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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
21–26 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
22–27 Aug
5.0 out of 5 average rating, 7 reviews
Superhost
Camper van/Motorhome in Sarasota
Mingo’s Micro Glamper!
1 bedroom, 1 single bed, 1 bathroom
28 Aug – 2 Sept
New place to stay
Top guest favourite
Home in Nokomis
Close to Beaches~ Downtown Venice~Bike Trail~Park
3 bedrooms, 4 beds, 2 bathrooms
21–26 Aug
5.0 out of 5 average rating, 46 reviews
Top guest favourite
Home in Sarasota
Siesta Breeze ~ Charming Coastal Cottage
2 bedrooms, 2 queen beds, 2 bathrooms
30 Aug – 4 Sept
4.99 out of 5 average rating, 137 reviews
Guest favourite
Home in Nokomis
Coastal Studio Getaway|5 Min to Beach|Pool
1 bedroom, 1 queen bed, 1 bathroom
24–29 Aug
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Apartment in Venice
1 block from Paradise, 3 blocks from Downtown
1 bedroom, 2 beds, 1 bathroom
25–30 Aug
5.0 out of 5 average rating, 54 reviews
Guest favourite
Home in Sarasota
Sarasota Silver Oasis - Private Pool Near Downtown
2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Sarasota
Books Tide Retreat - minutes from Siesta Beach
2 bedrooms, 2 beds, 2 bathrooms
30 Aug – 4 Sept
4.93 out of 5 average rating, 61 reviews
Guest favourite
Home in Nokomis
Front Unit Renovated Beach Duplex
2 bedrooms, 3 beds, 1 bathroom
31 Aug – 5 Sept
4.89 out of 5 average rating, 45 reviews
Top guest favourite
Home in Nokomis
Cool ranch home w/heated pool near beach
2 bedrooms, 4 beds, 2 bathrooms
26–31 Aug
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Home in Nokomis
The Nautilus Hacienda
3 bedrooms, 3 beds, 2 bathrooms
29 Aug – 3 Sept
5.0 out of 5 average rating, 47 reviews
Top guest favourite
Apartment in Nokomis
Private Studio (entire space)
1 bedroom, 1 queen bed, 1 bathroom
15–20 Sept
5.0 out of 5 average rating, 61 reviews
Top guest favourite
Home in Nokomis
Peaceful Getaway just minutes from the beach
3 bedrooms, 5 beds, 2 bathrooms
25–30 Aug
4.98 out of 5 average rating, 119 reviews
Top guest favourite
Home in Sarasota
Mid-Mod Coastal Charm - 10 mins to Siesta Key!
2 bedrooms, 3 beds, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 32 reviews
Top guest favourite
Guest house in Osprey
Our Paradise Place in Osprey
1 bedroom, 1 bed, 1 bathroom
22–27 Aug
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Home in Sarasota
Luxury Pool Family Paradise-Siesta Key Beach/DT
3 bedrooms, 4 beds, 2 bathrooms
31 Aug – 5 Sept
4.96 out of 5 average rating, 147 reviews
Top guest favourite
Home in Sarasota
Cozy Heaven Studio III
1 bedroom, 1 bed, 1 bathroom
22–27 Aug
4.92 out of 5 average rating, 171 reviews