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1,067 villas

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Family Reunion Villa on Anna Maria Island, Florida

Bradenton Beach villa

4 bedrooms
4 bathrooms

sleeps 12

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Price per night from

$574

Luxury lakefront Florida Bella Rosa 2B Villa, near tennis IMG Academy & beaches

Bradenton villa

2 bedrooms
2 bathrooms

sleeps 4

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Price per night from

$148

Bromeliad at The Wildflower

Siesta Key apartment

1 bedroom
1 bathroom

sleeps 4

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Price per night from

$490

Hibiscus at The Wildflower

Siesta Key apartment

1 bedroom
1 bathroom

sleeps 4

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Price per night from

$490

Pineapple at The Wildflower

Siesta Key apartment

1 bedroom
1 bathroom

sleeps 4

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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

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Price per night from

$230

Orchid at The Wildflower

Siesta Key apartment

1 bedroom
1 bathroom

sleeps 4

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Price per night from

$490

Coconut at The Wildflower

Siesta Key apartment

1 bedroom
1 bathroom

sleeps 4

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Price per night from

$490

Split Leaf at The Wildflower

Siesta Key apartment

1 bedroom
1 bathroom

sleeps 4

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Price per night from

$489

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

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

Siesta Key condo

3 bedrooms
4 bathrooms

sleeps 8

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Price per night from

$904

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

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

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

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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

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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

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Price per night from

$178

Luxury Resort Sleeps 26!

Palma Sola house

8 bedrooms
5 bathrooms

sleeps 26

Responds fast! avg. 3 hours 39 minutes

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Price per night from

$2,289

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

Siesta Key apartment

3 bedrooms
3 bathrooms

sleeps 9

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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

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Price per night from

$457

Off the Hook: By Beachside Management

Siesta Key house

4 bedrooms
4 bathrooms

sleeps 8

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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

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Price per night from

$148

Peaceful Home, close to siesta key and DT Sarasota

Fruitville house

3 bedrooms
2 bathrooms

sleeps 13

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Price per night from

$338

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 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

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Price per night from

$246

Luxury All Inclusive Fully Furnished House on the Gulf Coast in Venice Florida

Venice house

3 bedrooms
2 bathrooms

sleeps 2

Responds fast! avg. 54 minutes

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Price per night from

$268

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.

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Price per night from

$115

Florida Ocean Front Condo

Longboat Key condo

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$623

Gulfview/Bayfront Condo with Million Dollar Views on Siesta Key

Siesta Key condo

1 bedroom
1 bathroom

sleeps 6

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Price per night from

$109

March 23-March 30, 2024 Springbreak 3bdr on the beach Longboat key

Longboat Key cottage

3 bedrooms
2 bathrooms

sleeps 8

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Price per night from

$746

* SUPER SPECIAL RATES at Harbor Towers *

Siesta Key apartment

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 1 hour 56 minutes

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Price per night from

$114

Waves on Anna Maria

Anna Maria house

4 bedrooms
3 bathrooms

sleeps 8

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Price per night from

$975

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

Beachfront Condo Siesta Key

Siesta Key condo

2 bedrooms
2 bathrooms

sleeps 6

“Great place” We couldn't have a better time. The condo had everything you could possibly need for cooking, or going to the pool and beach. The condo is a 3 minute walk to the beach, and the weather was perfect. Village is a 5 minute drive and the restaurants were perfect for a family. Definitely coming back!

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Price per night from

$453