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Search results; Over 1,000 homes in Osprey

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Top guest favourite
Guest house in Osprey
Terrific Treehouse by the Bay
1 bedroom, 1 bed, 1 private bathroom
9–14 Sept
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4.99 out of 5 average rating, 143 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
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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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 Nokomis
Nokomis Serenity Oasis
3 bedrooms, 3 beds, 2 bathrooms
11–17 Sept
5.0 out of 5 average rating, 14 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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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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Home in Nokomis
Cool home w/heated pool near beach
2 bedrooms, 4 beds, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 17 reviews
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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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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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Home in Nokomis
The Pineapple Escape
3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
4.99 out of 5 average rating, 75 reviews
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Home in Nokomis
3BR Townhome with community pool Beaches close by
3 bedrooms, 3 beds, 2.5 bathrooms
15–22 Sept
5.0 out of 5 average rating, 4 reviews
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Top guest favourite
Home in Nokomis
Updated house close to the Beach
2 bedrooms, 3 beds, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 33 reviews
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Flat in Sarasota
Exclusive Living in Sarasota near Siesta Keys
1 bedroom, 1 queen bed, 1 bathroom
16–21 Sept
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Apartment in Sarasota
Peaceful retreat, pool, hot tub, near Siesta Key!
2 bedrooms, 3 beds, 2 bathrooms
14–19 Sept
4.96 out of 5 average rating, 82 reviews
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Guest suite in Sarasota
Suite Spot in Gulf Gate
1 bedroom, 1 bed, 1 bathroom
1–6 Sept
4.96 out of 5 average rating, 47 reviews
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Townhouse in Nokomis
Cozy, coastal retreat just minutes from shoreline!
3 bedrooms, 4 beds, 2.5 bathrooms
15–22 Sept
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Villa in Nokomis
Sarasota Villa 1 min to BEACH, king/qn/Pets/Yard!
1 bedroom, 2 beds, 1 bathroom
1–6 Sept
4.96 out of 5 average rating, 115 reviews
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Home in Venice
2 Kitchens + Pool + Ping-Pong + Corn Hole + BBQ
3 bedrooms, 4 beds, 2.5 bathrooms
17–22 Oct
4.96 out of 5 average rating, 57 reviews