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Search results; Over 1,000 homes in Osprey

Top guest favourite
Home in Osprey
Nokomis & Siesta Key Sand Dollar Retreat
4.94 out of 5 average rating, 33 reviews, 2 bedrooms, 3 beds, 1 bathroom
20–25 Jul
Guest favourite
Flat in Osprey
Windsor Lodge Unit #18, studio
5.0 out of 5 average rating, 7 reviews, 1 bedroom, 1 bed, 1 bathroom
21–26 Jul
Top guest favourite
Home in Nokomis
Close to Beaches~ Downtown Venice~Bike Trail~Park
5.0 out of 5 average rating, 42 reviews, 3 bedrooms, 4 beds, 2 bathrooms
22–27 Jul
Top guest favourite
Home in Sarasota
Family-Friendly Retreat Near Siesta Key+Beach Gear
4.97 out of 5 average rating, 70 reviews, 3 bedrooms, 3 beds, 3 bathrooms
31 Aug – 5 Sept
Guest favourite
Home in Sarasota
Beautiful Home on a prestigious 18 holes golf
5.0 out of 5 average rating, 8 reviews, 4 bedrooms, 4 beds, 3 bathrooms
20–26 Jul
Guest favourite
Home in Nokomis
Modern Pool Home in Nokomis
4.9 out of 5 average rating, 10 reviews, 3 bedrooms, 4 beds, 3 bathrooms
17–22 Aug
Guest favourite
Home in Sarasota
Mid-Mod Coastal Charm - 10 mins to Siesta Key!
5.0 out of 5 average rating, 30 reviews, 2 bedrooms, 3 beds, 2 bathrooms
5–10 Aug
Top guest favourite
Apartment in Sarasota
Lovely 2-Bedroom Condo, 7 min from Siesta Beach
4.98 out of 5 average rating, 129 reviews, 2 bedrooms, 3 beds, 2 bathrooms
21–26 Jul
Guest favourite
Home in Sarasota
Classy Comfortable Villa in Picturesque Paradise
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 2 beds, 2 bathrooms
15–20 Aug
Top guest favourite
Home in Nokomis
Coastal Retreat, 2 Blocks to Beach, Dining & More
5.0 out of 5 average rating, 39 reviews, 2 bedrooms, 5 beds, 1 bathroom
20–25 Jul
Top guest favourite
Home in Venice
Baycrest Bungalow | Walk to Beaches & Shops on Ven
5.0 out of 5 average rating, 13 reviews, 2 bedrooms, 3 beds, 2 bathrooms
20–25 Jul
Top guest favourite
Home in Nokomis
Peaceful Getaway just minutes from the beach
4.98 out of 5 average rating, 116 reviews, 3 bedrooms, 5 beds, 2 bathrooms
25–30 Aug
Top guest favourite
Home in Sarasota
Great Rates! Sunny Sarasota Villa! W/ 2 bicycles!
4.98 out of 5 average rating, 43 reviews, 2 bedrooms, 3 beds, 2 bathrooms
13–18 Sept
Top guest favourite
Guest house in Osprey
Our Paradise Place in Osprey
5.0 out of 5 average rating, 18 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Aug
Guest favourite
Home in Nokomis
Blue Heron Near Nokomis Beach
4.92 out of 5 average rating, 13 reviews, 3 bedrooms, 4 beds, 2 bathrooms
21–26 Jul
Top guest favourite
Flat in Nokomis
The Hub
4.97 out of 5 average rating, 35 reviews, 1 bedroom, 1 bed, 1 bathroom
20–25 Jul
Home in Nokomis
Amazing family paradise escape
2 bedrooms, 2 bathrooms
28 Jul – 4 Aug
Guest favourite
Home in Nokomis
Serenity on Stilts
4.89 out of 5 average rating, 9 reviews, 2 bedrooms, 3 beds, 2 bathrooms
22–27 Jul