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Search results; Over 1,000 homes in Osprey

Descriptions are based on details hosts provide
Guest favourite
Home in Osprey
LIME ON GREEN Osprey, Florida 34229
2 bedrooms, 3 beds, 1 private bathroom
15–20 Jul
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4.84 out of 5 average rating, 92 reviews
Top guest favourite
Home in Osprey
Old Florida cottage with kayak bay access
4.97 out of 5 average rating, 63 reviews, 2 bedrooms, 2 beds, 2 bathrooms
15–20 Jul
Top guest favourite
Cottage in Nokomis
Staycation Sanctuary
4.98 out of 5 average rating, 185 reviews, 1 bedroom, 2 beds, 1 bathroom
27 Jul – 1 Aug
Top guest favourite
Home in Nokomis
Saltwater pool and fruit trees near beach
5.0 out of 5 average rating, 12 reviews, 3 bedrooms, 3 beds, 2 bathrooms
28 Jul – 3 Aug
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
15–20 Jul
Top guest favourite
Home in Nokomis
Remodeled with a fenced yard and fire pit
4.97 out of 5 average rating, 34 reviews, 3 bedrooms, 5 beds, 2 bathrooms
26–31 Jul
Guest favourite
Home in Sarasota
Mid-Mod Coastal Charm - 10 mins to Siesta Key!
5.0 out of 5 average rating, 29 reviews, 2 bedrooms, 3 beds, 2 bathrooms
5–10 Aug
Top guest favourite
Guest house in Osprey
Private pool, two doors from the bay
5.0 out of 5 average rating, 18 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Aug
Top guest favourite
Townhouse in Nokomis
Heated Pool • Lakeview Escape • Near Nokomis Beach
5.0 out of 5 average rating, 16 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
29 Aug – 5 Sept
Top guest favourite
Apartment in Nokomis
Waterfront with kayaks near Nokomis Beach
5.0 out of 5 average rating, 61 reviews, 1 bedroom, 1 bed, 1 bathroom
10–15 Sept
Townhouse in Nokomis
Newly furnished and under 2 miles to beach
3 bedrooms, 4 beds, 2.5 bathrooms
1–6 Feb
Guest favourite
Flat in Sarasota
Family Nest Sarasota Beach | Pool • Tennis • Bikes
5.0 out of 5 average rating, 6 reviews, 2 bedrooms, 3 beds, 2 bathrooms
19–24 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
Gated golf-course home with private pool
5.0 out of 5 average rating, 8 reviews, 4 bedrooms, 4 beds, 3 bathrooms
15–21 Jul
Guest favourite
Home in Nokomis
Blue Heron Near Nokomis Beach
4.92 out of 5 average rating, 12 reviews, 3 bedrooms, 4 beds, 2 bathrooms
15–20 Jul
Apartment in Sarasota
Resort community minutes from Siesta Key
2 bedrooms, 3 beds, 2 bathrooms
31 Aug – 5 Sept
Top guest favourite
Guest house in Nokomis
Coastal Charm on Dona Bay walk to Venice hot spots
4.95 out of 5 average rating, 22 reviews, 1 bedroom, 2 beds, 1 bathroom
15–20 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
15–20 Jul
Top guest favourite
Home in Nokomis
2 blocks from Nokomis Beach
5.0 out of 5 average rating, 38 reviews, 2 bedrooms, 5 beds, 1 bathroom
19–24 Jul