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Holiday Rentals in Anna Maria

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533 rentals in Anna Maria.
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Close to beach, gorgeous 5 bd luxury home! Private Pool, Spa, and Putting Green!

Holiday Rental House
5 bedrooms
7 bathrooms
Sleeps 8
Match: Sleeps
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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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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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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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North Island Beach Escape

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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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Serendipity - Beach Front Home on Bean Point , Anna Maria

Holiday Rental House
4 bedrooms
8 bathrooms
Sleeps 8
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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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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Spoil yourselves on the GULF OF MEXICO SUNSET BEACH!

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 8
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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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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INCLUDED FREE Bikes+Tandem Kayak+Beach Cart! Heated Pool*103 degree Hot tub*Dock

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
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 Sanctuary #1 - World's Greatest Sunsets!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
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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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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Tucked Away in Anna Maria

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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NEW!! Amie’s House Modern Coastal Getaway

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Beach, Private Fishing dock, Heated Pool, Tropical Paradise

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Vacation Home with pool/canal front/3 blocks to Gulf beach on Anna Maria Island

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Castaway Cottage + Beach + Heated Private Pool&Spa = R & R! Close to Bean Point!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
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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Waterfront Luxury North End w/ Dock, Heated Pool, Spa and No Steps!

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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Waterfront Stunning New Luxury Home w/Pool, Spa, Dock, Elevator, Close to Pine

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful cottage w/ heated private pool - walk to beach, dining, Bayfront Park

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Jan, Feb, 1 month minimum, Contact for special rates $4K mo, $7500. 2 mo + tax

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Luxury Upscale Beach Home Steps from Gulf of Mexico, Heated Pool, Spa & Golfcart

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Dog-friendly house w/ private, heated pool & entertainment - walk to the beach!

Holiday Rental House
5 bedrooms
3 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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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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Grab your swimsuit!! Private heated pool is now open!!!

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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Blue Heron Cottage - Anna Maria Island

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Charming cottage with heated pool, tropical landscaping in prime location!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cute, Beachy, Canal-Front w/Dock on Historic Pine Ave! Steps to Beach and Pier!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Seahorse Cottage - 1820659

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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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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Family freindly adorable cottage steps to the beach, free trolly on island

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Bayside condo w/ a shared pool - close to the beach & restaurants

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
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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Adorable Vintage Anna Maria Cottage. Heated Pool! North End! 2 Blocks to Beach!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Stunning Canal front Luxury home! Beautiful tropical backyard Pool and Spa!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Dog-friendly beach bungalow with private, heated pool, balcony, and lanai

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Adorable Beach cottage just steps Bean Point beach! Great Pool, amazing Location

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
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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Frequently Asked Questions about Anna Maria