Vacation Rentals By Owner In Holmes Beach, FL

The Palms 2 by Anna Maria Island AccommodationsbrVRC16-000099brbrWelcome to The Palms 2, a beautifully updated second-level condo just one block from the stunning sands of Holmes Beach! Perfect for families or small groups, this refreshing Anna Maria Island retreat features two bedrooms and two bathrooms, offering comfort and convenience for your island adventure. With easy walking access to the beach, a community pool, and nearby shops and restaurants, The Palms 2 provides everything you need for a fun-filled island getaway!brbrHighlights br• 2-minute walk to Holmes Beach br• 2 bedroom / 2 bathroombr• 2 Queen beds, 1 Queen sleeper sofabr• Shared Poolbr• Shared BBQ grill br• Near local restaurants and shops br• Shared Outdoor patio areabr• Convenient location with trolley access for exploring the island br• 2 car parking spacesbrbrEnjoy your mornings with coffee in the Adirondack chairs just outside your door, overlooking lush surroundings. Take a dip in the semi-private pool or fire up the shared BBQ grill for a seafood feast or a casual cookout. Just a short walk from top restaurants, shops, and the grocery stores, this condo puts the best of Holmes Beach within easy reach. For outdoor fun, explore the bay or Anna Maria waters with paddleboards, kayaks, or even a private boat charter, making every day on Anna Maria Island an adventure.brbrStep inside to discover a cozy and inviting living room where you can unwind or plan your day of adventure. The modern kitchen with stainless steel appliances and generous counter space makes meal prep a breeze, from beach snacks to casual dinners. The kitchen island seats two, ideal for quick bites, while the adjoining dining table seats four for family meals or island takeout. Bright and cheerful, the space sets the tone for your relaxing island vacation!brbrThe primary bedroom is vibrant, with a queen-sized bed, ample storage, and a TV, ensuring restful nights after your days spent exploring. The en-suite bathroom features a walk-in shower for quick refreshes. The second bedroom captures the island vibe and offers a queen bed, TV, and convenient access to the second bathroom, which has a shower/tub combo, perfect for a relaxing refresh after a day at the beach. The living room also includes a queen sleeper sofa, providing an extra sleeping option for additional guests.brbrRoom Details br• Primary Bedroom: Queen bed, ensuite bathroombr• Second Bedroom: Queen bedbr• Living Room: Queen sleeper sofabrbrBook The Palms 2 today and enjoy a seamless blend of comfort, convenience, and coastal beauty. Whether relaxing by the pool, dining al fresco, or discovering nearby beaches, this condo gives you everything you need for a memorable Florida vacation. Reserve now and start planning your dream getaway!brbrbr-brThere are no pets allowed in this home.brbr*Please note: 2 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 Anna Maria Island Accommodations, 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 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.

Beautiful Condo with Pool, Just Steps to the Beach!

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$502.11

Ainsley Beach House by Anna Maria Island Accommodations brVRC16-000185 brbrWelcome to Ainsley Beach House, a charming three-bedroom, two-bath vacation home perfectly situated in the heart of Holmes Beach on Anna Maria Island. Just a five-minute stroll from the powder soft Gulf beaches, this inviting coastal retreat offers a private pool with a built-in tiki table, lush tropical landscaping, and vibrant indoor outdoor living spaces! You’ll love being close to the island’s main shopping plaza near Publix, featuring local boutiques, beach shops, and favorite dining spots. Making Ainsley Beach House the ideal home base for families or friends ready to relax and explore the best of Anna Maria Island. brbrHighlights br• 5-minute Walk to Holmes Beach br• 3 Bedroom / 2 Bathrooms br• 1 King, 1 Queen, 2 Twins and Queen Sleeper Sofa br• Private Pool with Sun Shelf and Tiki Table br• Outdoor Dining, Lounge Seating, and Grill br• Outdoor Shower br• Washer and Dryer br• Close to Shops, Dining and Trolley br• 2 Parking spots br• Pet-friendly with host approval and fee brbrStep into your private tropical backyard oasis. The inviting pool features a sun shelf and a unique in-water tiki table, ideal for lounging with a cold drink! Soak up the sun from the comfort of lounge chairs, fire up the BBQ grill for a backyard cookout, or rinse off the beach sand in the outdoor shower. In the evenings, gather around the outdoor dining table for meals under the stars and conversations you'll always remember. brbrInside, the open living area exudes coastal charm with beachy decor, a plush seating area, and a TV. The spacious kitchen is fully stocked with stainless steel appliances, cookware, utensils, and a large island for prepping meals or sharing drinks. The dining table seats the whole crew comfortably for breakfast before heading to the beach or game night after a day of adventures. brbrThe primary bedroom is a calming sanctuary with a king bed, TV, and an ensuite bathroom with a step-in shower. The second bedroom offers a cozy queen bed, while the third bedroom features two twin beds perfect for kids or friends. All rooms are styled with cheerful beach-themed decor, dressers, and TVs. The second full bathroom has a spacious walk-in shower. A queen sleeper sofa in the living room offers additional sleeping space, ideal for larger groups. brbrRoom Details br-Primary Bedroom: King bed, TV, and ensuite bathroom with step-in shower br-Second Bedroom: Queen bed br-Third Bedroom: Two Twin beds br-Living Room: Queen sleeper sofa brbrThis Anna Maria Island beach rental includes a washer and dryer, complimentary Wi-Fi, beach towels, and a peaceful residential setting close to everything. You’re just minutes from the island trolley, top-rated restaurants, cute island boutiques, and nearby attractions like Pine Avenue and Bridge Street. brbrReserve your dates today and make unforgettable memories at this charming Anna Maria Island vacation home with a private pool, close to beaches, dining, and island adventures. br br- brTwo exterior cameras are installed: one facing the street and one positioned over the entryway. These cameras record video only (no audio) and are not doorbell cameras. 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. brbr2 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 byAnna Maria Island Accommodations, 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 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.

Cottage

Vibrant Island Retreat with Pool, Tiki Table and Walk to Beach

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$514.4

Beach Retreat by Anna Maria Island Accommodations brVRC16-000857 brbrWelcome to Beach Retreat, a bright and spacious four-bedroom, three-bathroom vacation home just a short two-minute walk from Holmes Beach. This three-level coastal escape features an elevator, a private heated pool, and multiple balconies for enjoying the island's breeze. With room for up to eight guests, it’s perfect for families and groups seeking comfort, style, and easy access to Anna Maria Island’s stunning white-sand beaches and vibrant local attractions. brbrHighlights br• 2-minute walk to Holmes Beach br• 4 Bedroom / 3 Bathroom br• 2 King beds, 1 Queen bed, 2 Twin beds br• Private Heated Pool br• Elevatorbr• Xbox One and Game Pass br• Ping Pong Table and Cornhole br• Poolside Gamesbr• BBQ Grill and Covered Lanai br• Washer and Dryer br• 5 Parking Spaces brbrBeach Retreat combines fun and relaxation in one perfect setting. Spend your days splashing in the large heated pool surrounded by tropical palms and lounge seating or grill out and enjoy a meal under the covered lanai. Challenge friends to a round of ping pong or cornhole, and take advantage of the beach gear provided, including beach wagon, canopy, and toys. After a day in the sun, rinse off in the outdoor shower or take the island trolley, just steps away, to explore local shops and restaurants near Holmes Beach Towne Center and Pine Avenue. brbrInside, the home’s open concept living area features bright coastal decor, plenty of comfortable seating, and a TV for movie nights. The fully equipped kitchen includes stainless steel appliances, generous counter space, and an island with bar seating, making it easy to cook and socialize at the same time. Gather for meals around the dining table or enjoy dining on the covered patio. brbrThe primary bedroom, located on the third floor, offers a king bed, TV, comfortable seating, and a private balcony ideal for morning coffee. The ensuite bathroom features a walk-in shower and dual vanities. The second bedroom, also on the third floor, has a king bed, TV, and relaxing coastal furnishings. The third bedroom on the second floor includes a queen bed, TV, and private deck access for peaceful solitude in the ocean breeze. The fourth bedroom features two twin beds and a TV, making it the perfect space for younger guests. brbrRoom Details br-Primary Bedroom (3rd Floor): King bed, TV, ensuite bath with walk-in shower br-Second Bedroom (3rd Floor): King bed, TV br-Third Bedroom (2nd Floor): Queen bed, TV br-Fourth Bedroom (3rd Floor): Two twin beds, TV brbrThis home offers Wi-Fi, a washer and dryer, and parking for five vehicles. The elevator provides easy access between floors, ensuring everyone enjoys a stress-free stay. Located near Holmes Beach Towne Center, guests are minutes from restaurants, shops, and entertainment. Spend days kayaking, paddleboarding, or shelling along the shore, then unwind poolside as the sun sets. brbrWith its unbeatable location, spacious design, and endless amenities, Beach Retreat by Anna Maria Island Accommodations is the perfect home base for your next Anna Maria Island vacation. Whether you’re lounging by the pool, enjoying beach days, or exploring the island by trolley, this home has everything you need for a memorable getaway. brBook your stay today and experience the perfect blend of relaxation and fun at Beach Retreat! brbr- brThere are no pets allowed in this home. brbr*Please note: 5 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 Accommodations, 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 Accommodations Rental Policies for full details. brbrPlease Remember: brbrYou are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. brbr*Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

Beautiful home with pool, elevator, and ping pong table

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$473.17

Coral Palms by Anna Maria Island Accommodations brVRC16-000157brbrWelcome to Coral Palms, a beautiful ground level cottage split floorplan vacation home featuring three bedrooms and two bathrooms, perfect for families or groups seeking a relaxing escape on Anna Maria Island. Just a four-minute walk to the sparkling Gulf beach, this charming retreat boasts a private saltwater pool, spa, and outdoor showers. Located steps away from the free trolley stop makes shops, and waterfront dining minutes away. Coral Palms truly offers comfort, amenities, and effortless access to island adventures.brbrEnjoying outdoor living at its finest, guests can relax by the pool or hot tub soaking up the warm Florida sunshine, rinse off in one of the outdoor showers, and enjoy meals at the outdoor patio tables. When it's time for a little friendly competition, gather everyone for a game of chess, monopoly, or other child-friendly games!brbrInside, the home features a warm, welcoming sunroom space with cozy seating, a large flat-screen TV, electric fireplace and tropical decor perfect for unwinding after a day in the sun. The fully stocked kitchen has new stainless steel appliances, expansive granite countertops, and ample storage for all your culinary needs. Enjoy your favorite meals at the formal dining area or gather al fresco at one of the outdoor spaces, savoring the island breezes.brbrRetreat to the primary suite, which offers a king bed, a TV, and an ensuite bathroom with a walk-in shower, creating a luxurious and restful escape. Just off the primary suite is a room with twin trundle beds, perfect for children or extra guests. The second bedroom features a king bed and a TV for evening relaxation. The third bedroom includes a queen bed with a day bed and is ideal for additional guests. The hall bathroom with dual sinks and tub with shower offers added convenience for everyone.brbrRoom Detailsbr• Primary Bedroom: King bed, ensuite with walk-in showerbr• Adjacent to Primary: Trundle twin bedsbr• Second Bedroom: King bed, reclinerbr• Third Bedroom: Queen bed with day bedbrbrBook Coral Palms today and enjoy a luxurious, family-friendly vacation on Anna Maria Island. With its water access, outdoor amenities, and prime location, this home provides everything you need for an unforgettable getaway. Reserve your dates now and start creating lifelong memories in paradise!brbrHighlightsbr• 4-minute walk to Gulf beachbr• 3 Bedrooms / 2.5 Bathroomsbr• 2 Kings, 1 Queen, Twin trundlesbr• Private Saltwater Pool and Spabr• Two outdoor showersbr• 2 Dining tablesbr• Separate patio area with propane fire pit table and cushioned seatingbr• Combination washer and dryerbr• Dog friendlybr• Close to the free trolley stop, shops, dining, and local attractionsbr• 4 Parking spacesbr• Two car garage with half bath houses trolleys and beach equipment and chairs br• Fresh linens includedbrbr-br*Please note - the fireplace in the living area is not for guest use*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 street 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.

Updated Home with Private Pool! Near Gulf Beaches - Coral Palms

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$414.04

Attitude By Latitude by Anna Maria Island Accommodations brVRC16-000182brbrWelcome to Attitude by Latitude, three bedrooms, two and a half bathrooms coastal getaway just a short walk from the stunning Gulf beaches. Perfect for families or friends, this home offers a private heated pool, a fully stocked game room, and a covered outdoor entertainment area. With shopping, dining, and the Anna Maria Island Trolley all within walking distance, your ideal beach vacation starts here. brbrHighlights br-4-minute walk to Holmes Beach br-3 Bedrooms / 2.5 Bathrooms br-1 King bed, 1 Queen bed, 2 Twin beds, 1 Twin Daybed with trundle, 1 Queen sleeper sofa br-Private heated pool with waterfall br-Game room with pool table, ping pong, and foosball br-Elevator br-Covered patio with bar, fridge, BBQ grill, and TV br-Outdoor shower br-Laundry room with washer and dryer br-3 Parking spaces brbrSpend your days lounging by the sparkling pool or gather under the shaded patio for meals from the built in grill. The outdoor entertainment area includes a bar, fridge, comfortable seating, and a TV, making it the perfect place for evening gatherings. Challenge your group to friendly competition in the game room, equipped with a pool table, ping pong table, and foosball. brbrInside, the living room features two plush sofas, colorful artwork, and a large TV for cozy movie nights. The fully equipped kitchen boasts stainless steel appliances, custom cabinetry, and all the cookware essentials you need. Seating is available at the kitchen island, formal dining table, and the outdoor deck, giving you multiple spots to enjoy meals together. brbrThe private primary suite occupies the entire third floor and includes a king bed, a sitting area with two chairs, a twin daybed with a trundle, a TV, a work desk, and a private balcony with Gulf breezes. The luxurious ensuite bathroom features a soaking tub, walk-in shower, and a walk-in closet. The second bedroom offers a queen bed, while the third bedroom has two twin beds. These guest rooms share a hall bathroom with a shower/tub combo. A half bath is also available, along with a queen sleeper sofa in the living room for additional sleeping space. brbrRoom Details br-Primary Bedroom, 3rd Floor: King bed and twin daybed with a twin trundle, private balcony, ensuite with soaking tub and walk-in shower br-Second Bedroom, 2nd Floor: Queen bed br-Third Bedroom, 2nd Floor: Two twin beds br-Bonus, Living Room: Queen sleeper sofa brbrThis home includes a laundry room with washer and dryer, an elevator for easy access to all floors, and driveway parking for up to three vehicles. The location makes it simple to walk to the beach, explore local shops and restaurants, or hop on the free trolley to discover all corners of Anna Maria Island. brbrAttitude by Latitude by Anna Maria Island Accommodations is the ultimate Holmes Beach getaway. Book your stay today and experience the island lifestyle in style! brbr- brThere are no pets allowed in this home. brbr3 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 Accommodations, 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 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.

Holmes Beach Gem! Pool, Grill and Game Room!

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$293.43

Shamrock Palms by Anna Maria Island Accommodations brVRC16-000106brbrWelcome to Shamrock Palms, a charming ground level Florida retreat just a short, less than a 10-minute walk from Holmes Beach shoreline. This spacious three-bedroom, two-bathroom home offers a relaxing outdoor oasis with a private pool, rejuvenating spa, and plenty of space for fun and relaxation. Perfect for families or friends seeking a serene yet centrally located escape, Shamrock Palms provides modern coastal decor, an open floor plan, and easy access to fine dining, shopping, and island adventures on Anna Maria Island.brbrHighlights br• 10-minute walk to Holmes Beach br• Private in-ground pool with spabr• 3 bedroom / 2 bathroombr• 2 kings, 2 twin beds plus sleeper sofabr• Outdoor showerbr• Outdoor diningbr• Built-in BBQ grillbr• Near the free Island trolley stop for easy exploringbr• Close to beaches, restaurants, boutiques, and barsbr• 4 car parkingbrbrEnjoy Florida’s sunshine in your private backyard oasis, featuring a sparkling pool, soothing spa, loungers, and an outdoor dining area perfect for barbecues. After a day at the nearby beaches, rinse off in the outdoor shower and relax poolside before heading out to explore all that Anna Maria Island has to offer. The home’s excellent location near the trolley stop makes it easy to hop between beaches, shops, and eateries.brbrStep inside to find a beautifully designed, open floor plan that promotes relaxation and family fun. The front living room offers plush sofa seating and a large 55-inch HDTV, creating the perfect spot to unwind. The fully equipped kitchen features plenty of counter space, modern appliances, and a breakfast bar ideal for morning coffee or quick snacks. Open the patio doors to enjoy island breezes and easy access to the backyard for outdoor meals or poolside lounging.brbrRelax in the primary bedroom, decorated with charming sea-life themes, featuring a luxurious king-sized bed, pool deck access, and an ensuite bathroom with a walk-in shower and elegant vanity, your private retreat after a day exploring the island. The second bedroom offers a bright island ambiance with a king bed and TV, while the third bedroom has two twin beds and a TV for late-night entertainment. The main hallway bathroom provides a spa-like experience with a walk-in shower. A sleeper sofa is located off the laundry room and dining area, where you’ll also find a dedicated workspace in the same room. Ideal for remote work or extra guests. A washer and dryer are available for your convenience.brbrRoom Details br• Primary Bedroom: King bed, TV, ensuite with walk-in shower br• Second Bedroom: King bed, TV br• Third Bedroom: Two twin beds, TV br• Sleeper SofabrbrBook Shamrock Palms today and start planning your effortless, fun filled island vacation. With its thoughtfully designed outdoor space, modern interiors, and prime location just minutes from Holmes Beach’s white sandy beaches, this home is the perfect base for creating lifelong memories on Anna Maria Island!brbrbr-brThere are no pets allowed in this home.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.brbrThis home is managed by Anna Maria Island Accommodations, 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 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.

Spacious family home with heated Pool and Spa, Close to Beach! - Shamrock Palms

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$407.51

Bayshores by Anna Maria Island Accommodations brVRC18-000040 brbrWelcome to Bayshores by Anna Maria Island Accommodations, a charming three-bedroom, three-bathroom canal front home in Holmes Beach that captures the nostalgic charm of Old Florida while offering all the comforts of modern coastal living. Perfectly situated along serene waterways and just a short stroll from the white sands of Holmes Beach and the vibrant shops and dining along Pine Avenue, this home provides the perfect balance of relaxation and island adventure. Ideal for families or small groups, Bayshores features a private heated pool and spa, boat-friendly dock, and spacious interiors, creating the ultimate Anna Maria Island getaway for guests seeking sun, style, and comfort on the Florida Gulf Coast. brbrHighlights br• Canal front with private dock br• 6-minute walk to Holmes Beach br• 3 Bedrooms / 3 Bathrooms br• 1 King, 1 Queen, 2 Twin beds br• Private heated pool with in-ground spa br• Poolside bar and grill br• Elevator access br• Washer and dryer br• 3 parking spaces br• Balcony with water views brbrSpend your days soaking up the sunshine in your own tropical paradise, where the heated pool and in-ground spa overlook peaceful canal waters framed by swaying palms. Fire up the grill for a family cookout, sip cocktails at the poolside bar, or unwind in the bubbling spa as boats drift by. The private dock offers endless adventure, whether you’re launching kayaks and paddleboards or tying up a boat up to 23 feet to explore nearby Tampa Bay. Every feature of Bayshores is designed to make your island escape easy, relaxing, and unforgettable. brbrInside, the home welcomes you with an open concept design filled with natural light and panoramic water views. The living area features a cozy sectional, TV, and large sliding glass doors that are open to a furnished balcony, perfect for morning coffee or sunset cocktails. The kitchen includes stainless steel appliances, a spacious island, and a built-in bar with a wine fridge, making it easy to prepare meals or entertain friends. Gather in the nearby dining area for family dinners, creating a serene backdrop for every moment. brbrThe primary suite on the third floor is a peaceful retreat with a king bed, balcony access, and a quiet office nook for guests working remotely. Its ensuite bathroom features dual vanities, a walk-in shower, and a soaking tub for a true spa experience. On the second floor, a queen suite offers deck access and a private ensuite bathroom with a shower/tub combo, while the twin bedroom features two beds and balcony access, perfect for kids or friends. A third full bathroom with a walk-in shower and a laundry room complete this well-designed home, ensuring comfort for every guest. brbrRoom Details br- Primary Bedroom (3rd Floor): King bed, TV, private balcony, ensuite bathroom with walk-in shower and soaking tub. br-Second Bedroom (2nd Floor): Queen bed, deck access, ensuite bathroom with shower/tub combo. br-Third Bedroom (2nd Floor): Two twin beds, deck access. brbrBayshores offers an elevator, three parking spaces, and washer and dryer, providing convenience for extended stays. The canal depth may vary with tides, so guests bringing boats should verify conditions before arrival. Located just a short walk or trolley ride from Holmes Beach and Pine Avenue, guests can enjoy boutique shopping, local art galleries, and delicious dining with ease. brbrWith its private dock, pool and spa, and ideal Holmes Beach location, Bayshores by Anna Maria Island Accommodations delivers the perfect blend of coastal charm, relaxation, and island adventure. Create lasting memories with family and friends. brbrBook your stay today and experience the best of Anna Maria Island living! brbr- brDISCLAIMER: Depth of the canals and channels vary depending on tides, weather, and other circumstances beyond our control. At times this can result in a water level that is too low to support watercraft. It is the responsibility of the guest to review forecasts and make alternate arrangements for watercraft as necessary. brbrThere are no pets allowed in this home. brbr3 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 Anna Maria Island Accommodations, 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 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.

Luxury home with Pool, Spa, and Dock -Bayshores

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$487.37

Banana Cabana by Anna Maria Island Accommodations br brRelax and unwind at Banana Cabana, a charming three-bedroom, two-bath vacation home just minutes from Holmes Beach’s powdery Gulf beaches! This beautifully furnished retreat features a private pool, bubbling hot tub, outdoor bar, and multiple outdoor lounge and dining areas, perfect for family fun or a relaxing tropical getaway. Located within walking distance to beaches, parks, restaurants, and a trolley stop, Banana Cabana is your ideal island home for an unforgettable escape filled with sun, sea, and sand! brbrHighlights br• 6-minute walk to Holmes Beach br• 3 Bedroom / 2 Bath br• 2 Kings, 2 twin beds br• Private pool with in-ground spa br• Poolside bar and sun loungers br• Outdoor dining area and BBQ grill br• Ping pong table br• Beach toys, and a wagon included  br• Short walk or trolley ride to local shops, waterfront restaurants, and parks br• 4 Parking Spaces br brStep outside to your tropical backyard oasis, splash in the private pool, relax in the bubbling hot tub, or unwind in the shaded lounge chairs. Practice your cocktail making skills at the outdoor tiki bar or enjoy meals at the outdoor dining table. In the garage, find plenty of beach chairs, toys, and a wagon for easy beach trips. Explore nearby beaches, parks, and waterfront dining, or hop on the free trolley to discover Anna Maria Island’s scenic treasures each day.br brInside, the home features bright, tropical decor with a spacious living area, comfortable seating, and a large TV, perfect for relaxing or family movie nights. The fully stocked kitchen boasts stainless steel appliances, ample counter space, and a breakfast bar. The formal dining table seats six, with additional island seating for casual island dining in style. Large sliding doors open to a balcony or patio, offering refreshing breezes and scenic outdoor views. br brRetreat to the primary suite on the third floor, complete with a king sized bed, private balcony with a high top table, and a luxurious ensuite with a walk-in shower, tub, and dual vanities, your private sanctuary. The second bedroom features a king bed and a balcony accessible from the back, with a walk-in closet and shared hall bathroom with a shower/tub combo. The third bedroom offers two twin beds, perfect for kids or guests, with its own decor and ample storage. All rooms are designed for comfort with soft linens, dressers, and Roku TVs. brbrRoom Details br• Primary Bedroom (3rd floor): King bed, ensuite with walk-in shower and tub  br• Second Bedroom (2nd floor): King bed br• Third Bedroom (2nd floor): Twin bedsbr brBook Banana Cabana today and enjoy a fun, relaxing, and memorable island vacation! With luxurious water views, outdoor amenities, and close proximity to beaches, shops, and dining, this home offers everything needed for a perfect Gulf Coast retreat. Reserve now and start making lifelong memories in this tropical paradise! br brbr-br4 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 Anna Maria Island Accommodations, an Anna Maria Island property management company. brbrNo pets of any kind are allowed in this home. 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.

Holmes Beach Vacation Home with Pool, Ping Pong, and Tiki Bar! 6 minutes to Beac

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$437.21

Key Largo Cottage by Anna Maria Island Accommodations brVRC18-000120brbrDiscover the ultimate family getaway at Key Largo Cottage, a charming bungalow style vacation rental perfectly situated along Anna Maria Island’s peaceful streets. This spacious home features three bedrooms, three modern bathrooms, and a private heated pool with a swim up table and calming waterfall, all just a short stroll from the white sandy beaches of the Holmes Beach. Ideally located near top waterfront restaurants, boutique shops, parks, and water sports, Key Largo Cottage offers the perfect blend of style, comfort, and island adventure!brbrHighlights br• 8-minute walk to Holmes Beachbr• 3 Bedroom / 3 Bathbr• 2 King beds, 2 twin-twin bunk setsbr• Private heated pool with swim up tablebr• Outdoor dining area and grillbr• Outdoor showerbr• 5 bicycles providedbr• Walking distance to the Anna Maria Island trolley stopbr• Near parks, waterfront restaurants, and shopping with local flavor br• Washer and dryer br• 2 Parking SpacesbrbrEnjoy outdoor living in the lush backyard, featuring a private heated pool, sun pad, swim up table, and a soothing waterfall, perfect for leisure, family fun, or sunset cocktails. The outdoor patio, equipped with a gas grill and ample seating, is your ideal spot for outdoor dining or casual lounging. Walk just minutes to the beach, or hop on a bike to explore nearby shops, waterfront restaurants, parks, and water adventures like fishing, kayaking, and paddle boarding all from your doorstep. brbrInside, the inviting interior blends comfort and style. The cozy living room features plush seating, a large flat-screen TV, and a warm ambiance perfect for relaxing after a day in the sun. The fully equipped kitchen boasts stainless steel appliances and all essentials needed to prepare family favorites or island-inspired meals. Gather at the dining table for six, encouraging treasured family moments and shared meals.brbrRetreat to the two primary suites, each with a king-sized bed, elegant decor, and ensuite bathrooms featuring walk-in showers for a spa like experience. The third bedroom, perfect for kids or additional guests, features two twin bunk beds and an ensuite bathroom with a shower-tub combo. All bedrooms are thoughtfully decorated with plush linens and flat-screen TVs, ensuring restful nights and entertainment for everyone.brbrRoom Details br• Primary Bedroom (2nd floor): King bed, ensuite bathroom with walk-in shower br• Second Bedroom (1st floor): King bed, ensuite bathroom with walk-in shower br• Third Bedroom (2nd floor): Two Twin bunk beds, ensuite with shower-tub combobrbrBook Key Largo Cottage today and create unforgettable memories in a luxurious island setting. With its scenic water views, private pool, outdoor amenities, and proximity to the beach and charming shops, this home provides everything you need for the perfect Anna Maria Island vacation. Reserve your stay now and start living the island lifestyle you deserve!brbrbr-brThere are no pets allowed in this home.brbr2 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 Anna Maria Island Accommodations, 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 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.

Enjoy Endless Fun with a Private Heated Pool at Key Largo Cottage!

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$631.79

No Bad Days by Anna Maria Island Accommodations brVRC18-000057 brbrWelcome to No Bad Days by Anna Maria Island Accommodations, a beautiful four-bedroom, three-bath ground-level vacation home located just a four-minute walk from the soft white sands of Holmes Beach. Perfect for families or groups, this island retreat combines modern coastal design with a laid-back tropical atmosphere, creating the ideal setting for an unforgettable Anna Maria Island getaway. With a private pool and spa, open concept living spaces, and close proximity to the Anna Maria Island trolley stop, guests will enjoy both comfort and convenience throughout their stay. brbrHighlights br• 4-minute walk to Holmes Beach br• 4 Bedrooms / 3 Bathrooms br• 2 King, 1 Queen, 2 Twin beds br• Private pool with in-ground spa br• BBQ grill and outdoor dining area br• Outdoor shower br• Near Anna Maria Island trolley stop br• 4 parking spaces brbrYour private backyard oasis awaits at No Bad Days, featuring a sparkling pool with a built-in table, relaxing in-ground spa, and lush tropical landscaping. After a morning at the beach, rinse off in the outdoor shower, grill up fresh seafood on the BBQ, and gather for meals on the shaded patio surrounded by the gentle island breeze. With its inviting design, this home is made for sun-soaked afternoons and carefree evenings of island living. brbrStep inside to find a warm and inviting interior filled with natural light and coastal touches. The living area offers comfortable seating, a large TV. The modern kitchen is fully equipped with stainless steel appliances, granite countertops, and a spacious island with bar seating, making it perfect for preparing and sharing meals. A cozy dining area nearby provides plenty of space for family gatherings or game nights after a day in the sun. brbrTwo of the home’s bedrooms serve as luxurious primary suites, each featuring king beds, ensuite bathrooms with double vanities, and walk-in showers for ultimate comfort. The third bedroom includes a queen bed, while the fourth bedroom features two twin beds, ideal for kids or friends. Both guest rooms have easy access to a hall bathroom with a shower/tub combination. All bedrooms are equipped with TVs, soft linens, and ample storage, ensuring a restful night’s sleep for every guest. brbrRoom Details br-Primary Bedroom: King bed, TV, ensuite bathroom with walk-in shower br-Second Bedroom: King bed, TV, ensuite bathroom with walk-in shower br-Third Bedroom: Queen bed, TV br-Fourth Bedroom: Two Twin beds, TV brbrNo Bad Days offers four parking spaces, a washer and dryer, and convenient access to the island trolley, making it easy to explore all that Anna Maria Island has to offer. Spend the day strolling along Holmes Beach, visit the local boutiques and seafood restaurants on Pine Avenue, or simply relax poolside with family and friends. Whether you’re looking for adventure or tranquility, this Holmes Beach vacation home delivers the perfect blend of both. brbrWith its beautiful pool and spa, spacious layout, and prime location near the beach and trolley, No Bad Days by Anna Maria Island Accommodations offers everything you need for an effortless and memorable Anna Maria Island vacation. brBook your stay today and discover why at No Bad Days, every day feels like paradise! brbr- brThere are no pets allowed in this home. 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. brbrThis home is managed by AMI Accommodations, 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 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.

No Bad Days - 1.5 Blocks to Gulf Beaches, Private Heated Pool!

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$463.2

Sand Dollar by Anna Maria Island Accommodations brVR16-000117 brbrWelcome to Sand Dollar, a stunning vacation home featuring a sparkling pool and hot tub, just a short walk from Holmes Beach’s sugar-white sands! This three-bedroom, two-bath retreat offers a lush outdoor space with multiple seating areas, a charming tiki bar, and a screened-in patio. Conveniently located near shops, restaurants, and a trolley stop for exploring all seven miles of Anna Maria Island, Sand Dollar is your perfect island escape for relaxation, fun, and memorable adventures! br brHighlights br• 7-minute Walk to Holmes Beach  br• 3 Bedroom / 2 Bath br• 2 King beds, 2 Twin-Twin bunk beds br• Private pool and hot tub  br• Screened-in balcony  br• Ping pong and cornhole br• BBQ grill br• Close to Marina Drive and Pine Avenue shops, waterfront restaurants, and local attractions br• Near free Anna Maria trolley stop br• 3 Parking spots br brEnjoy outdoor living at its finest in the tropical backyard paradise. Lounge by the private pool and hot tub, gather at the outdoor dining table or relax at the tiki bar with drinks and snacks. Play ping pong with family and friends or retreat to the screened-in patio to enjoy the island breeze. The lush landscaping creates a serene setting for a peaceful island escape. br brStep inside this open, airy home and be greeted by vaulted ceilings, vibrant coastal artwork, and plenty of natural sunlight. The cozy living room features plush sofas, perfect for family movie nights or relaxing with friends. The fully equipped kitchen boasts stainless steel appliances, abundant granite countertops, and bar-height seating, ideal for preparing island-inspired meals or quick snacks. The dining room table seats the whole family for meals or board games while enjoying views of the lush backyard.br brRest peacefully in the tropically colored primary bedroom, featuring a king-sized bed, crisp linens, and a private balcony with seating, your personal retreat for morning coffee or evening chats. The ensuite bathroom offers a double vanity, walk-in shower, and a jetted bathtub for relaxing after beach or water adventures. The second bedroom, also with a king bed and balcony access, offers a bright and comfortable space. The third bedroom features a twin bunk bed, tropical decor, and a TV, making it perfect for kids or additional guests. The hall bathroom has a shower and tub combo, providing convenience and style. brbrRoom Details br• Primary Bedroom: King bed, ensuite bathroom  br• Second Bedroom: King bed  br• Third Bedroom: Two sets of Twin-over-twin bunks br brBook Sand Dollar today and enjoy a luxurious, fun-filled Anna Maria Island vacation. Whether swimming in your private pool, exploring local shops and restaurants, or taking part in water activities like sunset cruises or snorkeling trips, this home offers everything you need for an unforgettable stay! br brbr- br*Please note: 3 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. brbrThis home is managed by AMI Accommodations , an Anna Maria Island property management company. brbrThere are no pets allowed in this home. brbrWe do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. brbrPlease see our AMI 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.

Home with Private Pool and Hot Tub! 3 Blocks to Beach!

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$377.97

La Mer by Anna Maria Island Accommodations brVRC18-000126brbrWelcome to La Mer, a fabulous beach vacation home just a short stroll from the soft sandy beaches of Holmes Beach! This beautifully decorated, four-bedroom, three-bath estate offers a private pool with a built-in tiki bar, sun shelf, and hot tub. Just minutes from water adventures, local restaurants, parks, and the free Anna Maria Island trolley, La Mer provides everything you need for an extraordinary Gulf Coast escape with family or friends!brbrHighlights br• 7-minute walk to Holmes Beachbr• 4 Bedroom / 3 Bathbr• 3 King beds, 1 twin bunk bedbr• Private pool with sun shelf, hot tub, and built-in tiki bar br• Covered outdoor patio br• Close to shops, waterfront restaurants, parks, and the trolley stop for easy exploration br• 4 Parking SpacesbrbrRelax outdoors in your tropical backyard featuring a stunning pool with a sun shelf, hot tub, and plenty of lounge chairs. The covered patio with outdoor seating and a BBQ grill offers the perfect spot for meals, sunbathing, or evening drinks. Just a short walk to the beach, water activities, and the Holmes Beach shopping district; this retreat is your ideal base for Gulf Coast adventures.brbrStep inside this cheerful coastal retreat and enjoy a bright, open floor plan filled with natural light and tropical decor. The kitchen features stainless steel appliances, utility essentials, and island seating, perfect for island-inspired meals or casual conversations. The living area, with a plush sofa and a large TV, is ideal for relaxing after a fun day at the beach or gathering with friends around the indoor dining table.brbrUnwind in the primary bedroom, styled with soothing decor, a king bed, a TV, and an ensuite bathroom with a walk-in shower, your peaceful sanctuary. The second bedroom, on the first floor, features a king bed with easy access to the hall bathroom, which boasts a walk-in shower. On the second floor, the third bedroom showcases tropical ocean hues, a king bed, TV, and balcony access, offering a superb retreat. The fourth bedroom with a twin bunk bed and a TV is perfect for kids or singles, with hall access to the upscale hall bathroom featuring a walk-in, tiled shower and vanity.brbrRoom Details br• Primary Bedroom (2nd floor): King bed, ensuite with walk-in shower br• Second Bedroom (1st floor): King bedbr• Third Bedroom (2nd floor): King bed, balcony access br• Fourth Bedroom (2nd floor): Twin bunk bedbrbrBook La Mer today and enjoy an unforgettable Anna Maria Island escape. With its water views, outdoor amenities, and location near beaches, shops, and waterfront dining, this home offers everything you need for a relaxing, fun-filled vacation. Reserve your dates now and start creating lifelong memories in paradise!brbrbr-brThere are no pets allowed in this home.brbr*Please note: 4 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. brbrThis home is managed by AMI Accommodations, 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 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.

Villa with Heated Pool and Swim-up Tiki Bar! Close to Beach - La Mer

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$504.82

Seahorse Cove by Anna Maria Island Accommodations brVRC16-000109brbrWelcome to Seahorse Cove, a vibrant two-story duplex just three blocks from the gorgeous Holmes Beach and steps from the free Anna Maria Island trolley! This four-bedroom, three-bath coastal retreat boasts recently updated interiors and decor that create a bright, fresh island vibe. Featuring a large outdoor patio with a pool, loungers, outdoor dining, and a BBQ grill, it is the perfect setting for family gatherings or friends’ escapes. Located in the heart of Holmes Beach, Seahorse Cove offers effortless access to pristine beaches, boutique shopping, waterfront dining, and outdoor adventures on Anna Maria Island’s scenic seven miles.brbrHighlights br• 6-minute walk to Holmes Beach br• 4 Bedroom / 3 Bathbr• 1 King, 2 Queens, 2 Twin beds, 1 Twin sleeper sofabr• Shared outdoor pool br• Private balconiesbr• Close to Holmes Beach Towne Center shops and restaurantsbr• Near the Anna Maria Island trolley stop br• 2 car parking spotsbrbrRelax outdoors on the large open-air patio with a refreshing pool, sun loungers, and outdoor dining tables, perfect for family dinners or sunset cocktails. The tropical landscaping adds to the island vibe and privacy. Walk to the beaches, the trolley stop, and explore Anna Maria Island’s boutiques, ice cream shops, and water sport rentals await just minutes from your door. brbrStep inside this lively coastal home and enjoy a spacious, Florida-style living room with two comfortable sofas, a conversation area, and a TV, ideal for relaxing after a fun-filled beach day. The fully equipped kitchen features beautiful countertops, ample space for groceries, and all the essentials to prepare meals or snacks. Dine at the table with friends or family, then step onto the front-facing balcony to sip a drink while watching the sunset over the Gulf.brbrRetreat to the primary bedroom upstairs, where a king-sized bed, TV, and cozy sitting area create a peaceful sanctuary. The ensuite bathroom features a walk-in shower and a relaxing bathtub. The second and fourth bedrooms each have queen beds and TVs, offering bright island vibes and restful sleep options. The third bedroom, styled with nautical decor, is perfect for kids or younger travelers, equipped with two twin beds and a TV. There's a hall bathroom with a walk-in shower upstairs, and a second bathroom with a walk-in shower on the main floor for all your needs.brbrRoom Details br• Primary Bedroom (2nd floor): King bed, ensuite bathroom br• Second Bedroom (2nd floor): Queen bed br• Third Bedroom (2nd floor): Two Twin beds br• Fourth Bedroom (1st floor): Queen bed br• Bonus (1st floor): Twin sleeper sofabrbrBook Seahorse Cove today for an authentic Anna Maria Island experience! Whether enjoying days at the beach, shopping on Pine Avenue and Bridge Street, or exploring the bay’s calm waters, this duplex provides the perfect home base for your dream getaway. Reserve now and create lifelong memories in paradise!brbrbr-brThere are no pets allowed in this home.br br*Please note: 2 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. br brThis home is managed by AMI Accommodations, an Anna Maria Island property management company.br brWe 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.br brPlease see our AMI Accommodations Rental Policies for full details.br brPlease 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.

6 minutes to Beach! Screened-in and Heated Pool! - Seahorse Cove

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$475.08

Simply Chic by Anna Maria Island Accommodations brVRC16-000105 brbrDiscover Simply Chic, a stylish four-bedroom, three-bathroom ground-level vacation home located just a three-minute walk from Holmes Beach. Designed for relaxation and fun, this coastal retreat features a private pool, putting green, and outdoor games including ping pong and cornhole; perfect for a family-friendly Anna Maria Island getaway. With its bright, modern interior and inviting backyard, Simply Chic blends comfort, charm, and easy access to the white sand beaches. brbrHighlights br• 3-minute walk to Holmes Beach br• 4 Bedroom / 3 Bathroom br• 3 King beds, 2 Twin beds br• Private Heated Pool br• Putting Green br• Ping Pong Table and Cornhole br• Outdoor Shower and Grill br• Washer and Dryer br• 4 Parking Spaces brbrEnjoy your stay at Simply Chic, where sunny days are spent lounging by the private pool and evenings are filled with friendly games and outdoor dining. Fire up the grill for a family cookout, practice your swing on the putting green, or unwind on the patio surrounded by tropical landscaping. The outdoor dining area and lounge chairs create the perfect atmosphere for soaking up the Florida sunshine and enjoying time together. The home’s proximity to the free island trolley makes it easy to explore nearby shops, local restaurants, and Pine Avenue’s boutiques. brbrInside, guests are welcomed into a bright, open concept living space decorated in soothing coastal tones. The living room features plush sofas and a TV, ideal for gathering after a day in the sun. The fully equipped kitchen offers stainless steel appliances, ample counter space, and a kitchen island for casual bites or morning coffee. Enjoy meals at the indoor dining table or take them outside to the patio for an island-style dinner under the stars. brbrThe primary bedroom offers a luxurious retreat with a king bed, TV, and private patio access. The ensuite bathroom includes a walk-in shower and soaking tub, perfect for unwinding after a beach day. The second bedroom, also featuring a king bed and patio access, has a modern ensuite bathroom with a walk-in shower. The third bedroom provides another king bed and TV, while the fourth bedroom has two twin beds and a TV, making it ideal for children or single guests. The hall bathroom includes a walk in shower for added convenience. brbrRoom Details br-Primary Bedroom: King bed, TV, patio access, ensuite bath with walk-in shower and tub br-Second Bedroom: King bed, TV, patio access, ensuite bath with walk-in shower br-Third Bedroom: King bed, TV br-Fourth Bedroom: Two twin beds, TV brbrA washer and dryer, Wi-Fi, and four parking spaces add ease to your stay. From the backyard oasis to the short stroll to the beach, Simply Chic offers everything you need for a seamless and enjoyable island vacation. Guests can also enhance their stay with local experiences such as kayak rentals, dolphin tours, fishing charters, and sunset sails, easily arranged nearby. brbrExperience the perfect combination of fun, relaxation, and coastal charm at Simply Chic by Anna Maria Island Accommodations. Whether you’re practicing your putt, splashing in the pool, or watching the sunset over the Gulf, this Holmes Beach home ensures every moment feels effortless and unforgettable. brBook your stay today and start making memories at Simply Chic! brbr- brThere are no pets allowed in this home. brbr*Please note: 4 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. The shells are not a parking spot. Must use driveway. brbrThis home is managed by AMI Accommodations, 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. brbrPlease see our AMI Accommodations Rental Policies for full details. 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 refund.

Beautiful, Ground Level 4 bedroom/3 bath home, just a short block to the beach

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$264.56

Kismet by the Sea by AMI Locals br brExperience your perfect island escape at Kismet by the Sea, a charming three-bedroom, two-and-a-half-bathroom villa just a short walk from Anna Maria Islands beautiful Gulf beaches! Nestled in the heart of Holmes Beach, this coastal retreat features relaxed boho decor, a shared pool, private balconies, and endless nearby attractions. Whether you are seeking a family vacation or a friends getaway, Kismet by the Sea offers comfort and convenience in a prime location near Holmes Beach Town Center on Anna Maria Island! brbrHighlights br• 7-minute walk to Holmes Beach br• 3 Bedroom / 2.5 Bathroom br• 2 Kings, 1 Twin/ Full bunk, 1 Queen sleeper sofa  br• Shared pool br• Screened-in balcony br• Outdoor dining and BBQ grill br• Outdoor shower   br• Washer and dryer br• Dog friendly br• 2 Parking spaces br brRelax poolside in the shared pool or gather on the screened-in balcony for meals overlooking tropical landscaping. The outdoor porch area offers seating and a BBQ grill, perfect for casual island cookouts. Inside, the bonus living room provides additional space for relaxation or board games with family. The property’s ideal location near restaurants and parks makes it perfect for exploring all that Anna Maria Island has to offer. br brThe spacious open floor plan features a cozy living area with boho coastal accents and a dining space designed for family and friends. Large windows and sliding doors create an airy, inviting atmosphere. The fully equipped kitchen with modern appliances makes mealtime effortless, and the breeze from the screened-in balcony offers a relaxing indoor-outdoor flow. br brRetreat to the primary bedroom with a king bed and an ensuite bathroom with a walk-in shower, offering a peaceful sanctuary for restful nights. The second bedroom also has a king bed and shares a beautifully designed full hall bath with a shower-tub combo. The fun bunk room with a twin-over-full bunk bed is perfect for kids or extra guests, offering ample space and comfort. Each bedroom provides plenty of closet space and a relaxed atmosphere. For additional sleeping space, the living room is equipped with a queen sleeper sofa. brbrRoom Details br• Primary Bedroom: King bed, ensuite with walk-in shower  br• Second Bedroom: King bed br• Third Bedroom: Twin-over-full bunk br• Living Room: Queen sleeper sofa br brGuests love the outdoor shower, laundry facilities, and outdoor dining on the screened balcony. The shared pool, prime Holmes Beach location near top restaurants, parks, and beaches, and the relaxed coastal vibe make Kismet by the Sea a true island retreat. brbrBook your stay at Kismet by the Sea today and dive into the ultimate Anna Maria Island experience. Whether lounging poolside, dining on the balcony, or exploring the nearby beaches and attractions, this home provides everything needed for a memorable Gulf Coast escape. Reserve your dates now and start creating lifelong memories with loved ones! br brbr-brThis home is managed by AMI Locals, 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 AMI Locals Rental Policies for full details. brbr2 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. Please see our AMI Locals Rental Policies for full details. brbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

Experience Kismet by the Sea: Chic Holmes Beach Rental with Shared Pool

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$398.25

Very few beachfront vacation homes will get you as close to the sand as Hidden Cove #1— a beautiful 2-bedroom condominium with exquisite views and unlimited access to the aquamarine Gulf of Mexico. Located within a charming coastal community that also offers a crystal-clear swimming pool, your family will quickly fall in love with this gorgeous oasis and flawless central location. For an absolutely unforgettable getaway to the Gulf— pack your bags and book a stay at Hidden Cove #1. In the sunken, main living area, the floor plan is open and inviting, boasting ocean views from nearly every seat. A plush sofa and armchairs sit on the cool ceramic tile floors and face the large HDTV— perfect for a family movie night with a big bowl of popcorn. There's even a small desk area for getting a little work done— if you must.brbrUp a short flight of stairs is the living and dining area, complete with a formal dining table with seating for six and a pass-through bar area that leads into the kitchen and has bar stool seating for three. In the kitchen, pristine white cabinets are topped with glossy granite countertops. There's a premier GE electric range and matching microwave/vent hood as well as a dishwasher and a spacious refrigerator. This kitchen is the perfect spot to fix some snacks for the beach and brew the morning pot of coffee. Upstairs, the primary bedroom suite is an ultra-private oasis with exquisite gulf views. The luxurious king-size bed sits underneath a tropical-inspired ceiling fan, and there is a sun-kissed balcony overlooking the beach and a large HDTV. The ensuite bathroom features a marble vanity and a huge step-in glass shower. In the second bedroom, there are two twin-size beds, balcony access, and an attached full bathroom with a tub/shower combo. brbrBack downstairs, glass doors from the living area lead directly outside to your very own private, beachfront deck. Relaxing lounge chairs and an alfresco dining table allows you to kick back with your morning coffee or afternoon cocktail and gaze out at the rolling, turquoise waves and sparkling white sand. When it's time to get your toes sandy, the access to the beach is only a few short steps away! Guests of the Hidden Cove community also have access to the large, sun-drenched swimming pool that's surrounded by swaying palm trees. The location of this home also keeps you close to the delicious local dining, live music, eclectic shopping, and exciting entertainment on Anna Maria Island. 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.brbrBedroom & Bathrooms brPrimary Bedroom features a king-size bed, flat screen TV, ensuite bathroom and private balcony.brBedroom 2 features two twin beds.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.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: VRC23-000034brMax Occupancy: 4 Guests | Max Vehicles: 2brQuiet 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.

Beachfront - Hidden Cove Unit 1 by SeaBreeze Vacation

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$947.6

Featuring 6 bedrooms (sleeps 14), 5.5 baths and a fantastic location...NO STORM DAMAGE!!! - just a 1 minute walk to the white sands of the 65th St Beach Access! brbrThis vacation home offers a huge heated pool with spa, rock water slide and grotto waterfall. Covered outdoor entertaining area with outdoor TV and lounges next to the mini putt-putt and propane grill all surrounded by lush tropical landscaping for your privacy.brbrWell decorated and updated, this home has an open main level and a rooftop deck boasting breathtaking views of the tropical pool area and beautiful Anna Maria Island! You'll find the garage well stocked with a second refrigerator, beach chairs, umbrellas & pool toys for your use, as well as, bicycles to tour the island! brbrThis home can comfortably accommodate a group of 14 with plenty of space for everyone to enjoy their privacy while spending quality time together under one roof. Ideal for multiple families to share. Three bedrooms on the main floor all with en suite bathrooms; three bedrooms on the second floor with one featuring en suite bathroom, the other two bedrooms have access to the full hall bathroom across from the laundry room with full sized washer & dryer. Travelling with little ones We know you'll be back and forth to and from the beach a LOT! Which is great news because you'll only have about a minute walk each way. Too many luxury amenities to list them all. High speed WiFi, cable, and streaming TV’s. Take the worry out of packing your own sheets and beach towels knowing that when you arrive to your dream vacation rental, high quality bedding, bath towels, wash clothes and beach towels await for your stay. Free up luggage space and breathe easy knowing that everything is already taken care of for you. If you have any special requests for your stay, please send a message. brbrTake the free trolley to Bean Point, or down to historic Bridge Street. Eat at restaurants like Beach Bistro, Chateau Anna Maria, grab burger's at Skinny's, or watch the sunset at the Sandbar. Go parasailing, take a sunset cruise or paddleboard on the crystal clear blue waters in the Gulf of Mexico. Excellent fishing charters available daily from the island.brbrPlease let us know of any special requests or services that would make your stay even more enjoyable. Pets are welcome and must be declared and approved prior to booking. Rates shown are reflective of a standard minimum 7 night reservation, check in & out on Saturdays, and are subject to change. Additional fees may apply for non-standard reservation requests.

6 BR/5.5 Bth-Huge Heated Pool/Spa/Water Slide...Short -1 Min Walk to Beach

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$620.57

Summary:brbr✔️ 4BR Beachfront condo, Holmes Beachbrbr✔️ Sleeps 8 (2 King, Queen, 2 Twin)brbr✔️ Elevator accessbrbr✔️ 30ft large balcony, partial water view brbr✔️ Heated pool & Hot Tub brbr✔️ Direct beach access, pool-to-sandbrbr✔️ Free private parking (2 spots & guest)brbr✔️ Large living/entertainment areabrbr✔️ Full kitchen, dining for 10brbr✔️ In-unit washer/dryer brbr✔️ Perfect beachfront retreat | Beach gear providedbrbrbrbrThe Space:brbrA rental agreement must be completed before arrival and an ID provided. brbrbrbrIncredible beachfront condo located right on the white sands of Holmes Beach! This spacious 4-bedroom, 3-bathroom condo sleeps up to 8 guests comfortably and is perfect for families or groups.brbrbrbr Comfortable Accommodation:brbr* Bedroom 1: King bed, ensuite with walk-in shower, walk-in closet, Smart TVbrbr* Bedroom 2: King bed, ensuite with walk-in shower, water views, closet, Smart TVbrbr* Bedroom 3: Queen bed, Smart TVbrbr* Bedroom 4: Two twin beds, workstation desk, Smart TVbrbr* Hotel-quality linens, extra pillows, closets, and ceiling fans in every roombrbrbrbr Bathrooms:brbr* Bathroom 1: Toilet, standalone bidet, double vanity, walk-in shower with benchbrbr* Bathroom 2: Toilet, bathtub/shower combo, vanity, closetbrbr* Bathroom 3 (Hallway): Toilet, walk-in showerbrbrbrbr Interior Feeling:brbr* Open-concept living room with two seating areas, sofas, Smart TV, and fireplacebrbr* Full kitchen with fridge, cooktop, built-in microwave, dishwasher, toaster, and drip coffee makerbrbr* Cookware and dishware includedbrbr* Indoor dining area and balcony dining overlooking the beachbrbr* In-unit washer and dryer, ironing board, extra storagebrbrbrbr Outdoor Bliss:brbr* Private balcony with outdoor dining and lounge seatingbrbr* Direct beach accessbrbr* Shared heated pool and spabrbr* Short walk to Holmes Beach Towne Centerbrbr* There's no grill and no beach amenitiesbrbrbrbr✨ Delightful Extras:brbr* Workstation for remote work needsbrbr* Smart TVs in every roombrbr* Ceiling fans in every roombrbr* Extra pillows and hotel-quality linens providedbrbrbrbr Professional Cleaning:brbr* Toiletries, paper towels, toilet paper, beach towel and coffee providedbrbr* Regular pest control treatment in placebrbrbrbrℹ️ Additional Information:brbr* Free parking (unit may include a designated spot; additional parking nearby)brbr- Guest's can use the guest spot and a free spot through the gatebrbr- There's public parking space 7 minutes walk- Parking publico Anna Maria brbr* Steps from the white sands of Holmes BeachbrbrbrbrPLEASE NOTE:brbr* Additional supplies may be available conditionally, but we cannot guarantee them. Nearby stores are easily accessible.brbr* While we regularly treat for pests, occasional insects may appear due to the Florida climate. We will address any sightings promptly, but we do not offer refunds for this.brbrPlease note:brbr* La Plage has a community rule that electric golf carts are not permitted on the property.brbr* Some shared areas may have maintenance from time to time; we do our best to minimize disruption.brbr* While the pool and spa are generally open, hours may vary for cleaning or maintenance.brbrbrbrGuest Access:brbrGuests have full access to the entire condo.brbrbrbrThe Neighborhood:brbrThe condo is located in a prime beachfront area of Holmes Beach. Take a short walk to Holmes Beach Towne Center for shopping, dining, and local attractions. Stroll along the white sands, enjoy the calm Gulf waters, or explore nearby parks and recreational areas. Everything you need for a relaxing Florida getaway is right at your doorstep!brbrbrbrGetting Around:brbrGetting around Holmes Beach and the surrounding area is easy! The condo is centrally located on Gulf Drive, just a short walk to shops, restaurants, and the beach. Parking is available on-site. For exploring nearby areas, driving or rideshares (Uber/Lyft) are convenient. Sarasota and Anna Maria Island are just a short drive away, making day trips simple and stress-free.brbrbrbrOther Things to Note:brbr⚠️ Damage Waiver: Every reservation includes our Damage Waiver Program — you’re covered for up to $500 in accidental damage during your stay. Just relax and enjoy your trip, knowing little mishaps are taken care of. (Note, this is not insurance and does not replace travel or liability insurance; this self-funded protection covers up to $500 in accidental damage to contents only; examples included linens, towels, and wine. brbrbrbr Pest Note: We treat regularly, but Florida may have occasional pests. No refunds are issued for pest sightings, though we’re always happy to address concerns.brbrbrbr⚠️ Please be aware that certain situations beyond our control may occur, including construction or noise outside the unit, temporary closure of amenities, utility or city repairs, or other issues on neighboring properties or units. As these circumstances are beyond our control, we are unable to provide refunds for any related inconveniences resulting from these factors. brbrbrbr Pack ’n Plays must be requested in advance and are subject to availability. As these items are shared across our units, we kindly ask that you request one, at the time of booking to confirm availability. Please note that not all listings include them, so we recommend checking the amenities list or reaching out to our team in advance for confirmation.brbrbrbrPLEASE NOTE:brbr ️Additional supplies may be available upon request but are not guaranteed. If you run out, nearby stores are easily accessible. Towels are provided for approximately the first 2–3 days of your stay—please use the in-unit washer and dryer if available to refresh them. If your unit does not include laundry, on-site facilities may be available (fees may apply). For stays of 5 nights or longer, you may request replacement towels, subject to availability.brbrbrbrPlease note that not all listings include laundry, so we recommend checking the amenities or reaching out to our team in advance to confirm.brbrbrbr✓ ITEMS LEFT BEHIND. If a guest leaves personal items behind and requests their return, they are responsible for a $25 service fee plus packaging and shipping costs. We are not responsible for any loss or damage to left items once the guest has departed.brbrbrbrInteraction with Guests:brbrWe respect your privacy but are just a message or phone call away if you need anything during your stay. Whether it’s questions about the condo, local recommendations, or assistance with check-in/check-out, we’re happy to help. Our goal is to make your stay as comfortable and enjoyable as possible!

2500Sqft Beachfront Condo | Heated Pool & Hot Tub

Holmes Beach, Florida, United States

4

Bed

3

Bath

8

Sleeps

$294.91