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Search results; Over 1,000 homes in Osprey

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
Charming Florida Cottage - Kayaks Included
4.97 out of 5 average rating, 64 reviews, 2 bedrooms, 2 beds, 2 bathrooms
15–20 Jul
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Cottage in Nokomis
Staycation Sanctuary
4.98 out of 5 average rating, 185 reviews, 1 bedroom, 2 beds, 1 bathroom
27 Jul – 1 Aug
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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
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Home in Nokomis
Nokomis Serenity Oasis
5.0 out of 5 average rating, 12 reviews, 3 bedrooms, 3 beds, 2 bathrooms
28 Jul – 3 Aug
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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
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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
La Niña 5 minutes to Nokomis Beach Fenced In Yard
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
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Apartment in Nokomis
Private Studio (entire space)
5.0 out of 5 average rating, 61 reviews, 1 bedroom, 1 bed, 1 bathroom
10–15 Sept
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Home in Nokomis
The Nautilus Hacienda
5.0 out of 5 average rating, 45 reviews, 3 bedrooms, 3 beds, 2 bathrooms
26–31 Jul
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Villa in Nokomis
Oasis Getaway -Beautiful House-Infinity Pool-Beach
4.98 out of 5 average rating, 51 reviews, 4 bedrooms, 5 beds, 3 bathrooms
8–13 Aug
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Holiday home in Nokomis
Family Beach Vibes, Walk to Beach, Dining & More
4.98 out of 5 average rating, 121 reviews, 3 bedrooms, 3 beds, 2 bathrooms
19–24 Jul
Townhouse in Nokomis
Cozy, coastal retreat just minutes from shoreline!
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
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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
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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
Top guest favourite
Apartment in Nokomis
Private Waterfront 2 Bedroom Condo
5.0 out of 5 average rating, 48 reviews, 2 bedrooms, 5 beds, 1.5 bathrooms
22–27 Jul
Apartment in Sarasota
Renovated - Spanish Pine Villa #210
2 bedrooms, 3 beds, 2 bathrooms
31 Aug – 5 Sept