
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

Vitamin Sea: Private Pool, Downtown, and Beaches!

3bd 2th Solar Heat Pool Large home W/ big yard

Spacious 4BR Getaway – Perfect for Families!

Large 4 bedroom pool home tiki bar close to Ami

Charming 2BR Home + Private Pool

Beautiful House with Heated pool

Tropical Pool Vacation Getaway!

Beautiful, Spacious Heated Pool Home
Apartment rentals with a pool

Lovely Condo, Heated Pools, AMI, IMG, Top beaches

Condo With Heated Pool, Beaches Only Minutes Away

1 block from beach + pool - Cayman Cay #102

Lovely 2 bedroom condo with pool & tennis courts

Siesta Village Short Walk to Beach w heated Pool

Lakeside Condo. Beaches, Restaurants, IMG nearby.

Peaceful retreat, pool, hot tub, near Siesta Key!

Oceanfront Condo for Beach Lovers
Quick stats about holiday rentals with a pool in Osprey
Total rentals
50 properties
Nightly prices starting at
$81 SGD before taxes and fees
Total number of reviews
290 reviews
Family-friendly rentals
30 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
- Tampa Bay Holiday rentals
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- Rentals with a patio Osprey
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- Crescent Beach
- John's Pass
- Cortez Beach
- Bean Point Beach
- Lido Key Beach
- North Beach
- Vinoy Park
- Coquina Beach
- Fort De Soto Park
- Tropicana Field
- Manasota Key Beach
- Lakewood National Golf Club
- Streamsong Resort
- River Strand Golf and Country Club
- Englewood Beach
- Alafia River State Park
- Marie Selby Botanical Gardens
- Bayou Club
- Van Wezel Performing Arts Hall
- Sunken Gardens
- Tara Golf & Country Club
- North Beach At Fort DeSoto Park
- Del Tura Golf & Country Club
- Seminole Lake Country Club