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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
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
19–24 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
20–25 Aug
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Place to stay in Nokomis
Sunshine Cottage
1 bedroom, 2 beds, 1 bathroom
21–26 Aug
5.0 out of 5 average rating, 30 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
Top guest favourite
Home in Nokomis
Close to Beaches~ Downtown Venice~Bike Trail~Park
3 bedrooms, 4 beds, 2 bathrooms
19–24 Aug
5.0 out of 5 average rating, 46 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 Sarasota
Siesta Breeze ~ Charming Coastal Cottage
2 bedrooms, 2 queen beds, 2 bathrooms
27 Aug – 1 Sept
4.99 out of 5 average rating, 137 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
Flat in Longboat Key
Beachfront Bliss | Walk to the Water- 104
1 bedroom, 2 beds, 1 bathroom
23–28 Aug
New place to stay
Top guest favourite
Home in Nokomis
Cool ranch home w/heated pool near beach
2 bedrooms, 4 beds, 2 bathrooms
19–24 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
20–25 Aug
5.0 out of 5 average rating, 18 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 Sarasota
Palm Tree Haven
2 bedrooms, 2 beds, 2 bathrooms
7–12 Sept
4.99 out of 5 average rating, 102 reviews
Guest favourite
Home in Sarasota
Sunshine Slowdown
3 bedrooms, 5 beds, 2 bathrooms
19–24 Aug
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Flat in Sarasota
Cozy Stay Near Siesta Key & Downtown +Free Parking
1 bedroom, 1 queen bed, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 11 reviews
Guest favourite
Apartment in Sarasota
Peaceful Glamorous 2 Bed Resort
2 bedrooms, 3 beds, 2 bathrooms
19–24 Aug
4.96 out of 5 average rating, 84 reviews
Top guest favourite
Home in Sarasota
Cozy Heaven Studio III
1 bedroom, 1 bed, 1 bathroom
19–24 Aug
4.92 out of 5 average rating, 170 reviews