Holiday rentals with a pool in Osprey
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Osprey
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Osprey rentals with a pool
House rentals with a pool
Home
4.95 out of 5 average rating, 194 reviewsThe Oasis-Heated Private Pool Hot Tub-5mi to beach
Home in Nokomis
5 out of 5 average rating, 19 reviewsNo hurricane damage. 3-bedroom home with pool
Home in Nokomis
4.8 out of 5 average rating, 10 reviewsResort-like House
Home
5 out of 5 average rating, 10 reviewsCottage with Private Pool + Pickleball Court
Home
5 out of 5 average rating, 13 reviewsLake View, 6 Miles From Beach
Home in Nokomis
4.95 out of 5 average rating, 19 reviewsPets, Plunges & Peace on the Gulf of Mexico
Home
4.95 out of 5 average rating, 42 reviewsCreekside Paradise I
Home in Sarasota
4.9 out of 5 average rating, 10 reviewsSiesta Key Modern Retreat with Heated Pool & Spa
Apartment rentals with a pool
Apartment in Sarasota
4.97 out of 5 average rating, 187 reviewsGateway to Siesta Key - 1/2 Mile to the Beach
Apartment
4.83 out of 5 average rating, 207 reviewsNo Damage: Cozy 1BR Beach Condo on Siesta Key!
Apartment in Siesta Key
4.96 out of 5 average rating, 112 reviews2 Bed/2 Bath Condo Resort View on Siesta Key Beach
Apartment
4.9 out of 5 average rating, 101 reviews*Open* Crystal House on Siesta Key Beach
Apartment
4.8 out of 5 average rating, 104 reviewsLIDO KEY 1 BR/1Bath Heated Pool 16
Apartment
4.96 out of 5 average rating, 295 reviewsWE ARE OPEN—On the Beach; Siesta Key SunBum Studio
Apartment
4.94 out of 5 average rating, 189 reviewsSiesta key getaway!
Apartment
4.85 out of 5 average rating, 137 reviewsSiesta Key Ground Floor Condo 2BR On Trolley Line
Quick stats about holiday rentals with a pool in Osprey
Total rentals
50 properties
Nightly prices starting at
€ 57 before taxes and fees
Total number of reviews
300 reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Destinations to explore
- Rentals with pools United States
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