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Search results; Over 1,000 homes in Osprey

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Top guest favourite
Home in Osprey
Charming Florida Cottage - Kayaks Included
2 bedrooms, 2 beds, 2 private bathrooms
1–6 Oct
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4.97 out of 5 average rating, 66 reviews
Photo 1 of 29
Guest favourite
Home in Osprey
Nokomis & Siesta Key Sand Dollar Retreat
2 bedrooms, 3 beds, 1 bathroom
1–6 Oct
4.94 out of 5 average rating, 33 reviews
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Top guest favourite
Guest house in Osprey
Our Paradise Place in Osprey
1 bedroom, 1 bed, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 18 reviews
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Guest favourite
Flat in Osprey
Windsor Lodge Unit #18, studio
1 bedroom, 1 king bed, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 7 reviews
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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
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Home in Nokomis
Nokomis Sunset Retreat w/Patio 8 mins to Beach
1 bedroom, 2 beds, 1 bathroom
1–6 Oct
New place to stay
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Home in Sarasota
Cozy Sarasota Getaway.
2 bedrooms, 3 beds, 2 bathrooms
1–8 Oct
5.0 out of 5 average rating, 4 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 Oct
5.0 out of 5 average rating, 32 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
6–11 Oct
5.0 out of 5 average rating, 48 reviews
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Top guest favourite
Home in Nokomis
Nokomis Serenity Oasis
3 bedrooms, 4 beds, 2 bathrooms
1–7 Oct
5.0 out of 5 average rating, 15 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
1–6 Oct
4.94 out of 5 average rating, 34 reviews
Photo 1 of 29
Top guest favourite
Home in Nokomis
Updated house close to the Beach
2 bedrooms, 3 beds, 1 bathroom
1–8 Oct
5.0 out of 5 average rating, 33 reviews
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Home in Nokomis
3BR Townhome with community pool Beaches close by
3 bedrooms, 3 beds, 2.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 4 reviews
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Flat in Nokomis
Modern 2BR Apt | 5-Min Drive to Nokomis Beach
2 bedrooms, 2 beds, 1 bathroom
5–10 Oct
New place to stay
Photo 1 of 29
Guest favourite
Apartment in Sarasota
Peaceful Glamorous 2 Bed Resort
2 bedrooms, 3 beds, 2 bathrooms
1–6 Nov
4.96 out of 5 average rating, 84 reviews
Photo 1 of 29
Top guest favourite
Home in Nokomis
La Niña 5 minutes to Nokomis Beach Fenced In Yard
3 bedrooms, 5 beds, 2 bathrooms
17–22 Oct
4.97 out of 5 average rating, 37 reviews
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Guest favourite
Townhouse in Nokomis
Nokomis Escape! Close to Beach, Relaxation & Eats
3 bedrooms, 4 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 5 reviews
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Cottage in Sarasota
Private 1BR with Patio Near Siesta Key
1 bedroom, 1 queen bed, 1 bathroom
4–9 Oct
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Home in Sarasota
The Palms Away
2 bedrooms, 2 beds, 1.5 bathrooms
17–22 Oct
5.0 out of 5 average rating, 39 reviews