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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
11–16 Sept
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4.94 out of 5 average rating, 95 reviews
Home in Nokomis
Nokomis Sunset Retreat w/Pool - 8 mins to Beach
2 bedrooms, 4 beds, 2 bathrooms
22–27 Oct
New place to stay
Home in Nokomis
Nokomis Sunset Retreat w/Patio 8 mins to Beach
1 bedroom, 2 beds, 1 bathroom
14–19 Sept
New place to stay
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
Apartment in Nokomis
Family Friendly Beach Condo
3 bedrooms, 6 beds, 2.5 bathrooms
11–16 Sept
5.0 out of 5 average rating, 89 reviews
Top guest favourite
Cottage in Nokomis
Staycation Sanctuary
1 bedroom, 2 beds, 1 bathroom
11–16 Sept
4.98 out of 5 average rating, 189 reviews
Top guest favourite
Home in Nokomis
Close to Beaches~ Downtown Venice~Bike Trail~Park
3 bedrooms, 4 beds, 2 bathrooms
15–20 Sept
5.0 out of 5 average rating, 47 reviews
Top guest favourite
Camper van/Motorhome in Nokomis
"Nokomis Key" - Golf Cart Included (FREE)
1 bedroom, 4 beds, 1 bathroom
29 Sept – 4 Oct
4.91 out of 5 average rating, 81 reviews
Guest favourite
Home in Osprey
Nokomis & Siesta Key Sand Dollar Retreat
2 bedrooms, 3 beds, 1 bathroom
11–16 Sept
4.94 out of 5 average rating, 33 reviews
Flat in Sarasota
Exclusive Living in Sarasota near Siesta Keys
1 bedroom, 1 queen bed, 1 bathroom
16–21 Sept
Top guest favourite
Home in Venice
Venice Island Home w Heated Pool
2 bedrooms, 3 beds, 2 bathrooms
11–16 Sept
4.99 out of 5 average rating, 91 reviews
Flat in Nokomis
Modern 2BR Apt | 5-Min Drive to Nokomis Beach
2 bedrooms, 2 beds, 1 bathroom
11–16 Sept
New place to stay
Top guest favourite
Apartment in Sarasota
Peaceful retreat, pool, hot tub, near Siesta Key!
2 bedrooms, 3 beds, 2 bathrooms
14–19 Sept
4.96 out of 5 average rating, 83 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
Coastal Retreat, 2 Blocks to Beach, Dining & More
2 bedrooms, 5 beds, 1 bathroom
11–16 Sept
5.0 out of 5 average rating, 43 reviews
Top guest favourite
Home in Sarasota
Mid-Mod Coastal Charm - 10 mins to Siesta Key!
2 bedrooms, 3 beds, 2 bathrooms
16–21 Sept
5.0 out of 5 average rating, 32 reviews
Guest favourite
Flat in Osprey
Windsor Lodge Unit #18, studio
1 bedroom, 1 king bed, 1 bathroom
12–17 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Nokomis
Peaceful Getaway just minutes from the beach
3 bedrooms, 5 beds, 2 bathrooms
1–6 Nov
4.98 out of 5 average rating, 119 reviews
Guest favourite
Home in Nokomis
Relax and Unwind!
3 bedrooms, 6 beds, 2 bathrooms
11–16 Sept
4.98 out of 5 average rating, 46 reviews