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Search results; Over 1,000 homes in Osprey

Top guest favourite
Home in Osprey
Sarasota vacation Home!
3 bedrooms, 5 beds, 2.5 private bathrooms
25–30 Aug
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4.98 out of 5 average rating, 55 reviews
Top guest favourite
Home in Osprey
Nokomis & Siesta Key Sand Dollar Retreat
2 bedrooms, 3 beds
19–24 Aug
4.94 out of 5 average rating, 33 reviews
Top guest favourite
Home in Osprey
Charming Florida Cottage - Kayaks Included
2 bedrooms, 2 king beds
1–6 Sept
4.97 out of 5 average rating, 64 reviews
Guest favourite
Flat in Osprey
Windsor Lodge Unit #18, studio
1 bedroom, 1 king bed
20–25 Aug
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Nokomis
Close to Beaches~ Downtown Venice~Bike Trail~Park
3 bedrooms, 4 beds
19–24 Aug
5.0 out of 5 average rating, 46 reviews
Top guest favourite
Guest house in Osprey
Our Paradise Place in Osprey
1 bedroom, 1 bed
20–25 Aug
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
19–24 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Sarasota
Mid-Mod Coastal Charm - 10 mins to Siesta Key!
2 bedrooms, 3 beds
19–24 Aug
5.0 out of 5 average rating, 32 reviews
Top guest favourite
Home in Nokomis
Cool ranch home w/heated pool near beach
2 bedrooms, 4 beds
19–24 Aug
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Home in Nokomis
The Nautilus Hacienda
3 bedrooms, 3 beds
29 Aug – 3 Sept
5.0 out of 5 average rating, 47 reviews
Top guest favourite
Cottage in Sarasota
Bee Keepers Cottage
2 bedrooms, 3 beds
22–27 Aug
4.97 out of 5 average rating, 72 reviews
Top guest favourite
Home in Sarasota
Books Tide Retreat - minutes from Siesta Beach
2 bedrooms, 2 beds
30 Aug – 4 Sept
4.93 out of 5 average rating, 61 reviews
Top guest favourite
Home in Sarasota
The Palms Away
2 bedrooms, 2 beds
19–24 Aug
5.0 out of 5 average rating, 38 reviews
Guest favourite
Home in Sarasota
Sunshine Slowdown
3 bedrooms, 5 beds
19–24 Aug
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Home in Nokomis
La Niña 5 minutes to Nokomis Beach Fenced In Yard
3 bedrooms, 5 beds
19–24 Aug
4.97 out of 5 average rating, 35 reviews
Home in Sarasota
Furnished Model Home – Skye Ranch
2 bedrooms, 2 beds
10–15 Sept
Top guest favourite
Home in Nokomis
Peaceful Getaway just minutes from the beach
3 bedrooms, 5 beds
25–30 Aug
4.98 out of 5 average rating, 119 reviews
Home in Sarasota
Siesta Key Fully-Renovated Unit 5 min to the beach
2 beds
19–24 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Nokomis
The Pineapple Escape
3 bedrooms, 4 beds
24–29 Aug
4.99 out of 5 average rating, 74 reviews