This fun and convenient private home is a favorite amongst guests who return year after year! Located in the heart of Anna Maria Island, 'SURFSIDE' is close to all of the beach activities, shopping, dining, and entertainment. Amenities that set it apart include a LARGE, private fenced yard with...

At 4 bedrooms and 3 full bathrooms, this is one of the most charming rentals on Anna Maria Island!! Located a few houses from the beach, it is only a two minute walk until white powdery sand is between your toes! Easy on the kids and even easier on you! Around the corner from restaurants, pubs &...

This rental home on Anna Maria Island sleeps up to 20 and comes fully equipped. This Bradenton Beach vacation home is actually two rentals in one, in the middle of all the fun and beaches that Bradenton Beach can offer. The rental package sleeps up to 20, and everyone can enjoy the private...

*Please note, all guests occupying this property who are under the age of 25 must be accompanied by a parent or legal guardian. Thank you!* *Check in time is 4:30 PM ET - If Early check-in becomes available you will receive an email stating it is available. If you do not receive an email,...

Many homes with a high bedrooms count sprung out on the island lately, designed to maximize rents, they are built on very small lots normally 50 ft wide and packed upwards in three levels . This is a well reviewed house that I built for me and my family in 1998, it is the largest private rental...

4 Bedroom 5 bath luxury beach front house sleeping 8 with heated pool separate spa numerous decks and stunning beach views from every room. We are located on the desirable family friendly island of Anna Maria. The house is direct beach front on the quiet upmarket north end of the island. Recently...

This Beautiful new 4 bedroom 3 bathroom home ideally located just down the street from the white sand beaches, restaurants and shops. After a day of fun in the sun relax by the heated pool in your own backyard oasis. This house has every luxury you could want, Flat screen TV’s, stainless steel...

*Please note, all guests occupying this property who are under the age of 25 must be accompanied by a parent or legal guardian. Thank you!* *Check in time is 4:30 PM ET - If Early check-in becomes available you will receive an email stating it is available. If you do not receive an email,...

This is the luxury vacation rental home of your dreams! This custom bay-front home on the north end of Anna Maria Island offers 3600 square feet of luxury accommodations and has all the fine touches and professional craftsmanship one would expect in a high-end custom home. When walking into this...

This Bradenton Beach vacation home is actually two rentals in one, in the middle of all the fun and beaches that Bradenton Beach can offer. The rental package sleeps up to 20, and everyone can enjoy the 2 private swimming pools. This is a fully equipped rental home on Anna Maria Island, with...

Welcome to the Four Beach Lovers (Formerly Dawg Daze). Located at 2908 Avenue E in Holmes Beach, this gulf front tropical paradise features four well-appointed and comfortable one bedroom units. Each of the four units is fully equipped and tastefully furnished. All four units feature a private...

Limefish, from Pineapplefish is one of the most stunning beachfront holiday rentals on Anna Maria Island, with direct access to a beautiful, almost private beach. With spectacular views across the Gulf, Limefish has a wonderful and spacious decked area across the whole of the property, where you...

Located directly across from Tampa Bay, this gorgeous new custom luxury vacation rental looks out onto the beautiful bay waters from multiple large balconies. A rooftop deck provides outstanding 180 degree views of the turquoise waters, as well as the Anna Maria City Pier and the Sunshine Skyway...

Beautiful luxury beach front condominium for rent for the first time. There's only 2 condo's on the entire property. This condo is 3500 square feet including gourmet kitchen, dining room, living room with fireplace and built in flat screen TV. screened in lanai overlooking the Gulf of Mexico, den...

Villa Marisol, located at 797 North Shore Drive at the north end of Anna Maria Island and nestled on the shores of the Gulf of Mexico, offers breathtakingly beautiful views of the crystal blue waters of the gulf. This is unquestionably one of Anna Maria's loveliest homes. This spectacular home...

The MI Happy Place  is excited to be under new ownership and management, with new amenities and improvements to make a beautiful, convenient, and relaxing location even better! When renting MI Happy Place Island Resort you will have eight bedrooms and four bathrooms sleeping twenty two making...

Welcome to the Four Beach Lovers (Formerly Dawg Daze). Located at 2908 Avenue E in Holmes Beach, this gulf front tropical paradise features four well-appointed and comfortable one bedroom units. Each of the four units is fully equipped and tastefully furnished. All four units feature a private...

2016 New Custom 4 Bedrooms 4.5 Bathrooms resort size pool/spa Anna Maria Island home on a residential cul-de-sac and a boat dock in your back yard. This luxury home is quality built CBS and offers a chef's kitchen for all to enjoy. This Island retreat is located walking distance to the beach and...

OCEAN VIEW is a brand new construction home that features 6 bedrooms and 5.5 bathrooms and a fantastic location-just a 1 minute stroll to the White sandy beaches at the 65th st access! This lovely property offers a private heated pool with a spa, water slide and grotto. The backyard is an oasis...

Villa Marisol, located at 797 North Shore Drive at the north end of Anna Maria Island and nestled on the shores of the Gulf of Mexico, offers breathtakingly beautiful views of the crystal blue waters of the gulf. This is unquestionably one of Anna Maria's loveliest homes. This spectacular home...

The Beachcomber, located at 3306 4th Avenue in Holmes Beach is the ideal, dream vacation home. This recently built gulf front home features a heated salt water pool and spa nestled in a tropical setting. It does not get any better than this! Luxurious furnishings, an elevator, a gourmet kitchen, a...

Save 20% Off Now through Oct. 31st! Located on the tranquil north end of Anna Maria island with a Gilligan's Island feel, this four bedroom mid century modern sprawling house has 120' of sandy beach overlooking the Sunshine Skyway Bridge and over 4,494 sq. ft. of living space, the property...

Seagrass Flats Condo is a four unit complex located at 101 25th Street North in Bradenton Beach that features a large heated pool and bbq area. Immediately across from the beach, you can be on the sand in less than one minute. It’s a perfect vacation retreat for large family get- togethers and...

Mintfish is a fantastic 4-bedroom waterfront rental home on Anna Maria Island from Pineapplefish Villas. Our latest and one of our most exclusive offerings: this home enjoys and incredible waterfront location with spectacular views across Bimini Bay. A single-storey, spacious rental, with open...

The Blue Dolphin Inn, located at 780 Jacaranda and 404 Alamanda in the tranquil City of Anna Maria features four units surrounding a tropical heated pool with tiki huts, grills, rooftop observation decks and loads of charm. Each unit has its own private patio and charcoal grill for an evening of...

The Valhalla located at 3216 Gulf Drive in Holmes is a wonderful five bedroom, three bath Gulf front duplex on a secluded beach. While the Valhalla is tucked away in a quiet area, it is within walking distance to shopping and restaurants. The location is perfect! Each unit features a large...

The Beachcomber, located at 3306 4th Avenue in Holmes Beach is the ideal, dream vacation home. This recently built gulf front home features a heated salt water pool and spa nestled in a tropical setting. It does not get any better than this! Luxurious furnishings, an elevator, a gourmet kitchen, a...

510 Bayview - Private canal home 5 Bedroom / 5 Bath with private pool , maximum occupancy of 10 people. Island Elegance for the whole family!~ Distance to the Beach: 2 blocks Come to Anna Maria Island, bring family, friends and your boat to enjoy the simple pleasures of life: sun, sand, and...

This beautiful vacation home in Bradenton Beach, has been fully renovated with brand new furnishings, and is actually two homes in one! You can enjoy a fantastic pool area for relaxing days in the sun or after a day at the beach. Right next to the heated pool, is a covered outdoor seating area...

The Anna Cabana Resort, located at 3711 4th Avenue in Holmes Beach consists of four units, all located less than one block to the beach. All four units have been are decorated in a festive, tropical decor. There is also an onsite laundry room for provided for your use. A brand new heated pool has...

Seagrass Flats Condo is a four unit complex located at 101 25th Street North in Bradenton Beach that features a large heated pool and bbq area. Immediately across from the beach, you can be on the sand in less than one minute. It’s a perfect vacation retreat for large family get- togethers and...

Direct Beach Front Home with 180 degree Gulf Views. Your backyard is a Private Beach and a beautiful view of Egmont Key & the Skyway Bridge. Walk to the Rod & Reel Pier where dolphins frolic every afternoon or walk to Pine Avenue for some local shopping. The living level has a full size kitchen,...

This 3 bedroom 2 bath home is on the north end of Anna Maria Island and can be combined with Pirate Cove (a separate building ) to make a 5 bedroom beach front vacation home. All bedrooms in Hooks Haven are Queen size. Two bedrooms are on the main floor and one is on the second floor. Spiral...

THE MAP OF THIS PROPERTY IS INCORRECT THE HOUSE IS LOCATE AT 4118 5TH AVE HOLMES BEACH. This ideally located 6 Bedroom 3.5 Bathroom is an amazing place to escape and unwind. Perfect place to get away with friends or family with it's large open spaces and outdoor sitting area. Angel Sea has every...

Large 5 bedroom / 4.5 bath family home close to the best beach on AMI with a heated pool. The home is 130 steps to the beach, close to the stops for the free bus trolley which runs the island, close to the shops and restaurants of Pine Avenue. The home has a fully stocked kitchen, all the beach...

This brand new 6 bedroom 6.5 bathroom - SLEEPS 14 Comfortably. This home is ideally located just down the street from the white sand beaches, restaurants and shops. After a day of fun in the sun relax by the salt water heated pool in your own backyard oasis. This house has every luxury you could...

Relax and unwind in this brand new custom built and professionally decorated 6 bedroom 4 bath home located just steps from both the Gulf of Mexico and the bay. This coastal style property boast luxury views from each room and features smart T.V.s in all the bedrooms as well as the living room and...

2311 Ave C is a combination of Addy's Inn and Island Retreat on beautiful Anna Maria Island is the home you will want to come back to time and time again. We are family oriented With 6 bedrooms and 4 bathrooms. The open setting has room for everyone. The living room is equipped with a 50' flat...

The Valhalla located at 3216 Gulf Drive in Holmes is a wonderful five bedroom, three bath Gulf front duplex on a secluded beach. While the Valhalla is tucked away in a quiet area, it is within walking distance to shopping and restaurants. The location is perfect! Each unit features a large covered...

Have some fun entertaining friends under the covered patio next to the refreshing pool. Brand new 5 bedroom 4 bathroom vacation home in Holmes Beach, just steps from the beach with fantastic Gulf views. This home is the perfect beach getaway  with everything you could want while enjoying Anna...

*Please note, all guests occupying this property who are under the age of 25 must be accompanied by a parent or legal guardian. Thank you!* *Check in time is 4:30 PM ET - If Early check-in becomes available you will receive an email stating it is available. If you do not receive an email,...

The Anna Cabana Resort, located at 3711 4th Avenue in Holmes Beach consists of four units, all located less than one block to the beach. All four units have been are decorated in a festive, tropical decor. There is also an onsite laundry room for provided for your use. A brand new heated pool has...

Honeyfish is a fabulous, single storey vacation rental from Pineapplefish. Its location, on the edge of Bimini Bay, its nautically themed complete with boating artefacts, makes Honeyfish a water lover's dream luxury home on Anna Maria Island. Honeyfish is surrounded by the water and is perfect...

Cherryfish is the latest addition to the Pineapplefish collection of houses on Anna Maria Island. It is a spectacular 4 bedroom house, in a fantastic location, just one block from Tampa Bay Beach, the amazing Waterfront Restaurant and the island's most popular tourist destination - City Pier....

Pelican Roost 505 - Private canal home 5 Bedroom/ 5 Bath with private pool, maximum occupancy of 10 people. Distance to the Beach: 5 long blocks This gorgeous three story home in the city of Anna Maria, is an easy walk from Pine Avenue and the City Pier, with direct water views, front and rear,...

WELCOME TO ALL DECKED OUT! Whether getting away for a family vacation, with a group of friends, for a wedding or any other occasion, our gorgeous 5 Bedroom home offers everything you could want for a relaxing holiday on Anna Maria Island.... with incredible views of the Bay! Sit by the tropical...

A fantastic vacation rental for families or small groups that includes spacious patio area to enjoy your outdoor dining. Look forward to placing your your toes in the sand about one block away, or sailing on Sarasota Bay. Enjoy both units A & B when booking Beach Breeze Combo. Both units are easily...