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Search results; Over 1,000 homes in Osprey

Guest favorite
Apartment in Osprey
Great one bedroom apartment near beaches in Osprey
1 bedroom, 1 bed, 1 private bath
Aug 12 – 17
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4.71 out of 5 average rating, 142 reviews
Top guest favorite
Home in Osprey
Charming Florida Cottage - Kayaks Included
2 bedrooms, 2 king beds, 2 baths
Sep 1 – 6
4.97 out of 5 average rating, 64 reviews
Top guest favorite
Home in Osprey
Nokomis & Siesta Key Sand Dollar Retreat
2 bedrooms, 3 beds, 1 bath
Aug 16 – 21
4.94 out of 5 average rating, 33 reviews
Guest favorite
Apartment in Osprey
Windsor Lodge Unit #18, studio
1 bedroom, 1 king bed, 1 bath
Aug 12 – 17
5.0 out of 5 average rating, 7 reviews
Top guest favorite
Home in Nokomis
Close to Beaches~ Downtown Venice~Bike Trail~Park
3 bedrooms, 4 beds, 2 baths
Aug 12 – 17
5.0 out of 5 average rating, 45 reviews
Top guest favorite
Guesthouse in Osprey
Our Paradise Place in Osprey
1 bedroom, 1 bed, 1 bath
Aug 12 – 17
5.0 out of 5 average rating, 18 reviews
Top guest favorite
Home in Nokomis
Cool ranch home w/heated pool near beach
2 bedrooms, 4 beds, 2 baths
Aug 18 – 23
5.0 out of 5 average rating, 15 reviews
Superhost
Home in Sarasota
Sun Coast Oasis-Heated Pool-Pool Table-Arcade
3 bedrooms, 5 beds, 2 baths
Sep 9 – 14
5.0 out of 5 average rating, 4 reviews
Top guest favorite
Home in Nokomis
The Nautilus Hacienda
3 bedrooms, 3 beds, 2 baths
Aug 12 – 17
5.0 out of 5 average rating, 47 reviews
Top guest favorite
Home in Sarasota
Mid-Mod Coastal Charm - 10 mins to Siesta Key!
2 bedrooms, 3 beds, 2 baths
Aug 12 – 17
5.0 out of 5 average rating, 31 reviews
Top guest favorite
Condo in Nokomis
Private Studio (entire space)
1 bedroom, 1 queen bed, 1 bath
Sep 10 – 15
5.0 out of 5 average rating, 61 reviews
Home in Sarasota
Cozy Sarasota Getaway.
2 bedrooms, 3 beds, 2 baths
Aug 12 – 19
5.0 out of 5 average rating, 4 reviews
Top guest favorite
Home in Sarasota
Private Oasis: Mini Golf and firepit. 2 king beds.
3 bedrooms, 4 beds, 2 baths
Aug 22 – 27
5.0 out of 5 average rating, 46 reviews
Top guest favorite
Home in Sarasota
Siesta Breeze ~ Charming Coastal Cottage
2 bedrooms, 2 queen beds, 2 baths
Aug 27 – Sep 1
4.99 out of 5 average rating, 135 reviews
Guest favorite
Condo in Sarasota
Peaceful Glamorous 2 Bed Resort
2 bedrooms, 3 beds, 2 baths
Aug 12 – 17
4.96 out of 5 average rating, 84 reviews
Condo in Sarasota
Village Des Pins – Timberwood Villa #183
2 bedrooms, 3 beds, 2 baths
Aug 14 – 19
Top guest favorite
Home in Venice
Venice retreat-steps to Shamrock Park/Legacy Trail
2 bedrooms, 2 beds, 2 baths
Aug 12 – 17
5.0 out of 5 average rating, 45 reviews
Top guest favorite
Home in Nokomis
Charming vacation home, short walk to the beach
2 bedrooms, 5 beds, 2 baths
Aug 17 – 22
4.97 out of 5 average rating, 131 reviews
Top guest favorite
Home in Sarasota
The Palms Away
2 bedrooms, 2 beds, 1.5 baths
Sep 7 – 12
5.0 out of 5 average rating, 37 reviews