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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
18–23 Sept
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4.97 out of 5 average rating, 65 reviews
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Guest favourite
Home in Osprey
Nokomis & Siesta Key Sand Dollar Retreat
2 bedrooms, 3 beds
17–22 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
18–23 Sept
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
18–23 Sept
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
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
17–22 Sept
New place to stay
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Home in Osprey
Have your TINY house experience before you go TINY
1 queen bed
19–24 Sept
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Guest favourite
Townhouse in Nokomis
Nokomis Escape! Close to Beach, Relaxation & Eats
3 bedrooms, 4 beds
17–22 Sept
5.0 out of 5 average rating, 5 reviews
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Top guest favourite
Guest house in Nokomis
Pineapple and Palms
2 bedrooms, 2 queen beds
22–28 Nov
5.0 out of 5 average rating, 10 reviews
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Top guest favourite
Home in Nokomis
Close to Beaches~ Downtown Venice~Bike Trail~Park
3 bedrooms, 4 beds
17–22 Sept
5.0 out of 5 average rating, 47 reviews
Photo 1 of 29
Top guest favourite
Home in Nokomis
Nokomis Serenity Oasis
3 bedrooms, 4 beds
19–25 Sept
5.0 out of 5 average rating, 15 reviews
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Top guest favourite
Home in Sarasota
Mid-Mod Coastal Charm - 10 mins to Siesta Key!
2 bedrooms, 3 beds
17–22 Sept
5.0 out of 5 average rating, 32 reviews
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Top guest favourite
Home in Nokomis
Peaceful Getaway just minutes from the beach
3 bedrooms, 5 beds
15–20 Nov
4.98 out of 5 average rating, 119 reviews
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Home in Sarasota
Cozy Sarasota Getaway.
2 bedrooms, 3 beds
17–24 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
18–23 Sept
5.0 out of 5 average rating, 33 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
29 Sept – 4 Oct
4.97 out of 5 average rating, 37 reviews
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Townhouse in Nokomis
Cozy, coastal retreat just minutes from shoreline!
3 bedrooms, 4 beds
17–24 Sept
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Guest favourite
Apartment in Sarasota
Peaceful Glamorous 2 Bed Resort
2 bedrooms, 3 beds
1–6 Nov
4.96 out of 5 average rating, 84 reviews
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Guest favourite
Home in Nokomis
Nirvana In Nokomis
3 bedrooms, 4 beds
18–23 Sept
4.87 out of 5 average rating, 38 reviews