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Search results; Over 1,000 homes in Osprey

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Superhost
Home in Osprey
Pet-Friendly Modern Retreat Near Siesta Key
3 bedrooms, 6 beds, 2.5 private bathrooms
19–24 Oct
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4.83 out of 5 average rating, 42 reviews
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Guest favourite
Home in Osprey
Nokomis & Siesta Key Sand Dollar Retreat
2 bedrooms, 3 beds
1–6 Oct
4.94 out of 5 average rating, 33 reviews
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Top guest favourite
Home in Osprey
Charming Florida Cottage - Kayaks Included
2 bedrooms, 2 king beds
1–6 Oct
4.97 out of 5 average rating, 66 reviews
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Home in Nokomis
Nokomis Sunset Retreat w/Pool - 8 mins to Beach
2 bedrooms, 4 beds
30 Oct – 4 Nov
5.0 out of 5 average rating, 3 reviews
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Home in Nokomis
3BR Townhome with community pool Beaches close by
3 bedrooms, 3 beds
1–6 Oct
5.0 out of 5 average rating, 4 reviews
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Top guest favourite
Guest house in Osprey
Our Paradise Place in Osprey
1 bedroom, 1 bed
1–6 Oct
5.0 out of 5 average rating, 18 reviews
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Top guest favourite
Home in Nokomis
Close to Beaches~ Downtown Venice~Bike Trail~Park
3 bedrooms, 4 beds
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
1–7 Oct
5.0 out of 5 average rating, 15 reviews
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Home in Nokomis
Nokomis Sunset Retreat w/Patio 8 mins to Beach
1 bedroom, 2 beds
1–6 Oct
New place to stay
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Home in Venice
Venice Island Pool Home!
4 bedrooms, 5 beds
1–6 Oct
New place to stay
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Guest favourite
Villa in Sarasota
Sarasota Villa with Pool Access Tennis Near Beach
2 bedrooms, 3 beds
1–8 Oct
5.0 out of 5 average rating, 5 reviews
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Top guest favourite
Home in Nokomis
La Niña 5 minutes to Nokomis Beach Fenced In Yard
3 bedrooms, 5 beds
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
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
4–9 Oct
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Home in Sarasota
Palm Tree Haven
2 bedrooms, 2 beds
4–9 Oct
4.99 out of 5 average rating, 105 reviews
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Home in Osprey
Have your TINY house experience before you go TINY
1 queen bed
1–6 Oct
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Home in Sarasota
*BRAND NEW* heated pool, golf course views
3 bedrooms, 4 beds
20–25 Oct
New place to stay
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Guest favourite
Flat in Osprey
Windsor Lodge Unit #18, studio
1 bedroom, 1 king bed
1–6 Oct
5.0 out of 5 average rating, 7 reviews
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Flat in Nokomis
Modern 2BR Apt | 5-Min Drive to Nokomis Beach
2 bedrooms, 2 beds
5–10 Oct
New place to stay