Vacation Home Rentals By Owner In Holmes Beach, FL

Sun, Sand & Style at Holmes BeachbrbrRelax in this beautifully furnished 3-bedroom, 2.5-bath townhome with a private pool, just an 8 min walk to the beach! brbrSpend your days soaking up the sun, sailing on the Gulf, shopping, or golfing nearby—and enjoy the convenience of walking to local restaurants and beach bars.brNOTE: there are two separate rental units as noted in the listing (A and B) and EACH has it's OWN Private POOL.brbrThe SpacebrBedrooms: King bed in bedrooms 1 & 2, 2 twin beds in bedroom 3brHome Features: 4 Smart TVs, soaking tubs, chandeliers, board games, modern décorbrOutdoor Fun: Fenced pool with tanning chairs, furnished patio with dining set & gas grillbrKitchen: Fully equipped with stainless steel appliances, breakfast bar, essentials, and spicesbrGeneral: Free WiFi, washer & dryer, central AC & heating, towels & linens providedbrbrParking & Extrasbr- Driveway fits up to 4 vehicles br- No parking on the streetbr- Ring doorbell security camera (front exterior only)br- No Electric Golf Carts / Gas Golf Carts Only (no parking on the street)brbrHouse Rulesbr- Check-in: 4 PM | Check-out: 10 AMbr- No smoking, pets, events, or large gatheringsbr- Guests must be 25+ to bookbr- Stairs required for access; may be challenging for limited mobilitybrbrEscape to Holmes Beach for a worry-free getaway with all the comforts of home—and a little extra sunshine!brbrLooking for more space brAnother 3-bedroom home for up to 6 guests is available on-site—ask about booking both for larger groups.

Chic Holmes Beach #B Private Pool

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$424.94

Island Luxury Near the Beach | Private Pool & PatiobrbrEnjoy the best of Holmes Beach in this bright and stylish 3-bedroom, 2.5-bath home on beautiful Anna Maria Island & only an 8 min walk (or 2 min car ride) to the beach!brbrDesigned for relaxation, this coastal retreat features an open layout, high-end finishes, and a tropical backyard oasis complete with a private pool, grill, and plenty of lounge space. brNOTE: there are two separate rental units as noted in the listing (A and B) and EACH has it's OWN Private POOL.brbrStroll to local beaches, grab a bite at nearby cafes, or explore the island by bike. Whether you’re planning beach days, golf outings, or sunset cocktails, this home makes it easy to unwind and enjoy it all.brbrHighlights:br- Private fenced pool with sun loungers and outdoor diningbr- Fully equipped kitchen with stainless appliances and island seatingbr- 4 Smart TVs, board games, and cozy tropical décorbr- Two king bedrooms + twin bedroom for flexible sleeping arrangementsbr- Washer/dryer, free WiFi, central A/CbrbrGuest Notes:br- Gas only Golf Carts allowed (no street Parking)br- Driveway parking for 4 cars (no street parking)br- No pets, smoking, parties, or eventsbr- Must be 25+ to bookbr- Exterior Ring doorbell camera (front entry only)br- Stairs required for access

Chic Holmes Beach #A Private Pool

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$872.72

Island Escape by Beach Retreats Vacation Rentalsbr 307 65th St, Holmes Beach, FL 34217br VRC18-000047brYour dream getaway awaits on Anna Maria Island! This stunning 4-bedroom (+ bonus room), 4-bath luxury vacation home is just steps from the beach and close to the best dining, shopping, and island attractions. With a private heated pool featuring a waterfall, waterslide, and shaded lounge area, this home is the perfect mix of relaxation and fun for families and groups.brWhile most of our properties rent only from Saturday to Saturday, exceptions can be made. Please reach out to us prior to booking if you would like to arrive or depart on alternate dates, or stay for fewer than 7 nights. We would love to host you!br Highlightsbr Steps to the beachbr Private heated pool with waterfall, waterslide & grottobr Covered pool deck with outdoor TV & grillbr 5 bedrooms, 4 bathrooms br ‍ ‍ Perfect for large families & groupsbr Luxe linen service includedbr Free high-speed WiFibr Walk to restaurants, shops & the free island trolleybr This home can accommodate parking for up to 3 vehiclesbr Inside Your RetreatbrThis spacious and beautifully designed home features a bright open floor plan with high-end finishes throughout. The living area includes cozy sofas, a large Smart TV, and direct access to the outdoor pool deck.brThe fully equipped gourmet kitchen is stocked with stainless steel appliances, service for 12, and everything you need to enjoy home-cooked meals. A spacious dining area makes gathering for breakfast or dinner effortless.br Room DetailsbrMaster Suite: King bed, ensuite bathroom with dual sinks, walk-in closet.brBedroom 2: King bed, attached bathbrBedroom 3: King bed, ensuite bathroombrBedroom 4: King bed, shared bathbrBunk Room: 2 bunk beds (4 twins) with charming clapboard walls & bead-board ceilings — a fun kids' hideaway!brWith four King bedrooms and a bunk room, there's plenty of space for everyone to spread out while still enjoying time together.br Outdoor LivingbrThe backyard is your private tropical oasis. Spend your days splashing in the heated pool with grotto, waterfall, and waterslide, or relax on the covered pool deck while catching the game on the outdoor TV. Fire up the grill and enjoy meals al fresco under the shade.brBeach days are a breeze with provided gear including a beach cart, 4 chairs, umbrella, and wagon.br Location & Things to Dobr Steps to the free Anna Maria Island trolleybr Walk to award-winning restaurants like Chateau Anna Maria, The Feast, and Duffy's Tavernbr Live music, bars & shops within walking distancebr Activities include parasailing, paddleboarding, fishing, sunset cruises & morebrWhether you're chasing adventure or simply soaking up the Florida sun, this home places you right in the heart of it all.br✅ Important InfobrMax occupancy: 10 guestsbrNo cancellation fees!brCancel 60+ days before arrival → Full refundbrCancel within 60 days → No refundbrExtended stays & bookings $20,000+ → Full payment 90 days prior, non-refundablebr$500 deposit due at booking; balance due 60 days priorbrFor reservations 21+ nights or $20,000+ → 10% deposit due at time of booking.brThird party travel insurance cost is due at time of purchasebrThird-party travel insurance through Beach Retreats is non-refundablebrNo changes permitted within 60 days of arrival or during staybrWe highly recommend cancelation insurancebrGuests must be 25+ to book (or accompanied by parent/guardian)br Quiet hours: 10 PM – 7 AM; please respect neighborsbr Book your stay at Island Escape today and experience the best of Anna Maria Island — where coastal elegance meets fun in the sun! brWe prefer Saturday to Saturday rentals. If you're looking to stay other days, please give us a call.

307 65th Street managed by Beach Retreats FL Anna Maria Island

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$464.83

306 67th Street Unit B Holmes Beach, FL 34217brVRC 19-000277br Caribbean Surf by Beach Retreats Vacation Rentalsbrbr Holmes Beach, Anna Maria Islandbr 3 Bedrooms | 2 Bathrooms | Sleeps 6 | Private Heated Pool | Pet-Friendlybrbr✨ Your Anna Maria Island Bungalow Retreat ✨brWelcome to Caribbean Surf, a bright and inviting 3-bedroom, 2-bath bungalow just a short stroll from the sugar-white sands of Holmes Beach. With its cozy coastal charm, private heated pool, and family-friendly amenities, this home is the perfect place to relax, unwind, and enjoy everything Anna Maria Island has to offer.brbr While most of our properties rent only from Saturday to Saturday, exceptions can be made. Please reach out to us prior to booking if you would like to arrive or depart on alternate dates, or stay for fewer than 7 nights. We would love to host you!brbr HighlightsbrbrShort walk to Holmes BeachbrbrPrivate heated pool in your own fenced backyard oasisbrbr Pet-friendly + family-friendly yard space (Non refundable pet fee of $125/pet)brbrGrill, lounge chairs, and beach gear includedbrbrFree Wi-Fi, washer/dryer, central A/Cbrbr Inside Your HomebrbrBedroom 1: King bed + ensuite bathbrbrBedroom 2: King bedbrbrBedroom 3: Two twin bedsbrbrSpacious living area with flat-screen TV and comfortable seatingbrbrFully equipped kitchen for family meals and island dining nightsbrbr Outdoor LivingbrbrHeated pool with sun loungers and tropical landscapingbrbrPrivate fenced yard — perfect for kids or petsbrbrGrill + outdoor dining area for BBQ nights under the starsbrbrBeach chairs, umbrella, and wagon provided for seaside adventuresbrbr Explore Anna Maria IslandbrbrFrom Caribbean Surf, you're just minutes away from:brbrThe vibrant shops & eateries of Pine AvenuebrbrLocal favorites like Ginny's & Jane E's Café and The Sandbar RestaurantbrbrIsland adventures: fishing, kayaking, paddleboarding, biking, and dolphin toursbrbr Booking & CancellationbrbrNo cancellation fees!brCancel 60+ days before arrival → Full refundbrCancel within 60 days → No refundbrExtended stays & bookings $20,000+ → Full payment 90 days prior, non-refundablebr$500 deposit due at booking; balance due 60 days priorbrFor reservations 21+ nights or $20,000+ → 10% deposit due at time of booking.brThird party travel insurance cost is due at time of purchasebrThird-party travel insurance through Beach Retreats is non-refundablebrNo changes permitted within 60 days of arrival or during staybrWe highly recommend cancelation insurancebrbr This home can accommodate 2 vehiclesbrbr✨ Whether you're lounging poolside, strolling to Holmes Beach, or exploring the island's hidden gems, Caribbean Surf is your perfect home base for an unforgettable Anna Maria Island vacation.brbr Book now! br This home features Silicon Travel. With Silicon Travel's firewall place in place, you can prevent internet access to any malicious activity in a Vacation rental home. Any guest device (WebCam, Baby Monitor, etc) can be added for a set time and will be removed automatically upon departure.

Caribbean Surf managed by Beach Retreats FL Anna Maria Island

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$441.02

You, Me, and the Sea AMI by AMI Locals brVRC21-000081 brbrWelcome to You, Me, and the Sea AMI by AMI Locals, your perfect family retreat on beautiful Anna Maria Island. Just a one-minute walk to the soft Gulf sands, this elevated three-bedroom, two-bath vacation home blends modern coastal design with laid-back island comfort. Thoughtfully designed for families and multi-generational groups, it offers spacious living, a private pool with spa, and a prime Holmes Beach location close to everything that makes island life unforgettable. brbrHighlights br• 1-minute walk to Holmes Beach br• 3 Bedrooms / 2 Bathrooms br• 2 Kings / 1 Queen / 1 Full-over-Full bunk with Twin trundle br• Private pool with in-ground spa br• Balcony with outdoor dining and BBQ grill br• 2-minute walk to the Anna Maria Island trolley stop br• Parking available for 4 vehicles brbrStep into paradise with your very own private heated pool and spa, surrounded by lush tropical greenery that invites total relaxation. The balcony features a shaded dining area and grill, perfect for sharing alfresco meals and sunset cocktails after a fun-filled beach day. brbrInside, you’ll find a bright open floor plan designed for comfort and togetherness. The living room offers cozy seating and a TV for movie nights, while the fully equipped kitchen features stainless steel appliances, generous counter space, and a dining table set for family gatherings. A small workspace next to the kitchen provides a convenient spot to catch up on emails or jot down vacation plans, making this home functional as it is relaxing. Whether preparing breakfast or enjoying evening dinners, this space makes island living effortless. brbrThe primary suite is ideal for parents and kids, featuring a king bed, full-over-full bunk bed with twin trundle, and an ensuite bathroom with a double vanity and walk-in shower. The second bedroom includes a king bed, while the third bedroom offers a queen bed. Both share a hallway bathroom with a walk-in shower, making it easy for everyone to have their own space and comfort. brbrRoom Details br• Primary Bedroom (2nd floor): King bed, Full-over-Full bunk with Twin trundle, ensuite bathroom with walk-in shower br• Second Bedroom (2nd floor): King bed br• Third Bedroom (2nd floor): Queen bed br• Hall bathroom with walk-in shower brbrThis home provides a washer and dryer, Wi-Fi, and beach essentials for guest use. Guests can easily explore Anna Maria Island with the island trolley, just steps away. Located near restaurants such as Skinny's Place and Double Deez Chicago Style Restaurant, or parks like Grassy Pointe Preserve, you’ll have local dining and outdoor activities at your fingertips for the perfect island experience. brbrFrom peaceful mornings on the balcony to sunset swims in the pool, You, Me, and the Sea AMI by AMI Locals offers everything you need for an unforgettable Anna Maria Island vacation rental. Make lifelong memories with your loved ones and book your stay today! brbr- brThis home is managed by AMI Locals, an Anna Maria Island property management company. brbr4 cars maximum can 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. 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. brbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise respectful 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 a refund.

You, Me, and the Sea AMI - Elevated Beach Home with Pool and Spa Steps from Beac

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$366.25

Top Reasons to Book:br-Only 1.5 Blocks to the Beachbr-Private Pool with Swim-Up Tiki Table (Free Pool Heat in Cooler Months)br-3 Bedrooms + Sleeper Sofa – Sleeps Up to 6br-All Bedrooms Have Ensuite Bathroomsbr-Fully Equipped Kitchen with Island Seatingbr-Multiple Outdoor Spaces Including Front Deck & Private Backyardbr-Close to Manatee Public Beach, Dining, Shops & Free AMI TrolleybrbrWelcome to Blue Martini, a bright and inviting two-level beach home just steps from the Gulf. Vaulted ceilings, tropical backyard views, and an open living area create a relaxing coastal retreat. The fully equipped kitchen features stainless steel appliances, ample counter space, and island seating—perfect for meals and entertaining.brbrThree comfortable bedrooms each include an ensuite bathroom, and the primary suite features a private balcony and walk-in shower. A sleeper sofa in the living room provides flexible accommodations.brOutside, enjoy your own private oasis with a heated pool, swim-up tiki table, loungers, and a gas grill for fresh island meals. Multiple dining areas—indoors and out—let you take advantage of the island breeze all day long.brbrManatee County Beach is minutes away, along with great restaurants, shops, and access to the free island trolley. Enjoy kayaking, paddleboarding, tours, golf, boat charters, and all that Anna Maria Island has to offer.brbrBedrooms & Baths:br-Primary Bedroom, 1st Floor: King bed, TV, private balcony, ensuite bath with walk-in showerbr-Second Bedroom, 1st Floor: King bed, TV, ensuite bath with walk-in showerbr-Third Bedroom, 2nd Floor: Queen bed, TV, ensuite bath with shower/tubbr-Living Area: Queen sleeper sofabr (Sleeps 6 total)brbrImportant Notes:br-No Pets Allowedbr-Parking: Max 3 cars (no overnight street or additional parking)br-TVs use Roku for streaming (no traditional cable)br-Complimentary starter kit provided; guests replenish as neededbr-Pool Heat: Free during cooler season

Beautiful 3 Bedroom 3 Bath Home Steps Away from the White Sands of Holmes Beach!

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$384.11

Cuddlefish Cove Your flip flops have found a new retreat by the beach! Stay for a week or a month at this dazzling Key West inspired, 3 bedroom beach house with New heated pool, all within minutes from the most amazing beach on the Gulf of Mexico. You will feel relaxed within minutes of arriving! brbrThe morning sun illuminates the open sitting and dining area where large ceiling fans provide a relaxing breeze that you’ll come to love at Cuddlefish Cove. The large, well appointed kitchen with fully equipped stainless steel appliances is inviting and the long island bar is where friends and family will gather. Looking for that perfect place for afternoon cocktails Sneak away to the rooftop deck with fabulous views of the Gulf of Mexico and Tampa Bay. brbrAs a place to be inspired and relaxed you’ll find all the amenities of home including: large screen TV, DVD, wireless internet, and washer/dryer. Enjoy your afternoon siesta in one of three bedrooms with all new ensuite bathrooms, comfortable beds and walk out decks. The main floor master suite with luxury mattress king bed has a gorgeous Juliet balcony to enjoy the tropical breeze. The main floor boasts two bedrooms one with a king size bed and walk in shower and the other bedroom with twin beds and full bath. brbrA new heated pool surrounded by a garden full of palms and hibiscus is perfect to enjoy the sun as well as a covered lanai by the pool is perfect for those who want to get out of the sun! A perfect blend of interior meets the outdoors with relaxing patio furniture and a large flat screen television. brbrTake a walk, bike or free trolley to the village and stop in one of the beach side cafes, Ice-cream, or boutiques, famous piers and so much more! Take the virtual tour and see why Cuddlefish Cove will become your family and friend’s special place on the Island. Sleeps six.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.br*Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.brbrVRC16-000222

Cuddlefish Cove: Heated Pool, rooftop deck, gorgeous views!

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$187.38

266 South Harbor - Anna Maria Island - 3 Bedroom/ 2 Bath, maximum occupancy of 6 people. VRC# 20-000032br No Pool - Distance to the Beach: 3 blocksbr Please ask for Long-term specials. br br This elevated home is in the city of Holmes Beach. Nice open floor plan with spacious kitchen and new stainless steel appliances. The two car garage features one side long enough to accommodate a truck with a boat trailer. Take advantage of the roomy deck. Visit and relax with friends and family.br Grill the day's catch, and dine under the stars.br br Enjoy many activities on your visit: swimming, snorkeling, beautiful sunsets, fishing, boating, shopping, watching wildlife, golfing, bicycling, tennis, and more. The free island trolley has convenient stops the length of the island.br br You are vacationing in a residential area where homes are in close proximity to each other. Please be a good neighbor by keeping the noise to a respectful level during the day and night. A violation of the city's noise control ordinance shall subject the violator to the issuance of a notice of violation or citation. Noise is measured at the property line of the property generating the noise.br Amenities Include:br - # Bedrooms: 3br - Bed Sizes: Queen, twinsbr - Sofa Sleeper: Futon in denbr - # Baths: 2br - Tub or Shower: bothbr - Balcony: Yes-largebr - #of units in complex: single homebr - Tennis: public nearbybr - BBQ Grill: yes Gas grillbr - Square Feet: 1522 / 3646br - Floor Number: elevated homebr - Distance to Beach: 3 blocksbr - Internet: wifibr - View: neighborhoodbr - washer dryer: Yesbr - Dishwasher: Yesbr - Boat Dock: neighborhoodbr - Maximum Persons: 6br - DVD/VCR: Yes-Blue Raybr - TV: living room,master,dbr - Hairdryer: yesbr - Type of Parking: 2 car garagebr - Coffee maker: yes regularbr - Blender: yes Ninja

266 S. Harbor - Anna Maria Island- Private home 3 Bedroom/ 2 Bath , maximum occupancy of 6 people.

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$737.76

6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS!brAll Drivers must be over the age of 21. Drivers must provide valid Driver's License and Vehicle Insurance. To drive the golf cart, non-US driver license holders are required to pay an additional $25 per day instead of providing vehicle insurance. The golf cart $25 fee is per golf cart, not per driver. This cost covers the extra insurance required. brbrWelcome to It's Miller Time, a stunning 4-bedroom, 4.5-bath vacation retreat located in the heart of Holmes Beach on beautiful Anna Maria Island. Designed for relaxation, comfort, and easy island living, this pet-friendly home (up to two dogs) offers everything you need for the perfect beach escape.brbrStep outside to your private, resort-style lanai, an expansive outdoor space perfect for gathering, dining, or simply enjoying the island breeze. The large, heated pool features a unique in-water dining table and a hot tub for unwinding after a day in the sun. With plenty of lounge seating, this backyard is your personal paradise. Grab a paddle and enjoy a game of ping pong, which is located in the garage.brbrInside, a serene lower-level seating area welcomes guests looking for a quiet seating area to read, relax, or take a break from the group. Head upstairs to the main living floor where an open-concept layout creates a warm, connected space for everyone to enjoy. The gourmet kitchen boasts a large island with abundant seating, a Sub-Zero refrigerator, and all the essentials needed to host family meals or casual snacks after the beach. The living room features a spacious sectional and opens to a breezy balcony—perfect for morning coffee or sunset cocktails. A convenient half bath is located just off the living area.brbrThis home sleeps up to 12 guests comfortably, offering plenty of room for families or groups:brPrimary Suite: King bed, ensuite bathroom with a luxurious soaking tub and separate walk-in shower.brBedroom 2: King bed with ensuite bathroom and walk-in shower.brBedroom 3: King bed with ensuite bathroom and walk-in showerbrBedroom 4: Queen-over-queen bunk with ensuite shower, perfect for kids or extra guests.brbrJust a short stroll away, you'll find Holmes Beach with its powder-soft sand and sparkling Gulf waters. Spend your days swimming, shelling, and soaking up the Florida sunshine before heading back to your private haven for a dip in the pool or a rest on a sun-lounger. Whether you're here for family fun, relaxation, or a little of both, It's Miller Time promises a memorable Anna Maria Island vacation. Soak it up, settle in, and enjoy every moment!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. brbrThe 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. Our 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.brbrThis property features an EV charger for our environmentally savvy guests! You can charge your electric vehicles right on-site, ensuring you're always charged up and ready to explore. It's not just about convenience; it's about making a positive impact on the planet while providing top-notch service. So, get ready to plug in, charge up, and embark on eco-friendly adventures with us! For more info or to add EV Charging, contact SeaBreeze Vacation Reservations prior to 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: VRC23-000026brMax Occupancy: 12 Guests | Max Vehicles: 5brQuiet 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.

It's Miller Time by SeaBreeze Vacation

Holmes Beach, Florida, United States

Bed

Bath

8

Sleeps

$552.9

Welcome to your perfect coastal getaway on beautiful Holmes Beach, just one block from the shimmering Gulf of Mexico with its turquoise-blue waters and powdery white sand. This charming 3-bedroom, 2.5-bath single-family home captures the essence of Anna Maria Island living, featuring soft pastel interiors and decor that echo the island's breezy, relaxing vibe. With plenty of space for family and friends, this home offers comfort, style, and all the amenities needed for a memorable stay.brbrSleeping Arrangements:brPrimary Suite: King bed with a private ensuite bathroombrBedroom 2: King bed brBedroom 3: Queen bed with half bathroom ensuitebrbrThe spacious kitchen is equipped with stainless steel appliances, ample counter space, and everything you need to entertain or prepare delicious island meals. Step outside to your own tropical oasis: a screened-in heated pool and lanai that provide the ideal spot to relax day or night. Enjoy meals at the large outdoor dining table, where everyone can gather comfortably while the screened enclosure keeps the island's insects at bay. Rinse off the beach sand using the convenient outdoor shower after a day by the Gulf. This home offers the perfect blend of coastal charm, modern comfort, and unbeatable location—your ideal retreat on Anna Maria Island.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: brPer 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: VRC16-000906brMax Occupancy: 8 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.

Perfect Coastal Getaway by SeaBreeze Vacation

Holmes Beach, Florida, United States

3

Bed

2

Bath

6

Sleeps

$628.17

Summary:brbrEscape to Beach Escape, a charming 3-bedroom, 3-bathroom Mediterranean-style house in the heart of Holmes Beach, Florida. Enjoy easy access to the pristine beach, walkable dining and shopping, and a free trolley stop. This home offers a private outdoor oasis with a heated pool, outdoor dining, and a gas grill. Explore the island with a complimentary golf cart and bikes. Experience the perfect blend of relaxation and adventure in this guest-friendly location.brbrbrbrThe Space:brbrThe Home This charming 3-bedroom, 3-bath Mediterranean-style retreat is tucked away on a quiet cul-de-sac—offering peaceful privacy while still being right in the heart of Holmes Beach. Bright, coastal interiors inspired by the Gulf Fully equipped kitchen with stainless steel appliances Multiple balconies for morning coffee or sunset breezes Smart TVs + high-speed WiFi throughoutbrbrbrbrGuest Access:brbrGuests have access to the entire private house, including the heated outdoor pool, surrounded by lush tropical landscaping. Enjoy the outdoor dining area with a gas grill, perfect for al fresco meals. The property is located in a quiet, relaxing setting, just steps from the beach.brbrbrbrThe Neighborhood:brbrEnjoy the prime location of our Holmes Beach home, just a stone's throw from the beautiful public beach! You'll have easy, stress-free access to the sand and surf, perfect for a relaxing day by the water. Nearby, you'll find convenient public amenities such as restrooms, showers, and lifeguards. Indulge in the local culinary scene with a variety of restaurants, cafes, and beach bars within walking distance. Plus, you're close to shops and essential services, making your stay convenient and enjoyable.brbrbrbrGetting Around:brbrGetting around Anna Maria Island is easy and enjoyable. The free island trolley runs daily along the island and is just a short walk away, offering convenient access to beaches, shops, dining, and local favorites from the City of Anna Maria to Bradenton Beach. Complimentary bikes are provided, and ride shares, taxis, and personal vehicles are also readily available. On-site parking is available for up to four vehicles. For a classic island experience, guests may rent a golf cart from our preferred provider, Coconut Rentals. Be sure to mention Serendipity when booking to receive a preferred guest discount (subject to availability).brbrbrbrOther Things to Note:brbrWeekly Rentals Only: This home is subject to a 7-night minimum stay in accordance with City of Holmes Beach regulations. brbrbrbrOccupancy Limits: Maximum occupancy is 2 guests per bedroom plus up to 2 additional guests, not to exceed 12 total, whichever is less. Limits are strictly enforced. brbrbrbrParking: On-site parking is available for up to 4 vehicles in designated areas only. brbrbrbrNo Pets: Only service animals are allowed on the property, and must be registered prior to check in brbrbrbrNoise Ordinance: This is a quiet residential neighborhood. Local noise limits apply (65 dBA from 7 AM–10 PM; quiet hours 10 PM–8 AM). brbrbrbrSelf Check-In: Easy arrival with smart-lock self check-in. Entry details are provided prior to arrival once pre-arrival requirements are completed. brbrbrbrPre-Arrival Requirements: A signed rental agreement, valid government ID, and signed waivers are required for all adults prior to check-in.brbrbrbrPool Safety: Swim at your own risk. No glass permitted in or around the pool. Children must be supervised at all times.brbrbrbrInteraction with Guests:brbrThis home is professionally managed to ensure a seamless, luxury stay while respecting your privacy. Guests enjoy a self-directed experience, with no on-site interaction unless requested. brbrbrbrOur team is available 7 days a week from 8 AM to 4 PM to assist with questions or needs. Outside of regular hours, after-hours support is available for true emergencies only.

Beach Escape, Family Home

Holmes Beach, Florida, United States

3

Bed

3

Bath

8

Sleeps

$1225.7

Slice of Paradise by Duncan Real Estate! Welcome to this stunning custom built luxury home on Anna Maria Island with four-bedrooms, five full bathrooms and two half baths. We are re-defining a high quality of coastal living!Relax and unwind in the outdoor tropical oasis with a private pool with water features, outdoor kitchen and catwalk that leads to a bar and large TV so you can enjoy the game. More luxury features at Slice of Paradise are the roof top deck, elevator to every floor, large balconies, ping pong table, pack and play and a high chair.HIGHLIGHTS Luxury Vacation Rental Property Private pool (25x9 ft.) Catwalk to covered pool deck bar Water views from roof top deck Elevator Game room with ping pong table Pack and Play High Chair Centrally locatedbrbrLIVING SPACE 3762 sq. ft. Smart TVs in every bedroom Rooftop Deck Washer/Dryer located in the house Fully equipped kitchen Work spaceBEDROOMS Sleeps 8 Primary Bedroom: Ensuite King Second Bedroom: Ensuite Queen Third Bedroom: Ensuite Queen Fourth Bedroom: Ensuite Twin Bunk Beds and Single bedBATHROOMS Primary Bathroom: Walk-in Shower Second Bathroom: Walk-in Shower Third Bathroom: Walk-in Shower Fourth Bathroom: Shower/Tub Fifth Bathroom: Half Bathroom Sixth Bathroom: Half BathroomOUTDOOR LIVINGLarge BalconiesFive expansive balconies, one off the great room, one off the main bedroom, one off the front of the house and two on the roof top, features panoramic views. Ideal for sunrise coffee or sunset cocktails.Ground Level Pool & Outdoor KitchenAn entertainer's haven connecting seamlessly from the back balcony to the catwalk and covered pool deck area.Poolside bar area: Custom cabinetry, bar stools, fridge, workstation, sink with water, a large outdoor TV and a large indoor dining area for shaded meals. There is also a gas grill.Pool Area: Large wrap around pool, separate hot tub, outdoor bar and kitchen area, generous seating, outdoor shower. Soft night lighting for evening ambiance.Rooftop DeckCrowning the home with 360-degree Gulf and island views, the rooftop deck offers seating. The perfect space for entertaining, yoga, or stargazing.Slice of Paradise draws from coastal modernism, geometric rooflines and inviting living spaces. Elevated above the garages, it's surrounded by mature palms and tropical landscaping. Located in a central location and a short walk to the white sand beaches of Anna Maria Island, the property offers privacy while remaining close to the Holmes Beach boutiques, cafs, and beachside charm. Slice of Paradise embodies the essence of modern coastal life.The weekly pool and spa heat is $150 which will be set at 86 F for the pool and 102 F for the spa.Pool equipment is locked for safety and controls must not be tampered with. Pool alarms are mandated per city licensing ordinance and cannot be disarmed. Pools are professionally serviced weekly. Debris due to tropical climate might occur in between service days. Pool equipment does not run 24 hours and water temperature can vary as pool heaters operate ONLY when the pool pump is running. The spa is integrated with the pool and its body of water and requires the pool heater to be on in order to warm up. The spa has to be turned on manually and will run in increments. Pool equipment does not run 24 hrs. and water temperature can vary as pool heaters operate ONLY when the pool pump is running. Please note if cold days/nights occur, water temperatures will drop and may stay cooler longer. When the ambient temperature falls below 60 degrees F, the pool heater may not function and even switch off. Duncan Real Estate will expedite repairs of reported malfunctions, but no refund will be made for circumstances beyond our control.This property is protected by video surveillance in the front parking area.VRC21-000047brbrAmenities Include:brbr- Bedroom 1 Kingbrbr- Bedroom 2 Kingbrbr- Bedroom 3 Queenbrbr- Bedroom 4 Bunkbed, single twinbrbr- Pack N Playbrbr- Bathroom 1 Walk in shower and soaking tubbrbr- Bathroom 2 Walk-in-Showerbrbr- Bathroom 3 walk in showerbrbr- Bathroom 4 Shower/tubbrbr- Half Bathbrbr- Hot Waterbrbr- Beach Access 0.1 milebrbr- Elevatedbrbr- Elevator Ybrbr- Central A Cbrbr- Cental Heatbrbr- Ceiling Fan Living Areabrbr- Sqft under a c 2669brbr- Free Parkingbrbr- Parking Spots 4brbr- Garagebrbr- Self Check Inbrbr- Keyless Entrybrbr- Bath Towelsbrbr- Beach Towelsbrbr- Quality Linensbrbr- Hair Dryerbrbr- Hangersbrbr- Refrigeratorbrbr- Ice Makerbrbr- Wine Fridgebrbr- Stovebrbr- Ovenbrbr- Cookwarebrbr- Toasterbrbr- Blenderbrbr- Keurigbrbr- Drip Coffee makerbrbr- Dishwasherbrbr- Microwavebrbr- Garbage Disposalbrbr- Dining Tablebrbr- Breakfast Barbrbr- High Chairbrbr- High Speed WIFIbrbr- TV 6brbr- Cable Channelsbrbr- Washerbrbr- Dryerbrbr- Ironbrbr- Ironing Boardbrbr- Cleaning Kitbrbr- Fire Extinguisherbrbr- Smoke Alarmbrbr- Carbon Monoxide Alarmbrbr- Private Pool Ybrbr- Hot Tub Ybrbr- Pool Alarmsbrbr- Sun Loungersbrbr- Balconybrbr- Outdoor Kitchenbrbr- Outdoor Diningbrbr- Deckbrbr- Rooftop Deckbrbr- Propane Grillbrbr- Beach Amenitiesbrbr- Game Roombrbr- Ping Pongbrbr

Slice of Paradise by Duncan Real Estate

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$964.54

Octopus Cottage by Anna Maria Life Vacation Rentalsbr209 69th St, Holmes Beach, FL 34217brbrWhat You'll Love About This Home:brLocation! 1.5 Blocks to the Beach!br4 Bedrooms / 4.5 Bathroomsbr4 KingsbrPrivate Heated Pool & SpabrPool LoungersbrCovered Poolside Lounge Area with TVbrAdirondack Chairs around Fire PitbrCovered Patio Verandah Dining for 6brGas GrillbrElevator (all floors)br8 Hole Mini Putt-Putt CoursebrPing Pong, Pool, Cornhole, Connect FourbrProfessional Linen Service, Washer & DryerbrComplimentary WIFIbrBeach Towels, Beach Chairs, Beach WagonbrParking for 5 Cars MaxbrbrDetails:brOctopus Cottage is a delightful beach house located 1.5 blocks from the sparkling clear waters and sugar sand beaches of the Gulf of Mexico.brbrThe kitchen overlooks the dining area with seating for six, plus additional seating at the island. The living room offers a comfortable space to gather. Patio doors open to a verandah with outdoor dining for six, a gas grill, and a wet bar. An elevator provides easy access to the main living area for guests, groceries, and luggage.brbrAll four bedrooms feature a king bed, private ensuite bathroom, and TV. Linens and towels are provided through a professional linen service. Guests also have complimentary WiFi and access to a washer and dryer.brbrThe backyard is designed for both relaxation and entertainment. Enjoy the private pool and spa, lounge chairs, and a swim-up table. The covered poolside area includes seating and a TV. In the yard, you'll find an 8-hole mini putt-putt course, yard Connect 4, cornhole, ping pong, and a firepit for evening gatherings. Inside, a pool table adds even more space for friendly competition.brbrOctopus Cottage is within walking distance to the free island trolley, which runs the full 7-mile length of the island with stops for beaches, shopping, and dining. A convenient location for your next beach getaway.brbrBedroom 1 - King Bed, Ensuite Bathroom, TV - Floor 2brBedroom 2 - King Bed, Ensuite Bathroom, TV - Floor 2brBedroom 3 - King Bed, Ensuite Bathroom, TV - Floor 2brBedroom 4 - King Bed, Ensuite Bathroom, TV - Floor 2brbrPlease note:brThis home is not pet friendly.brThe left-hand side garage is not for guest use.brAmenities are subject to change.brDriveway parking is available for a maximum of 4 cars. Garage Parking for 1 car. Parking for additional vehicles is not availablebrbrYou 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. The minimum requirement for this home is no less than seven nights. The maximum occupancy is eight.brbrVRC18-000139brIMPORTANT INFORMATION: brbrYour booking is with Anna Maria Life Vacation Rentals. We will send you check-in instructions 14 days prior to your arrival date. We will send you our rental agreement in an electronic signature document. Please review and return to us by following the instructions.brbr** Your signed rental agreement must be returned in order to receive your check-in details. brbrVRBO BOOKINGSbrbrAnna Maria Life Vacation Rentals will charge your credit card for your deposit payment. You will also see a separate charge by VRBO for their service fee. brbrYour final balance is due 60 days prior to your arrival date. We will send you a final payment reminder 90 days prior to arrival. We do not automatically charge your card for your final balance. brbrThe instructions for making your final payment will be included in your final payment reminder.brbrPlease review the cancellation policy prior to booking. brbrGOOGLE VACATION RENTAL BOOKINGSbrbrYour payment is due in full at the time of booking and the final balance information above does not apply to your reservation.

Octopus Cottage: 1.5 Blocks to Beach, Pool & Spa by Anna Maria Life Vacation Rentals

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$378.47

Casa Bella by AMI Locals brVRC22-000114 br brExperience the ultimate island retreat at Casa Bella, a luxurious corner lot vacation home located just three blocks from the pristine Gulf in Holmes Beach. This stunning four-bedroom, three-bath home offers modern coastal elegance, a private pool, and easy access to parks, beaches, and local attractions. Perfect for families and groups seeking relaxation and adventure in Anna Maria Island, Casa Bella is a true seaside paradise with stylish decor and spacious outdoor living! brbrHighlights br• 5-minute walk to Holmes Beachbr• 4 Bedroom / 3 Bathroom br• 3 Kings, 2 Twin/ Twin bunks br• Private pool with pool loungers  br• Screened-in lanai  br• Near popular parks br• Ping pong table br• Washer and dryer br• Short drive to Holmes Beach Town Center shopping, dining, and local attractions br• 3 Parking spacesbr brEnjoy resort inspired amenities including a sparkling private pool, a screened-in lanai, and a game room featuring a ping pong table. The backyard is perfect for lounging, outdoor games, and socializing, while the nearby parks and promenade provide endless opportunities for outdoor adventures. The home’s coastal decor and open floor plan make it an inviting setting for creating lifelong memories with friends and family. brbrThe main living area welcomes you with stunning blue hues, engaging artwork, and plush sectional seating that creates a relaxing atmosphere. The fully equipped kitchen features stainless steel appliances, a custom backsplash, stone countertops, and a coastal dining table, plus outside dining on the balcony. Large sliding doors connect indoor comfort to outdoor living, perfect for vacation relaxation and entertainment. br brThe third-floor primary bedroom is a tranquil oasis with a King bed, private balcony, and an ensuite bathroom with a soaking tub, walk-in shower, and double vanity. The second bedroom on the third floor offers a King bed and a TV, while the third bedroom, also on the third floor, is ideal for kids with two twin over twin bunk beds. The fourth bedroom on the second floor features a King bed and a TV, with easy access to the hallway bathroom that includes a shower and bath combo. Every bedroom offers comfortable linens, ample closet space, and a relaxing retreat to rest after a day of island adventures. brbrRoom Details br• Primary Bedroom (3rd floor): King bed, balcony, ensuite with soaking tub and walk-in shower  br• Second Bedroom (3rd floor): King bed brThird Bedroom (3rd floor): Two twin-over-twin bunk beds  br• Fourth Bedroom (2nd floor): King bed br brThis home provides a washer and dryer, a screened in porch, a ping pong table in the game room, and plenty of outdoor space for poolside lounging and backyard games. Beach chairs and outdoor seating are included to enhance your stay, while the home’s convenient location makes exploring Anna Maria Island easy and enjoyable. br brBook your stay at Casa Bella today and immerse yourself in the charm of Holmes Beach. With effortless access to the beach, parks, and local shops and dining, this stylish coastal retreat offers endless opportunities for adventure and relaxation. Slip into island time and create unforgettable vacation memories at Casa Bella on Anna Maria Island! br brbr- brThere are no pets allowed in this home.brbr*Please note: 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. brbrThis home is managed by AMI Locals, an Anna Maria Island property management company. 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. brbrPlease 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.

Perfect Family Vacation Home with Private Pool and Tropical Landscaping

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$372.1

Beach Bellini is a 3 bedroom/3 bathroom private home in Holmes Beach. Just an 8 minute walk to the beach, pull into the paver driveway with a one-car garage and enter this light and airy home with wood floors and wood plank ceilings. The fully-stocked kitchen has stainless steel appliances, granite counters, bar counter seating as well as a dining table with seating for six. There's a washer and dryer right off the kitchen that allows the convenience for you. Three lovely bedrooms; one with a king and two bedrooms with queen beds and each bedroom having their own ensuite bathroom. After a day at the beach, head outdoors in the private backyard and there's a heated pool and outdoor seating as well as a grill. Truly a vacation home for you and your family to make memories.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.brbrThe 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. Our 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: VRC18-000197brMax 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.

Pool - Beach Bellini by SeaBreeze Vacation

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$1172.5

Anna Maria Wave by Anna Maria Island Accommodations brbrWelcome to Anna Maria Wave by Anna Maria Island Accommodations, a spectacular four-bedroom, four-bathroom beachfront home that captures the essence of coastal luxury on beautiful Anna Maria Island. Perfect for families and groups, this contemporary retreat combines modern design, breathtaking Gulf views, and thoughtful amenities that make every moment unforgettable. Enjoy direct beach access, a heated beachfront pool, and multiple balconies designed for soaking in golden sunsets; creating an island getaway like no other on the Florida Gulf Coast. brbrHighlights br• Direct beachfront home br• 4 Bedrooms / 4 Bathrooms br• 4 King beds, Twin Lounge Seat br• Heated beachfront pool br• Stunning beach and Gulf views br• Poker table and outdoor TV/bar br• Beachfront dining area br• Dog friendly (with approval and additional fee) br• Elevator access br• 4 parking spaces brbrStep outside to your private paradise where the heated beachfront pool overlooks the turquoise Gulf waters, providing the perfect spot for a refreshing swim or lazy afternoon under the sun. Dine outdoors at the beachfront dining area, unwind at the outdoor bar, or gather for game night around the poker table. As the sun sets, relax with your favorite drink by the outdoor TV and watch the sky transform with color. Every detail of Anna Maria Wave was designed for unforgettable beachfront living, combining comfort, fun, and breathtaking scenery. brbrInside, the open concept design perfectly frames the ocean views from nearly every angle. The modern kitchen features sleek cabinetry, stainless steel appliances, and plenty of counter space, making it easy to prepare family meals or entertain guests. Multiple living areas and balconies create space for both connection and relaxation, while large glass doors let in the island breeze and endless natural light. With stylish finishes and a soothing coastal palette, every corner of Anna Maria Wave invites guests to unwind in comfort and style. brbrEach of the home’s four bedrooms offers a luxurious king bed, three with ensuite bathrooms, one with access to the hall bathroom, ensuring privacy and relaxation for every guest. The third-floor primary suite stands out with a panoramic Gulf-front balcony, perfect for morning coffee or evening cocktails as the sun sets over the horizon. Every bedroom is thoughtfully designed with plush bedding, TVs, and plenty of space to unpack and settle in for your stay on Anna Maria Island. brbrRoom Details br-Primary Bedroom (3rd Floor): King bed, ensuite bathroom with walk-in shower, Gulf-facing balcony br-Second Bedroom (3rd Floor): King bed, ensuite bathroom with walk-in shower br-Third Bedroom (2nd Floor): King bed br-Fourth Bedroom (2nd Floor): King bed, ensuite bathroom with walk-in shower br-Bonus: Twin lounge seat brbrAnna Maria Wave offers an elevator, dog-friendly accommodation (with approval and fee), and four parking spaces. Located directly on the beach, guests can enjoy sunrise walks, swim in the Gulf, or stroll to nearby restaurants and shops in Holmes Beach. Whether you’re lounging by the pool, playing poker with friends, or exploring the vibrant local scene, this home delivers the ultimate Anna Maria Island accommodations experience. brbrWith its direct beachfront setting, luxury amenities, and stunning Gulf views, Anna Maria Wave by Anna Maria Island Accommodations is the perfect choice for families and groups seeking a one-of-a-kind coastal escape. Wake up to the sound of the waves, unwind in your private pool, and let every sunset remind you that you’ve found paradise. brbrBook your stay today and experience beachfront living at its finest on Anna Maria Island! brbr- brThis home is managed by Anna Maria Island Accommodations, an Anna Maria Island property management company. 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 Island Accommodations Rental Policies for full details. brbr4 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. 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. brbrPlease see our Anna Maria Island Accommodations 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.

Anna Maria Wave: Stunning Beachfront Home with Pool and Poker Room

Holmes Beach, Florida, United States

Bed

Bath

8

Sleeps

$216.68

Gertie's Lime HousebrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrWelcome to your cozy and historic Florida-style duplex in the heart of Holmes Beach just steps away from the beautiful beaches. This comfortable home offers a perfect blend of comfort and convenience, ensuring a memorable stay.brbrRelax and unwind in the inviting living space, complete with a sofa bed, TV for entertainment, and central AC to keep you cool on warm Florida days. The well-equipped kitchen features modern appliances including a fridge, stove, oven, dishwasher, microwave, coffee maker, and more, making meal preparation a breeze.brbrStep outside to your private patio area perfect for enjoying your morning coffee or evening cocktails. Take a refreshing dip in the pool or head to the beach for a day of sun and sand. With beach access and being located on a bike path, outdoor adventures are right at your doorstep.brbrExplore the charming town of Holmes Beach with its entertainment, dining, and activities just a stone's throw away. For those seeking more excitement, attractions like theme parks, zoos, restaurants, and cinemas are within easy reach. Outdoor enthusiasts will love the proximity to activities such as horseback riding, sailing, paddle boarding, kayaking, and more.brbrWhether you're looking for a relaxing beach getaway or an action-packed adventure, this is the perfect home base for your Florida vacation. Book now and start planning your unforgettable stay in Holmes Beach!brbrThings to know:brThis property requires a 7-night minimum stay.brThis property's maximum occupancy is limited to 4 guests.brCode enforcement notification: 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.brCity/town permit number: VRC24-000088brbrParking notes: There is free parking available for 1 vehicle.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.

Comfortable and relaxing with pool and just steps from the beaches

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$375.18

Steps from beach access! Welcome to `Pineapple Paradise` at the Gulf Drive Inn - a spacious 1 bedroom/1 bathroom suite with a sleeper sofa, full kitchen and living area. This duplex style bungalow has resort-like amenities with a shared backyard space including a heated saltwater pool, spa and gas grill. brWhether you`re celebrating a birthday, anniversary, or simply in need of an extended beachside stay, The Gulf Drive Inn has it all! Inquire for short or longer stays!br⭐️Super host Property + Verified for Cleanliness + Communication⭐brbr`Pineapple Paradise ` is one of four resort suites at The Gulf Drive Inn. Please inquire to reserve more than one suite for larger parties! brThe spacebr 3014 Gulf Drive Unit B - `Pineapple Paradise` at the Gulf Drive Inn.brbrThis duplex style resort property with a private entrance comes with one parking space with easy access to everything.br✦ Located minutes from the beach and across the street from the Grassy Point Preserve, an ecological park with a nature trail and boardwalk perfect for morning walks.br✦ The fully equipped kitchen has everything you need – Featuring stainless steel appliances, coffee maker, full-size fridge/freezer with ice maker, microwave, dishwasher, oven, and all the essential cookware and utensils.brbr✦ Resort-Style Amenities - Guests have access to a heated, shared pool, complete with a poolside grill and comfortable patio furniture – a great way to cool off or gather for a laid-back meal.brbr✦ Close to the free trolley stop which is only one block away running north and south on AMI, shops and restaurants.brWelcome book with wifi and local information will be in the rentalbrFor your convenience, the home includes a beach wagon with beach chairs, a beach umbrella, and all bath towels, beach towels, and linens—everything ready for a relaxing stay!brbrPlease note a starter set of toiletries and supplies are left for your arrival. The complimentary starter set includes: brTwo rolls of toilet paper per bathroom, small hand soap, one paper towel roll, two garbage bags, small dish soap and two pods for the dishwasher. With a Publix grocery store located nearby for anything else desired.brbrPools are heated October - April at no additional costs. Full disclosure if temperate drop below 60 heaters do not work at full capacity fighting the ambient temp. Below 60 the heaters do not come on until temperatures risebrbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level. Noise ordinance is in effect 10pm to 7am. Excessive and unreasonable noise can result in disciplinary actions including fines and/or termination of your rental agreement without refund.brbrVRC23-000127brQuiet hours between 10pm - 6ambrNo partiesbrNo smoking

250 steps to the Beach | Heated pool + spa

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$348.73

Steps from beach access! Welcome to `Pirates Den` at the Gulf Drive Inn - a spacious 1 bedroom/1 bathroom suite with a sleeper sofa, full kitchen and living area. This duplex style bungalow has resort-like amenities with a shared backyard space including a heated saltwater pool, spa and gas grill. brWhether you`re celebrating a birthday, anniversary, or simply in need of an extended beachside stay, The Gulf Drive Inn has it all!. Please inquire to reserve more than one suite for larger parties or shorter stays! br⭐️Super host Property + Verified for Cleanliness + Communication⭐brbrbrThe spacebr 3016 Gulf Drive Unit A - `Pirates Den` at the Gulf Drive Inn.brbrThis duplex style resort property with a private entrance comes with one parking space with easy access to everything.br✦ Located minutes from the beach and across the street from the Grassy Point Preserve, an ecological park with a nature trail and boardwalk perfect for morning walks.br✦ The fully equipped kitchen has everything you need – Featuring stainless steel appliances, coffee maker, full-size fridge/freezer with ice maker, microwave, dishwasher, oven, and all the essential cookware and utensils.brbr✦ Resort-Style Amenities - Guests have access to a heated, shared pool, complete with a poolside grill and comfortable patio furniture – a great way to cool off or gather for a laid-back meal.brbr✦ Close to the free trolley stop which is only one block away running north and south on AMI, shops and restaurants. Steps from beach access!brFor your convenience, the home includes a beach wagon with beach chairs, a beach umbrella, and all bath towels, beach towels, and linens—everything ready for a relaxing stay!brbrPlease note a starter set of toiletries and supplies are left for your arrival. The complimentary starter set includes: brTwo rolls of toilet paper per bathroom, small hand soap, one paper towel roll, two garbage bags, small dish soap and two pods for the dishwasher. With a Publix grocery store located nearby for anything else desired.brbrPools are heated October - April at no additional costs. Full disclosure if temperate drop below 60 heaters do not work at full capacity fighting the ambient temp. Below 60 the heaters do not come on until temperatures risebrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level. Noise ordinance is in effect 10pm to 7am. Excessive and unreasonable noise can result in disciplinary actions including fines and/or termination of your rental agreement without refund.brVRC23-000120brQuiet hours between 10pm - 6ambrNo partiesbrNo smoking

Central location|Walk to beach, trolley stop & restaurants

Holmes Beach, Florida, United States

1

Bed

1

Bath