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Anna Maria Luxury Holiday Homes

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744 rentals in Anna Maria.
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Beautiful, Gulf-Front Home on Bean Point--Halcyon House
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Castaway Cottage + Beach + Heated Private Pool & Spa = R & R! Near Bean Point!
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Seaside Sanctuary #1 - World's Greatest Sunsets!
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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A bird's view of Dragonfly from the north
Dragonfly in the Evening
Enjoying an Evening on the Beaches of Bean Point
Dragonfly - Southern charm on the North end of Anna Maria Island
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Anna Maria-Villa Tarpon- Ground Level Private Canal/Dock, Saltwater Heated pool
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Calling all water lovers! Plus free bikes+tandem kayaks+beach cart+hot tub+dock
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Spectacular Beachfront House with Pool
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Sea Garden Cottage with Direct Beach Access,AC & WiFi - North End Anna Maria Fl
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Private heated salt pool at OHasis Getaway and only 200 steps from the Beach!
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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SPOIL YOURSELVES AND VACATION DIRECTLY ON THE GULF OF MEXICO BEACH!
Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 8
Match: Sleeps
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Save time - get the best Anna Maria rentals sent straight to your email!
Steps to Bean Point Beach, Pineapple Breeze is a quaint home with private pool
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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MI Oasis Getaway! Just 200 Steps to the Beach on a very quiet street
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Spacious Canal Front Home w/ Private Heated Pool on AMI
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Anna Maria, Prive Heated Pool, Lanai
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Spoonbill Hideaway-*WINTER SPECIAL*/Huge Pool/Spa/Across from Gulf Beach
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Bungalow On The Bayou (Best Location on the Island)
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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North End of AMI, Heated/Chilled Pool, Ocean Views, Tropical Oasis with elevator
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Luxury Beach Cottage for Families on the North Shore of Anna Maria Island
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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North Island Beach Escape
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Luxury Upscale Beach Home Steps from Gulf of Mexico, Heated Pool, Spa & Cabana
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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$200 towards a private fishing charter with Captain Josh with 2020 reservation
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Island Living, refreshing outdoor shower and pool , pet friendly if approved
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Beautiful, decorated and furnished, spacious Great Room family & kid friendly,
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Anna Maria Island Rentals - Beach Front - 'Angels Envy'
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Seaside Maison, Family Friendly, 3 Blocks to Gulf, 2 Blocks to Rest. & Pine St.
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Sea La Vie Beach House - Stunning New Luxury Waterfront Home w/Pool, Dock, Eleva
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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BEAUTIFUL BEAN POINT LOCATION 200 FEET TO ROD AND REEL PIER! EVERYTHING INCLUDED
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Beautiful 4-BR, Very Close to Gulf Beach, Large Heated Pool
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Northshore Beach House near Pine Ave, north end of Anna Maria Island
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Sept 17 - 24 Deal! - Waterfront/Backyard Beach/Hot Tub/Pool/Dock/Putting Green!
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Private heated pool with this charming bungalow!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beach, Private Fishing dock, Heated Pool, Tropical Paradise
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Canalfront Anna Maria Cottage w/ Pool & Hot Tub!
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Gulf front, charming home right on the beach - stunning views & dogs welcome!
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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AMI North End Private Heated Pool. Great location to beach
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Charming Beach Home-with a large, Private Pool -3 Houses to the Beach!!!
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Amie House Chef’s kitchen, 2 King suites walk to beach/Stunning Pool
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Anna Belle by Beach Boutique Rentals
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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3 blocks to sugar sand beach! Large, heated pool and 20 ft dock.
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
More info
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Bay-Canal Waterfront! Tiki Bar 5BR, 2 King Sleeprs, 5BA Heated Pool, 2 Kitchens
Holiday Rental House
7 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
More info
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Blue Heron Cottage - Anna Maria Island
Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Tucked Away in Anna Maria
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Come relax at the amazing and beautiful Cast Away Cove - 2min walk from beach
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Yellowbird: AMI North End, Gulf Views, Pool, Tiki Hut, Elevator by Anna Maria Li
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Brand New Renovation Sea Breeze Cottage With Private Dock, Access To Bimini Bay
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Cloud 9- beachfront/heated pool/ 4 plus bedroom - Beach Front/Hot Tub/Golf Cart/
Holiday Rental House
5 bedrooms
12 bathrooms
Sleeps 8
Match: Sleeps
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Charming cottage located close to beach - private heated pool
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Seahorse Cottage - 1820659
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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New Luxury-Professionally Decorated Home Pool/Spa 5 Minutes walk to beach
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Perfect Location!! 3 BED, 2BA on North Side between Beach and Anna Maria Pier
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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