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Search results; Over 1,000 homes in Osprey

Top guest favourite
Home in Osprey
Sarasota vacation Home!
3 bedrooms, 5 beds, 2.5 private bathrooms
25–30 Aug
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4.98 out of 5 average rating, 55 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
11–16 Aug
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Nokomis
Close to Beaches~ Downtown Venice~Bike Trail~Park
3 bedrooms, 4 beds, 2 bathrooms
11–16 Aug
5.0 out of 5 average rating, 45 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
Cool ranch home w/heated pool near beach
2 bedrooms, 4 beds, 2 bathrooms
18–23 Aug
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Home in Sarasota
Mid-Mod Coastal Charm - 10 mins to Siesta Key!
2 bedrooms, 3 beds, 2 bathrooms
10–15 Aug
5.0 out of 5 average rating, 31 reviews
Top guest favourite
Home in Sarasota
Palm Tree Haven
2 bedrooms, 2 beds, 2 bathrooms
22–27 Aug
4.99 out of 5 average rating, 101 reviews
Top guest favourite
Home in Sarasota
Spacious Cozy Tropical Retreat!
2 bedrooms, 3 beds, 2 bathrooms
26–31 Aug
5.0 out of 5 average rating, 29 reviews
Top guest favourite
Guest house in Osprey
Our Paradise Place in Osprey
1 bedroom, 1 bed, 1 bathroom
11–16 Aug
5.0 out of 5 average rating, 18 reviews
Guest favourite
Townhouse in Nokomis
Nokomis Escape! Close to Beach, Relaxation & Eats
3 bedrooms, 4 beds, 2 bathrooms
19–24 Aug
5.0 out of 5 average rating, 5 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
Guest favourite
Apartment in Sarasota
Peaceful Glamorous 2 Bed Resort
2 bedrooms, 3 beds, 2 bathrooms
10–15 Aug
4.96 out of 5 average rating, 84 reviews
Top guest favourite
Home in Nokomis
Charming vacation home, short walk to the beach
2 bedrooms, 5 beds, 2 bathrooms
13–18 Aug
4.97 out of 5 average rating, 131 reviews
Top guest favourite
Home in Sarasota
Books Tide Retreat - minutes from Siesta Beach
2 bedrooms, 2 beds, 2 bathrooms
18–23 Aug
4.95 out of 5 average rating, 59 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 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
Top guest favourite
Apartment in Sarasota
Peaceful retreat, pool, hot tub, near Siesta Key!
2 bedrooms, 6 beds, 2 bathrooms
26–31 Aug
4.96 out of 5 average rating, 81 reviews