Search results; Over 1,000 homes in Osprey

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Guest favorite
Home in Osprey
Sarasota vacation Home!
8 guests3 bedrooms5 beds2.5 baths
Aug 15 – 20
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Aug 15 – 20
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R23,310 ZAR for 5 nights

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Top guest favorite
Guesthouse in Osprey
Private Coastal Getaway - Your Home Away from Home
2 queen beds
Aug 15 – 20
R13,171 ZAR for 5 nights
5.0 out of 5 average rating, 12 reviews
Top guest favorite
Guesthouse in Osprey
Cozy Cottage by the Bay
1 queen bed
Aug 19 – 24
R8,467 ZAR for 5 nights
4.99 out of 5 average rating, 335 reviews
Superhost
Camper/RV in Osprey
Thyme on Green
1 bed
Aug 15 – 20
R7,108 ZAR for 5 nights
New place to stay
Top guest favorite
Home in Osprey
Secluded 3R Pool Home Retreat Near Sarasota
3 beds
Aug 15 – 20
R23,404 ZAR for 5 nights
5.0 out of 5 average rating, 43 reviews
Top guest favorite
Cottage in Osprey
Mattie’s Cottage by the Bay
1 queen bed
Sep 1 – 6
R11,812 ZAR for 5 nights
4.97 out of 5 average rating, 63 reviews
Top guest favorite
Room in Sarasota
Stay with Diem Kieu Thi
Sarasota private room near beach
Aug 16 – 21
R7,004 ZAR for 5 nights
5.0 out of 5 average rating, 9 reviews
Top guest favorite
Room in Venice
Stay with ChandlerAssociate architect,
Coastal 70s Florida Getaway
Aug 19 – 24
R3,485 ZAR for 5 nights
4.96 out of 5 average rating, 68 reviews
Guest favorite
Home in Osprey
Private house with loft
3 beds
Sep 2 – 7
R13,892 ZAR for 5 nights
4.93 out of 5 average rating, 83 reviews
Top guest favorite
Home in Osprey
Sand Dollar Retreat
3 beds
Aug 18 – 23
R15,052 ZAR for 5 nights
5.0 out of 5 average rating, 19 reviews
Home in Nokomis
Parkview Cottage - NEW Home
4 beds
Aug 15 – 20
R17,143 ZAR for 5 nights
New place to stay
Superhost
Home in Nokomis
Waterfront Home, Walk to the Beach & Dining
2 beds
Sep 2 – 7
R20,697 ZAR for 5 nights
New place to stay
Townhouse in Nokomis
Coastal Retreat in Nokomis
4 beds
Aug 15 – 20
R20,972 ZAR for 5 nights
New place to stay
Guest favorite
Home in Sarasota
☀Coastal Gem☀Heated pool & amazing location!☀
3 beds
Sep 4 – 9
R17,874 ZAR for 5 nights
4.93 out of 5 average rating, 366 reviews
Guest favorite
Apartment in Sarasota
Pets friendly modern studio 5 mi to Siesta Key
2 beds
Aug 17 – 22
R11,776 ZAR for 5 nights
4.89 out of 5 average rating, 166 reviews
Top guest favorite
Room in Nokomis
Stay with MandyHosting for 8 years,
Cheerful, bright queen bedroom in sparkling house
Sep 2 – 7
R6,063 ZAR for 5 nights
4.89 out of 5 average rating, 19 reviews
Apartment in Sarasota
Suite Retreat Near Siesta Key!
2 beds
Aug 15 – 20
R14,592 ZAR for 5 nights
New place to stay
Top guest favorite
Condo in Sarasota
Lovely 2-Bedroom Condo, 7 min from Siesta Beach
3 beds
Aug 17 – 22
R16,202 ZAR for 5 nights
4.98 out of 5 average rating, 113 reviews
Top guest favorite
Home in Osprey
Charming Florida Cottage - Kayaks Included
2 king beds
Aug 15 – 20
R23,100 ZAR for 5 nights
4.98 out of 5 average rating, 48 reviews