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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
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
14–19 Aug
5.0 out of 5 average rating, 7 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 Nokomis
Close to Beaches~ Downtown Venice~Bike Trail~Park
3 bedrooms, 4 beds, 2 bathrooms
13–18 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
27 Aug – 1 Sept
4.99 out of 5 average rating, 136 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
Cool ranch home w/heated pool near beach
2 bedrooms, 4 beds, 2 bathrooms
18–23 Aug
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Guest house in Sarasota
Coastal Hideaway: Guest House 5 min to NBP & UTC!
2 bedrooms, 2 king beds, 1 bathroom
18–23 Aug
4.98 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
13–18 Aug
4.95 out of 5 average rating, 59 reviews
Top guest favourite
Guest house in Osprey
Our Paradise Place in Osprey
1 bedroom, 1 bed, 1 bathroom
14–19 Aug
5.0 out of 5 average rating, 18 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, 101 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, 37 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
Home in Sarasota
Heated Pool Retreat | Siesta Key & Downtown
3 bedrooms, 5 beds, 2 bathrooms
8–13 Sept
New place to stay
Top guest favourite
Apartment in Nokomis
Private Studio (entire space)
1 bedroom, 1 queen bed, 1 bathroom
10–15 Sept
5.0 out of 5 average rating, 61 reviews
Top guest favourite
Home in Sarasota
Quiet Family Home w/ Pool Near Pinecraft
3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.83 out of 5 average rating, 40 reviews
Top guest favourite
Home in Venice
2 Kitchens + Pool + Ping-Pong + Corn Hole + BBQ
3 bedrooms, 4 beds, 2.5 bathrooms
30 Aug – 4 Sept
4.96 out of 5 average rating, 55 reviews