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Air conditioning
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Cot available
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Staffed property
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Beach or lakeside relaxation
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849 houses

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A Pearl of a Beach Home - now with luxury Saltwater heated pool and hot tub

Holmes Beach house

3 bedrooms
3 bathrooms

sleeps 6

“Perfect Luxury” Our 5-week stay at this vacation rental was absolutely perfect. The house was everything you could ask for and more. We have stayed in many vacation rentals in the last 20 or so years that we have been coming to anna Maria Island and I have to say this one was right at the top of the list. The kitchen was outfitted with everything you could want. The beds were very comfortable. The neighborhood was nice and quiet. Short walk to the beach. The owners were very nice to deal with and always responded quickly and were very warm and helpful. Definitely can recommend this vacation rental.

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Price per night from

$476

Newly renovated beach house near AMI free trolley stop with Private pool

Holmes Beach house

3 bedrooms
3 bathrooms

sleeps 8

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Price per night from

$562

Super Cute Cottage--Private--Walk/Bike to Beach

Siesta Key house

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$258

Off the Hook: By Beachside Management

Siesta Key house

4 bedrooms
4 bathrooms

sleeps 8

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Price per night from

$515

Luxury Resort Sleeps 26!

Palma Sola house

8 bedrooms
5 bathrooms

sleeps 26

Responds fast! avg. 3 hours 39 minutes

Match: Rental types Linen provided Table tennis

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Price per night from

$2,289

Las Palmas; by Beachside Management

Siesta Key house

7 bedrooms
8 bathrooms

sleeps 16

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Price per night from

$1,202

Serendipity

Anna Maria house

4 bedrooms
4 bathrooms

sleeps 8

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Price per night from

$1,260

Luxury Modern Oasis in Heart of Sarasota

Sarasota house

2 bedrooms
2 bathrooms

sleeps 4

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Price per night from

$1,031

Waves on Anna Maria

Anna Maria house

4 bedrooms
3 bathrooms

sleeps 8

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Price per night from

$975

Beautiful Longboat Key Home!

Bradenton Beach house

3 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 27 minutes

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Price per night from

$516

Bromeliad at The Wildflower

Siesta Key apartment

1 bedroom
1 bathroom

sleeps 4

2 of 3 match: Rental types, Linen provided, Table tennis

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Price per night from

$490

Hibiscus at The Wildflower

Siesta Key apartment

1 bedroom
1 bathroom

sleeps 4

2 of 3 match: Rental types, Linen provided, Table tennis

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Price per night from

$490

Pineapple at The Wildflower

Siesta Key apartment

1 bedroom
1 bathroom

sleeps 4

2 of 3 match: Rental types, Linen provided, Table tennis

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Price per night from

$490

Sunsets on Beach Siesta Key top floor #402

Siesta Key condo

2 bedrooms
1 bathroom

sleeps 6

2 of 3 match: Rental types, Linen provided, Table tennis

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Price per night from

$230

Beachplace Building 3 unit 302

Longboat Key condo

2 bedrooms
2 bathrooms

sleeps 4

2 of 3 match: Rental types, Linen provided, Table tennis

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Price per night from

$187

Orchid at The Wildflower

Siesta Key apartment

1 bedroom
1 bathroom

sleeps 4

2 of 3 match: Rental types, Linen provided, Table tennis

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Price per night from

$490

Coconut at The Wildflower

Siesta Key apartment

1 bedroom
1 bathroom

sleeps 4

2 of 3 match: Rental types, Linen provided, Table tennis

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Price per night from

$490

Split Leaf at The Wildflower

Siesta Key apartment

1 bedroom
1 bathroom

sleeps 4

2 of 3 match: Rental types, Linen provided, Table tennis

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Price per night from

$489

Shorewalk Condo ED near the Beaches Anna Maria Island, Longboat Key, IMG, Shops

Bradenton apartment

2 bedrooms
2 bathrooms

sleeps 4

2 of 3 match: Rental types, Linen provided, Table tennis

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Price per night from

$402

Amazing Gulf Beech Rental with Fantastic FREE Amenities!!!

Longboat Key condo

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$436

Gulf and Bay Club 3bdrm “E” Luxury END CORNER Unit - RIGHT ON BEACH

Siesta Key condo

3 bedrooms
4 bathrooms

sleeps 8

2 of 3 match: Rental types, Linen provided, Table tennis

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Price per night from

$904

Bird of Paradise at The Wildflower

Siesta Key apartment

1 bedroom
1 bathroom

sleeps 4

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Price per night from

$490

Stunning & Serene +++ Minutes from Anna Maria Island, IMG Academy and more!

Bradenton apartment

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 2 hours 9 minutes

2 of 3 match: Rental types, Linen provided, Table tennis

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Price per night from

$114

Modern Lakerfront Condo! 2x Pools~WiFi~Lanai. By IMG~Beaches~Restaurants~AMI~SRQ

Bradenton apartment

2 bedrooms
2 bathrooms

sleeps 4

Responds fast! avg. 11 minutes

2 of 3 match: Rental types, Linen provided, Table tennis

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Price per night from

$138

+++ Clean & Bright +++ Minutes to Anna Maria Island

Bradenton apartment

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 2 hours 9 minutes

2 of 3 match: Rental types, Linen provided, Table tennis

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Price per night from

$178

Waterview Oasis Retreat, minutes to Anna Maria Island and IMG

Bradenton condo

2 bedrooms
2 bathrooms

sleeps 6

2 of 3 match: Rental types, Linen provided, Table tennis

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Price per night from

$109

Siesta Key Beach : 2 Bedroom, 3 Beds, 3 Bathroom Duplex & Heated Pool

Siesta Key apartment

2 bedrooms
3 bathrooms

sleeps 6

2 of 3 match: Rental types, Linen provided, Table tennis

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Price per night from

$182

A Somewhere Is Here - Changes in Attitude: By Beachside Management

Siesta Key apartment

3 bedrooms
3 bathrooms

sleeps 9

2 of 3 match: Rental types, Linen provided, Table tennis

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Price per night from

$411

A Somewhere is Here - Changes in Latitude: By Beachside Management

Siesta Key apartment

3 bedrooms
3 bathrooms

sleeps 9

2 of 3 match: Rental types, Linen provided, Table tennis

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Price per night from

$457

Beach Walk: By Beachside Management

Siesta Key townhouse

3 bedrooms
3 bathrooms

sleeps 8

2 of 3 match: Rental types, Linen provided, Table tennis

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Price per night from

$515

Florida Palms Heaven 2B Villa, near tennis IMG Academy & beaches

South Bradenton apartment

2 bedrooms
2 bathrooms

sleeps 4

2 of 3 match: Rental types, Linen provided, Table tennis

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Price per night from

$148

Newly discounted rates! Gorgeous one bedroom across from beach, near village!

Siesta Key condo

1 bedroom
1 bathroom

sleeps 3

“Anniversary Trip” Had a wonderful time at LA Siesta Condominiums for our anniversary vacation. Beautifully furnished and do close to the best beach in the USA

2 of 3 match: Rental types, Linen provided, Table tennis

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Price per night from

$246

Family Reunion Villa on Anna Maria Island, Florida

Bradenton Beach villa

4 bedrooms
4 bathrooms

sleeps 12

2 of 3 match: Rental types, Linen provided, Table tennis

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Price per night from

$574

Just Minutes from the White Sandy Siesta Beach

Siesta Key condo

1 bedroom
1 bathroom

sleeps 4

“It was very cozy and comfortable apartment!” We loved to spend our vacation at this place. Really close to the beach, to different restaurants, and all kind of stores.

2 of 3 match: Rental types, Linen provided, Table tennis

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Price per night from

$115