Best price vacation rentals in Osprey, FL, USA • 150 Listings
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Osprey, FL, USA Vacation Rentals | 

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0.0 (0)
Direct Beachfront on Siesta Key, FL
Up to 6 guests
EstimatedVerified Host$171
Average Nightly Rate
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5.0 (43)
Jamaica Royale 052 Great updates and close to the pool!
Up to 4 guests
Airbnb$160
Vrbo$198
Average Nightly Rate
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5.0 (8)
Enjoy the fantastic view from Siesta Dunes 5-307 overlooking the Gulf of Mexico.
Up to 6 guests
Airbnb$357
Vrbo$465
Average Nightly Rate
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5.0 (61)
Pool Home with Hot Tub⭐ - Very Close to Siesta Key!
Up to 6 guests
Vrbo$369
Airbnb$393
Average Nightly Rate
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5.0 (76)
Midnight Cove II 333F - Bayside Beauty!
Up to 6 guests
Airbnb$179
Vrbo$209
Average Nightly Rate
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5.0 (40)
Come get your beach on! 4 minute flip flop walk to the #1 beach!
Up to 6 guests
Airbnb$273
Vrbo$273
Average Nightly Rate
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5.0 (64)
"West of Trail" home close to Crescent Beach and Siesta Key with water access
Up to 6 guests
Vrbo$299
Airbnb$301
Average Nightly Rate

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5.0 (48)
Paradise Villa on Siesta Key
Up to 8 guests
Airbnb$242
Vrbo$269
Average Nightly Rate
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5.0 (23)
Siesta Key Beach Front Condo! Breathtaking view!
Up to 6 guests
Airbnb$222
Vrbo$364
Average Nightly Rate

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5.0 (30)
VACATION COUNTRY HOUSE ON EQUINE RANCH
Up to 9 guests
Airbnb$313
Vrbo$313
Average Nightly Rate
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5.0 (1)
Traditional Unit Overlooking Gulf of Mexico
Up to 4 guests
Airbnb$317
Vrbo$429
Average Nightly Rate
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5.0 (11)
Ideal location Siesta Key
Up to 4 guests
Vrbo$140
Airbnb$142
Average Nightly Rate
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5.0 (6)
Sarasota Villa w/ Pool Access ~4 Mi to Beach!
Up to 6 guests
Airbnb$173
Vrbo$183
Average Nightly Rate
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5.0 (5)
VERY Private Casey Key Luxury Home with 2 Masters (All Bedroom Suites) + Pool
Up to 8 guests
Vrbo$571
Airbnb$591
Average Nightly Rate
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5.0 (35)
Front Unit of Renovated Beach Duplex in Historic Downtown Nokomis, Florida
Up to 6 guests
Airbnb$100
Vrbo$129
Average Nightly Rate
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5.0 (11)
CocoBayou Cottage | Private Home w/ Pool, Walk to Crescent Beach & South Village
Up to 10 guests
Vrbo$1,687
Airbnb$2,787
Average Nightly Rate
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5.0 (6)
Sandpiper Cottage | Large Sarasota House, Private Pool, Roof Porch, 2 Story Loft
Up to 14 guests
Vrbo$974
Airbnb$1,608
Average Nightly Rate
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5.0 (29)
13 min to Siesta Key!65'' TV!Great heated pool!Jacuzzi!
Up to 6 guests
Airbnb$326
Vrbo$350
Average Nightly Rate
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5.0 (1)
Vista Hermosa 189, Wireless Internet, 2 Bedrooms, Pool, Sleeps 6
Up to 6 guests
Airbnb$128
Vrbo$217
Average Nightly Rate
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5.0 (2)
Beautiful 5 Bedroom Home In Sunny Sarasota FL, Peaceful Views, Golf and More
Up to 10 guests
Airbnb$425
Vrbo$485
Average Nightly Rate
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5.0 (49)
4 Bedroom Beach House w/ Dock on Canal, West of 41, Less than 1mile to Casey Ke
Up to 12 guests
Airbnb$350
Vrbo$350
Average Nightly Rate
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5.0 (37)
SPRING BREAK! 4 minute flip flop walk to the beach!
Up to 10 guests
Airbnb$530
Vrbo$530
Average Nightly Rate
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5.0 (5)
Waterfront One Room Bungalow with Private Beach Access
Up to 2 guests
Airbnb$325
Vrbo$375
Average Nightly Rate
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5.0 (114)
Casa El Sueño - 8 min to Siesta Key - Intracoastal
Up to 7 guests
Airbnb$114
Vrbo$125
Average Nightly Rate
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5.0 (9)
Super South Sarasota Location minutes to Amenities
Up to 4 guests
Airbnb$175
Vrbo$220
Average Nightly Rate
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  2. Florida
  3. Osprey Vacation Rental Price Comparison

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