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Search results; Over 1,000 homes in Osprey

Photo 1 of 29
Top guest favourite
Home in Osprey
5 mins to the beach! Come relax!
3 bedrooms, 4 beds, 2 bathrooms
11–16 Sept
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5.0 out of 5 average rating, 30 reviews
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Home in Nokomis
Nokomis Sunset Retreat w/Pool - 8 mins to Beach
2 bedrooms, 4 beds, 2 bathrooms
12–17 Sept
New place to stay
Photo 1 of 29
Top guest favourite
Home in Osprey
Nokomis & Siesta Key Sand Dollar Retreat
2 bedrooms, 3 beds, 1 bathroom
1–6 Sept
4.94 out of 5 average rating, 33 reviews
Photo 1 of 29
Top guest favourite
Home in Osprey
Charming Florida Cottage - Kayaks Included
2 bedrooms, 2 king beds, 2 bathrooms
1–6 Sept
4.97 out of 5 average rating, 64 reviews
Photo 1 of 29
Top guest favourite
Home in Nokomis
Nokomis Serenity Oasis
3 bedrooms, 3 beds, 2 bathrooms
11–17 Sept
5.0 out of 5 average rating, 14 reviews
Photo 1 of 19
Guest favourite
Townhouse in Nokomis
Nokomis Escape! Close to Beach, Relaxation & Eats
3 bedrooms, 4 beds, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 5 reviews
Photo 1 of 29
Top guest favourite
Home in Nokomis
Close to Beaches~ Downtown Venice~Bike Trail~Park
3 bedrooms, 4 beds, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 46 reviews
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Top guest favourite
Home in Nokomis
Cool home w/heated pool near beach
2 bedrooms, 4 beds, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 17 reviews
Photo 1 of 29
Top guest favourite
Home in Sarasota
Spacious Cozy Tropical Retreat!
2 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 32 reviews
Photo 1 of 24
Guest favourite
Flat in Osprey
Windsor Lodge Unit #18, studio
1 bedroom, 1 king bed, 1 bathroom
2–7 Sept
5.0 out of 5 average rating, 7 reviews
Photo 1 of 13
Top guest favourite
Home in Nokomis
The Pineapple Escape
3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
4.99 out of 5 average rating, 75 reviews
Photo 1 of 29
Top guest favourite
Home in Sarasota
Mid-Mod Coastal Charm - 10 mins to Siesta Key!
2 bedrooms, 3 beds, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 32 reviews
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Guest favourite
Villa in Sarasota
Sarasota Villa with Pool Access Tennis Near Beach
2 bedrooms, 3 beds, 2 bathrooms
5–12 Sept
5.0 out of 5 average rating, 5 reviews
Photo 1 of 29
Top guest favourite
Apartment in Sarasota
Waterfront w/ Pool, mins to SK Beaches, bikes/sups
2 bedrooms, 2 beds, 1 bathroom
3–8 Sept
4.94 out of 5 average rating, 34 reviews
Photo 1 of 29
Home in Nokomis
3BR Townhome with community pool Beaches close by
3 bedrooms, 3 beds, 2.5 bathrooms
15–22 Sept
5.0 out of 5 average rating, 4 reviews
Photo 1 of 29
Top guest favourite
Home in Nokomis
Updated house close to the Beach
2 bedrooms, 3 beds, 1 bathroom
2–7 Sept
5.0 out of 5 average rating, 33 reviews
Photo 1 of 23
Top guest favourite
Home in Venice
Venice Island Home w Heated Pool
2 bedrooms, 3 beds, 2 bathrooms
9–14 Sept
4.99 out of 5 average rating, 91 reviews
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Home in Sarasota
Cozy Sarasota Getaway.
2 bedrooms, 3 beds, 2 bathrooms
1–8 Sept
5.0 out of 5 average rating, 4 reviews
Photo 1 of 29
Top guest favourite
Home in Nokomis
Coastal Retreat, 2 Blocks to Beach, Dining & More
2 bedrooms, 5 beds, 1 bathroom
4–9 Sept
5.0 out of 5 average rating, 42 reviews