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Search results; Over 1,000 homes in Osprey

Guest favourite
Home in Osprey
Creekside Paradise I
3 bedrooms, 3 beds, 2 private bathrooms
4–11 Sept
,
4.96 out of 5 average rating, 52 reviews
Top guest favourite
Home in Osprey
Nokomis & Siesta Key Sand Dollar Retreat
2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
4.94 out of 5 average rating, 33 reviews
Guest favourite
Flat in Osprey
Windsor Lodge Unit #18, studio
1 bedroom, 1 king bed, 1 bathroom
3–8 Aug
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Sarasota
Mid-Mod Coastal Charm - 10 mins to Siesta Key!
2 bedrooms, 3 beds, 2 bathrooms
5–10 Aug
5.0 out of 5 average rating, 31 reviews
Townhouse in Nokomis
Nokomis Escape! Close to Beach, Relaxation & Eats
3 bedrooms, 4 beds, 2 bathrooms
3–8 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Nokomis
Close to Beaches~ Downtown Venice~Bike Trail~Park
3 bedrooms, 4 beds, 2 bathrooms
11–16 Aug
5.0 out of 5 average rating, 44 reviews
Top guest favourite
Home in Nokomis
Charming vacation home, short walk to the beach
2 bedrooms, 5 beds, 2 bathrooms
10–15 Aug
4.97 out of 5 average rating, 130 reviews
Guest favourite
Home in Nokomis
Serenity on Stilts
2 bedrooms, 3 beds, 2 bathrooms
2–7 Aug
4.89 out of 5 average rating, 9 reviews
Flat in Sarasota
Exclusive Living in Sarasota near Siesta Keys
1 bedroom, 1 queen bed, 1 bathroom
8–13 Aug
New place to stay
Top guest favourite
Guest house in Osprey
Our Paradise Place in Osprey
1 bedroom, 1 bed, 1 bathroom
3–8 Aug
5.0 out of 5 average rating, 18 reviews
Guest favourite
Villa in Sarasota
Sarasota Villa with Pool Access Tennis Near Beach
2 bedrooms, 3 beds, 2 bathrooms
2–9 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Sarasota
3614 Pine Point
2 bedrooms, 3 beds, 2 bathrooms
2–9 Aug
4.92 out of 5 average rating, 36 reviews
Top guest favourite
Home in Nokomis
Nirvana In Nokomis
3 bedrooms, 4 beds, 3 bathrooms
3–8 Aug
4.87 out of 5 average rating, 38 reviews
Top guest favourite
Home in Nokomis
The Nautilus Hacienda
3 bedrooms, 3 beds, 2 bathrooms
3–8 Aug
5.0 out of 5 average rating, 47 reviews
Top guest favourite
Home in Nokomis
Nokomis Serenity Oasis
3 bedrooms, 3 beds, 2 bathrooms
12–18 Aug
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Home in Nokomis
Coastal Retreat, 2 Blocks to Beach, Dining & More
2 bedrooms, 5 beds, 1 bathroom
14–19 Aug
5.0 out of 5 average rating, 40 reviews
Guest favourite
Home in Sarasota
Relaxing Lakefront 3bd Heated Pool Near Siesta Key
3 bedrooms, 4 beds, 2 bathrooms
2–7 Aug
5.0 out of 5 average rating, 6 reviews
Apartment in Sarasota
Renovated - Spanish Pine Villa #210
2 bedrooms, 3 beds, 2 bathrooms
4–9 Sept
Top guest favourite
Home in Venice
5-min to Venice Beach/EV Charger/fast Wi-fi/3bd
3 bedrooms, 5 beds, 2 bathrooms
10–15 Aug
4.9 out of 5 average rating, 92 reviews