Osprey Rentals

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703 Houses

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

Sarasota Stoneybrook Golf Condo, overlooking #3 Hole, near Siesta Key

Osprey condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$161

Great rentals within 20 miles that match your search

Beautiful Location On Bay Side, Water View, Pool

Sarasota villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

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Price per night from

$229

Park Model with lanai, large deck, block from pool

Venice house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$121

Venice Florida Condo

Venice condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$126

Amazing Beachfront Condo, Siesta Key,

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$344

Stay near the heart of Sarasota

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$115

FANTASTIC VACATION! STEPS FROM THE POOL AND BEACH, VERY CLEAN CONDO!

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$271

New 6 Bedroom, Luxury Home in Gated Community

Siesta Key house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

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Price per night from

$999

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

Lido Sunshine L

Lido Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$171

Spacious Apt. #1 Historic Walkable Downtown, between Siesta & Lido Beach

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$482

Charming Private Studio in Historic Downtown Area

Sarasota studio

  • Studio
  • 1 bathroom
  • sleeps 3

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Price per night from

$258

Manasota Beachy Cottage

Manasota Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

“Our 2017 vacation” This was our first time ever renting a house. Peter was the best. This house had everything we need or wanted. It was super clean and beautiful. The screened porch was perfect to drink coffee in the morning. Didn't have to worry about the bugs or anything. Beach was a short walk around the corner over a bridge. The town was great and hardly no traffic. Safe for younger kids to play in the yard. Can't wait to rent again next year. Thank you!!

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Price per night from

$155

Perfect vacation spot

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Good location. Nice host.” Location to near by beaches and downtown were just perfect. It was comfortable and had all we needed for our visit with a lovely host. Definitely would stay here again if we visit Sarasota again.

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Price per night from

$155

Quiet pool home with lake view, close to beaches

Venice house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$229

Tara Golf & Country Club Condo

Bradenton condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Wonderful, peaceful location and beautiful condo.” This condo is wonderful and has everything anyone would want or need for a wonderful stay. We loved the property and the owners. It is located in a private championship golf course community and is just across the street from all the amenities. The amenities include tennis, pool, workout room, and of course golf at its best. There is a wonderful grill room and beautiful dining room facing the driving range. Very close to a hugh shopping area and enclosed mall. Very convenient to travel anywhere from here. Very nice rental in a wonderful area.

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Price per night from

$144

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

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Price per night from

$144

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Price per night from

$284

Serene Sarasota Getaway near shopping and golfing.

Fruitville villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$127

Piece of Paradise

Sarasota condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 3 minutes

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Price per night from

$95

Beautiful, Affordable Close to famous Siesta Beach

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“It was wonderful!” Everything about the trip and condo was great! Mike met us to give us the keys and we called him for suggestions about restaurants, etc. and he was very helpful. The condo was very clean and had everything we needed. It was also great that we were able to use the beach chairs and umbrella. I am already trying to figure out when we can go again.

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Price per night from

$163

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

Sarasota condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$161

Quiet and Comfortable Condo Near Turtle Beach

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Siesta sweet spot” Great value for location. Nice pool, visits with the manitees. Close to everything. This time of year ocean water was amazing

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Price per night from

$201

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. 2 hours 9 minutes

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Price per night from

$92

All Inclusive Executive Rental

Sarasota apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 2 hours 9 minutes

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Price per night from

$166

Luxury Sarasota Golf Home

Sarasota house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$368

Siesta Vacation Home - 3 miles to beach

Venice house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$211

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Price per night from

$149

****Walk to Beach-5min! Waterfront Canal! Private Pool~spa~Kayaks, Bikes!

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$454

Lido Sunshine M

Lido Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$182

Responds fast! avg. 0 minutes

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Price per night from

$229

Shorewalk waterfront Condo Bradenton

Bradenton condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Nice and affordable condo convenient to shopping and restaurants.” This unit has been updated and is a very comfortable place to stay. The owner responded promptly when we contacted him.

Responds fast! avg. 2 hours 1 minutes

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Price per night from

$95

Jamaica Royale #104! Completely renovated, Gulf side, beautiful 2b/2b Condo!

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$337

Viewing 38 of 703
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