee (plus 13% tax)./pbrbrp dir=ltrWe treat for mosquitos from May through August./pbrbrp dir=ltrYou are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property./pbrbrp dir=ltrNOISE ORDINANCE: Anna Maria Island has a zero tolerance policy for noise after 9 PM. Please show consideration for your neighbors. No loud music, parties or playing in pools after 9 PM. If a neighbor complains the Police Department has no choice but to file a complaint. strongAny tickets issued by the police department for noise violations will be the responsibility of the guest and may result in immediate eviction with no refunds of rent or deposits./strong/pbrbrp dir=ltrBy City Regulation, a 7 night minimum stay is required with a maximum occupancy of 6 persons. strongViolation of the occupancy limit may result in immediate eviction with no refunds of rent or deposits./strong/pbrbrp dir=ltrLicense #: VRC17-000051/pbrbrpbr/p
Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
Slider Thumb
Exceptional(48)

$346.4

/ Nightly
Private Vacation Home

Private Pool/Spa - A Wave From It All by SeaBreeze Vacation

Holmes Beach, Florida, United States

New Name - A Wave From It All, formerly known as Island Dream, is a recently updated custom home nestled in the quiet residential area in the heart of Holmes Beach. Offering 3 bedrooms/2 bathrooms. You will find that this home has everything you need for your perfect Anna Maria Island vacation! From the heated pool and spa, gourmet kitchen, full-size washer & dryer, balcony, and gas outdoor grill. The list goes on with the amazing amenities - what more could you possibly need to make your tropical island vacation perfect!brbrThe property is located in a great location for a great family vacation. The world-renowned white sandy beaches of the Gulf of Mexico and great restaurants and shopping in Holmes Beach is just a short walk away. Make memories as a family that will last a lifetime! Vacations are for fun and relaxation. The outdoor area at A Wave From It All provides just that. Have fun in the pool which is heated year round for your enjoyment. The family dogs are welcome to join you here and with the Central Dog Park located just a short distance from your front door. The entire family, including the dogs, are sure to have a great time and never want the vacation to end.brbrCancellation Policy - SeaBreeze Vacation has spent a great deal of time and effort into formulating a cancellation policy for you. SeaBreeze Vacation has the most flexible cancellation policy on the Island. You are allowed to cancel your reservation up to 14 days prior to check-in to receive a refund. Additional terms and conditions apply. brbrThis property participates in our Professional Linen Program. SeaBreeze Vacation strives to bring only the best quality experience to our guests. To do so, we provide a professional linen service at this property to better enhance your enjoyment while staying here. This luxury amenity provides you high quality linens that are in place and ready for your use upon your arrival. These high-quality linens are laundered in a commercial setting that uses only hypoallergenic, perfume & dye-free soaps assuring all of our guests a comfortable stay. brbrWith all SeaBreeze Vacation properties, we think of the little things to make your vacation special. Included to get you started are the following: brbrPer Guest: 1 Bath Towel, 1 Hand Towel, 1 Washcloth, 1 Pool/Beach TowelbrPer Full Bathroom: 2 Rolls of Toilet Paper, Hand Soap, Shower Products Set (including trial size shampoo, conditioner, shower gel, and body lotion), Cosmetic Cloth, Bath MatbrPer Kitchen: 2 Rolls of Paper Towels, Hand Soap, Dish Soap, Sponge, Dishwasher Pods (x4), Laundry Detergent Pods (x4), All-Purpose Disinfectant, Microfiber Cloth, 2 Kitchen TowelsbrbrWe also offer a range of supplemental services including pre-stock grocery shopping and babysitting. Need a pack and play or high chair, etc. These are available for a small additional fee and will be waiting in the home on your arrival.brbrThe weight limit per dog is 30 lbs. brbrYou are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property.brbrCity of Holmes Beach Vacation Rental License: VRC18-000023brMax Occupancy: 6 Guests | Max Vehicles: 4brQuiet Hours: 10 p.m. - 7 a.m. - please respect our island communitybrMin stay requirements vary by city ordinance and are often 7 nights. Please contact our office with any questions.
Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
Slider Thumb
Exceptional(138)

$542.4

/ Nightly
Private Vacation Home

Private paradise w/ all the beach supplies & toys!

Holmes Beach, Florida, United States

Casa Laguna is a privately owned home with private amenities and entry via smart locks. The home is surrounded by lush palms ands vegetation offering. Creating a feeling of your own private paradise. brbrWe welcome you and your family to take a break, relax and feel safe in your own private paradise. brbrAnna Maria Island is a family-oriented vacation destination with a laid-back feel. The island has a very relaxing atmosphere. The beautiful, world-famous white beaches and friendly character of the island will make you want to come back again and again.brBEDROOMSbr5 Bedrooms/ 8 Beds & Upstairs retreatbrOur home has 5+ bedrooms that are all comfortably apart from each other in the house, accommodating for the privacy of members of your group. AL. TV's in every bedroom Netflix, or HULU ready. The master suite has a medium firm memory foam king bed, and a master bath equipped with two shower heads, and penny tiled flooring. Also, the master bath is connected to the outdoor bamboo shower. Bedroom two is upstairs off the kitchen and has a queen bed that easily glides out from the wall. Partitioned from the rest of the room by collapsable doors is a sleeping nook with fun lighting includes a cozy double bed for the kids or your own cozy solace. This bedroom also comes with an ensuite two person deluxe shower with wall-mounted shower jets, bluetooth shower music system, and optional blue LED lighting. Bedrooms three & four both have queen beds. Bedroom five is the kids' sanctuary with a queen and double on the loft-like bunk bed. brKITCHENbrThe new kitchen has an open-air feel and plenty of space for a large group. There are granite counter tops, new stainless steel appliances, and all the necessary utensils you may need. The kitchen eating area accommodates six, and the rest of the gang can hang around the granite island which seats 2-4, or the foyer cocktail table that seats 4 more. Do not forget the larger outside table.brLIVING ROOMbrWatch television on the large 75 flat screen smart TV. There is a large sectional likely to fit the whole crew. At the end of the room is a closet packed full with board games.brHEATED POOL/ SPAbrFinally, relax in your private lagoon-like pool with a tanning ledge, swim up tiki table, infinity edge hot tub/spa, waterfall, deck jets, There is LED pool and spa lighting with variable color settings with the touch of a button. Landscape lighting provides a resort-like feel and is throughout the property. The pool is heated year round to 84 degrees or better at no additional charge. Forget your worries, you're on island time and yes, you'll be back again. brTiki Bar off the back side of the pool.brOTHERSbrIt is just three blocks to white sandy beaches of the Gulf of Mexico. Take a 5-6 minute walk or a 90 second golf cart ride. Golf Carts are easily rented and delivered by my friend at Beac’N Rides. Just goole search their company. Easy parking at the beach access. There are many beach toys and supplies available for you to you use. Including a cooler. The bikes are there but guests & groups are typically hard on them so they are not a guarantee. We only ask that you please treat all the gear well and wash off the salt water after use. Thanks in advance.brNearby are the wonderful shops, and restaurants that Holmes Beach has to offer. PUBLIX shopping center is 1.2 miles away. brWiFi internet access provided. brTop of the line front loader washer and dryer brA collapsable baby cribs (or pack-n-play's) are there for your use as well. brWeber grill and three lounge chairs on the patio. brWe update our house regularly to ensure it is in in prime condition so guests can have their best stay. The home went through $100,000+ repair/ renovation post hurricane Helene and looks and smells like new because much of it is.
Bed 4

Bed

Bath 4

Bath

Sleep 8

Sleeps
Slider Thumb
Exceptional(50)

$846.59

/ Nightly
Private Vacation Home

Sunsets on Carissa - Coastal Retreat w/ Heated Pool, Game Room & Steps from Gulf

Holmes Beach, Florida, United States

Welcome to Sunsets on Carissa!brOn Anna Maria Island (Holmes Beach, FL)brbrThe SpacebrEvery corner of this home is designed to bring people together. The open-concept layout connects the kitchen, dining, and living areas, so laughter and conversation flow as easily as the island air. The furnishings are comfortable yet refined, and natural light fills each space with warmth and calm.brbrSliding doors lead out to the backyard, where the pool and patio area become the natural heart of the home — ideal for mid-day swims, grilled dinners, and lingering evenings spent beneath the palms.brbrPerfect for: Families, couples, and small friend groups seeking comfort, connection, and easy access to the beach.brbrHighlightsbr- Steps to the Gulf beaches — easy access to soft white sand and unforgettable sunsetsbr- Heated private pool with sun shelf, dining area, and covered lounge spacebr- Bonus game room with ping pong table and hangout seatingbr- Three bedrooms and two full baths, comfortably sleeping up to 6 guestsbr- Private deck balcony off Primary SuitebrbrInterior Spacesbr- Living Area: Open and airy with coastal-inspired décor, plush seating, and a large TV for family movie nights.br- Dining Area: A table for six sits just off the kitchen, perfect for shared meals or evening board games.brbrBedrooms:br- Primary Suite: King bed, TV, en-suite bath with oversized shower and double vanity, walk-in closet, and private balcony.br- Queen Bedroom: Bright and comfortable with a TV and generous closet space.br- Twin Bedroom: Two twin beds, TV, and plenty of room for little travelers.brbrBathrooms: One full bath on each level; both with fresh towels and essentials provided through our Professional Linen Program.brbrLayout Overviewbr- Ground Level: Covered pool patio, bonus game room with ping pong table, garage parking.br- Main Level: Open kitchen, dining, and living area; queen bedroom; twin bedroom; full hallway bath.br- Upper Level: Master suite with private balcony and en-suite bath.brbrOutdoor LivingbrJust outside, the heated private pool offers a peaceful retreat surrounded by tropical landscaping. Spend your mornings on a lounge chair with coffee, afternoons splashing in the water, and evenings gathered around the outdoor table as the sky turns shades of gold and coral.brbrThe ping pong table and shaded patio make this space just as fun as it is relaxing — a spot where everyone can connect and create new memories together.brbrKitchen & DiningbrThe fully equipped kitchen includes:br- Stove, oven, microwave, and refrigerator with ice makerbr- Dishwasher and garbage disposalbr- 12-cup coffeemaker, toaster, blender, and full cookware setbr- Spacious island with bar seating for casual breakfastsbrbrWhether you're cooking a seafood dinner or plating takeout from your favorite island café, you'll find everything you need to make mealtime easy and enjoyable.brbrAdditional Amenitiesbr- Washer/dryer for guest usebr- Cable TV and high-speed Wi-Fibr- A/C and heat for year-round comfortbr- Hair dryer, iron, and ironing boardbr- Professionally laundered linens and towelsbr- Enjoy complimentary beach chairs and an umbrella, along with a beach gear rental credit included with every staybrbrParkingbrTwo-car garage and two additional driveway spaces (max 3 vehicles)brbrWrite your vacation story at Sunsets on Carissa, where every sunset calls you back to what matters most — time together.brbrPoliciesbrbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.brbrNO PETS. NO SMOKING.brbrBooking & Fee PolicybrInclude all guests and pets in your reservation request for accurate pricing. Additional fees apply for extra occupancy (over 2 guests per bedroom) or undeclared pets.brbrOptional Services (subject to approval)brEarly check-in/late departure, elevator access, and mid-stay cleaning for stays of 28+ days. Fees for approved add-ons are collected after booking.brbrReservations & Guest RequirementsbrMost stays are 7 nights, Saturday–Saturday, though flexible dates may be available outside peak/holiday weeks—confirm before booking, as changes are not always possible afterward. Guests must be 25+, provide valid ID, and remain for the full stay. Standard occupancy is 2 per bedroom; extra guests are $25/person/night up to the maximum allowed.brbrQuiet Hoursbr10 PM–8 AM. Maintain reasonable noise at all times to respect neighbors; excessive noise is not permitted.brbrCleaning & LinensbrHome is professionally cleaned and sanitized between stays. Starter amenities provided; daily service available for a fee. Stays of 28+ days require a mid-stay clean. Linens/towels are commercially laundered through our Professional Linen Program; no extra sets stored onsite.brbrGolf Cart RentalsbrExplore the island with ease! After booking, reserve a golf cart through our sister company, Once Upon A Beach Carts, and enjoy an exclusive discount available only to our vacation rental guests.brbrPool & SpabrPool heated year-round to 82–85°F; heating may be affected by cooler weather. Heaters/filters off during quiet hours (10 PM–8 AM). Spa, if available, is part of the pool, seasonal, not a commercial hot tub, and may be unavailable in summer. Guests may not adjust equipment; violations may result in fines or damages.brbrProperty SecuritybrExterior cameras may monitor entries, driveways, pool equipment, and backyard access for security, deliveries, and occupancy compliance. Cameras do not face private areas.brbrPayments & Cancellation PolicybrPolicies updated October 6, 2025 — see full Terms & Conditions for details.brbrPayment SchedulebrDepositbr- Reservations up to 20 days: 50% of total amount due at time of booking.brRemaining Balancebr- Reservations up to 20 days: Remaining 50% due 30 days prior to check-in.brbrCancellation PolicybrFor Reservations of 20 Days or Lessbr- More than 30 days before arrival: Full refund of deposit (including taxes) minus non-refundable booking administration fee.br- 14–29 days before arrival: Refund of 50% of total rental, fees, and taxes, minus non-refundable booking administration fee.br- Less than 14 days before arrival: Refunds only for base rental rate, fees, and taxes for nights we are able to rebook, minus non-refundable booking administration fee.br- Please note: While we make every effort to rebook, we cannot guarantee the same rate or number of nights. For any nights that cannot be re-rented, as well as for non-arrivals, late arrivals, early departures, or alterations resulting in lost revenue, no refunds or price adjustments will be made.brbrTravel InsurancebrCSA Travel Insurance is available to U.S. guests (except NY and HI residents) and is strongly encouraged to protect your trip from unforeseen events. No refunds are given for COVID-19, weather, or beach conditions outside our cancellation policy. Hurricane season runs June 1–Nov 30; insurance can safeguard your plans. In the event of a mandatory evacuation, home unavailability, or government order halting vacation rentals, guests receive a full refund of base rate, applicable fees (minus booking fee), and taxes.brbrAdditional TermsbrNo refunds for events beyond our control (weather, red tide, travel issues, etc.). Cancellation requests must be submitted in writing by the registered guest—phone/text not accepted.brbrHolmes Beach Vacation Rental License: VR20-000090brMax Occupancy: 6 Guests | Max Vehicles: 3brInformation deemed reliable but not guaranteed; subject to change or withdrawal without notice.
Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
No Image
Exceptional(34)

$468.38

/ Nightly
Private Vacation Home

Fins Up – AMI Cozy Island Retreat w/ Private Pool & 4-Min Walk To Beach

Holmes Beach, Florida, United States

Welcome to Fins Up!brOn Anna Maria Island (Holmes Beach, FL)brbr​​​​​​​The SpacebrYour serene island retreat where simplicity meets comfort. Tucked within the heart of Holmes Beach and just two blocks from the sand, this coastal home balances calm, convenience, and connection. Soaring ceilings, natural light, and soothing tones create an inviting backdrop for days spent at the beach and evenings gathered by the pool.brbrPerfect for: couples seeking renewal, small families craving quality time, or travelers looking for calm, connection, and comfort.brbrHighlightsbr- Private heated pool with sun shelf, covered seating, and outdoor barbr- 2 bedrooms / 2 bathrooms + queen sleeper sofa (approx. 1,250 sq. ft.)br- Two en-suite bedrooms — ideal for shared comfort and privacybr- Open-concept living area with vaulted ceilings and Smart TVbr- Fully equipped kitchen with stainless-steel appliances and quartz countertopsbr- Washer and dryer in-unitbr- Two blocks from the beach and steps from the free island trolleybrbrInterior Spacesbr- A space designed for presence — light, calm, and ease.br- The open-concept layout connects the kitchen, dining, and living areas under vaulted ceilings, creating a sense of airiness and flow. Sliding glass doors open to the balcony, welcoming the Florida sunshine and gentle island breeze.br- King Bedroom: Spacious and restful with Smart TV, en-suite bath featuring a walk-in shower, and direct access to a covered deck — perfect for morning coffee or quiet evenings.br- Bunk Room: Full-over-full bunk beds, Smart TV, and en-suite bath with walk-in shower — ideal for kids or guests.br- Living Area: Comfortable sofa (queen sleeper), Smart TV, and open sightlines to the kitchen for easy togetherness.brbrSubtle coastal décor, crisp finishes, and thoughtful details make this home a relaxing environment that feels as refreshing as a morning swim.brbrLayout Overviewbr- Single-level elevated home (approx. 1,250 sq. ft.)br- Two bedrooms, both with en-suite bathsbr- Open living, dining, and kitchen areabr- Balcony overlooking pool and tropical landscapingbr- Ground-level outdoor living area with private pool and bar seatingbrbrThis thoughtful layout provides privacy when desired and connection when it matters most.brbrOutdoor Livingbr- Your own private island sanctuary awaits below.br- Heated private pool with sun shelf and surrounding lounge areabr- Covered patio with outdoor bar, TV, and dining space for shaded relaxationbr- Outdoor shower for a refreshing rinse after the beachbr- Gas grill and dining area for easy poolside mealsbr- Tropical landscaping that adds to the sense of peace and seclusionbrbrIt's a place to pause, breathe, and reconnect — whether lounging in the shade or sharing laughter under the palm trees.brbrKitchen & DiningbrA bright and functional kitchen sits at the heart of the home, bringing everyone together for meals, conversation, and moments that linger.br- Stainless-steel appliances: stove, oven, dishwasher, microwave, refrigerator with ice makerbr- 12-cup coffee maker, blender, toaster, and full kitchenwarebr- Solid wood cabinets and quartz countertopsbr- Dining table with seating for four + bar seating for twobrbrFrom morning smoothies to seafood dinners, the space is designed to make cooking easy and connection effortless.brbrAdditional Amenitiesbr- Central A/C & heatbr- Smart TVs and high-speed Wi-Fibr- Linens, towels, and starter amenities providedbr- Hair dryer, iron & ironing boardbr- Washer and dryer for guest usebr- Beach gear credit through VayKLife Gear (chairs, umbrella, bikes, etc.) delivered before arrivalbrbrOnce Upon A Beach provides trusted, hands-on local support — ensuring your stay is seamless, relaxed, and memorable.brbrParkingbr- Two-car garage and space for two additional vehicles in the drivewaybr- No street or overnight parking permittedbrbrAt Fins Up, mornings start with sunlight and the sound of palms, and end with a quiet swim beneath the stars.brIt's where time slows, balance returns, and every day feels like a breath of fresh air.brbrWrite Your Vacation Story.brbrPoliciesbrbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.brbrNO SMOKING. NO PETS.brbrBooking & Fee PolicybrInclude all guests and pets in your reservation request for accurate pricing. Additional fees apply for extra occupancy (over 2 guests per bedroom) or undeclared pets.brbrOptional Services (subject to approval)brEarly check-in/late departure, elevator access, and mid-stay cleaning for stays of 28+ days. Fees for approved add-ons are collected after booking.brbrReservations & Guest RequirementsbrMost stays are 7 nights, Saturday–Saturday, though flexible dates may be available outside peak/holiday weeks—confirm before booking, as changes are not always possible afterward. Guests must be 25+, provide valid ID, and remain for the full stay. Standard occupancy is 2 per bedroom; extra guests are $25/person/night up to the maximum allowed.brbrQuiet Hoursbr10 PM–8 AM. Maintain reasonable noise at all times to respect neighbors; excessive noise is not permitted.brbrCleaning & LinensbrHome is professionally cleaned and sanitized between stays. Starter amenities provided; daily service available for a fee. Stays of 28+ days require a mid-stay clean. Linens/towels are commercially laundered through our Professional Linen Program; no extra sets stored onsite.brbrGolf Cart RentalsbrExplore the island with ease! After booking, reserve a golf cart through our sister company, Once Upon A Beach Carts, and enjoy an exclusive discount available only to our vacation rental guests.brbrPool & SpabrPool heated year-round to 82–85°F; heating may be affected by cooler weather. Heaters/filters off during quiet hours (10 PM–8 AM). Spa, if available, is part of the pool, seasonal, not a commercial hot tub, and may be unavailable in summer. Guests may not adjust equipment; violations may result in fines or damages.brbrProperty SecuritybrExterior cameras may monitor entries, driveways, pool equipment, and backyard access for security, deliveries, and occupancy compliance. Cameras do not face private areas.brbrPayments & Cancellation PolicybrPolicies updated October 6, 2025 — see full Terms & Conditions for details.brbrPayment SchedulebrDepositbr- Reservations up to 20 days: 50% of total amount due at time of booking.brRemaining Balancebr- Reservations up to 20 days: Remaining 50% due 30 days prior to check-in.brbrCancellation PolicybrFor Reservations of 20 Days or Lessbr- More than 30 days before arrival: Full refund of deposit (including taxes) minus non-refundable booking administration fee.br- 14–29 days before arrival: Refund of 50% of total rental, fees, and taxes, minus non-refundable booking administration fee.br- Less than 14 days before arrival: Refunds only for base rental rate, fees, and taxes for nights we are able to rebook, minus non-refundable booking administration fee.br- Please note: While we make every effort to rebook, we cannot guarantee the same rate or number of nights. For any nights that cannot be re-rented, as well as for non-arrivals, late arrivals, early departures, or alterations resulting in lost revenue, no refunds or price adjustments will be made.brbrTravel InsurancebrCSA Travel Insurance is available to U.S. guests (except NY and HI residents) and is strongly encouraged to protect your trip from unforeseen events. No refunds are given for COVID-19, weather, or beach conditions outside our cancellation policy. Hurricane season runs June 1–Nov 30; insurance can safeguard your plans. In the event of a mandatory evacuation, home unavailability, or government order halting vacation rentals, guests receive a full refund of base rate, applicable fees (minus booking fee), and taxes.brbrAdditional TermsbrNo refunds for events beyond our control (weather, red tide, travel issues, etc.). Cancellation requests must be submitted in writing by the registered guest—phone/text not accepted.brbrCity of Holmes Beach Vacation Rental License: VRC18-000018brMax Occupancy: 6 Guests | Max Vehicles: 3brInformation deemed reliable but not guaranteed; subject to change or withdrawal without notice.
Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps
Slider Thumb

$1645.08

/ Nightly
Private Vacation Home

Beach Haven~Waterslide! Pool/Spa

Holmes Beach, Florida, United States

Summary:brbrBeach Haven is an 8BR/7.5BA luxury retreat with just a 5-minute walk to the beach ️! Enjoy a heated pool with waterslide , in-ground spa, swim-up tiki table , game area with pool table & foosball , and a rooftop deck with stunning Gulf & Bay views . Walk to restaurants and shops, relax in spacious king suites, and create unforgettable island memories . Ideal for large groups and family stays too!brbrbrbrThe Space:brbr Beach Haven | Rooftop Views • Waterslide • Walk to Beach ️brbr 5501 Holmes Blvd, Holmes Beach, FLbrbr✅ VRC #: VRC18-000066brbrbrbrWelcome to Beach Haven, an extraordinary 8-bedroom, 7.5-bath luxury retreat just a 5-minute stroll to the sugar-white beaches of Anna Maria Island . Perfect for large families or group getaways, this spacious multi-level home is packed with resort-style amenities including a heated pool, waterslide, in-ground spa, rooftop deck, and multiple entertainment areas. With its walkable location near shops and restaurants, Beach Haven is where coastal comfort meets unforgettable fun.brbrbrbrStep into your private tropical oasis . Spend sunny days splashing in the pool, relaxing at the swim-up tiki table, or soaking in the spa. Under the covered patio, enjoy lounge seating, a bar with TV, pool table, and foosball, making it easy to entertain guests of all ages. Head up to the rooftop deck for sunset cocktails and sweeping views of both the Gulf and Tampa Bay.brbrbrbrInside, the open-concept living space features bright coastal décor, plush seating, and a large TV for movie nights. The fully equipped kitchen boasts stainless steel appliances, custom cabinetry, generous counter seating, and a vibrant dining area ideal for group meals ️. Sliding glass doors lead to a balcony with Adirondack chairs overlooking the pool area.brbrbrbrWith seven king suites and a dedicated bunk room, Beach Haven offers space, privacy, and comfort for everyone. Whether you’re planning a family reunion, milestone celebration, or friends’ retreat, this island escape delivers luxury, location, and laid-back Florida charm.brbrbrbr✨ Highlights ✨brbrbrbr• ️ 5-minute walk to Anna Maria Island beachesbrbr• ️ 8 Bedrooms / 7.5 Bathroomsbrbr• 7 King beds + ️ 2 Twin-over-Twin bunksbrbr• Rooftop deck with Gulf & Bay viewsbrbr• Heated pool with waterslide & in-ground spabrbr• Swim-up tiki table & outdoor barbrbr• Pool table & foosballbrbr• Pet-friendly with host approvalbrbr• 4 parking spacesbrbr• ️ Walk to dining, parks & shoppingbrbrbrbr ️ Bedrooms ️brbrbrbr• Primary Bedroom (3rd Floor): King bed, private balcony, ensuite bath with double vanity & walk-in showerbrbr• Bedroom 2 (3rd Floor): King bed, ensuite bath with walk-in showerbrbr• Bedroom 3 (3rd Floor): King bed, balcony accessbrbr• Bedroom 4 (3rd Floor): King bedbrbr• Bedroom 5 (2nd Floor): King bed, ensuite bath with double vanity & walk-in showerbrbr• Bedroom 6 (2nd Floor): King bed, ensuite bath with walk-in showerbrbr• Bedroom 7 (2nd Floor): King bed, ensuite bath with walk-in showerbrbr• Bedroom 8 (2nd Floor): Two twin-over-twin bunk beds, ensuite bath with walk-in showerbrbrbrbrOther Things to Note:brbr ️ Beach-Ready Convenience brbrTo make your stay effortless, the home is fully stocked with 4 beach chairs, a beach cart, and a beach umbrella, plus all bath towels, beach towels, and linens—just pack your bags and enjoy island time ☀️ brbrbrbr Parking InformationbrbrParking is available for up to 4 vehicles maximum. Please plan ahead and coordinate with your group accordingly.brbrbrbr Friendly Island ReminderbrbrThis home is located in a residential neighborhood. We kindly ask guests to be respectful of our neighbors by keeping noise at a considerate level day and night. Thank you for helping preserve the peaceful island atmosphere brbrbrbrInteraction with Guests:brbrIf you need anything during your stay, I’m always here to help! You can call or text me directly on my cell anytime. I’m available 24/7 to answer questions, share local tips ️, or assist with anything that comes up. Your comfort and peace of mind are my top priority! ✨
Bath 8

Bath

Sleep 16

Sleeps
Slider Thumb
Exceptional(42)

$532.46

/ Nightly
Private Vacation Home

Putting Green - Flip Flops Forever by SeaBreeze Vacation

Holmes Beach, Florida, United States

Recently renovated! Flip Flops Forever is a traditional Florida home just steps from the beach nestled in the quiet residential area in the heart of Holmes Beach. Offering 5 bedrooms/3 bathrooms, Flip Flops Forever is located in the perfect location for a great family vacation. Only a few seconds walk (around 200 steps) from the world-renowned white sandy beaches of the Gulf of Mexico. This home offers enough space for everyone to have their privacy while still enjoying quality time together. Sit back and relax - you are on vacation! Flip Flops ensures you have it all. Make memories as a family that will last a lifetime! Vacations are for fun and relaxation. The outdoor area at Flip Flops Forever provides just that. Have fun in the pool which is heated year round for your enjoyment or play on the mini golf hole.br brThe family dogs are welcome to join you here. The weight limit per dog is 30 lbs. The entire family, including the dogs, are sure to have a great time and never want the vacation to end.brbrCancellation Policy - SeaBreeze Vacation has spent a great deal of time and effort into formulating a cancellation policy for you. SeaBreeze Vacation has the most flexible cancellation policy on the Island. You are allowed to cancel your reservation up to 14 days prior to check-in to receive a refund. Additional terms and conditions apply. Please note: For reservations longer than 28 nights or more than $20,000, a different cancellation policy applies - please see the Rental Agreement under the House Rules on the check-out page.brbrThis property participates in our Professional Linen Program. SeaBreeze Vacation strives to bring only the best quality experience to our guests. To do so, we provide a professional linen service at this property to better enhance your enjoyment while staying here. This luxury amenity provides you high quality linens that are in place and ready for your use upon your arrival. These high-quality linens are laundered in a commercial setting that uses only hypoallergenic, perfume & dye-free soaps assuring all of our guests a comfortable stay. brbrWith all SeaBreeze Vacation properties, we think of the little things to make your vacation special. Included to get you started are the following: brbrPer Guest: 1 Bath Towel, 1 Hand Towel, 1 Washcloth, 1 Pool/Beach TowelbrPer Full Bathroom: 2 Rolls of Toilet Paper, Hand Soap, Shower Products Set (including trial size shampoo, conditioner, shower gel, and body lotion), Cosmetic Cloth, Bath MatbrPer Kitchen: 2 Rolls of Paper Towels, Hand Soap, Dish Soap, Sponge, Dishwasher Pods (x4), Laundry Detergent Pods (x4), All-Purpose Disinfectant, Microfiber Cloth, 2 Kitchen TowelsbrbrWe also offer a range of supplemental services including pre-stock grocery shopping and babysitting. Need a pack and play or high chair, etc. These are available for a small additional fee and will be waiting in the home on your arrival.brbrBedrooms & BathroomsbrThis 5 bedroom/3 bathroom home sleeps 10. brPrimary bedroom is located on the second features a king bed, flat screen TV and private balcony to watch the sunset. brThere are also 2 twin beds located off the primary bedroom with private closet.brBedroom 2 is located on the second floor and features a queen-size bed and flat screen TV. brBathroom 1 is located on the second floor and has a walk-in shower with a separate vanity area.brBedroom 3 is located downstairs and features a king-size bed and flat screen TV.brBedroom 4 is located downstairs and features 2 twin beds and flat screen TV. brBedroom 5 is located downstairs and features a queen-size bed and flat screen TV. brBathroom 2 is located downstairs with a walk-in shower and single vanity. brBathroom 3 is located downstairs with a shower/tub combo and full vanity.brbrYou are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property.brbrCity of Holmes Beach Vacation Rental License: VRC19-000079brMax Occupancy: 10 Guests | Max Vehicles: 6brQuiet Hours: 10 p.m. - 7 a.m. - please respect our island communitybrMin stay requirements vary by city ordinance and are often 7 nights. Please contact our office with any questions.
Bed 5

Bed

Bath 3

Bath

Sleep 10

Sleeps
Slider Thumb
Exceptional(1)

$673.58

/ Nightly
Private Vacation Home

Family-Friendly Waterfront Paradise!

Holmes Beach, Florida, United States

Coral Castle by AMI Locals brVRC16-000158brbrWelcome to Coral Castle, a luxurious waterfront retreat in the heart of Anna Maria Island, where you can spot gentle manatees gliding by from your private dock! This five-bedroom, three-and-a-half-bathroom haven is just a three-minute walk to the powdery sands of Manatee Beach. With a private pool, spa, rooftop deck, and private dock, this coastal gem blends upscale comfort with tropical charm, perfect for families or groups seeking a dream island getaway. brbrHighlights br • 3-minute walk to Manatee Beach br • 5 Bedroom / 3.5 Bath br • 3 Kings, 2 Fulls br • Rooftop deck with Gulf and Bay views br • Heated pool and in-ground spa br • Private dock for up to 20ft boat br • Outdoor dining area and grill br • Beach chairs provided br • Washer and dryer br • 5 Parking Spaces brbrThe rooftop deck invites guests to take in jaw-dropping views of the Gulf and Bay. It’s the perfect spot to sip morning coffee or watch the sunset with a chilled drink in hand. Outside, the tropical backyard features a heated pool, spa, lounge seating, and a BBQ grill, ideal for relaxing after a day of beach fun or boating. Best of all, keep an eye out for manatees cruising by from the private dock, a magical touch to your island escape! brbrStep inside this spacious island-style home, where the airy living area features plush seating, TV, and sliding doors that lead to the outdoor patio. The gourmet kitchen includes stainless steel appliances, ample counter space, and a wine fridge. Share meals at the dining table or outside under the stars on the covered patio. brbrThis home features three king bedrooms, including a primary suite with a private balcony, walk-in closet, and spa-style ensuite with a soaking tub and walk-in shower. The additional two full bedrooms are connected by a Jack-and-Jill bathroom with a shower/tub combo, perfect for kids or additional guests. brbrRoom Details br• Primary Bedroom: King bed, ensuite bathroom with soaking tub and walk-in shower br• Second Bedroom: King bed, Jack-and-Jill bathroom with walk-in shower br• Third Bedroom: King bed, Jack-and-Jill bathroom with walk-in shower br• Fourth Bedroom: Full bed, shares Jack-and-Jill bathroom with shower/tub combo br• Fifth Bedroom: Full bed, shares Jack-and-Jill bathroom with shower/tub combo brbrEnjoy mornings from the dock or head just a few minutes down the street to explore Pine Ave and Bridge Street’s local shops and restaurants. Whether you’re boating, relaxing in the spa, or enjoying the rooftop views, Coral Castle offers a perfect blend of luxury and island adventure. brbrBook Coral Castle now and start making unforgettable family memories in paradise! brbr- brThis home is managed by AMI Locals, an Anna Maria Island property management company. brbrThis property does not allow pets of any kind. brbr5 cars maximum are able to park at this home. One side of the garage is available for guest use. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. brbrThese premises are under active video surveillance in public approach areas and the dock. brbrWe do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please see our AMI Locals Rental Policies for full details. brbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.
Bed 5

Bed

Bath 3

Bath

Sleep 10

Sleeps
Slider Thumb
Exceptional(4)

$792.47

/ Nightly
Private Vacation Home

Island Girl East & West – AMI Retreat w/ Heated Pool, Covered Porches & Walk To Beach

Holmes Beach, Florida, United States

Welcome to Island Girl East & West!brOn Anna Maria Island (Holmes Beach, FL)brbrThis listing is for BOTH units: Island Girl East & Island Girl WestbrbrThe SpacebrWith room for up to 10 guests, Island Girl East & West is thoughtfully designed for shared experiences and easy island living. Each side of this home mirrors the other, allowing everyone to gather together while still enjoying their own space. Inside, bright open-concept living areas invite conversation, laughter, and long dinners that stretch into the evening. Outside, the deck and pool patio set the stage for laid-back afternoons under the palms.brbrPerfect for: Families traveling together • Multi-generational groups • Friends seeking shared space and privacybrbrHighlightsbr- Two complete homes—rent both sides for exclusive usebr- Heated saltwater pool with sun loungers and outdoor diningbr- Two king master suites with ensuite bathsbr- Steps to the beach (just five houses away!)br- Beach gear credit includedbr- On-site grill, private decks, and tropical landscapingbr- Washer & dryer in each unitbrbrInterior Spacesbr- Living Areas: Each home features an inviting living room with comfortable seating and Smart TV—perfect for movie nights or unwinding after a day by the Gulf.br- Dining Areas: Gather around dining tables that seat six, or combine both spaces to host a full family meal.br- Bathrooms: Four full bathrooms in total, each stocked with fresh linens and thoughtful amenities.brbrBedrooms:br- Two king master suites, each with private ensuite bath.br- One queen bedroom (West unit).br- One bedroom with two twin beds (East unit).br- Two twin hotel-quality rollaway beds available for groups over eight.brbrLayout Overviewbr- Island Girl East: King ensuite, twin bedroom, two full bathrooms, open living/dining/kitchen area, washer/dryer.br- Island Girl West: King ensuite, queen bedroom, two full bathrooms, open living/dining/kitchen area, washer/dryer.brbrTogether, they offer double the comfort and connection—ideal for families or groups traveling together.brbrOutdoor LivingbrStep out to a private tropical yard with a heated saltwater pool, surrounded by lush landscaping, sun loungers, and shaded seating areas. Fire up the grill for fresh-caught seafood or enjoy a quiet morning coffee on the deck overlooking the pool.brbrJust five houses away, a convenient public beach access leads you to the white sands and turquoise waters of Holmes Beach. Return home for sunset swims and stories shared beneath the soft glow of the patio lights.brbrKitchen & Diningbr- Each side of the duplex offers a fully equipped gourmet kitchen with:br- Stove/Oven, Dishwasher, Microwave, Refrigerator w/ Ice & Waterbr- Coffeemaker (12-cup), Blender, Toaster, and full kitchenwarebr- Open layout with counter seating and adjacent dining tablebrbrPrepare shared meals with ease, or let everyone create their own favorites—there's plenty of space for both collaboration and comfort.brbrAdditional Amenitiesbr- High-speed WiFibr- Cable TVbr- Central A/C & Heatbr- Linens, towels, hair dryers, and irons providedbr- Beach gear rental credit included (chairs, umbrellas, carts, bikes, and more)br- Professional cleaning between staysbrbrParkingbrDriveway parking available for 1–2 cars per unit (4 total). Garage is used for storage and not available for vehicles.brbrAt Island Girl East & West, mornings begin with coffee shared across sunlit porches and the gentle hush of waves nearby.brDays unfold between the pool and the shore, where laughter drifts as easily as the sea breeze.brEvenings bring everyone back together—grilling, storytelling, and soaking in the glow of another island sunset.brbrWrite Your Vacation Story.brbrPoliciesbrbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.brbrNO SMOKING.brbrPets are welcome with prior approval, provided they meet our pet policy guidelines. We allow a maximum of one pet, weighing under 65 lbs. A pet fee applies based on the length of your stay: $100 for stays under 4 days, $200 for stays of 4-14 days, and $400 for stays of 15+ days, per pet.brbrBooking & Fee PolicybrInclude all guests and pets in your reservation request for accurate pricing. Additional fees apply for extra occupancy (over 2 guests per bedroom) or undeclared pets.brbrOptional Services (subject to approval)brEarly check-in/late departure, elevator access, and mid-stay cleaning for stays of 28+ days. Fees for approved add-ons are collected after booking.brbrReservations & Guest RequirementsbrMost stays are 7 nights, Saturday–Saturday, though flexible dates may be available outside peak/holiday weeks—confirm before booking, as changes are not always possible afterward. Guests must be 25+, provide valid ID, and remain for the full stay. Standard occupancy is 2 per bedroom; extra guests are $25/person/night up to the maximum allowed.brbrQuiet Hoursbr10 PM–8 AM. Maintain reasonable noise at all times to respect neighbors; excessive noise is not permitted.brbrCleaning & LinensbrHome is professionally cleaned and sanitized between stays. Starter amenities provided; daily service available for a fee. Stays of 28+ days require a mid-stay clean. Linens/towels are commercially laundered through our Professional Linen Program; no extra sets stored onsite.brbrGolf Cart RentalsbrExplore the island with ease! After booking, reserve a golf cart through our sister company, Once Upon A Beach Carts, and enjoy an exclusive discount available only to our vacation rental guests.brbrPool & SpabrPool heated year-round to 82–85°F; heating may be affected by cooler weather. Heaters/filters off during quiet hours (10 PM–8 AM). Spa, if available, is part of the pool, seasonal, not a commercial hot tub, and may be unavailable in summer. Guests may not adjust equipment; violations may result in fines or damages.brbrProperty SecuritybrExterior cameras may monitor entries, driveways, pool equipment, and backyard access for security, deliveries, and occupancy compliance. Cameras do not face private areas.brbrPayments & Cancellation PolicybrPolicies updated October 6, 2025 — see full Terms & Conditions for details.brbrPayment SchedulebrDepositbr- Reservations up to 20 days: 50% of total amount due at time of booking.brRemaining Balancebr- Reservations up to 20 days: Remaining 50% due 30 days prior to check-in.brbrCancellation PolicybrFor Reservations of 20 Days or Lessbr- More than 30 days before arrival: Full refund of deposit (including taxes) minus non-refundable booking administration fee.br- 14–29 days before arrival: Refund of 50% of total rental, fees, and taxes, minus non-refundable booking administration fee.br- Less than 14 days before arrival: Refunds only for base rental rate, fees, and taxes for nights we are able to rebook, minus non-refundable booking administration fee.br- Please note: While we make every effort to rebook, we cannot guarantee the same rate or number of nights. For any nights that cannot be re-rented, as well as for non-arrivals, late arrivals, early departures, or alterations resulting in lost revenue, no refunds or price adjustments will be made.brbrTravel InsurancebrCSA Travel Insurance is available to U.S. guests (except NY and HI residents) and is strongly encouraged to protect your trip from unforeseen events. No refunds are given for COVID-19, weather, or beach conditions outside our cancellation policy. Hurricane season runs June 1–Nov 30; insurance can safeguard your plans. In the event of a mandatory evacuation, home unavailability, or government order halting vacation rentals, guests receive a full refund of base rate, applicable fees (minus booking fee), and taxes.brbrAdditional TermsbrNo refunds for events beyond our control (weather, red tide, travel issues, etc.). Cancellation requests must be submitted in writing by the registered guest—phone/text not accepted.brbrCity of Holmes Beach Vacation Rental Licenses: VRC17-000038 & VRC17-000039brMax Occupancy: 10 Guests | Max Vehicles: 4brInformation deemed reliable but not guaranteed; subject to change or withdrawal without notice.
Bed 4

Bed

Bath 4

Bath

Sleep 10

Sleeps
Slider Thumb
Exceptional(3)

$485.96

/ Nightly
Private Vacation Home

Island Girl West – Spacious Retreat w/ Deck, Heated Pool & Just Steps To The Beach

Holmes Beach, Florida, United States

Welcome to Island Girl West!brOn Anna Maria Island (Holmes Beach, FL)brbrThis listing is for ONE unit: Island Girl WestbrbrStep inside Island Girl West, where natural textures, sunlight, and soft coastal hues set the tone for your stay. The open layout invites easy flow between kitchen, dining, and living spaces—perfect for shared meals or quiet mornings with coffee and conversation. Whether you're capturing golden-hour light on the wraparound deck or creating simple meals that turn into long dinners, this home offers both comfort and inspiration.brbrPerfect for: Couples • Small families • Friends seeking a bright and beautiful escapebrbrHighlightsbr- Just five houses from Holmes Beach accessbr- Shared heated saltwater pool and patiobr- King master suite with ensuite bathbr- Queen bedroom + rollaway bed for groups of up to fivebr- Wraparound deck overlooking lush tropical yardbr- Beach gear credit includedbr- Washer & dryer in unitbrbrInterior Spacesbr- Living Room: Bathed in natural light, with soft furnishings and textures that echo the shoreline. A Smart TV and plush seating make it the perfect space to relax after the beach.br- Dining Area: Designed for connection, this open space blends form and function—ideal for casual meals or quiet journaling in the morning light.brbrBedrooms:br- King master suite with ensuite bath and elegant simplicity.br- Queen bedroom with bright, serene décor.br- Twin rollaway available for an additional guest.br- Bathrooms: Two full bathrooms with crisp design, fresh towels, and quality linens provided through our Professional Linen Program.brbrLayout Overviewbr- Open-concept kitchen, dining, and living areasbr- Two bedrooms, two bathroomsbr- Ground-level access to shared outdoor spacesbr- Washer and dryer in unitbrbrOutdoor LivingbrStep outside to a wraparound deck surrounded by palms and filtered sunlight. Mornings begin here—barefoot and peaceful—with the smell of salt in the air. Evenings bring shared dinners and the gentle sound of island life winding down.brbrThe shared heated saltwater pool offers a tranquil spot to unwind, with loungers, shaded seating, and a grill for fresh-caught seafood. When both sides of the home are occupied, the space still feels open and welcoming—each guest enjoying their own rhythm under the same island sky.brbrKitchen & DiningbrThe fully equipped kitchen invites both creativity and simplicity, featuring:br- Stove/Oven, Dishwasher, Microwave, Refrigerator w/ Ice & Waterbr- Coffeemaker (12-cup), Blender, Toaster, KitchenwarebrbrPrepare island-inspired meals with ease or let the day's adventures inspire your dinner menu. Dine indoors with soft lighting or take your plates to the deck for al fresco evenings that feel like a work of art.brbrAdditional Amenitiesbr- High-speed WiFibr- Cable TVbr- Central A/C & Heatbr- Linens, towels, and starter supplies includedbr- Beach gear rental credit for chairs, umbrellas, carts, and morebr- Professionally cleaned between staysbrbrParkingbr- Driveway parking for 1–2 vehicles. Garage reserved for storage; not available for parking.brbrAt Island Girl West, sunlight spills across every surface and laughter fills the air.brMornings start with inspiration, afternoons flow with ease, and evenings unfold on the deck beneath painted skies.brIt's a home that reminds you that beauty isn't just seen—it's felt.brbrPoliciesbrbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.brbrNO SMOKING. NO PETS WHEN ONLY RENTING ONE UNIT.brbrIf you're reserving both units of this property (Island Girl East & West) and plan to enjoy your stay as one unified group, please let us know in advance. This allows our team to make any necessary preparations and ensure a seamless, comfortable experience for your entire party.brbrWhen both sides are rented together, the property is fully reserved for your group only—no other guests will occupy the space during your stay, and the owner will not be present.brbrIf you're renting just one side of the duplex, please note that the other side may be occupied by another vacation rental guest, and a small ground-level area of the property may be intermittently used by the owner as a private residence. In those instances, the outdoor spaces—including the pool and deck—may be shared with up to two additional, independent parties.brbrBooking & Fee PolicybrInclude all guests and pets in your reservation request for accurate pricing. Additional fees apply for extra occupancy (over 2 guests per bedroom) or undeclared pets.brbrOptional Services (subject to approval)brEarly check-in/late departure, elevator access, and mid-stay cleaning for stays of 28+ days. Fees for approved add-ons are collected after booking.brbrReservations & Guest RequirementsbrMost stays are 7 nights, Saturday–Saturday, though flexible dates may be available outside peak/holiday weeks—confirm before booking, as changes are not always possible afterward. Guests must be 25+, provide valid ID, and remain for the full stay. Standard occupancy is 2 per bedroom; extra guests are $25/person/night up to the maximum allowed.brbrQuiet Hoursbr10 PM–8 AM. Maintain reasonable noise at all times to respect neighbors; excessive noise is not permitted.brbrCleaning & LinensbrHome is professionally cleaned and sanitized between stays. Starter amenities provided; daily service available for a fee. Stays of 28+ days require a mid-stay clean. Linens/towels are commercially laundered through our Professional Linen Program; no extra sets stored onsite.brbrGolf Cart RentalsbrExplore the island with ease! After booking, reserve a golf cart through our sister company, Once Upon A Beach Carts, and enjoy an exclusive discount available only to our vacation rental guests.brbrPool & SpabrPool heated year-round to 82–85°F; heating may be affected by cooler weather. Heaters/filters off during quiet hours (10 PM–8 AM). Spa, if available, is part of the pool, seasonal, not a commercial hot tub, and may be unavailable in summer. Guests may not adjust equipment; violations may result in fines or damages.brbrProperty SecuritybrExterior cameras may monitor entries, driveways, pool equipment, and backyard access for security, deliveries, and occupancy compliance. Cameras do not face private areas.brbrPayments & Cancellation PolicybrPolicies updated October 6, 2025 — see full Terms & Conditions for details.brbrPayment SchedulebrDepositbr- Reservations up to 20 days: 50% of total amount due at time of booking.brRemaining Balancebr- Reservations up to 20 days: Remaining 50% due 30 days prior to check-in.brbrCancellation PolicybrFor Reservations of 20 Days or Lessbr- More than 30 days before arrival: Full refund of deposit (including taxes) minus non-refundable booking administration fee.br- 14–29 days before arrival: Refund of 50% of total rental, fees, and taxes, minus non-refundable booking administration fee.br- Less than 14 days before arrival: Refunds only for base rental rate, fees, and taxes for nights we are able to rebook, minus non-refundable booking administration fee.br- Please note: While we make every effort to rebook, we cannot guarantee the same rate or number of nights. For any nights that cannot be re-rented, as well as for non-arrivals, late arrivals, early departures, or alterations resulting in lost revenue, no refunds or price adjustments will be made.brbrTravel InsurancebrCSA Travel Insurance is available to U.S. guests (except NY and HI residents) and is strongly encouraged to protect your trip from unforeseen events. No refunds are given for COVID-19, weather, or beach conditions outside our cancellation policy. Hurricane season runs June 1–Nov 30; insurance can safeguard your plans. In the event of a mandatory evacuation, home unavailability, or government order halting vacation rentals, guests receive a full refund of base rate, applicable fees (minus booking fee), and taxes.brbrAdditional TermsbrNo refunds for events beyond our control (weather, red tide, travel issues, etc.). Cancellation requests must be submitted in writing by the registered guest—phone/text not accepted.brbrCity of Holmes Beach Vacation Rental License: VRC17-000039brMax Occupancy: 5 Guests | Max Vehicles: 2brInformation deemed reliable but not guaranteed; subject to change or withdrawal without notice.
Bed 2

Bed

Bath 2

Bath

Sleep 5

Sleeps
Slider Thumb
Exceptional(4)

$476.82

/ Nightly
Private Vacation Home

Island Girl East – Coastal Retreat w/ Pool, Deck & Short Walk To Beach

Holmes Beach, Florida, United States

Welcome to Island Girl East!brOn Anna Maria Island (Holmes Beach, FL)brbrThis listing is for ONE unit: Island Girl EastbrbrDiscover Island Girl East, a bright coastal retreat just five houses from the beach. Here, mornings begin with the sound of swaying palms, and afternoons drift between the pool and the sea. With light-filled interiors, thoughtful details, and shared access to a heated saltwater pool, this home offers an easy balance of rest, renewal, and connection.brbrPerfect for: Small families • Couples • Friends seeking a peaceful island escapebrbrHighlightsbr- Just five houses from the beachbr- Shared heated saltwater pool and outdoor living areabr- King master suite with ensuite bathbr- Twin bedroom + rollaway bed for groups of up to fivebr- Washer & dryer in unitbr- Beach gear credit includedbr- Professionally cleaned and locally managedbrbrInterior Spacesbr- Living Room: Bright and inviting, with comfortable seating and a Smart TV for movie nights or quiet mornings.br- Dining Area: Open to the kitchen for easy flow, perfect for shared meals or board games after a day on the sand.brbrBedrooms:br- King master suite with private ensuite bathroom.br- Second bedroom with two twin beds.br- One twin rollaway bed available for groups of five.brbrBathrooms: Two full bathrooms, each with ample counter space and fresh linens provided through our Professional Linen Program.brbrLayout Overviewbr- Open-concept living, dining, and kitchen areabr- Two bedrooms and two bathroomsbr- Ground-level access with shared pool and patio areabr- In-unit washer and dryerbrbrOutdoor LivingbrStep out to a shared heated saltwater pool surrounded by lush palms and gentle island breezes. Enjoy sun loungers, outdoor seating, and a grill for easy afternoons by the water.brbrAfter a short walk to the beach—just five houses away—return home for an evening swim or al fresco dinner beneath the string lights on the shared deck. Whether you're connecting with loved ones or soaking in a little solitude, this is island living at its most peaceful.brbrKitchen & DiningbrThe fully equipped kitchen includes everything you need for simple meals and late-night snacks:br- Stove/Oven, Dishwasher, Microwave, Refrigerator w/ Ice & Waterbr- Coffeemaker (12-cup), Blender, Toaster, Kitchenwarebr- Cook together and share meals at the dining table or take your plates outside for an easy island dinner under the palms.brbrAdditional Amenitiesbr- High-speed WiFibr- Cable TVbr- Central A/C & Heatbr- Linens, towels, and starter supplies includedbr- Beach gear rental credit for chairs, umbrellas, carts, and morebr- Shared access to heated pool and outdoor lounge areabrbrParkingbrDriveway parking for 1–2 vehicles. Garage is used for storage only and not available for parking.brbrAt Island Girl East, mornings start with sunlight and sea breeze, and evenings settle into laughter by the pool.brIt's where stillness finds you, and every day feels like a breath of fresh air.brbrPoliciesbrbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.brbrNO SMOKING. NO PETS.brbrIf you're reserving both units of this property (Island Girl East & West) and plan to enjoy your stay as one unified group, please let us know in advance. This allows our team to make any necessary preparations and ensure a seamless, comfortable experience for your entire party.brbrWhen both sides are rented together, the property is fully reserved for your group only—no other guests will occupy the space during your stay, and the owner will not be present.brbrIf you're renting just one side of the duplex, please note that the other side may be occupied by another vacation rental guest, and a small ground-level area of the property may be intermittently used by the owner as a private residence. In those instances, the outdoor spaces—including the pool and deck—may be shared with up to two additional, independent parties.brbrBooking & Fee PolicybrInclude all guests and pets in your reservation request for accurate pricing. Additional fees apply for extra occupancy (over 2 guests per bedroom) or undeclared pets.brbrOptional Services (subject to approval)brEarly check-in/late departure, elevator access, and mid-stay cleaning for stays of 28+ days. Fees for approved add-ons are collected after booking.brbrReservations & Guest RequirementsbrMost stays are 7 nights, Saturday–Saturday, though flexible dates may be available outside peak/holiday weeks—confirm before booking, as changes are not always possible afterward. Guests must be 25+, provide valid ID, and remain for the full stay. Standard occupancy is 2 per bedroom; extra guests are $25/person/night up to the maximum allowed.brbrQuiet Hoursbr10 PM–8 AM. Maintain reasonable noise at all times to respect neighbors; excessive noise is not permitted.brbrCleaning & LinensbrHome is professionally cleaned and sanitized between stays. Starter amenities provided; daily service available for a fee. Stays of 28+ days require a mid-stay clean. Linens/towels are commercially laundered through our Professional Linen Program; no extra sets stored onsite.brbrGolf Cart RentalsbrExplore the island with ease! After booking, reserve a golf cart through our sister company, Once Upon A Beach Carts, and enjoy an exclusive discount available only to our vacation rental guests.brbrPool & SpabrPool heated year-round to 82–85°F; heating may be affected by cooler weather. Heaters/filters off during quiet hours (10 PM–8 AM). Spa, if available, is part of the pool, seasonal, not a commercial hot tub, and may be unavailable in summer. Guests may not adjust equipment; violations may result in fines or damages.brbrProperty SecuritybrExterior cameras may monitor entries, driveways, pool equipment, and backyard access for security, deliveries, and occupancy compliance. Cameras do not face private areas.brbrPayments & Cancellation PolicybrPolicies updated October 6, 2025 — see full Terms & Conditions for details.brbrPayment SchedulebrDepositbr- Reservations up to 20 days: 50% of total amount due at time of booking.brRemaining Balancebr- Reservations up to 20 days: Remaining 50% due 30 days prior to check-in.brbrCancellation PolicybrFor Reservations of 20 Days or Lessbr- More than 30 days before arrival: Full refund of deposit (including taxes) minus non-refundable booking administration fee.br- 14–29 days before arrival: Refund of 50% of total rental, fees, and taxes, minus non-refundable booking administration fee.br- Less than 14 days before arrival: Refunds only for base rental rate, fees, and taxes for nights we are able to rebook, minus non-refundable booking administration fee.br- Please note: While we make every effort to rebook, we cannot guarantee the same rate or number of nights. For any nights that cannot be re-rented, as well as for non-arrivals, late arrivals, early departures, or alterations resulting in lost revenue, no refunds or price adjustments will be made.brbrTravel InsurancebrCSA Travel Insurance is available to U.S. guests (except NY and HI residents) and is strongly encouraged to protect your trip from unforeseen events. No refunds are given for COVID-19, weather, or beach conditions outside our cancellation policy. Hurricane season runs June 1–Nov 30; insurance can safeguard your plans. In the event of a mandatory evacuation, home unavailability, or government order halting vacation rentals, guests receive a full refund of base rate, applicable fees (minus booking fee), and taxes.brbrAdditional TermsbrNo refunds for events beyond our control (weather, red tide, travel issues, etc.). Cancellation requests must be submitted in writing by the registered guest—phone/text not accepted.brbrCity of Holmes Beach Vacation Rental License: VRC17-000038brMax Occupancy: 5 Guests | Max Vehicles: 2brInformation deemed reliable but not guaranteed; subject to change or withdrawal without notice.
Bed 2

Bed

Bath 2

Bath

Sleep 5

Sleeps
Slider Thumb

$614.69

/ Nightly
Private Vacation Home

Tie Dye Sky AMI Beach Home, Family-Friendly, Private Heated Pool, Walk to Beach!

Holmes Beach, Florida, United States

Anna Maria Island Beach House | Family-Friendly | Heated Pool | Walk to BeachbrbrLooking for the perfect Anna Maria Island vacation rental for your family Enjoy sunny pool days, beach sunsets, and a fully equipped home designed for comfort, convenience, and fun.brbrWelcome to Tie Dye Sky, a 4 bedroom, 3 bathroom beach house that sleeps 8, ideal for families, groups, and multi-generational vacations.brbrPrime LocationbrbrSteps to soft sandy famous AMI Gulf beachesbrWalk to Manatee Public Beach, restaurants, grocery stores, and shopsbrCentrally located near the free island trolleybrbrSpacious & Luxurious Bedroomsbrbr2 King suites with private bathroomsbrTwin room with trundle (4 twin beds)brTower bedroom with king bed & panoramic viewsbrTVs and ceiling fans in all roomsbrbrFamily-Friendly AmenitiesbrbrCrib, stroller, high chair, monitor, toddler dining gearbrPool alarms for safetybrBeach toys and baby beach gearbrbrOutdoor LivingbrbrPrivate heated pool and lanai with waterfall and bar seatingbrRooftop crow’s nest with ocean viewsbrGas and charcoal grillsbrbrEntertainment & ComfortbrbrGame room with Pac Man, ping pong, basketball, jumbo gamesbrFast WiFi, fully stocked kitchen, laundry roombrAll beach gear included (chairs, toys, essentials)brbrRelax, explore, and make memories at Tie Dye Sky on AMI, your ultimate Florida Gulf Coast beach getaway.brbrbrbrMaximum Occupancy Limit of Property: 8 peoplebrbrMaximum Parking Available on Property: 4 vehiclesbrbrMinimum Stay Requirement: 7 daysbrbrbrPlease note: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property.brbrbrWe can’t wait for you to visit us—see you soon!brbrVRC#18-000200
Bed 4

Bed

Bath 3

Bath

Sleep 8

Sleeps
Slider Thumb

$475.12

/ Nightly
Private Vacation Home

Waterfront home with a dock and heated pool.

Holmes Beach, Florida, United States

“A Shore Thing” – Waterfront Pool Home on Anna Maria IslandbrbrA Shore Thing is exactly that—your perfect place to create unforgettable beach vacation memories. This newly renovated ground-level waterfront home features a fresh coastal décor and no stairs, making it ideal for families and multi-generational groups.brThe open floor plan offers plenty of space for gathering, relaxing, or playing games. Enjoy time together in the living room, Florida room, or screened lanai. The living room features a 72” flat-screen Smart TV, and cable and high-speed wireless internet are available throughout the home.brbrSleeping Arrangements (Sleeps 6)brbrPrimary bedroom: King bed with private en-suite bathbrbrSecond bedroom: Queen bedbrbrThird bedroom: Two queen beds—perfect for kids or teensbrbr2 new bathrooms with a guest bathroom which offers direct pool access, double sinks, and a large glass walk-in shower—ideal after a day in the sun. There’s also a private study with a desk and reading chair, perfect for remote work or quiet relaxation with a cocktail.brbrKitchen & AmenitiesbrbrThe fully equipped kitchen includes:brbrGas range for gourmet cookingbrbrRefrigerator with ice and water dispenserbrbrOven, dishwasher, and ample cookware and serving warebrKeurig coffee maker and tea kettle brbrA brand-new washer and dryer are conveniently located just steps away in the freshly painted garage.brbrWaterfront Living, Kayaking & Outdoor FunbrbrLocated on a wide canal, this waterfront home with dock is ideal for kayaking, fishing, and boating. The private dock is perfect for kayaks, paddleboards, and easy water access.brbr(Boat lift is not operational; boats may be tied to the lift for dock access.)brbrYou’re just minutes from Bimini Bay, Tampa Bay, and the Gulf of Mexico, making this an excellent boaters’ and anglers’ retreat.brbrThe expansive backyard is a true highlight:brbrOne of the largest heated pools on Anna Maria Island (9 ft deep)brbrFish from the dockbrbrGrill your catch on the gas grillbrbrRelax in the lanai or on your own private sandy “beach”brbrBeach wagon, chairs, and umbrellas are provided for easy trips to some of the most beautiful beaches in the world.brbrLocationbrbrWalk to downtown Holmes Beach, or hop on the free island trolley to explore Pine Avenue or Bradenton Beach. Whether you’re shopping, dining, boating, or beachcombing—you’ll have a blast.brbrAdditional DetailsbrbrPet friendlybrbr4 parking spacesbrbr1-month minimum staybrbrCity of Holmes Beach Notice:brYou are vacationing in a residential neighborhood. Please be a good neighbor by keeping noise at a respectful level day and night.brbrVRC20-000145brbrbr- Pet Policy: **This property is dog friendly. If you will be bringing your dog, please reach out to us for the breed/weight restrictions. Please note: Non-Refundable dog fees apply - maximum of 2 dogs allowed. $200.00 for the first dog & $100.00 for the second dog. Please note: without prior knowledge to Love rentals there will be a minimum of a Non-Refundable $500 and possible eviction so please ensure you advise us BEFORE you travel. Dog owner accepts full responsibility for the dog. Aggressive breeds are NOT allowed.brbrThe LoveRentals portfolio is comprised of curated, professionally managed vacation rental homes around the world. We only select professional property managers that meet our high standards. Book with peace of mind knowing that you will have the very best vacation.brbrLoveRentals - Find Your Bliss.
Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
Slider Thumb
Exceptional(56)

$1830.06

/ Nightly
Private Vacation Home

Family Tides, Great for groups, Ocean View, Pool/Waterfall, Spa, Golf Cart Incl.

Holmes Beach, Florida, United States

Perfect for large families or groups, this property delivers a unique holiday experience bolstered by standout features such as an 8-person spa and a large, heated pool, intricately detailed with a waterfall and LED lighting perfect for an evening dip. brbrOur 5-suite property enjoys prime location convenience, nestled close by to the beach and affording ample secure parking. Revel under the sun at our phenomenal rooftop patio designed with scenic ocean views, an outdoor turf playground with water table and toys, and included with the rental a new 6-seater golf cart at your disposal, explore the island to your heart`s content.brbrEach suite within our property is designed as a luxurious enclave fitted with private kitchens, exquisitely furnished living spaces, and modern state-of-the-art finishes. The distinct composition of the property caters to your varying travel needs, making it an ideal home away from home for large groups, families, or friends who appreciate both communal and private spaces.brbrOur property`s crown jewel is the impressive 1500 sq. ft. Swordfish Suite. This space is generously fitted with 3 bedrooms, 3 full baths, a private covered porch, and breathtaking views of the rolling ocean waves right from the comfort of your living room, porch, and master suite.brbrOther highlights include the Coral Suite and the Turtle Suite which boast of scenic views and plush furnishing. The former showcases two king bedrooms with a full kitchen, while the latter houses a king bedroom and a secondary bedroom with a queen-sized and bunk bed.brbrThe Starfish Suite and the Flip-Flop Suite further accentuate the property`s exclusivity, making every guest feel special. High-speed internet and smart TVs are standard, keeping you entertained throughout your stay.brbrOutdoor relaxation is a sophisticated affair with our splendid patio space, complete with lounge areas, dining settings, and a tiki bar. A temperate pool and mesmerizing rock waterfall cater for sun-soaked dips during the day and memory-filled night swims.brbrElevate your mobility convenience with our sleek 6-seater golf cart, providing ready access to all corners of the island. A pristine sandy beach is just a stone`s throw away. We have beach essentials in lock and key, including chairs, umbrellas, toys, life jackets, and a spacious cart for your convenience.brbrOur central location guarantees a 5-minute stroll to amenities such as grocers, unique beach shops, and popular eateries. An AMI trolley stop across the property provides leisurely island tours.brbrWith 8 parking spaces, an array of fun rental options such as golf carts and scooters, and a commitment to your privacy, our property lives up to the mantra of luxury and convenience. This is the vacation you`ve been waiting for.brbrPlease note our licensing details: Unit A - VRC17-000136, Unit B - VRC22-000028, Unit C - VRC22-000029, Unit D - VRC22-000030.brbr*Kindly adhere to the local noise ordinance to respect the tranquil residential setting and to ensure the peaceful enjoyment of our neighbors.
Bed 10

Bed

Bath 9

Bath

Sleep 24

Sleeps
Slider Thumb
Exceptional(8)

$362.32

/ Nightly
Private Vacation Home

A Shore Thing - Relaxing Island Living , Large Heated Pool, Boat Lift

Holmes Beach, Florida, United States

This beach house is A Shore Thing for creating fantastic vacation memories. This newly furnished ground level home is decorated in coastal living motif and has no stairs to climb. The open floor plan is ideal for one or two families to have a fantastic vacation. The living room, Florida room and screened in lanai provide areas for entertaining, relaxing or playing games. The living room is equipped with a 60 inch flat screen Smart TV. Cable and wireless interned access are available throughout the entire home. On that evening when you have an extra guest, the Queen sleeper sofa in the Florida room will come in handy.brbrThe three bedrooms include a master with a king bed, 46 flat screen LCD TV and private bath. The second bedroom has a queen bed and 24 flat screen LCD TV. The third bedroom is equipped with 2 sets of bunk beds, each consisting of a double bed on the bottom and a twin on the top with a 24 flat screen LCD TV and is perfect for the kids. A brand new bathroom provides direct access to the pool and features double sinks and a large glass stand-up shower. Additionally, there is a study with desk and reading chair if you must keep up with work while away or just want a quiet reading area to relax and sip a cocktail!brbrThe kitchen is equipped with a gas range for that gourmet cook and a refrigerator with on-door water and ice, oven, and dishwasher. It is filled with cooking equipment and entertainment ware for even the most discriminating chef and host. The brand new Samsung washer and dryer are just steps away in the newly painted garage.brbrSituated on a wide canal, the house is perfect for the boating and/or fishing enthusiast and just minutes from Bimini Bay, Tampa Bay and the Gulf of Mexico! Bring your boat ad utilize the 8000 pound boat lift which is free with the home but does require a $500 security deposit. Also available are two floating docks for Wave Runners or Kayaks. Parking is also ample at the house for your boat trailer and multiple cars.brbrOnce back on land, enjoy your own oasis in the expansive backyard. Fish from the dock, swim in one of the largest heated pools on Anna Maria Island that is 9' deep, grill the fish you just caught on the provided gas grill, relax in the lanai or sit on your own private sandy beach. For those seeking adventures outside of your vacation retreat, take the beach wagon with chairs and umbrellas 5 minutes to one of the most beautiful beaches in the world. If you want to shop, walk to downtown Holmes Beach or jump on the free trolley to visit Pine Ave or venture down to Bradenton Beach. Whatever your choice, you will have a blast!brbrSmall Pets considered.br1 month minimum.
Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
Slider Thumb
Exceptional(1)

$386.58

/ Nightly
Private Vacation Home

Blue Haven Beach House: 3BR/3BA Pool Home Steps to Beach

Holmes Beach, Florida, United States

Blue Haven Beach House is a beautifully updated, elevated home located in the heart of Holmes Beach—just steps from the sugar-white sands of the Gulf and walking distance to shops, restaurants, and the free island trolley. Designed with comfort and convenience in mind, this coastal retreat features four bedrooms, three bathrooms, and a spacious open layout perfect for relaxing with family and friends.brbrThe main living area is bright and welcoming, with plenty of natural light, comfortable seating, and a Smart TV. The adjacent kitchen is fully stocked with everything you need to cook meals at home, including granite countertops, stainless appliances, and island seating for casual dining. Just off the kitchen, a screened lanai offers a peaceful spot to enjoy morning coffee or an evening drink with peek-a-boo Gulf views.brbrDown the hall on the main floor, you'll find a guest bedroom with two bedrooms that are two twins each and a full hallway bath. Upstairs, the primary suite features a king bed, sitting area, and private balcony overlooking the Gulf of Mexico. Its en-suite bathroom is a comfortable retreat after a long beach day. A second upstairs bedroom includes a queen bed and private bath, offering a quiet, restful space for guests.brbrOutdoors, a private heated pool invites you to relax and unwind. A covered patio area provides shade and includes comfortable seating and a propane grill for easy outdoor dining.brbrThis home also includes an elevator for convenience, though it is not ADA compliant and should not be relied upon for guests with mobility concerns. Garage and driveway parking are available.brbrPETS: Please note this property does NOT allow pets. brbrPARKING: 3 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles.brbr***OVERCROWDING CONSEQUENCES***brMaximum occupancy of rental homes on Anna Maria Island are set by the Cities and are strictly enforced. An occupant is any person staying overnight, regardless of the number of nights. Due to recent issues of overcrowding in the area, if maximum occupancy is exceeded during your stay, a $1000 (one thousand dollar) overcrowding fee will be charged to the payment method on file and your party will be immediately evicted. We appreciate your understanding and cooperation to keep Anna Maria Island enjoyable for everyone.brbrYou are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property.brbr*Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.brbrbrVRC19-000076
Bed 4

Bed

Bath 3

Bath

Sleep 8

Sleeps
Slider Thumb

$611.0

/ Nightly
Private Vacation Home

February & March Special: Luxury Canal Home with Pool & Deck

Holmes Beach, Florida, United States

Welcome to Woodside Beach House, a luxury waterfront retreat in the heart of Holmes Beach. Designed with comfort and elegance in mind, this spacious 4-bedroom, 4.5-bathroom home offers the perfect blend of modern amenities and island charm.brbrNestled on a large canal that feeds directly into Bimini Bay, the property is ideal for boating enthusiasts and those who enjoy serene water views. The chef’s kitchen is fully equipped with high-end appliances and finishes, making it a dream for cooking and entertaining. Each bedroom features its own private ensuite, ensuring comfort and privacy for all guests.brbrStep outside to a truly exceptional outdoor living space. The private heated pool is surrounded by a very large multi-level deck with plenty of room to spread out. Enjoy al fresco dining overlooking the water, gather around the fire pit in the evenings, or relax in one of the comfortable lounge areas. This inviting setting is perfect for making the most of Florida’s beautiful weather, whether you’re soaking up the sun or winding down under the stars.brbrLocated in a quiet residential neighborhood, Woodside Beach House offers both privacy and convenience. The Gulf beaches are just a 15-minute walk away, and local shops and restaurants are within easy reach.brbrWith a 28-night rental minimum, this stunning home is designed for an extended island escape where you can truly relax, recharge, and live like a local.brbrPARKING: 4 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles.brbr *Note that the garage is owner-use only and is not available for parkingbrbrDOCK/BOATS: Dock is approximately 20ft. brbrNOTE: For security and insurance purposes, there are exterior-only video cameras on the premises.brbr***OVERCROWDING CONSEQUENCES***brMaximum occupancy of rental homes on Anna Maria Island are set by the Cities and are strictly enforced. An occupant is any person staying overnight, regardless of the number of nights. Due to recent issues of overcrowding in the area, if maximum occupancy is exceeded during your stay, a $1000 (one thousand dollar) overcrowding fee will be charged to the payment method on file and your party will be immediately evicted. We appreciate your understanding and cooperation to keep Anna Maria Island enjoyable for everyone.brbrYou are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property.brbr*Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.brbrVRC-
Bed 4

Bed

Bath 4

Bath

Sleep 8

Sleeps
Slider Thumb
Exceptional(39)

$456.46

/ Nightly
Private Vacation Home

Dream luxury home on Anna Maria Island, heated private pool - pet friendly!

Holmes Beach, Florida, United States

This lovely new island 2 bedrooms, 2.5 baths luxury home with private heated pool is a dream. Fishful Thinking is positioned in a superb location just steps to the white sands of the gulf-side pristine beaches, nearby trolley stop, and shops of Holmes Beach. The home offers every comfort you can imagine with an open concept living, dining, and kitchen, and tile floors throughout. The spacious 2 bedroom 2 bath home has a kitchen, living room, dining room and two bedrooms with king beds, 2 full baths and a large laundry room. The kitchen is equipped with stainless appliances, granite counter tops and all the conveniences to cook a meal in. You're welcome to make use of the large garage and amazing outdoor space with private heated pool, grill, outdoor seating. This island gem is stocked with beach towels, beach chairs, beach cart, and linens for your use during your stay. It is located just minutes from the Manatee Bridge and entrance to Anna Maria Island along with the local grocery store, pharmacy, & public beach and Skate Park. The home is literally just up the street from the public beach access. It is located to a nearby free trolley stop that runs the length of the island and is a very short distance to the local beer and wine store, as well as several bars and restaurants. Don't miss this dream home. Dogs are welcome. Pet fee is $200 per pet plus taxes, maximum of 2 pets unless otherwise approved by FDR. brbrAccommodates up to 4 people. Minimum Stay Required: 1 Week. brMax. parking: 2; VRC #18-000021brbrYou are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property.brbr* Cancellation more than 90 days prior to arrival will receive a deposit refund less a $250 cancellation fee. Cancellation less than 90 days prior to arrival will forfeit all deposit received. Cancellation less than 60 days prior to arrival will forfeit all monies on account. Cancellations must be confirmed in writing.
Bed 2

Bed

Bath 2

Bath

Sleep 4

Sleeps
Slider Thumb
Exceptional(1)

$332.92

/ Nightly
Private Vacation Home

Single-Level Beach Home, Short Walk to Sand! Close to Dining, Shopping, and More

Holmes Beach, Florida, United States

Sea Place by Anna Maria Vacations brHome in Holmes Beach, Florida brVRC16-000265 brbrWelcome to Sea Place, a beautiful island bungalow with a private heated pool, tropical style, and all the comforts of home. Just a short 3-minute walk from the beach, this three-bedroom, two-bathroom ground level retreat is perfect for families or small groups seeking a laid back Anna Maria Island getaway in the heart of Holmes Beach! brbrHighlights br• 3-minute walk to the beach br• 3 Bedroom / 2 Bath br• 2 Queens, 2 Twin beds br• Private heated pool with sun shelf br• Swim-up table and gas grill br• Garage br• Washer and dryer br• Dog-friendly with host approval br• Complimentary Wi-Fi br• On our Professional Linen Program br• Centrally located near shops and restaurants br• 2 Parking spaces brbrOutside, your private heated pool awaits, complete with a sun shelf, swim up table and umbrella, and plenty of poolside seating. Fire up the grill and enjoy a meal under the Florida sun. Whether you're taking a dip or lounging with a good book, this backyard oasis is built for vacation vibes. brbrStep inside to discover a cheerful, coastal space with granite countertops, tile floors, updated furnishings, and HD flat-screen TVs throughout. The open concept living area allows for easy flow between the kitchen, dining, and lounge spaces. The fully equipped kitchen comes stocked with cookware, modern appliances, and everything you need for a stress free stay. brbrThe primary bedroom features a queen bed, tranquil decor, and an ensuite bathroom with a shower and tub combination. The second bedroom is coastally decorated and incudes a queen bed while the third bedroom includes two twin beds, perfect for additional friends or family. These two bedrooms share a hall bathroom, complete with a shower/tub combo. A washer and dryer are conveniently located in the garage for easy access after long beach days. brbrRoom Details br• Primary Bedroom: Queen bed, ensuite bathroom with shower/tub combo br• Second Bedroom: Queen bed br• Third Bedroom: Two Twin beds brbrAs part of our Professional Linen Program, Sea Place includes premium, hotel-quality linens, bath towels, and beach towels professionally laundered and ready for use upon your arrival. Adding a luxurious touch to your island stay. Enjoy complimentary Wi-Fi and garage access at Sea Place! brbrWhen you're ready to explore, take a quick stroll to the sugar sand beaches of Anna Maria Island, or walk 10 minutes to The Ugly Grouper, a favorite local hangout with live music, tropical cocktails, and fresh seafood. With shops, cafes, parks, and trolley stops nearby, Sea Place is your perfect home base for an unforgettable beach vacation. brbrBook your stay and enjoy a private, pet-friendly island oasis just steps from the beach. Experience everything Anna Maria Island has to offer sun, sand, and serenity await! br br- brThis property participates in our Professional Linen Program. In Anna Maria Vacation's continuous effort to bring only the best quality experience to our guests, we are proud to offer a professional linen service at this property to better enhance your enjoyment while staying here. This luxury amenity provides you with high-quality linens; including bedding, bath towels, washcloths, and beach towels that are in place and ready for your use upon your arrival. These high-quality linens are washed in a commercial setting using the latest and best technology. brbrReady for some fun under the sun Poolside furniture, a stainless-steel grill, and a swim-up pool table are all features that add to the perfect island retreat. You can even walk to the beach in as little as three minutes. The Ugly Grouper, a local favorite known for its laid-back vibes, live music, and fresh seafood, is just a 10-minute walk away! You won’t believe how many attractions are just minutes from your doorstep. Come enjoy this private beach bungalow on Anna Maria Island! brbrWith host approval before check-in, this property accepts dogs only (No cats or other animals are allowed). An additional pet fee will apply. See our Anna Maria Vacations Rental Policies for full details. brbrYou are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. This property requires a 7-night minimum stay as set forth by Holmes Beach’s Land Development Code. Occupancy may not exceed 6.
Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps

Home Rent a place that suits your needs

Condo

Condo

View 309 Condo
Cottage

Cottage

View 52 Cottage
Private vacation home

Private vacation home

View 729 Private vacation home
Villa

Villa

View 43 Villa

Home Most popular vacation rentals in Holmes Beach

Slider Thumb
Exceptional(1)

$1793.37

/ Nightly
Private vacation home

Limefish Luxury | Gulf-Front | Pool | Iconic Sunsets

Holmes Beach, Florida, United States

Bed 3

Bed

Bath 3

Bath

Sleep 8

Sleeps
Slider Thumb
Exceptional(1)

$1806.16

/ Nightly
Private vacation home

Malibu Beach ~ Waterslide/Rooftop Views/Walk to Beach

Holmes Beach, Florida, United States

Bed 8

Bed

Bath 7

Bath

Sleep 16

Sleeps
Slider Thumb
Exceptional(1)

$1830.06

/ Nightly
Private vacation home

Family Tides, Great for groups, Ocean View, Pool/Waterfall, Spa, Golf Cart Incl.

Holmes Beach, Florida, United States

Bed 10

Bed

Bath 9

Bath

Sleep 24

Sleeps
Slider Thumb
Exceptional(1)

$1957.32

/ Nightly
Private vacation home

Pool with with water slide & grotto! Sleeps 14! Walk to Beach!

Holmes Beach, Florida, United States

Bed 4

Bed

Bath 5

Bath

Sleep 14

Sleeps
Slider Thumb
Exceptional(1)

$2304.07

/ Nightly
Private vacation home

PERFECT BEACH HOME! Heated pool/spa! Just steps to beach & Stunning views!

Holmes Beach, Florida, United States

Bed 5

Bed

Bath 3

Bath

Sleep 8

Sleeps
Slider Thumb
Exceptional(1)

$2771.73

/ Nightly
Private vacation home

The Palace ~ Walk to Beach/Rooftop Views

Holmes Beach, Florida, United States

Bed 7

Bed

Bath 7

Bath

Sleep 14

Sleeps
Slider Thumb
Exceptional(1)

$464.10

/ Nightly
Apartment

Sand & Sea Oasis: Condo with Private Beach Access

Holmes Beach, Florida, United States

Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps
Slider Thumb
Exceptional(1)

$469.77

/ Nightly
Private vacation home

Pool - The Sea Pearl by SeaBreeze Vacation

Holmes Beach, Florida, United States

Bed 3

Bed

Bath 3

Bath

Sleep 6

Sleeps
Slider Thumb
Exceptional(1)

$468.70

/ Nightly
Condo

GULF FRONT Beautiful Condo w/Heated Pool, FREE WiFi & Trolley, Great Sunsets!

Holmes Beach, Florida, United States

Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps
Slider Thumb
Exceptional(1)

$468.48

/ Nightly
Condo

Anna Maria Island Beachfront Condo | Gulf Views, Heated Pool, 3BR at Gulf Place 18 |Great Sunsets!

Holmes Beach, Florida, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps

Most Popular Cities in Florida