Vacation Rentals By Owner In Holmes Beach, FL

**ASK ABOUT LAST MINUTE DEALS!brbrForget your cares at this thoughtfully renovated 3 bedroom, 3 bath, pool home in the heart of Holmes Beach. Located just one block away from the Island's sugar sand beaches, with easy walk to several shopping plazas and restaurants. Hop the free trolley, just a block away, to see the rest of the island.brbrInside you'll find an open floor plan with vaulted ceilings and plenty of room to relax. The main floor is tastefully decorated, featuring two bedrooms, each with a king bed and en suite baths, a beautifully appointed open kitchen, and comfortable living and dining areas. brbrUpstairs is the perfect hideaway for the children, in this spacious loft bedroom, en suite bath, and two queen beds. Relax to smart TVs in the living room as well as in each of the bedrooms.brbrThe lovely outdoor living areas will truly increase your enjoyment of this home! Start your day with breakfast on the deck, right off the kitchen, then retreat to the lush tropical shade of the pool-side patio with lots of comfortable seating, plus a 55 TV, Corn Hole, and sun loungers by the pool. Lush tropical landscaping, a fenced yard, and a heatable pool make Ride the Tide the vacation home you'll want to call your own when you visit Anna Maria Island!brbrA NOTE ABOUT POOL HEAT: If you book online, your reservation will automatically populate with a pool heat charge for one week. If your reservation is for a longer period, someone on our staff will adjust the pool heat rate to reflect the longer stay. We recommend pool heat at this property, regardless of the time of year, as pools near shady trees stay cooler, even in the summer.brbr*PET OWNERS: This property is dog friendly for one dog with a maximum weight of 25 pounds and a non-refundable pet fee of $150 for the first week. There is a $50 fee per week for any additional weeks booked. Also, certain breeds are excluded. It is necessary that you check with our office prior to your trip for details on weight and breed limitations.brbrOur Cancellation Policy: In order to protect our owners from loss of income, ALL MONIES PAID TOWARDS YOUR RESERVATION MAY BE NON-REFUNDABLE AFTER A CERTAIN DATE! FULL AND PARTIAL REFUNDS MAY BE GIVEN UNDER CERTAIN CONDITIONS. Ask our office for details, or check your rental agreement.brbrNOTICE TO VISITORS OF HOLMES BEACH:brbr1. Per City of Holmes Beach ordinances: 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. brbr2. Per City of Holmes Beach ordinances, this unit cannot exceed 6 occupants. This amount includes adults and children of all ages. brbr3. Per City of Holmes Beach ordinances, we are required to tell you the minimum stay requirement for this property is one week.

Beautiful 3Bed/3 Bath, Heated Pool, WiFi & Trolley, Stroll to Pristine Beach, NO Roads to Cross, Dog*(See Note)Allow

Holmes Beach, Florida, United States

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Bath

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$943.27

3BR · 2.5BA · Sleeps 6 · Direct Gulf Front · Private Deck · Post-Hurricane 2025 Restoration · New Kitchen · Outdoor Shower · brbrSome homes are more than just a place to stay — they hold a story. Breakers 1 is one of the last true Old Florida beach homes on Anna Maria Island, standing on the Gulf while everything around it has been replaced with newer construction. After the 2024 hurricanes, the home was restored — new kitchen, fresh updates throughout — while keeping the bones, the character, and the feel that guests have been returning for year after year.brbrStep off the deck and you're on the sand. No streets to cross, no path to navigate — the Gulf of Mexico is right there. The private Gulf-front deck is where the day ends at Breakers 1, whether that means morning coffee in the quiet before anyone else is up or an evening watching the sun drop into the water.brbrThe home sleeps six across three bedrooms. The master suite has a king bed, an en-suite bath, and Gulf views. The guest room has two twin beds — right for families with younger kids. The loft has a queen bed with water views — open loft with no door, worth knowing if you're traveling with light sleepers or anyone who needs full privacy. The living area has vaulted ceilings, original details, and smart TVs throughout.brbrThe kitchen is brand new — one of the most tangible improvements from the 2025 restoration. Fully equipped for a week of meals at home. An outdoor shower handles the sand. The garage provides covered parking for one car with two additional spaces outside — rare for a direct beachfront property on AMI.brbrThe walkability here is exceptional even by Holmes Beach standards. Publix is within walking distance. CVS nearby. The free Anna Maria Island trolley stops close by for exploring the full length of the island without moving your car. Guests consistently report parking on arrival and never needing their car again until checkout.brbrA 5% military discount is available — contact IVP directly to apply.brbrBreakers 1 requires a one-week minimum stay with parking for 3 vehicles. Not pet-friendly.brbr*Final payments are due 60 days prior to arrival payable by personal check or Echeck (which will incur a $1.00 processing fee) we do takebrcredit cards for final payment with a 3% fee on the balance due.

Breakers 1 · Old Florida Home · Gulf Front - Fully Restored

Holmes Beach, Florida, United States

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Bath

Sleeps

$303.74

Welcome to Tropical Sunset 4, a refreshed and inviting two-bedroom, two-bath retreat just a quick two-minute walk from Holmes Beach. This third-floor condo blends comfort, style, and convenience, offering beautiful water views along with access to a heated community pool, BBQ grills, and a picnic area. It's the ideal spot for families, couples, or friends looking to relax and explore Anna Maria Island. Please be advised that the balcony is currently not accessible at this time.brbrInside, the open layout feels bright and breezy, with calming coastal colors, a comfortable seating area with a flat-screen TV, and a fully equipped kitchen featuring stainless steel appliances and all the cookware you'll need. Whether you're enjoying a casual breakfast at the kitchen bar or gathering for dinner at the dining table, the space is designed to make you feel right at home.brbrThe primary bedroom offers a peaceful escape with a king bed, TV, plenty of storage, and an ensuite bathroom with a walk-in shower. The second bedroom is just as welcoming, with a full bed, a sleeper sofa for extra guests, a TV, and large windows that bring in natural light. A second full bathroom with a walk-in shower and an in-unit washer and dryer add convenience during your stay. Step onto the balcony to take in the ocean views, or head downstairs to enjoy a poolside afternoon or a casual meal at the community BBQ area. With shops, restaurants, and cafes all within easy reach, you'll have endless ways to spend your days, whether you prefer sunrise beach walks, exploring island boutiques, or simply soaking up the sun.brbrTropical Sunset 4 offers the perfect blend of modern updates, outdoor amenities, and unbeatable proximity to the beach. Book your stay today and experience the relaxed rhythm of island living, your Florida getaway awaits!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.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: VRC16-000347brMax Occupancy: 5 Guests | Max Vehicles: 3brQuiet 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.

Condo

Tropical Sunset 4 by SeaBreeze Vacation

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$237.65

Welcome to The White Pelican, your charming retreat on Anna Maria Island! Nestled just 1000 feet from the pristine sands of the island`s renowned beaches, this original duplex offers the quintessential coastal getaway experience.brbrStep inside The White Pelican to discover a cozy yet airy ambiance, with one bedroom and one bath awaiting to cocoon you in comfort after a day of seaside adventures. The interior exudes a laid-back coastal vibe, adorned with beachy decor and furnishings that invite relaxation.brbrEquipped with everything you need for a perfect beach day, from towels to beach chairs, umbrellas, and even a cooler, The White Pelican ensures you can effortlessly soak up the sun and surf.brbrConveniently located within walking distance of many shops and restaurants, The White Pelican puts you at the heart of Anna Maria Island`s vibrant community. Explore local eateries serving up fresh seafood delicacies, browse eclectic shops, or simply meander along the picturesque streets lined with swaying palms.brbrWhether you`re seeking a romantic getaway for two or a solo escape to recharge by the sea, The White Pelican promises an unforgettable island retreat. Come experience the magic of Anna Maria Island from your own beachside haven.brManaged by Doreste PropertiesbrNo smoking. Pets are not allowed.

White Pelican - 1000 Feet to the Beach

Holmes Beach, Florida, United States

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Bath

Sleeps

$270.4

We have a great view of the Gulf of Mexico With easy access to the beach and heated pool. Full laundry and the kitchen is equipped for family meals. There is a free trolley that runs the length of the island and it stops right out front.brbrMinimum stay is 7 daysbrMaximum occupancy 6 peoplebrMaximum parking 2 spacesbrbrbrThe City of Holmes Beach has established a noise ordinance to protect the rights of citizens to enjoy a peaceful, quiet environment. brbrThe ordinance applies to all places of business, public and private property, and other areas in the city. No person shall cause, suffer, allow, or permit any unreasonable noise that is audible beyond the boundaries of their property without the express written consent of the owner or occupier of the affected properties. brbr Noise is defined as any sound which is audible beyond the boundaries of the property producing the sound. Unreasonable noise is defined as any sound that is loud, raucous, jarring, or shrill enough to disturb the peace and quiet of any person or persons in the vicinity. The following activities are prohibited: -Loud music, including amplified musical instruments, musical instruments, radios, televisions, or other sound equipment. -Loud and unnecessary vehicle noises, such as loud engine revving, honking of horns, loud exhaust systems, and screeching tires. -Loud shouting, yelling, or screaming. -The use of loudspeakers or other sound equipment for commercial advertising.

Condo

Duckbow Properties, Beachfront Condo, Anna Maria Island VRC22-000184

Holmes Beach, Florida, United States

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Bath

Sleeps

$617.82

Welcome to Sandy Pants!brOn Anna Maria Island (Holmes Beach, FL)brbrThe SpacebrWhere creativity meets coastal calm, Sandy Pants brings modern design and island ease together just steps from the Gulf. Every detail feels intentional — from the natural light streaming through open spaces to the textures and tones that invite connection, rest, and inspiration.brbrPerfect for: design lovers, families who value connection, and travelers seeking inspiration near the sea.brbrHighlightsbr- Prime beach block location — just a few homes from the soft quartz sand of the Gulf of Mexicobr- Heated private pool surrounded by tropical landscaping and lounge spacebr- Outdoor dining area, hammock, built-in grill, and outdoor showerbr- Stylish open-concept living area with natural light and TV for relaxing eveningsbr- Three comfortable bedrooms plus additional sleeping flexibility with a sleeper sofabr- Washer and dryer, Wi-Fi, and complimentary beach gear creditbrbrInteriorbrInside, the heart of Sandy Pants is an open, artfully designed living area that brings the whole group together. Coastal décor meets modern comfort, with soft neutrals and textures inspired by the sea. A spacious living room offers plush seating and a smart TV, while wide windows fill the room with natural light.brbrThe kitchen features stainless steel appliances, sleek cabinetry, and generous counter space — designed for effortless meal prep or morning coffee rituals. The adjacent dining area brings everyone together to share meals, laughter, and stories after a day in the sun.brbrKitchen & Diningbr- The kitchen is fully equipped and ready to inspire your inner chef or host:br- Stove, oven, and microwavebr- Refrigerator/freezerbr- 12-cup coffeemaker and Keurigbr- Blender, toaster, and full kitchenware setbrbrThe open layout keeps you connected as meals come together — from quick breakfasts before the beach to laid-back dinners after sunset. Dine indoors at the coastal-style table or outside beneath the palms for a true island experience.brbrEach bedroom feels like a personal sanctuary, designed with care and creativity in mind:br- King Bedroom: A serene retreat with simple elegance and plush comfort.br- Queen Bedroom: Modern and cozy, offering easy access to shared spaces.br- Custom Bunk Room: Designed for kids and groups with three twin beds and two double beds — both playful and practical.br- Sleeper Sofa: Offers extra flexibility for larger groups or extended family.brbrLayout Overviewbr- Main Level: Open kitchen, dining, and living areas with access to the backyard and pool.br- Bedroom Wing: King bedroom, queen bedroom, and custom bunk room with shared access to full bathrooms.br- Outdoor Connection: Every space within the home leads seamlessly to the tropical pool area — the centerpiece of the property.brbrOutdoor LivingbrStep outside and feel the gentle rhythm of the island. The private heated pool is framed by palms and lush greenery, creating an inviting atmosphere for sunbathing or a refreshing swim. Enjoy long afternoons in the hammock or relaxed evening gatherings around the outdoor dining table.brbrThe built-in grill and prep area make it easy to cook outside, while the outdoor shower adds convenience after a beach day. Whether you're reading poolside, sipping something cool, or floating beneath the stars, this backyard was designed for both play and peace.brbrAdditional Amenitiesbr- Air conditioning and heatingbr- Cable television and Wi-Fibr- Washer and dryerbr- Linens, towels, hair dryer, iron, and ironing boardbr- Beach gear rental credit included (chairs, cart, umbrella, bikes, coolers, games, etc.)br- Some items may be on-site but are not guaranteedbrbrParkingbr2 off-street driveway parking spacesbrbrEvery moment at Sandy Pants is an invitation to create — to gather, to breathe, to dream — and to write your vacation story, one beautiful detail at a time.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.brbrCity of Anna Maria Vacation Rental License: VRC18-000131brMax Occupancy: 8 Guests | Max Vehicles: 2brInformation deemed reliable but not guaranteed; subject to change or withdrawal without notice.

Sandy Pants – Tropical Oasis Beach Block Home w/ Heated Pool, Steps to Gulf

Holmes Beach, Florida, United States

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Bath

Sleeps

$318.44

ATTENTION: We rent with 1 week minimum: Saturday to SaturdaybrOld Florida Feeling: bungalow right on the beach on level - d. H. no trepidation to the beach. Unit 3 with a bedroom, kitchen bathroom is on the garden side (20!Meters to the beach :-) with a beautiful terrace in the garden with a pavilion and fountain. The beach lovers are on a quiet side street - you hear no traffic, only the waves. brIf you are looking for vacation away from the hustle and bustle with stunning beach and great evening Sonnenutergängen, you are right on the Gulf of Mexico. And there on Anna Maria Island: Connected to the mainland by two roads.brbr

Closer to the beach does not work: comfortable apartment at ground level on the beach.

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$321.72

Isle Haven B will let you make beautiful memories - it's the perfect beach getaway to relax and enjoy the classic Florida charm of Anna Maria Island. The 2 bedroom 2 bath duplex offers all the amenities you may think of. The master bedroom has a king size bed, the second bedroom a queen and a bunk bed if your kids prefer this. The location cannot be any better. The beach is just a short walk down the street, the same goes for bars, restaurants and shops in Holmes Beach. The free trolley as well stops very close by the house. The kitchen is fully stocked, linens, towels, cookware, beach equipment and of course free Wi-Fi is all provided. You can't go wrong with this rental.brDogs up to 40lb are welcome. Pet fee is $200 per pet plus taxes, maximum of 2 pets unless otherwise approved by FDR. brbrAccommodates up to 6 people. Minimum Stay Required: 1 Week. brMax. 2 parking; VRC #18-000064brbrYou 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.

Lovely 2 bedroom duplex on Anna Maria Island, great location, pet friendly!

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$301.76

VRC16-000503brbr1BR · 1.5BA · Sleeps 4 · Gulf Front · Beachfront Balcony · Heated Pool · Pack-N-Play & High Chair · No EVs or Golf Carts · For Sale — Showings with 24-Hr Notice · 1 Parking Space · Shared Ground Level Laundry.brbrImportant before booking: Seaside Beach House #102 is currently listed for sale. Occasional showings may be scheduled during your stay with a minimum of 24 hours notice. If that's a concern, worth knowing before you book.brbrA Gulf-front condo in the northern end of Holmes Beach on a quiet side street with heated pool overlooking the shoreline and the same direct beachfront balcony. This unit is the one-bedroom configuration, sleeping four on a king bed and a living room sofa bed.brbrThe Pack-N-Play and high chair are provided — making this the better fit for guests traveling with infants or toddlers. The beachfront balcony faces the Gulf directly for morning coffee and evening sunsets. The kitchen has been recently updated and is fully equipped for meals at home. One and a half bathrooms. Flat-screen TVs in the living room and bedroom. High-speed WiFi. On-site shared laundry.brbrPlease note: this property is not suitable for electric vehicles or electric golf carts. One parking space included. Non-smoking property.brbrSeaside Beach House #102 requires a one-week minimum stay. Not pet-friendly.brbr*Final payments are due 60 days prior to arrival payable by personal check or Echeck (which will incur a $1.00 processing fee) we do takebrcredit cards for final payment with a 3% fee on the balance due

Seaside Beach House 102 · Gulf Front · For Sale · Families

Holmes Beach, Florida, United States

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Bath

Sleeps

$358.33

Welcome to Loggerhead Beach House just a few houses from the Gulf beaches on Anna Maria Island. Loggerhead Beach House is a ground level half duplex with 2 bedrooms, 1 and a half baths and its own private patio with lots of shade where you can enjoy the heated pool and outdoor shower. You can enjoy a day at the beach with the provided beach wagon, chairs and umbrella located in the garage. Inside you will find the fully equipped kitchen with bar seating for 4 is open to the spacious living area for easy entertaining. In the evening you can retreat to the master suite where you will enjoy the comfortable king size bed complete with 600 thread count prima cotton wrinkle free sheets. Linens, towels and beach towels are included in this house.brbrLizzie Lu's Island Retreat is a full-service property manager on Anna Maria Island to ensure our guests enjoy some of the nicest, well stocked homes on the island. For an additional cost, we offer GEM cars among other services. Rest assured we are here to assist as needed in the most efficient manner possible. While vacationing on Anna Maria Island, please adhere to our local rules and regulations for our residential community which are included in our homes as well as our arrival information.brbrCity ordinance requires us to inform you that 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. brHolmes Beach Rental License VRC16-000372

Two Bedroom Cozy Island Home Right Around the Corner from Gulf Beaches. Lots of Amenities!

Holmes Beach, Florida, United States

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Bath

Sleeps

$736.05

Welcome to Sunset Beach House just a few steps away from the Gulf beaches of Anna Maria Island. Sunset Beach is a 4 bedroom, 4 bath half duplex with its own private patio surrounded by tropical landscaping where you can enjoy the heated pool, outdoor shower, picnic table and Weber grill. Enjoy a day at the beach with the provided beach wagon, chairs and umbrella located in the garage. Inside you will find the fully equipped kitchen with bar seating for 4 and a dining table for 6. The kitchen is open to the spacious living area which has sliding doors onto the back deck overlooking the backyard oasis. There are 2 bedrooms on the main floor, one with twin bunks and attached bathroom and the other with a queen bed and attached bathroom.brbrThe two master suites are located upstairs. You can relax in the comfortable king size beds complete with 600 thread count prima cotton wrinkle free sheets. Both master suites have beautiful views of the Gulf as well as access to the second floor patio. For your convenience there is a coffee bar located in the hallway. Linens, towels and beach towels are included in this home.brbrLizzie Lu's Island Retreat is a full-service property manager on Anna Maria Island to ensure our guests enjoy some of the nicest, well stocked homes on the island. For an additional charge, we offer GEM cars among other services. Rest assured we are here to assist as needed in the most efficient manner possible.brWhile vacationing on Anna Maria Island, please adhere to our local rules and regulations for our residential community which are located in our homes as well as our arrival information.brbrCity ordinance requires us to inform you that 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. brHolmes Beach Rental License VRC16-000379

One house to the Beach with expansive heated pool!! Sleeps 8

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$266.94

VRC16-000511brbr2BR + Den · 2BA · Sleeps 6 · Heated Saltwater Pool · Reading Nook · Gas Grill · Pet-Friendly ($150 · 1 Small Pet) · 2.5 Blocks to Beach · Shared Washer/Dryer · Quiet Lakeside NeighborhoodbrbrA heated saltwater pool in a quiet lakeside neighborhood in Holmes Beach — the pool deck at A Wright Place has lush island landscaping and a reading nook tucked in for the afternoons when the beach has worn you out. The beach is 2.5 blocks away.brbrThe poolside den is a flexible third sleeping space — futon, ground level, and connected to the pool area — that works for a sixth guest or as a quiet retreat when the main bedrooms are occupied. The main unit has a king bed in the primary bedroom and two twin beds in the second bedroom. Two full bathrooms. A washer and dryer is on-site.brbrThe kitchen is fully equipped for meals at home. The living room has a flat-screen TV. High-speed WiFi included. A gas grill is at poolside for evening cookouts.brbrPlease note: rates are higher during peak periods — March, July, and the holiday weeks of Easter, July 4th, Thanksgiving, and Christmas. Bookings generally run Saturday to Saturday during busy months.brbrOne small pet is welcome with a $150 non-refundable fee. Parking for two vehicles.brbrA Wright Place requires a one-week minimum stay.brbr*Final payments are due 60 days prior to arrival payable by personal check or Echeck (which will incur a $1.00 processing fee) we do takebrcredit cards for final payment with a 3% fee on the balance due

A Wright Place · Saltwater Pool · 2.5 Blocks · Pets

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$316.73

Welcome to Yellowfin Cottage located just 2 houses from the Gulf beaches on Anna Maria Island. Yellowfin Cottage is a ground floor half duplex with 2 beds, 1 bath and its own private patio surrounded by tropical landscaping where you can enjoy the heated pool and outdoor shower. Inside you will find a generous amount of space through out the living room and kitchen area. The kitchen area includes bar seating and is open to the living area for easy entertaining. During the day take the provided beach wagon, chairs and umbrella down to the beach or enjoy some time around the pool. Relax in the living room or retreat to the master suite where you will enjoy our comfortable beds complete with 600 thread count wrinkle free sheets. This home includes a fully equipped kitchen, linens, towels, beach towels, and a Weber grill.brbrLizzie Lu's Island Retreat is a full-service property manager on Anna Maria Island to ensure our guests enjoy some of the nicest, well stocked homes on the island. For an additional charge, we offer GEM cars among other services. Rest assured we are here to assist as needed in the most efficient manner possible.brWhile vacationing on Anna Maria Island, please adhere to our local rules and regulations for our residential community which are included in our homes as well as our arrival information.brbrCity ordinance requires us to inform you that 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. brHolmes Beach Rental License VRC16-000331

Cozy Cottage for 4 located steps from the beach. Heated Pool in private Patio.

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$369.91

Welcome to Bluefin Cottage located a few houses from the Gulf beaches of Anna Maria Island. Bluefin Cottage is a half duplex with 2 beds, 2 baths, and its own private patio surrounded by tropical landscaping where you can enjoy the heated pool and outdoor shower. Inside you will find a generous amount of space throughout the living room and kitchen area. The kitchen area includes bar seating along with a dining area for family meals and is open to the living area for easy entertaining. During the day take the provided beach wagon, chairs and umbrella down to the beach or enjoy some time around the heated pool. Relax in the evening in our spacious living room or retreat to the master suite where you will enjoy our comfortable beds complete with 600 thread count prima cotton wrinkle free sheets. This home includes a fully equipped kitchen, linens, towels, beach towels, and a Weber grill.brbrLizzie Lu's Island Retreat is a full-service property manager on Anna Maria Island to ensure our guests enjoy some of the nicest, well stocked homes on the island. For an additional charge, we offer GEM cars among other services. Rest assured we are here to assist as needed in the most efficient manner possible. brWhile vacationing on Anna Maria Island, please adhere to our local rules and regulations for our residential community which are included in our homes as well as our arrival information. brbrCity ordinance requires us to inform you that 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. brHolmes Beach Rental License VRC16-000330

Island Cottage with open living area, pool, ground floor very close to beach located in Holmes Beach

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$248.96

VRC16-000556brbr2BR · 1BA · Sleeps 6 · 50 Seconds to Gulf · 2025 Remodel · 712 Sq Ft + 326 Sq Ft outdoor Patio · Full/Full Bunk + Trundle · King Bed · Gas Grill · Heated Pool · 8-Unit Complex · 1 Parking SpacebrbrYour 50-second walk to the beach starts here.brSea Pirate 3 just completed a total 2025 transformation. Brand-new kitchen with navy shaker cabinets, white herringbone backsplash, quartz counters, and stainless appliances. Redesigned bathroom with double-sink navy vanity, patterned cement tile, and frameless glass shower. Gray wood-look LVP flooring throughout. New beds — actually new mattresses, which was the number one complaint from old reviews and is now completely solved. The result is 712 square feet that looks like it belongs in a design magazine and lives like a genuine beach home.brbrWalk out the front door, cross Gulf Drive — one quiet residential street — and 50 seconds later you're standing on Holmes Beach. No parking lots to navigate, no hauling gear for blocks. No public beach parking nearby means the sand stays uncrowded even when the rest of the island is busy. Mornings feel private. Afternoons stay peaceful. This is the beach access most AMI visitors never find.brbrThe 326-square-foot patio is the outdoor room that makes this unit work for families. Gas grill for cookouts. Ample seating for sunset cocktails. Storage for all the beach gear — wagon and chairs live here. Load up, walk across the street, unload on the sand. At day's end, rinse everything off, leave it on the patio, repeat. Families with young children come back year after year specifically because of this setup — you can run to the unit for snacks or sunscreen without dismantling the entire beach operation.brbrThe unit sleeps six. The primary bedroom has a king bed, TV, and direct patio access. The bunk room has a full-over-full bunk with a twin trundle — sleeping four in one room, with a desk for remote work and its own TV. The living room queen sleeper sofa handles the sixth guest. One well-designed bathroom serves everyone.brbrSea Pirate has just eight units. The heated pool never feels crowded. Walgreens and Skinny's Place are an easy walk. The free island trolley stops nearby for getting around without a car. One parking space is included — tight but manageable for a week.brbrSea Pirate 3 requires a one-week minimum stay. Not pet-friendly.brbr*Final payments are due 60 days prior to arrival payable by personal check or Echeck (which will incur a $1.00 processing fee) we do takebrcredit cards for final payment with a 3% fee on the balance due

Condo

Sea Pirate 3 · 50 Sec to Beach · 2025 Remodel

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$349.26

Welcome to the Starfish Shack located just a few houses from the Gulf beaches of Anna Maria Island. The Starfish Shack is a ground level half duplex with 2 bedrooms, 1 and a half baths, and its own private full sun patio surrounded by tropical landscaping where you can enjoy the heated pool, outdoor shower and Weber grill. During the day enjoy the beach with the provided beach wagon, chairs and umbrella located in the garage. Inside you will find an open living area and kitchen which is great for easy entertaining. In the evening, retreat to the master suite where you will enjoy the comfortable bed complete with 600 thread count prima cotton wrinkle free sheets. This home includes a fully equipped kitchen, linens, towels and beach towels.brbrLizzie Lu's Island Retreat is a full-service property manager on Anna Maria Island to ensure our guests enjoy some of the nicest, well stocked homes on the island. For an additional charge, we offer GEM cars among other services. Rest assured we are here to assist as needed in the most efficient manner possible.brWhile vacationing on Anna Maria Island, please adhere to our local rules and regulations for our residential community which are included in our homes as well as our arrival information.brbrCity ordinance requires us to inform you that 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. brHolmes Beach Rental License VRC16-000370

Holmes Beach Cottage Steps to the Beach with Heated Pool!

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$279.93

The cozy front porch of Gulf Winds A invites you to have your morning coffee or your evening cocktail and in the back yard you can enjoy your dinner and make use of the gas grill. A huge table umbrella provides you with shade if needed. The two bedroom two bath unit is located on a very quiet street. The Master bedroom has a king size bed and the guest bedroom has a queen. The home has been totally remodeled, everything is new from furniture to floors and appliances. There are TV's in the master bedroom and the living room, and of course there is free WiFi. Everything you need to enjoy your visit is provided: dishes, cookware, linens, towels, beach chairs and beach towels, etc.brGulf Winds is a short walk away from the white sandy beaches of the Gulf of Mexico. Just take the short-cut through North Beach Village to get to the beach. The Holmes Beach Dog Park is another short walk down the street across Marina Drive. The bus stop of the free Island Trolley is close by as well as restaurants, shops and bars. Do not miss this GEM. For bigger parties you may also book Gulf Winds B.brDogs up to 25lb 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.

Cozy cottage on Anna Maria Island, 2 bedroom - pet friendly

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$370.61

Welcome to Seahorse Beach House located just a few houses from the Gulf beaches of Anna Maria Island. Seahorse Beach House is a half duplex with 2 bedrooms, 1 and a half baths and its own private shady patio with tropical landscaping where you can enjoy the heated pool, outdoor shower, and Weber grill. Inside you will find the spacious living area with sliding doors to the patio area. The kitchen has bar seating for 4 and is open to the living area which is good for easy entertaining. You can enjoy a day at the beach with the provided beach wagon, chairs and umbrella located in the garage. In the evening you can retreat to the bedrooms where you will enjoy our comfortable beds complete with 600 thread count prima cotton wrinkle free sheets. This home includes a fully equipped kitchen, linens, towels and beach towels.brbrLizzie Lu's Island Retreat is a full-service property manager on Anna Maria Island to ensure our guests enjoy some of the nicest, well stocked homes on the island. For an additional charge, we offer GEM cars among other services. Rest assured we are here to assist as needed in the most efficient manner possible.brWhile vacationing on Anna Maria Island, please adhere to our local rules and regulations for our residential community which are included in our homes as well as our arrival information.brbrCity ordinance requires us to inform you that 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. brVRC16-000373

Beautiful cottage just around the corner from the beach with Private Pool!

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$858.74