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215 houses

A Wonderful Pool House on a lake full of wildlife.

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Location location” Great house convincent , clean , close to everything

Match: Rental types Pool or snooker table

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Price per night from

$121

Discover the perfect beachfront getaway with a private pool & hot tub.

Siesta Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$852

3 bedrooms luxurious home,2 full bath, swimming pool, fully remodeled,pool table

Gulf Gate Estates house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$544

Indulge in a spacious 4-bedroom rental with private pool and beach access!

Siesta Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$972

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Hibiscus at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Rental types, Pool or snooker table

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Price per night from

$489

Bromeliad at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Rental types, Pool or snooker table

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Price per night from

$489

Pineapple at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Rental types, Pool or snooker table

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Price per night from

$489

Sunsets on Beach Siesta Key top floor #402

Siesta Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Rental types, Pool or snooker table

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Price per night from

$229

Orchid at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Rental types, Pool or snooker table

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Price per night from

$489

Coconut at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Rental types, Pool or snooker table

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Price per night from

$489

Split Leaf at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Rental types, Pool or snooker table

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Price per night from

$489

Ideal Retreat next to USA's #1 Beach—Siesta Key

Sarasota condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Rental types, Pool or snooker table

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Price per night from

$160

St.Armands Circle condo ( Kingston Arms )

Sarasota apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 25 minutes

1 of 2 match: Rental types, Pool or snooker table

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Price per night from

$258

Amazing Gulf Beech Rental with Fantastic FREE Amenities!!!

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Rental types, Pool or snooker table

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Price per night from

$435

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

Siesta Key condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Rental types, Pool or snooker table

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Price per night from

$901

Bird of Paradise at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Rental types, Pool or snooker table

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Price per night from

$489

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

Siesta Key apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Rental types, Pool or snooker table

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Price per night from

$182

4 Bedroom with Gulf View Siesta Key FL Beach Fun

Siesta Key apartment

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

“Fantastic Location and Beautiful Accomodations” Our daughters and their families stayed here in February. The condo was everything we expected and more. It has a breathtaking view of the Gulf from the screened in lani which runs the width of the unit. The four bedrooms were perfect for our group of nine and the kitchen / dining area was well stocked with appliances , pots & pans , dishes , glassware , etc. Condo has easy access to heated pool and ample parking. Owner made the rental process smooth as silk , and we all felt right at home as soon as we had checked in. Right across street from world famous Siesta Beach. Would highly recommend.

1 of 2 match: Rental types, Pool or snooker table

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Price per night from

$514

Clean comfort in Sarasota-book now for comfort

Sarasota caravan/mobile home

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Rental types, Pool or snooker table

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Price per night from

$134

“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

1 of 2 match: Rental types, Pool or snooker table

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Price per night from

$245

Gulfview/Bayfront Condo with Million Dollar Views on Siesta Key

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

1 of 2 match: Rental types, Pool or snooker table

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Price per night from

$109

*** SUPER SPECIAL RATES at Harbor Towers ***

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 56 minutes

1 of 2 match: Rental types, Pool or snooker table

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Price per night from

$114

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!

1 of 2 match: Rental types, Pool or snooker table

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Price per night from

$452

Gorgeous Direct Gulf/Beach Front 2 Bedroom Condo on Siesta Key, Amazing views!

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 1 minutes

1 of 2 match: Rental types, Pool or snooker table

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Price per night from

$266

Convenient + Cozy + Quite + Comfortable :-)

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 1 hour 55 minutes

1 of 2 match: Pool or snooker table, Rental types

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Price per night from

$315

New 6 Bedroom, Luxury Home in Gated Community

Siesta Key house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

1 of 2 match: Pool or snooker table, Rental types

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Price per night from

$998

Charming Lido Key Beach House 5 min Walk to Beach!

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Pool or snooker table, Rental types

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Price per night from

$409

Luxury Sarasota Golf Home

Sarasota house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Pool or snooker table, Rental types

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Price per night from

$367

Downtown Sarasota five star home

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pool or snooker table, Rental types

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Price per night from

$195

A Siesta Tropical Retreat - Island Pool Oasis in Village & 2 blocks to Beach

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

“Your best choice for location!” We stayed for 10 lovely days in this home and I have to say It was an even better location than I expected. Everything you could want to do is in walking distance or you can walk to the village (maybe a 3 minute walk)and hop in a free taxi . The house is well appointed and beds are very comfortable. We traveled with a 10 yr.old, 11yr. old , and 15 yr. old my 15 yr. old niece slept in the trundle bed and commented on how comfortable the bed was. In the kitchen you will find a drawer full of menus for the many nearby restaurants and information for water activities. I highly recommend parasailing while your there ! Considering how close everything is the street is very quiet and the owners were great to deal with. Thanks Kathi and Grant!

1 of 2 match: Pool or snooker table, Rental types

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Price per night from

$550

Three bedroom house directly on beach with gulf vi

Siesta Key house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 7

1 of 2 match: Pool or snooker table, Rental types

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Price per night from

$401

Lovely 3 BR Home with Office & Heated Pool at Tara

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pool or snooker table, Rental types

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Price per night from

$166

Stunning 2,550 Sq.ft House, FL

Bradenton house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Pool or snooker table, Rental types

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Price per night from

$285

Downtown Sarasota Historic Burns Court Adorable Bungalow

Sarasota house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Pool or snooker table, Rental types

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Price per night from

$294

Siesta Key Beach Condo, 2Br/2Ba Direct Beach Front

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“What a great view” We usually rent a house one block from the main Siesta Key beach area. This year friends rented the house and my husband and I stayed in this condo for a week. Loved the view of the beach from the living room! Loved the lani! Location was great. Pool was massive compared to our usual house pool, however we did have to walk thru parking lot to get there. The noise from the hall was annoying. And I did miss my temperpedic mattress, but had a great relaxing time.

1 of 2 match: Pool or snooker table, Rental types

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Price per night from

$327

Renovated Beach Front 2BR/2BA Condo, Steps to beach, Gulf of Mexico Views

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pool or snooker table, Rental types

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Price per night from

$277

Beach house for rent in siesta key beach.

Siesta Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

Responds fast! avg. 2 hours 0 minutes

1 of 2 match: Pool or snooker table, Rental types

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Price per night from

$1,001

The MacGregor House is 1925 Old Florida elegance

Sarasota house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 2 match: Pool or snooker table, Rental types

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Price per night from

$315

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