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Search results; Over 1,000 homes in Osprey

Guest favourite
Home in Osprey
Private house with loft
1 bedroom, 3 beds, 1 private bathroom
1–6 Sept
,
4.9 out of 5 average rating, 101 reviews
Top guest favourite
Home in Osprey
Nokomis & Siesta Key Sand Dollar Retreat
2 bedrooms, 3 beds, 1 bathroom
1–6 Sept
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 Sept
5.0 out of 5 average rating, 7 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
Superhost
Apartment in Sarasota
NEW! Beachfront Ground Floor: Million $ Views
2 bedrooms, 3 beds, 2 bathrooms
1–8 Sept
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
Guest house in Osprey
Our Paradise Place in Osprey
1 bedroom, 1 bed, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 18 reviews
Flat in Sarasota
Exclusive Living in Sarasota near Siesta Keys
1 bedroom, 1 queen bed, 1 bathroom
13–18 Sept
Top guest favourite
Home in Nokomis
Close to Beaches~ Downtown Venice~Bike Trail~Park
3 bedrooms, 4 beds, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 46 reviews
Top guest favourite
Camper van/Motorhome in Nokomis
"Nokomis Key" - Golf Cart Included (FREE)
1 bedroom, 4 beds, 1 bathroom
26 Sept – 1 Oct
4.91 out of 5 average rating, 76 reviews
Home in Sarasota
Cozy Sarasota Getaway.
2 bedrooms, 3 beds, 2 bathrooms
1–8 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Apartment in Sarasota
Amazing Gulf Views Condo, Siesta Key,
2 bedrooms, 4 beds, 2 bathrooms
1–8 Sept
4.98 out of 5 average rating, 95 reviews
Guest favourite
Home in Nokomis
Pet Friendly With Resort Amenities
2 bedrooms, 3 beds, 1 bathroom
1–6 Sept
4.88 out of 5 average rating, 8 reviews
Top guest favourite
Home in Nokomis
The Nautilus Hacienda
3 bedrooms, 3 beds, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 47 reviews
Top guest favourite
Home in Sarasota
Siesta Key Tropical Escape | Private Pool Oasis
3 bedrooms, 4 beds, 1 bathroom
8–15 Sept
5.0 out of 5 average rating, 11 reviews
Flat in Longboat Key
Beachfront Bliss | Walk to the Water- 104
1 bedroom, 2 beds, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Venice
Venice Island Home w Heated Pool
2 bedrooms, 3 beds, 2 bathrooms
1–6 Sept
4.99 out of 5 average rating, 90 reviews
Top guest favourite
Home in Sarasota
The Palms Away
2 bedrooms, 2 beds, 1.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 38 reviews
Guest favourite
Townhouse in Nokomis
Nokomis Escape! Close to Beach, Relaxation & Eats
3 bedrooms, 4 beds, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 5 reviews