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Search results; Over 1,000 homes in Osprey

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Top guest favourite
Home in Osprey
5 mins to the beach! Come relax!
3 bedrooms, 4 beds, 2 bathrooms
1–6 Sept
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5.0 out of 5 average rating, 30 reviews
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Home in Nokomis
Nokomis Sunset Retreat w/Pool - 8 mins to Beach
2 bedrooms, 4 beds, 2 bathrooms
12–17 Sept
New place to stay
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Home in Osprey
Charming Florida Cottage - Kayaks Included
2 bedrooms, 2 king beds, 2 bathrooms
1–6 Sept
4.97 out of 5 average rating, 64 reviews
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Home in Osprey
Nokomis & Siesta Key Sand Dollar Retreat
2 bedrooms, 3 beds, 1 bathroom
1–6 Sept
4.94 out of 5 average rating, 33 reviews
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Apartment in Nokomis
Family Friendly Beach Condo
3 bedrooms, 6 beds, 2.5 bathrooms
6–11 Sept
5.0 out of 5 average rating, 88 reviews
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Top guest favourite
Home in Nokomis
Peaceful Getaway just minutes from the beach
3 bedrooms, 5 beds, 2 bathrooms
1–6 Sept
4.98 out of 5 average rating, 119 reviews
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Guest house in Osprey
Our Paradise Place in Osprey
1 bedroom, 1 bed, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 18 reviews
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Flat in Osprey
Windsor Lodge Unit #18, studio
1 bedroom, 1 king bed, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 7 reviews
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Top guest favourite
Home in Nokomis
Close to Beaches~ Downtown Venice~Bike Trail~Park
3 bedrooms, 4 beds, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 46 reviews
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Home in Sarasota
Mid-Mod Coastal Charm - 10 mins to Siesta Key!
2 bedrooms, 3 beds, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 32 reviews
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Apartment in Sarasota
Waterfront w/ Pool, mins to SK Beaches, bikes/sups
2 bedrooms, 2 beds, 1 bathroom
2–7 Sept
4.94 out of 5 average rating, 34 reviews
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Home in Venice
Venice Island Home w Heated Pool
2 bedrooms, 3 beds, 2 bathrooms
9–14 Sept
4.99 out of 5 average rating, 91 reviews
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Home in Nokomis
Amazing family paradise escape
2 bedrooms, 2 bathrooms
19–26 Sept
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Guest favourite
Townhouse in Nokomis
Nokomis Escape! Close to Beach, Relaxation & Eats
3 bedrooms, 4 beds, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 5 reviews
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Cottage in Nokomis
Staycation Sanctuary
1 bedroom, 2 beds, 1 bathroom
7–12 Sept
4.98 out of 5 average rating, 188 reviews
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Holiday home in Nokomis
Family Beach Vibes, Walk to Beach, Dining & More
3 bedrooms, 3 beds, 2 bathrooms
16–21 Sept
4.98 out of 5 average rating, 125 reviews
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Camper van/Motorhome in Nokomis
"Nokomis Key" - Golf Cart Included (FREE)
1 bedroom, 4 beds, 1 bathroom
26 Sept – 1 Oct
4.91 out of 5 average rating, 79 reviews
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Home in Nokomis
Pet Friendly With Resort Amenities
2 bedrooms, 3 beds, 1 bathroom
2–7 Sept
4.78 out of 5 average rating, 9 reviews
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Top guest favourite
Home in Nokomis
Cool home w/heated pool near beach
2 bedrooms, 4 beds, 2 bathrooms
3–8 Sept
5.0 out of 5 average rating, 17 reviews