filters

Search results; Over 1,000 homes in Osprey

Top guest favourite
Guest house in Osprey
Cozy Cottage by the Bay
1 bedroom, 1 bed, 1 private bathroom
25–30 Aug
,
4.99 out of 5 average rating, 365 reviews
Top guest favourite
Home in Osprey
Charming Florida Cottage - Kayaks Included
2 bedrooms, 2 king beds, 2 bathrooms
1–6 Sept
4.97 out of 5 average rating, 64 reviews
Top guest favourite
Home in Osprey
Nokomis & Siesta Key Sand Dollar Retreat
2 bedrooms, 3 beds, 1 bathroom
20–25 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
21–26 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
20–25 Aug
5.0 out of 5 average rating, 46 reviews
Home in Sarasota
Siesta Key Fully-Renovated Unit 5 min to the beach
2 beds, 1 bathroom
27 Aug – 1 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Apartment in Sarasota
Waterfront w/ Pool, mins to SK Beaches, bikes/sups
2 bedrooms, 2 beds, 1 bathroom
8–13 Sept
4.94 out of 5 average rating, 33 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
Home in Nokomis
Cool ranch home w/heated pool near beach
2 bedrooms, 4 beds, 2 bathrooms
20–25 Aug
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Guest house in Osprey
Our Paradise Place in Osprey
1 bedroom, 1 bed, 1 bathroom
21–26 Aug
5.0 out of 5 average rating, 18 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 Sarasota
Coastal Hideaway: Guest House 5 min to NBP & UTC!
2 bedrooms, 2 king beds, 1 bathroom
29 Aug – 3 Sept
4.98 out of 5 average rating, 47 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
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 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
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
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
Home in Sarasota
Palm Tree Haven
2 bedrooms, 2 beds, 2 bathrooms
7–12 Sept
4.99 out of 5 average rating, 102 reviews