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Anna Maria, FL Apartments and Holiday Rentals
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533 rentals
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Close to beach, gorgeous 5 bd luxury home! Private Pool, Spa, and Putting Green!
20 reviews
Holiday Rental House
5 bedrooms
7 bathrooms
Sleeps 8
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Dragonfly - Southern charm on the North end of Anna Maria Island
146 reviews
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
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Sea Garden Cottage with Direct Beach Access,AC & WiFi - North End Anna Maria Fl
118 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
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Private heated salt pool at OHasis Getaway and only 200 steps from the Beach!
97 reviews
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
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Steps to Bean Point Beach, Pineapple Breeze is a quaint home with private pool
85 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
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North Island Beach Escape
84 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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Anna Maria, Prive Heated Pool, Lanai
112 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
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Serendipity - Beach Front Home on Bean Point , Anna Maria
74 reviews
Holiday Rental House
4 bedrooms
8 bathrooms
Sleeps 8
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Spoonbill Hideaway-*WINTER SPECIAL*/Huge Pool/Spa/Across from Gulf Beach
79 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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Bungalow On The Bayou (Best Location on the Island)
78 reviews
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
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MI Oasis Getaway! Just 200 Steps to the Beach on a very quiet street
75 reviews
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
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Spoil yourselves on the GULF OF MEXICO SUNSET BEACH!
79 reviews
Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 8
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$200 towards a private fishing charter with Captain Josh with 2020 reservation
75 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
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North End of AMI, Heated/Chilled Pool, Ocean Views, Tropical Oasis with elevator
50 reviews
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 10
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Luxury Beach Cottage for Families on the North Shore of Anna Maria Island
47 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
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INCLUDED FREE Bikes+Tandem Kayak+Beach Cart! Heated Pool*103 degree Hot tub*Dock
158 reviews
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
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Anna Maria Island Rentals - Beach Front - 'Angels Envy'
85 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
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Seaside Sanctuary #1 - World's Greatest Sunsets!
140 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
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Spectacular Beachfront House with Pool
106 reviews
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
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Seaside Maison, Family Friendly, 3 Blocks to Gulf, 2 Blocks to Rest. & Pine St.
49 reviews
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
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Tucked Away in Anna Maria
43 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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NEW!! Amie’s House Modern Coastal Getaway
39 reviews
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 10
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Beach, Private Fishing dock, Heated Pool, Tropical Paradise
55 reviews
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
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Vacation Home with pool/canal front/3 blocks to Gulf beach on Anna Maria Island
64 reviews
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
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Castaway Cottage + Beach + Heated Private Pool&Spa = R & R! Close to Bean Point!
148 reviews
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
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Gulf front, charming home right on the beach - stunning views & dogs welcome!
86 reviews
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
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Waterfront Luxury North End w/ Dock, Heated Pool, Spa and No Steps!
46 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
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Island Living, refreshing outdoor shower and pool , pet friendly if approved
88 reviews
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
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Waterfront Stunning New Luxury Home w/Pool, Spa, Dock, Elevator, Close to Pine
44 reviews
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
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Beautiful cottage w/ heated private pool - walk to beach, dining, Bayfront Park
60 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
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Jan, Feb, 1 month minimum, Contact for special rates $4K mo, $7500. 2 mo + tax
137 reviews
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 5
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Luxury Upscale Beach Home Steps from Gulf of Mexico, Heated Pool, Spa & Golfcart
70 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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Dog-friendly house w/ private, heated pool & entertainment - walk to the beach!
48 reviews
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 8
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Charming cottage located close to beach - private heated pool
76 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
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Charming Beach Home-with a large, Private Pool -3 Houses to the Beach!!!
90 reviews
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
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Grab your swimsuit!! Private heated pool is now open!!!
79 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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Canalfront Anna Maria Cottage w/ Pool & Hot Tub!
52 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
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Blue Heron Cottage - Anna Maria Island
27 reviews
Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 4
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Charming cottage with heated pool, tropical landscaping in prime location!
40 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
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Cute, Beachy, Canal-Front w/Dock on Historic Pine Ave! Steps to Beach and Pier!
42 reviews
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
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Seahorse Cottage - 1820659
74 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
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Come relax at the amazing and beautiful Cast Away Cove - 2min walk from beach
103 reviews
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
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Family freindly adorable cottage steps to the beach, free trolly on island
51 reviews
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
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Bayside condo w/ a shared pool - close to the beach & restaurants
53 reviews
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
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Anna Maria-Villa Tarpon- Ground Level Private Canal/Dock, Saltwater Heated pool
118 reviews
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
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Adorable Vintage Anna Maria Cottage. Heated Pool! North End! 2 Blocks to Beach!
60 reviews
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
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Stunning Canal front Luxury home! Beautiful tropical backyard Pool and Spa!
37 reviews
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
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Dog-friendly beach bungalow with private, heated pool, balcony, and lanai
54 reviews
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
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Adorable Beach cottage just steps Bean Point beach! Great Pool, amazing Location
44 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
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Perfect Location!! 3 BED, 2BA on North Side between Beach and Anna Maria Pier
40 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
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Frequently Asked Questions about Anna Maria
Do any holiday rentals in Anna Maria have a pool?
Yes, here are some popular holiday rentals in Anna Maria that have a pool:\n
\n
Gorgeous views,spectacular home!
\n
Enjoy our Beach, Pool and Dock! 100 5-Star Reviews!
\n
'Island Oasis' A single family North end canal home with pool
\n
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See all holiday rentals with a pool in Anna Maria on Tripadvisor
Do any holiday rentals in Anna Maria have internet access?
Yes, here are some popular holiday rentals in Anna Maria that have internet access:\n
\n
Jacaranda Artist Retreat
\n
Gorgeous views,spectacular home!
\n
Enjoy our Beach, Pool and Dock! 100 5-Star Reviews!
\n
\n
See all holiday rentals in Anna Maria on Tripadvisor
What are the best pet friendly rentals in Anna Maria?
The best pet friendly rentals in Anna Maria are:\n
\n
Jacaranda Artist Retreat
\n
Gorgeous views,spectacular home!
\n
Sand Castle well appointed home steps from beaches
\n
\n
See all pet friendly holiday rentals in Anna Maria on Tripadvisor
What are some great rentals in Anna Maria that are kid friendly?
Some of the most popular kid friendly rentals in Anna Maria are:\n
\n
Gorgeous views,spectacular home!
\n
Enjoy our Beach, Pool and Dock! 100 5-Star Reviews!
\n
Blue Heron Waterfront House Anna Maria island
\n
\n
See all kid friendly holiday rentals in Anna Maria on Tripadvisor