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Search results; Over 1,000 homes in Osprey

Top guest favourite
Cottage in Osprey
Mattie’s Cottage by the Bay
1 bedroom, 1 bed, 1 private bathroom
10–15 Sept
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4.94 out of 5 average rating, 95 reviews
Guest favourite
Home in Osprey
Nokomis & Siesta Key Sand Dollar Retreat
2 bedrooms, 3 beds
10–15 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
12–17 Sept
New place to stay
Top guest favourite
Guest house in Osprey
Our Paradise Place in Osprey
1 bedroom, 1 bed
14–19 Sept
5.0 out of 5 average rating, 18 reviews
Guest favourite
Townhouse in Nokomis
Nokomis Escape! Close to Beach, Relaxation & Eats
3 bedrooms, 4 beds
15–20 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Nokomis
Close to Beaches~ Downtown Venice~Bike Trail~Park
3 bedrooms, 4 beds
16–21 Sept
5.0 out of 5 average rating, 47 reviews
Top guest favourite
Home in Nokomis
Nokomis Serenity Oasis
3 bedrooms, 3 beds
11–17 Sept
5.0 out of 5 average rating, 14 reviews
Home in Nokomis
3BR Townhome with community pool Beaches close by
3 bedrooms, 3 beds
15–20 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Nokomis
Cool home w/heated pool near beach
2 bedrooms, 4 beds
10–15 Sept
5.0 out of 5 average rating, 17 reviews
Guest favourite
Flat in Osprey
Windsor Lodge Unit #18, studio
1 bedroom, 1 king bed
10–15 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Nokomis
The Pineapple Escape
3 bedrooms, 4 beds
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
10–15 Sept
5.0 out of 5 average rating, 33 reviews
Guest favourite
Home in Nokomis
You get 2 homes! Beach house w/bonus guest house!
4 bedrooms, 4 beds
22–27 Nov
4.97 out of 5 average rating, 35 reviews
Home in Nokomis
Amazing family paradise escape
2 bedrooms
19–26 Sept
Top guest favourite
Villa in Sarasota
Vacation Villa/Resort Pool 4 miles to Siesta Key
2 bedrooms, 3 beds
20–25 Sept
4.98 out of 5 average rating, 50 reviews
Top guest favourite
Home in Sarasota
Books Tide Retreat - minutes from Siesta Beach
2 bedrooms, 2 beds
10–15 Sept
4.94 out of 5 average rating, 65 reviews
Top guest favourite
Home in Nokomis
Coastal Retreat, 2 Blocks to Beach, Dining & More
2 bedrooms, 5 beds
10–15 Sept
5.0 out of 5 average rating, 42 reviews
Flat in Nokomis
Modern 2BR Apt | 5-Min Drive to Nokomis Beach
2 bedrooms, 2 beds
10–15 Sept
New place to stay
Top guest favourite
Apartment in Sarasota
Lovely 2-Bedroom Condo, 7 min from Siesta Beach
2 bedrooms, 3 beds
26 Sept – 1 Oct
4.98 out of 5 average rating, 131 reviews