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Search results; Over 1,000 homes in Osprey

Top guest favourite
Home in Osprey
Nokomis & Siesta Key Sand Dollar Retreat
4.94 out of 5 average rating, 33 reviews, 2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
Guest favourite
Flat in Osprey
Windsor Lodge Unit #18, studio
5.0 out of 5 average rating, 7 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Aug
Townhouse in Nokomis
Nokomis Escape! Close to Beach, Relaxation & Eats
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 4 beds, 2 bathrooms
3–8 Aug
Top guest favourite
Home in Nokomis
The Nautilus Hacienda
5.0 out of 5 average rating, 47 reviews, 3 bedrooms, 3 beds, 2 bathrooms
1–6 Aug
Top guest favourite
Home in Nokomis
Close to Beaches~ Downtown Venice~Bike Trail~Park
5.0 out of 5 average rating, 44 reviews, 3 bedrooms, 4 beds, 2 bathrooms
11–16 Aug
Top guest favourite
Home in Sarasota
Mid-Mod Coastal Charm - 10 mins to Siesta Key!
5.0 out of 5 average rating, 31 reviews, 2 bedrooms, 3 beds, 2 bathrooms
5–10 Aug
Top guest favourite
Home in Nokomis
Nokomis Serenity Oasis
5.0 out of 5 average rating, 13 reviews, 3 bedrooms, 3 beds, 2 bathrooms
12–18 Aug
Top guest favourite
Guest house in Osprey
Our Paradise Place in Osprey
5.0 out of 5 average rating, 18 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Aug
Home in Nokomis
Amazing family paradise escape
2 bedrooms, 2 bathrooms
1–8 Aug
Guest favourite
Home in Sarasota
Beautiful Home on a prestigious 18 holes golf
5.0 out of 5 average rating, 8 reviews, 4 bedrooms, 4 beds, 3 bathrooms
4–10 Aug
Top guest favourite
Home in Sarasota
Family-Friendly Retreat Near Siesta Key+Beach Gear
4.97 out of 5 average rating, 71 reviews, 3 bedrooms, 3 beds, 3 bathrooms
31 Aug – 5 Sept
Top guest favourite
Home in Nokomis
Peaceful Getaway just minutes from the beach
4.98 out of 5 average rating, 117 reviews, 3 bedrooms, 5 beds, 2 bathrooms
25–30 Aug
Guest favourite
Villa in Sarasota
Sarasota Villa with Pool Access Tennis Near Beach
5.0 out of 5 average rating, 5 reviews, 2 bedrooms, 3 beds, 2 bathrooms
2–9 Aug
Top guest favourite
Home in Nokomis
Nirvana In Nokomis
4.87 out of 5 average rating, 38 reviews, 3 bedrooms, 4 beds, 3 bathrooms
1–6 Aug
Guest favourite
Villa in Sarasota
7845 Timberwood Cir, Sarasota, FL 34238
4.95 out of 5 average rating, 21 reviews, 2 bedrooms, 3 beds, 2 bathrooms
1–8 Aug
Top guest favourite
Cottage in Nokomis
Pink Pineapple Cottage
4.99 out of 5 average rating, 84 reviews, 1 bedroom, 2 beds, 1 bathroom
1–6 Aug
Guest favourite
Home in Nokomis
Serenity on Stilts
4.89 out of 5 average rating, 9 reviews, 2 bedrooms, 3 beds, 2 bathrooms
1–6 Aug
Townhouse in Nokomis
Cozy, coastal retreat just minutes from shoreline!
3 bedrooms, 4 beds, 2.5 bathrooms
1–6 Feb