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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
Nokomis & Siesta Key Sand Dollar Retreat
4.94 out of 5 average rating, 33 reviews, 2 bedrooms, 3 beds, 1 bathroom
12–17 Jul
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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
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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
Home in Nokomis
The Nautilus Hacienda
5.0 out of 5 average rating, 45 reviews, 3 bedrooms, 3 beds, 2 bathrooms
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
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
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
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
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
Home in Nokomis
Family Friendly Salty Getaway, 3/2 private pool
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
Top guest favourite
Home in Nokomis
Coastal Retreat, 2 Blocks to Beach, Dining & More
5.0 out of 5 average rating, 37 reviews, 2 bedrooms, 5 beds, 1 bathroom
12–17 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
Home in Venice
Venice Island Home w Heated Pool
4.99 out of 5 average rating, 84 reviews, 2 bedrooms, 3 beds, 2 bathrooms
19–24 Jul
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Home in Nokomis
Updated house close to the Beach
5.0 out of 5 average rating, 33 reviews, 2 bedrooms, 3 beds, 1 bathroom
16–21 Jul
Guest favourite
Home in Sarasota
Classy Comfortable Villa in Picturesque Paradise
5.0 out of 5 average rating, 6 reviews, 2 bedrooms, 2 beds, 2 bathrooms
4–9 Aug
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
Home in Sarasota
Books Tide Retreat - minutes from Siesta Beach
4.96 out of 5 average rating, 53 reviews, 2 bedrooms, 2 beds, 2 bathrooms
9–14 Aug
Top guest favourite
Home in Nokomis
Peaceful Getaway just minutes from the beach
4.98 out of 5 average rating, 115 reviews, 3 bedrooms, 5 beds, 2 bathrooms
1–6 Aug