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Search results; Over 1,000 homes in Osprey

Top guest favourite
Home in Osprey
Charming Florida Cottage - Kayaks Included
2 bedrooms, 2 beds, 2 private bathrooms
18–23 Sept
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4.97 out of 5 average rating, 65 reviews
Guest favourite
Home in Osprey
Nokomis & Siesta Key Sand Dollar Retreat
2 bedrooms, 3 beds, 1 bathroom
15–20 Sept
4.94 out of 5 average rating, 33 reviews
Home in Nokomis
Nokomis Sunset Retreat w/Patio 8 mins to Beach
1 bedroom, 2 beds, 1 bathroom
15–20 Sept
New place to stay
Home in Nokomis
Nokomis Sunset Retreat w/Pool - 8 mins to Beach
2 bedrooms, 4 beds, 2 bathrooms
30 Oct – 4 Nov
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Guest house in Osprey
Our Paradise Place in Osprey
1 bedroom, 1 bed, 1 bathroom
16–21 Sept
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Home in Nokomis
Close to Beaches~ Downtown Venice~Bike Trail~Park
3 bedrooms, 4 beds, 2 bathrooms
15–20 Sept
5.0 out of 5 average rating, 47 reviews
Guest favourite
Townhouse in Nokomis
Nokomis Escape! Close to Beach, Relaxation & Eats
3 bedrooms, 4 beds, 2 bathrooms
15–20 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Nokomis
Nokomis Serenity Oasis
3 bedrooms, 4 beds, 2 bathrooms
17–23 Sept
5.0 out of 5 average rating, 15 reviews
Home in Nokomis
3BR Townhome with community pool Beaches close by
3 bedrooms, 3 beds, 2.5 bathrooms
15–20 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Nokomis
La Niña 5 minutes to Nokomis Beach Fenced In Yard
3 bedrooms, 5 beds, 2 bathrooms
15–20 Sept
4.97 out of 5 average rating, 37 reviews
Top guest favourite
Home in Sarasota
Mid-Mod Coastal Charm - 10 mins to Siesta Key!
2 bedrooms, 3 beds, 2 bathrooms
16–21 Sept
5.0 out of 5 average rating, 32 reviews
Guest favourite
Flat in Osprey
Windsor Lodge Unit #18, studio
1 bedroom, 1 king bed, 1 bathroom
16–21 Sept
5.0 out of 5 average rating, 7 reviews
Home in Sarasota
Cozy Sarasota Getaway.
2 bedrooms, 3 beds, 2 bathrooms
15–22 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Nokomis
Updated house close to the Beach
2 bedrooms, 3 beds, 1 bathroom
16–21 Sept
5.0 out of 5 average rating, 33 reviews
Top guest favourite
Home in Nokomis
Coastal Retreat, 2 Blocks to Beach, Dining & More
2 bedrooms, 5 beds, 1 bathroom
15–20 Sept
5.0 out of 5 average rating, 43 reviews
Top guest favourite
Cottage in Nokomis
Staycation Sanctuary
1 bedroom, 2 beds, 1 bathroom
25–30 Sept
4.98 out of 5 average rating, 189 reviews
Cottage in Sarasota
Private 1BR with Patio Near Siesta Key
1 bedroom, 1 queen bed, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Venice
Venice Island Home w Heated Pool
2 bedrooms, 3 beds, 2 bathrooms
15–20 Sept
4.99 out of 5 average rating, 91 reviews
Home in Osprey
Have your TINY house experience before you go TINY
1 queen bed, 1 bathroom
19–24 Sept