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Search results; Over 1,000 homes in Osprey

Top guest favourite
Guest house in Osprey
Terrific Treehouse by the Bay
1 bedroom, 1 bed, 1 private bathroom
3–8 Aug
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4.99 out of 5 average rating, 141 reviews
Top guest favourite
Home in Osprey
Charming Florida Cottage - Kayaks Included
4.97 out of 5 average rating, 63 reviews, 2 bedrooms, 2 beds, 2 bathrooms
14–19 Jul
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
13–18 Jul
Top guest favourite
Home in Sarasota
Family-Friendly Retreat Near Siesta Key+Beach Gear
4.97 out of 5 average rating, 69 reviews, 3 bedrooms, 3 beds, 3 bathrooms
31 Aug – 5 Sept
Top guest favourite
Home in Nokomis
The Nautilus Hacienda
5.0 out of 5 average rating, 45 reviews, 3 bedrooms, 3 beds, 2 bathrooms
14–19 Jul
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
14–20 Jul
Top guest favourite
Home in Nokomis
Coastal Retreat, 2 Blocks to Beach, Dining & More
5.0 out of 5 average rating, 38 reviews, 2 bedrooms, 5 beds, 1 bathroom
13–18 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
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
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
13–18 Jul
Top guest favourite
Home in Venice
Baycrest Bungalow | Walk to Beaches & Shops on Ven
5.0 out of 5 average rating, 12 reviews, 2 bedrooms, 3 beds, 2 bathrooms
15–20 Jul
Home in Sarasota
Siesta Key Oasis| Hot tub| Fire Pit| BBQ| Games
New place to stay, 3 bedrooms, 5 beds, 2 bathrooms
19–24 Jul
Top guest favourite
Apartment in Sarasota
Peaceful retreat, pool, hot tub, near Siesta Key!
4.96 out of 5 average rating, 81 reviews, 2 bedrooms, 6 beds, 2 bathrooms
17–22 Jul
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
13–18 Jul
Superhost
Home in Sarasota
The Siesta Key Retreat - An Island Garden Oasis!
New place to stay, 4 bedrooms, 4 beds, 2 bathrooms
26–31 Jul
Home in Nokomis
Amazing family paradise escape
2 bedrooms, 2 bathrooms
28 Jul – 4 Aug
Top guest favourite
Home in Sarasota
Freda’s Sarasota Oasis! Private Pool & Lounge Area
4.94 out of 5 average rating, 17 reviews, 3 bedrooms, 5 beds, 3 bathrooms
13–18 Jul
Top guest favourite
Home in Nokomis
Cool ranch home w/heated pool near beach
5.0 out of 5 average rating, 13 reviews, 2 bedrooms, 4 beds, 2 bathrooms
17–22 Jul
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
18–23 Jul