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Search results; Over 1,000 homes in Osprey

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, 145 reviews
Top guest favourite
Guest house in Osprey
Our Paradise Place in Osprey
1 bedroom, 1 bed, 1 bathroom
14–19 Sept
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Home in Osprey
Nokomis & Siesta Key Sand Dollar Retreat
2 bedrooms, 3 beds, 1 bathroom
9–14 Sept
4.94 out of 5 average rating, 33 reviews
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
Guest favourite
Flat in Osprey
Windsor Lodge Unit #18, studio
1 bedroom, 1 king bed, 1 bathroom
10–15 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Nokomis
Nokomis Serenity Oasis
3 bedrooms, 3 beds, 2 bathrooms
11–17 Sept
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Home in Nokomis
Cool home w/heated pool near beach
2 bedrooms, 4 beds, 2 bathrooms
9–14 Sept
5.0 out of 5 average rating, 17 reviews
Guest favourite
Townhouse in Nokomis
Nokomis Escape! Close to Beach, Relaxation & Eats
3 bedrooms, 4 beds, 2 bathrooms
15–20 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Nokomis
The Pineapple Escape
3 bedrooms, 4 beds, 2 bathrooms
10–15 Sept
4.99 out of 5 average rating, 76 reviews
Top guest favourite
Home in Nokomis
Updated house close to the Beach
2 bedrooms, 3 beds, 1 bathroom
10–15 Sept
5.0 out of 5 average rating, 33 reviews
Home in Nokomis
3BR Townhome with community pool Beaches close by
3 bedrooms, 3 beds, 2.5 bathrooms
15–20 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Nokomis
Close to Beaches~ Downtown Venice~Bike Trail~Park
3 bedrooms, 4 beds, 2 bathrooms
16–21 Sept
5.0 out of 5 average rating, 47 reviews
Top guest favourite
Home in Sarasota
Spacious Cozy Tropical Retreat!
2 bedrooms, 3 beds, 2 bathrooms
10–15 Sept
5.0 out of 5 average rating, 32 reviews
Top guest favourite
Home in Nokomis
Coastal Retreat, 2 Blocks to Beach, Dining & More
2 bedrooms, 5 beds, 1 bathroom
9–14 Sept
5.0 out of 5 average rating, 42 reviews
Top guest favourite
Home in Sarasota
Books Tide Retreat - minutes from Siesta Beach
2 bedrooms, 2 beds, 2 bathrooms
9–14 Sept
4.94 out of 5 average rating, 65 reviews
Home in Sarasota
Cozy Sarasota Getaway.
2 bedrooms, 3 beds, 2 bathrooms
9–16 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Nokomis
You get 2 homes! Beach house w/bonus guest house!
4 bedrooms, 4 beds, 3 bathrooms
22–27 Nov
4.97 out of 5 average rating, 35 reviews
Townhouse in Nokomis
Cozy, coastal retreat just minutes from shoreline!
3 bedrooms, 4 beds, 2.5 bathrooms
15–22 Sept
Flat in Sarasota
Exclusive Living in Sarasota near Siesta Keys
1 bedroom, 1 queen bed, 1 bathroom
16–21 Sept