
Holiday rentals with a pool in Westchester
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Westchester
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 Westchester rentals with a pool
House rentals with a pool

Casa Cascada in Coral Gables Area

Private Pool and Tropical Garden Oasis

Casa De Miller

Miami Oasis: Charming home with private pool

Luxury Oasis in Brickell - Only 3 min to Ocean

Centrally Located Resort Style Miami home

The Miami Designer Cove

My Own Miami/Downton/Minigolf/HeatedPool/ Arcades
Apartment rentals with a pool

Feels Like Summer ~ Panoramic Water Views! 2BR

Chic Studio 5 Icon Brickell Amazing View

Incredible 49th Flr Bay & Pool Views | Free Spa!

Luxury Condo in Hotel, amenities Downtown/Brickell

Modern and comfortable Studio In Downtown Doral

Modern DT Studio | Near Port Miami + Free Parking

Upper Penthouse Corner Unit 2B/2B | Icon Brickell

★King Suite★ Located at SLS LUX Brickell Building
Quick stats about holiday rentals with a pool in Westchester
Total rentals
50 properties
Nightly prices starting at
$38 SGD before taxes and fees
Total number of reviews
3K reviews
Family-friendly rentals
50 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
40 properties have a dedicated workspace
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- South Beach
- Fort Lauderdale Beach
- Bayfront Park
- Miami Beach Convention Center
- Haulover Beach
- Everglades National Park
- Hard Rock Stadium
- Bal Harbour Beach
- Miami Design District
- Port Everglades
- John Pennekamp Coral Reef State Park
- Zoo Miami
- Ocean Terrace Public Beach
- Trump National Doral Miami
- Dania Beach
- Crandon Beach
- Phillip and Patricia Frost Museum of Science
- Key Biscayne Beach
- Coral Castle
- Jungle Island
- Biscayne National Park
- Hobie Island Beach Park North
- Cannon Beach
- Biltmore Golf Course Miami