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Search results; Over 1,000 homes in Osprey

Top guest favourite
Guest house in Osprey
Cozy Cottage by the Bay
1 bedroom, 1 bed, 1 private bathroom
13–18 Aug
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4.99 out of 5 average rating, 364 reviews
Top guest favourite
Home in Osprey
Nokomis & Siesta Key Sand Dollar Retreat
2 bedrooms, 3 beds, 1 bathroom
16–21 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, 2 bathrooms
9–14 Aug
4.97 out of 5 average rating, 64 reviews
Guest favourite
Flat in Osprey
Windsor Lodge Unit #18, studio
1 bedroom, 1 king bed, 1 bathroom
10–15 Aug
5.0 out of 5 average rating, 7 reviews
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Home in Nokomis
Close to Beaches~ Downtown Venice~Bike Trail~Park
3 bedrooms, 4 beds, 2 bathrooms
11–16 Aug
5.0 out of 5 average rating, 45 reviews
Guest favourite
Townhouse in Nokomis
Nokomis Escape! Close to Beach, Relaxation & Eats
3 bedrooms, 4 beds, 2 bathrooms
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, 2 bathrooms
9–14 Aug
5.0 out of 5 average rating, 31 reviews
Top guest favourite
Guest house in Osprey
Our Paradise Place in Osprey
1 bedroom, 1 bed, 1 bathroom
10–15 Aug
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Place to stay in Nokomis
Sunshine Cottage
1 bedroom, 2 beds, 1 bathroom
21–26 Aug
5.0 out of 5 average rating, 30 reviews
Guest favourite
Villa in Sarasota
Sarasota Villa with Pool Access Tennis Near Beach
2 bedrooms, 3 beds, 2 bathrooms
9–16 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Nokomis
The Nautilus Hacienda
3 bedrooms, 3 beds, 2 bathrooms
10–15 Aug
5.0 out of 5 average rating, 47 reviews
Top guest favourite
Home in Nokomis
Charming vacation home, short walk to the beach
2 bedrooms, 5 beds, 2 bathrooms
10–15 Aug
4.97 out of 5 average rating, 131 reviews
Top guest favourite
Home in Nokomis
Cool ranch home w/heated pool near beach
2 bedrooms, 4 beds, 2 bathrooms
18–23 Aug
5.0 out of 5 average rating, 15 reviews
Guest favourite
Apartment in Sarasota
Peaceful Glamorous 2 Bed Resort
2 bedrooms, 3 beds, 2 bathrooms
9–14 Aug
4.96 out of 5 average rating, 84 reviews
Home in Sarasota
Siesta Key Fully-Renovated Unit 5 min to the beach
2 beds, 1 bathroom
9–14 Aug
5.0 out of 5 average rating, 4 reviews
Home in Sarasota
Amazing Heated Pool & Game Room
3 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
Apartment in Sarasota
Renovated - Spanish Pine Villa #210
2 bedrooms, 3 beds, 2 bathrooms
4–9 Sept
Top guest favourite
Cottage in Nokomis
Pink Pineapple Cottage
1 bedroom, 2 beds, 1 bathroom
9–14 Aug
4.99 out of 5 average rating, 85 reviews
Top guest favourite
Home in Nokomis
Nokomis Serenity Oasis
3 bedrooms, 3 beds, 2 bathrooms
27 Aug – 2 Sept
5.0 out of 5 average rating, 14 reviews