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Search results; Over 1,000 homes in Osprey

Top guest favourite
Home in Osprey
Secluded 3R Pool Home Retreat Near Sarasota
3 bedrooms, 3 beds, 2 private bathrooms
18–25 Jul
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5.0 out of 5 average rating, 45 reviews
Top guest favourite
Home in Osprey
Nokomis & Siesta Key Sand Dollar Retreat
2 bedrooms, 3 beds, 1 bathroom
18–23 Jul
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
19–24 Jul
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
22–27 Jul
5.0 out of 5 average rating, 42 reviews
Guest favourite
Home in Sarasota
Beautiful Home on a prestigious 18 holes golf
4 bedrooms, 4 beds, 3 bathrooms
18–24 Jul
5.0 out of 5 average rating, 8 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, 70 reviews
Guest favourite
Home in Sarasota
4mi to Siesta key|sleeps 8|Renovated Coastal Home
3 bedrooms, 8 beds, 2 bathrooms
30 Jul – 4 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Nokomis
Coastal Retreat, 2 Blocks to Beach, Dining & More
2 bedrooms, 5 beds, 1 bathroom
19–24 Jul
5.0 out of 5 average rating, 38 reviews
Guest favourite
Home in Sarasota
Mid-Mod Coastal Charm - 10 mins to Siesta Key!
2 bedrooms, 3 beds, 2 bathrooms
5–10 Aug
5.0 out of 5 average rating, 29 reviews
Guest favourite
Apartment in Sarasota
Peaceful Glamorous 2 Bed Resort
2 bedrooms, 3 beds, 2 bathrooms
20–25 Jul
4.96 out of 5 average rating, 84 reviews
Top guest favourite
Home in Nokomis
Updated house close to the Beach
2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
5.0 out of 5 average rating, 33 reviews
Guest favourite
Home in Nokomis
Blue Heron Near Nokomis Beach
3 bedrooms, 4 beds, 2 bathrooms
18–23 Jul
4.92 out of 5 average rating, 12 reviews
Top guest favourite
Guest house in Osprey
Our Paradise Place in Osprey
1 bedroom, 1 bed, 1 bathroom
1–6 Aug
5.0 out of 5 average rating, 18 reviews
Home in Nokomis
Coastal Retreat Near Nokomis Beach
2 bedrooms, 3 beds, 2 bathrooms
20–25 Jul
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Sarasota
Classy Comfortable Villa in Picturesque Paradise
2 bedrooms, 2 beds, 2 bathrooms
15–20 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
29 Jul – 3 Aug
5.0 out of 5 average rating, 29 reviews
Home in Sarasota
Siesta Key Oasis| Hot tub| Fire Pit| BBQ| Games
3 bedrooms, 5 beds, 2 bathrooms
19–24 Jul
New place to stay
Top guest favourite
Home in Sarasota
3614 Pine Point
2 bedrooms, 3 beds, 2 bathrooms
19–26 Jul
4.92 out of 5 average rating, 36 reviews
Top guest favourite
Home in Sarasota
Great Rates! Sunny Sarasota Villa! W/ 2 bicycles!
2 bedrooms, 3 beds, 2 bathrooms
13–18 Sept
4.98 out of 5 average rating, 43 reviews