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Search results; Over 1,000 homes in Osprey

Guest favourite
Home in Osprey
Creekside Paradise I
3 bedrooms, 3 beds, 2 private bathrooms
4–11 Sept
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4.96 out of 5 average rating, 52 reviews
Top guest favourite
Home in Osprey
Nokomis & Siesta Key Sand Dollar Retreat
2 bedrooms, 3 beds, 1 bathroom
20–25 Aug
4.94 out of 5 average rating, 33 reviews
Guest favourite
Flat in Osprey
Windsor Lodge Unit #18, studio
1 bedroom, 1 king bed, 1 bathroom
21–26 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, 2 bathrooms
20–25 Aug
5.0 out of 5 average rating, 46 reviews
Guest favourite
Townhouse in Nokomis
Nokomis Escape! Close to Beach, Relaxation & Eats
3 bedrooms, 4 beds, 2 bathrooms
20–25 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, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 32 reviews
Top guest favourite
Guest house in Osprey
Our Paradise Place in Osprey
1 bedroom, 1 bed, 1 bathroom
21–26 Aug
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Home in Nokomis
The Nautilus Hacienda
3 bedrooms, 3 beds, 2 bathrooms
29 Aug – 3 Sept
5.0 out of 5 average rating, 47 reviews
Top guest favourite
Home in Nokomis
Cool ranch home w/heated pool near beach
2 bedrooms, 4 beds, 2 bathrooms
20–25 Aug
5.0 out of 5 average rating, 17 reviews
Guest favourite
Home in Sarasota
Sunshine Slowdown
3 bedrooms, 5 beds, 2 bathrooms
20–25 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, 2 bathrooms
20–25 Aug
4.97 out of 5 average rating, 35 reviews
Home in Sarasota
Furnished Model Home – Skye Ranch
2 bedrooms, 2 beds, 2.5 bathrooms
10–15 Sept
Top guest favourite
Apartment in Sarasota
Peaceful retreat, pool, hot tub, near Siesta Key!
2 bedrooms, 6 beds, 2 bathrooms
26–31 Aug
4.96 out of 5 average rating, 81 reviews
Top guest favourite
Cottage in Nokomis
Staycation Sanctuary
1 bedroom, 2 beds, 1 bathroom
20–25 Aug
4.98 out of 5 average rating, 187 reviews
Guest favourite
Apartment in Sarasota
Peaceful Glamorous 2 Bed Resort
2 bedrooms, 3 beds, 2 bathrooms
20–25 Aug
4.96 out of 5 average rating, 84 reviews
Top guest favourite
Home in Nokomis
The Pineapple Escape
3 bedrooms, 4 beds, 2 bathrooms
24–29 Aug
4.99 out of 5 average rating, 74 reviews
Home in Sarasota
Siesta Key Fully-Renovated Unit 5 min to the beach
2 beds, 1 bathroom
27 Aug – 1 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Holiday home in Nokomis
Family Beach Vibes, Walk to Beach, Dining & More
3 bedrooms, 3 beds, 2 bathrooms
20–25 Aug
4.98 out of 5 average rating, 124 reviews
Top guest favourite
Apartment in Nokomis
Family Friendly Beach Condo
3 bedrooms, 6 beds, 2.5 bathrooms
22–27 Aug
5.0 out of 5 average rating, 88 reviews