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Search results; Over 1,000 homes in Osprey

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Top guest favourite
Cottage in Osprey
Mattie’s Cottage by the Bay
1 bedroom, 1 bed, 1 private bathroom
24–29 Sept
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4.94 out of 5 average rating, 96 reviews
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Top guest favourite
Home in Osprey
Charming Florida Cottage - Kayaks Included
2 bedrooms, 2 king beds, 2 bathrooms
19–24 Sept
4.97 out of 5 average rating, 66 reviews
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Guest favourite
Home in Osprey
Nokomis & Siesta Key Sand Dollar Retreat
2 bedrooms, 3 beds, 1 bathroom
19–24 Sept
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
20–25 Sept
5.0 out of 5 average rating, 18 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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Guest favourite
Flat in Osprey
Windsor Lodge Unit #18, studio
1 bedroom, 1 king bed, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 7 reviews
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Home in Nokomis
Nokomis Sunset Retreat w/Patio 8 mins to Beach
1 bedroom, 2 beds, 1 bathroom
19–24 Sept
New place to stay
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Home in Osprey
Have your TINY house experience before you go TINY
1 queen bed, 1 bathroom
19–24 Sept
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Top guest favourite
Home in Nokomis
The Bayshore Beach Get Away
2 bedrooms, 2 beds, 2 bathrooms
20–25 Sept
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, 2 bathrooms
19–24 Sept
5.0 out of 5 average rating, 47 reviews
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Top guest favourite
Home in Nokomis
Nokomis Serenity Oasis
3 bedrooms, 4 beds, 2 bathrooms
21–27 Sept
5.0 out of 5 average rating, 15 reviews
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Guest favourite
Townhouse in Nokomis
Nokomis Escape! Close to Beach, Relaxation & Eats
3 bedrooms, 4 beds, 2 bathrooms
19–24 Sept
5.0 out of 5 average rating, 5 reviews
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Top guest favourite
Home in Nokomis
Updated house close to the Beach
2 bedrooms, 3 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 33 reviews
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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
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Top guest favourite
Home in Nokomis
Peaceful Getaway just minutes from the beach
3 bedrooms, 5 beds, 2 bathrooms
15–20 Nov
4.98 out of 5 average rating, 119 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, 2 bathrooms
29 Sept – 4 Oct
4.97 out of 5 average rating, 37 reviews
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Top guest favourite
Home in Sarasota
Mid-Mod Coastal Charm - 10 mins to Siesta Key!
2 bedrooms, 3 beds, 2 bathrooms
19–24 Sept
5.0 out of 5 average rating, 32 reviews
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Home in Sarasota
Cozy Sarasota Getaway.
2 bedrooms, 3 beds, 2 bathrooms
19–26 Sept
5.0 out of 5 average rating, 4 reviews
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Top guest favourite
Villa in Sarasota
Vacation Villa/Resort Pool 4 miles to Siesta Key
2 bedrooms, 3 beds, 2 bathrooms
28 Sept – 3 Oct
4.98 out of 5 average rating, 50 reviews