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155 Houses

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LUX VILLAs close to sparkling Siesta Key Beach.

Osprey villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$161

Coral Reef Cutie 2Bedroom Bungalow - 4 Miles to Siesta Key

Osprey cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 2 hours 14 minutes

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Price per night from

$132

Great rentals within 20 miles that match your search

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Price per night from

$229

Newly Remodeled Spacious Loft in Sarasota!

Sarasota apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$295

Stay near the beach and downtown

Sarasota house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$69

Monthly Rental, 2 bed, 2 bath, Ocean view.

Sarasota condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$115

3BR/4BA TOWNHOUSE - POOL VIEW PARADISE - PRIVATE BEACH ACCESS

Siesta Key townhouse

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 38 minutes

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Price per night from

$430

Cumberland Road Paradise

Venice apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 1

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Price per night from

$103

Siesta Key 2 Bedroom 1 Bath Modern/Contemporary Decor Apartment

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

“Amazing!” I stayed here with my husband and we had a great time! We were in Orlando visiting family and we decided to arrange some us time. The condo was excellent and very clean! Kathy and her husband were very informative, respond quickly,and available when we needed them. What was great was that we had all beach items available to us and were very useful. We were in close proximity to everything and the beach and restaurants were great! Everyone in the area was very friendly and my husband and I want to definitely come back!

Responds fast! avg. 1 hour 14 minutes

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Price per night from

$224

Sandy Toes Town Home

Siesta Key townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Time in Paradise” We recently had the luck to spend two months in paradise. This condo was comfortably appointed, well stock to meet all our needs, and most importantly in the perfect location. The beach was a short walk to the left and stores and restaurants were just a short walk to the right. We had a great time and enjoyed everything Sarasota, Siesta Key, and this Sandy Toes Condo had to offer. Thanks Mark!

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Price per night from

$272

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!

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Price per night from

$500

Siesta Key private beach access

Siesta Key villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

“Siesta Key Townhouse” This was a wonderful place to stay! The house was very clean and spacious and had everything we needed for a week at the beach.

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Price per night from

$509

Clean comfort in Sarasota-book now for comfort

Sarasota caravan/mobile home

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

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Price per night from

$134

Siesta Key Townhouse across from Pristine Sands of Siesta Key 2B/2B sleeps 6

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Fantastic week in Siesta Key” The townhouse was fantastic and fully equipped with everything we needed for a very comfortable week. The location was outstanding - right across from the beach and the free trolley to the Village stopped right outside. The garage had everything the family needed to take to the beach and we met some lovely people around the pool. Thank you Michelle for your hospitality - we hope to be back soon.

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Price per night from

$189

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

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Price per night from

$266

Responds fast! avg. 54 minutes

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Price per night from

$267

Three bedroom house directly on beach with gulf vi

Siesta Key house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 7

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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

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Price per night from

$166

Charming Lido Key Beach House 5 min Walk to Beach!

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$409

Manasota Beach Vacation Rental

Englewood house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$269

Brand new villa with heated pool for swimmers

Venice house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$189

Serene Sarasota Getaway near shopping and golfing.

Fruitville villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$127

Ohana

Sarasota condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$144

Great Location and Best Price in Sarasota

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 1 hour 57 minutes

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Price per night from

$92

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Price per night from

$149

Heritage Oaks

Heritage Oaks Golf and Country Club condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 3 hours 56 minutes

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Price per night from

$98

Port Charlotte 3 bedroom, 2 bathroom heated pool villa

Port Charlotte villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$99

Fanta-Sea 47; By Beachside Management

Siesta Key townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$457

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

Cozy & Bright+++Minutes to 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

$117

Lookout: By Beachside Management

Siesta Key house

  • 4 bedrooms
  • 6 bathrooms
  • sleeps 10

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Price per night from

$744

Living the Dream - Mermaid: By Beachside Management

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$343

Banana Cabana: By Beachside Management

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$240

Bianco Sands - 2 Bedroom - Poolside: By Beachside Management

Siesta Key villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Match: Bicycles available

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Price per night from

$331

Bianco Sands - 1 Bedroom 1 Bath: By Beachside Management

Siesta Key villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Bicycles available

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Price per night from

$251

Crescent Beach Villas - La Perlita: By Beachside Management

Siesta Key villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$274

Living the Dream - Starfish: By Beachside Management

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Bicycles available

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Price per night from

$343

Jamaica Royale - Beachfront Tower: By Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Bicycles available

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Price per night from

$377

Viewing 38 of 155
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