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 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...

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...

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...

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...

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...

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...

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 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...

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...

If you're looking for luxury, then this Anna Maria Island vacation rental home is the perfect getaway! With a private pool, ocean views, and even roof top deck, you'll have everything you need for a memorable stay. Located on the coveted west of Gulf Drive strip, you'll be just steps from the...

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,...

Following an extensive renovation in 2018, Dragonfly Harbour is now a handsome four-bedroom, five-bathroom private vacation home situated on a deep water canal in close proximity to Bimini Bay. This is a venue designed to allow our guests every opportunity to enjoy all facets of beautiful Anna...

Coconut Breeze is a custom home on the north end of Anna Maria in the quiet residential area in the sought after City Of Anna Maria. Offering 4 bedrooms / 4 bathrooms. You will find that this home has everything you need for your perfect Anna Maria Island vacation! From the luxurious heated pool,...

For your next Anna Maria Island adventure, enjoy a stunning, one-of-a-kind vacation destination. From an oceanfront location to a private pool and original antiques, you won’t another Florida home like this one! Built by Emma Palmer in 1912, this home is one of four Anna Maria cottages known as...

Located at the prestigious north end of Anna Maria, Blue Waters is a beautiful resort-style villa, just minutes walk from the gorgeous white sand beaches of Anna Maria Island and a few blocks away from the individual shops and restaurants of Pine Avenue. Situated on a peaceful residential street,...

A special time awaits you at this updated beach house on Anna Maria Island. Featuring a dog-friendly attitude, a private lagoon pool, and easy access to Bean Point Beach, this house will leave you dreaming about the tropics for weeks after your trip. Located at the tip of Anna Maria Island, a...

Welcome to Yellowbird; your home away from home at the north end of beautiful Anna Maria Island. Here you will enjoy unforgettable views and sunsets over the white sands of the Gulf from the home's multiple decks. This 4 bedroom custom home is the perfect rental for a family vacation or reunion...

Welcome to Pier to Pier Paradise! This beautiful brand new luxury home is one of a kind!  Three stories high and ideally situated on Anna Maria's North end, the property is tucked into a quiet little neighborhood across the street from the beach and a short walk from the Rod and Reel pier, the...

Take just four steps from Wave Crest's back door and sink your toes into the white sand beach of Anna Maria Island or enjoy views of the Gulf of Mexico from the deck, Florida room, or the four Adirondack chairs right on the sand. This gulf-front cottage is located directly on the beach and will...

The perfect spot for a large family getaway, this canalfront Anna Maria Island vacation rental home has room for everyone! Offering a dog-friendly atmosphere (dogs up to 50 lbs. are welcome with a small pet fee), parking for five vehicles, a private pool, and tons of space for the whole group, you...

The Azure Seas is a glorious three bedroom, two bath Gulf front home located at 779 North Shore Drive in the much desired and tranquil northern end of Anna Maria Island. Tropical paradise found!! This is the perfect place to forget your troubles and soak in the unbelievable views of the Gulf of...

This delightful Anna Maria Island duplex is the perfect destination for your next group Florida vacation. Comprising both Sugar Plum Hideaway West and Sugar Plum Hideaway East, this spacious rental offers room for up to 12 guests - and their dogs! Plus, you'll enjoy a big fenced backyard, a shared...

Get ready for an island getaway unlike any other with this stunning gulf-front bungalow! Completely repainted and renovated, this gem of a home combines old Florida charm with brand new furniture, appliances, and kitchen, along with a private sundeck that leads directly out onto the beach and the...