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Search results; Over 1,000 homes in Osprey

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
1–6 Aug
5.0 out of 5 average rating, 7 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, 43 reviews
Top guest favourite
Home in Nokomis
The Nautilus Hacienda
3 bedrooms, 3 beds, 2 bathrooms
1–6 Aug
5.0 out of 5 average rating, 46 reviews
Guest favourite
Villa in Sarasota
7845 Timberwood Cir, Sarasota, FL 34238
2 bedrooms, 3 beds, 2 bathrooms
1–8 Aug
4.95 out of 5 average rating, 21 reviews
Top guest favourite
Guest house in Osprey
Our Paradise Place in Osprey
1 bedroom, 1 bed, 1 bathroom
1–6 Aug
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Flat in Nokomis
Pool, by Nokomis Beach - Flamingo Bay - UNIT A
3 bedrooms, 5 beds, 2 bathrooms
1–6 Aug
5.0 out of 5 average rating, 21 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
Family-Friendly Retreat Near Siesta Key+Beach Gear
3 bedrooms, 3 beds, 3 bathrooms
31 Aug – 5 Sept
4.97 out of 5 average rating, 71 reviews
Top guest favourite
Home in Sarasota
Books Tide Retreat - minutes from Siesta Beach
2 bedrooms, 2 beds, 2 bathrooms
13–18 Aug
4.96 out of 5 average rating, 56 reviews
Top guest favourite
Home in Venice
5-min to Venice Beach/EV Charger/fast Wi-fi/3bd
3 bedrooms, 5 beds, 2 bathrooms
1–6 Aug
4.9 out of 5 average rating, 91 reviews
Top guest favourite
Home in Sarasota
Quiet Family Home w/ Pool Near Pinecraft
3 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
4.82 out of 5 average rating, 38 reviews
Flat in Siesta Key
Villa with private beach, 3 pools complex on beach
2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
New place to stay
Top guest favourite
Home in Sarasota
3614 Pine Point
2 bedrooms, 3 beds, 2 bathrooms
1–8 Aug
4.92 out of 5 average rating, 36 reviews
Top guest favourite
Place to stay in Nokomis
Sunshine Cottage
1 bedroom, 2 beds, 1 bathroom
1–6 Aug
5.0 out of 5 average rating, 29 reviews
Top guest favourite
Home in Sarasota
Modern Pool House Sealand 3/2 near Siesta
3 bedrooms, 4 beds, 2 bathrooms
1–6 Aug
4.98 out of 5 average rating, 99 reviews
Home in Sarasota
Siesta Key Oasis| Hot tub| Fire Pit| BBQ| Games
3 bedrooms, 5 beds, 2 bathrooms
13–18 Aug
New place to stay
Top guest favourite
Home in Venice
Bright New Home • Family Oasis Near the Shore
3 bedrooms, 5 beds, 2 bathrooms
12–17 Aug
5.0 out of 5 average rating, 18 reviews