
Vacation 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.

Stunning Studio w/Bay & City View Free Park/Pool
INCREDIBLE VALUE! First, a $30 gift card to our restaurant GreenStreet and a bottle of champagne will be awaiting you in your room! in Coconut Grove, this privately owned & renovated deluxe bright studio on the 15th floor of a luxurious waterfront property offers breathtaking bay & city views, is equipped for 2 guests w/king size bed, full kitchen, full bath & balcony. Enjoy all the luxury amenities we offer, pool & hot-tub w/ incredible bay views, penthouse gym, sauna, business center, squash.

Guesthome w/ Heated Pool 5 mins from Miami Airport
This home is located just 5 minutes from the Miami Airport and is central to many attractions here in Miami. Take a walk down Calle Ocho, swim at Miami Beach, enjoy a game at Marlins baseball stadium or American Airlines Arena (home to the Miami Heat), and dine at one of the many popular restaurants such as Versailles. These are all within 15 minutes of this private comfortable home. Come enjoy a location that provides a rich experience into the vibrant hispanic culture that Miami radiates.

The Lux Paradise Miami
Enjoy a stylish experience at this centrally-located place. Located in the heart of Miami, our property is close to all the main attractions the city has to offer. Whether you’re looking to explore vibrant neighborhoods like Little Havana and Coconut Grove, enjoy the stunning beaches of Miami Beach, or visit popular spots like the Miami Zoo, Vizcaya Museum, and the bustling Brickell area, you’ll find everything within easy reach. Perfect for those who want to experience the best of Miami!

Miami Palm House with HEATED POOL & BBQ/BAR
Bring the whole family and friends to this Tropical Miami Home with lots of room for gatherings and entertainment! Enjoy the entire house with a stunning backyard, salt pool and gazebo! FREE PARKING 12 Guests. 4 Bedrooms. 9 Beds. 2 Baths Patio: Large Salt Pool (child friendly) BBQ Grill, Fridge, Wine Cooler, Bar Counter, Outdoor Lounge Furniture, Mini Golf Area Rooms: Bedroom 1: 1 Queen Bed Bedroom 2: 1 Queen Bed 1 Twin Bed Bedroom 3: 1 Queen Bed Bedroom 4: 5 Twin beds & (Game Room)

Sanctuary Salt water heated pool BBQ Grill Oasis
Come and create unforgettable memories in this modernly designed single-family home with a spacious layout and a range of comfortable bedrooms. It features two king-size beds, one queen-size bed, and a twin fold-up bed, as well as an Italian queen-size sofa bed. The house is bathed in natural light and boasts modern amenities that cater to your convenience. Located in a prime location, this house is close to all the tourist areas!! The pool is salt water with heater, Also a grill area

Luxe Pool & Fire Pit | 5 min to Dolphin Mall
Experience sun-soaked luxury in Miami! Dive into the refreshing saltwater pool or unwind on one of the poolside lounge chairs. Newly renovated in 2022, this 4 bed/3.5 bath home comfortably accommodates 10 guests. For endless entertainment, compete in games of ping pong, sing your heart out with the karaoke machine, enjoy board games, or shoot some hoops. Presented by SuCasa Vacay, every detail has been thoughtfully chosen for an unforgettable Miami stay. Property Name: SuCasa Palmas

Heated pool home only 7 miles from MIA Airport
A block a way from the Famous Calle OCHO . The Property is located in the heart of Miami. Property is only 6.4 miles away from Miami International Airport. ONLY 14 MILES AWAY FROM SOUTH BEACH Property is close to lots of restaurants and shopping centers. great location and property. Property Very comfortable and spacious with a private pool. You will love it because of the cleanliness & comfort, its for family, couples,friends,business travelers.Equipped kitchen for cooking.

Miami Tropical Villa -Pool & BBQ
Welcome to "Miami Tropical Villa" – Miami's ultimate tropical escape! Immerse in luxury with the stunning blue pool, a haven of relaxation under the Florida sun. Poolside loungers invite you to unwind. Beyond the villa, Miami's treasures await. From South Beach nightlife to the Wynwood art scene, adventure is at your doorstep. This Tropical Villa invites you to make unforgettable memories in a tropical paradise that transcends the ordinary. Your escape to luxury begins here!

Dharma | 20% off Monthly Charming 2B | South Miami
Spacious, comfortable, upscale, and ideally located, Dharma Home Suites at Red Road Commons are the furnished accommodations you’ve been looking for. Quality living is at the forefront of this apartment community and we’ve made sure its modern and cozy interior offers the perfect home away from home for all travelers. Immerse yourself in Coral Gables’ vibrant surroundings, enjoy resort-style amenities and beautiful surroundings in the heart of South Miami.

The Miracle Cottage & Pool on Acre Miami Florida
Beautiful, brand new PRIVATE cottage on an acre property situated in million dollar neighborhood. Perfect place to relax and enjoy the Miami sun. This is a little piece of heaven in the heart of a magical city. Come & enjoy your best vacation. Charming , peaceful & comfortable . Cottage is a completely separate building from the main house. It’s 900 sf of living area. Cleaning & Decontamination as per CDC guidelines before every check in.

Magnolia House Heated Pool with Slide/Gazebo/ BBQ
Magnolia House Miami features a beautiful heated pool with slide, large Gazebo, Brazilian BBQ, Domino Table, Sunbeds & lots of outside seating & tables. This is a spacious 4 bedroom 2 bathroom home, with a large kitchen. Very Close to Miami Airport, Cruise Port, & South Beach, Little Havana, Coral Gables, all hot spots & major attractions. Large driveway with ample parking & High speed WiFi. The pool and patio is very private.

Marriott Villas at Doral 2BD sleeps 8
Located in one of the most prestigious areas of Miami, Marriott's Villas at Doral are a tranquil hideaway; only 13 miles from the sizzling excitement of Miami Beach, yet a world away. Sharing the 650-acre lush landscape is the celebrated Trump National Doral Miami, a Trump-managed resort. There, you have access to four championship courses, a classic European spa, a water recreation playground and several restaurants.
Popular amenities for Westchester rentals with a pool
House rentals with a pool

Spacious MIAMI private home with pool and parking.

Tropical Oasis Getaway w/ Heated Pool and Hot Tub

“MIA Paradise: Heated Pool+Spa, Prime Location

Miami Oasis: Charming home with private pool

Sunset Retreat at Heart of Miami with pool

Centrally Located Resort Style Miami home

Waterfront Home 3/3.5 Resort Style-Heated Pool*

Aurea | 12 PPL | Pool | BBQ |Playground |Mini Golf
Condo rentals with a pool

Lovely 1 Bedroom apartment/Pool,Heart of Wynwood

Luxury Condo - 3B/3B with Amazing Skyline View

Stylish Studio Icon, Waterfront Building

NEW Apartment in Downtown Doral 1512

Modern Apartment in Downtown Doral

Stunning Views 2 Bdrms Condo|Miami Design District

Brickell Condo 28th floor! New AKA Hotel 5-Star

Luxury Miami Studio 3013 View, Pool, Gym Amenities
Other vacation rentals with a pool

Luxury Lakefront Getaway

The Sunflower Inn

Lake Of Dreams Miami House - The Perfect Place

Miami Favorite Stay | Heated Pool & Game Room

Escape to Miami/Heather+Pool/9pl/BBQ/pool table.

Lakefront Glow Villa | 5BR · Cinema · Heated Pool

3 BR Cozy Miami Home with Pool

Luxe collection home in Miami.
When is the best time to visit Westchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $478 CAD | $539 CAD | $570 CAD | $470 CAD | $550 CAD | $506 CAD | $511 CAD | $521 CAD | $427 CAD | $470 CAD | $495 CAD | $681 CAD |
| Avg. temp | 20 °C | 22 °C | 23 °C | 25 °C | 27 °C | 28 °C | 29 °C | 29 °C | 28 °C | 27 °C | 24 °C | 22 °C |
Quick stats about vacation rentals with a pool in Westchester

Total vacation rentals
Explore 60 vacation rentals in Westchester

Nightly prices starting at
Westchester vacation rentals start at $55 CAD per night before taxes and fees

Verified guest reviews
Over 3,880 verified reviews to help you choose

Family-friendly vacation rentals
50 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
60 of Westchester vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Westchester rentals

4.8 Average rating
Westchester stays are highly rated by guests—averaging 4.8 out of 5!
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- South Beach
- Fort Lauderdale Beach
- Bayfront Park
- Bayside Marketplace
- The Tides on Hollywood Beach
- Kaseya Center
- Brickell City Centre
- Miami Beach Convention Center
- Hard Rock Stadium
- Port Everglades
- Midtown
- Everglades National Park
- Haulover Beach
- University of Miami
- Ocean Reserve Condominium
- Miami Design District
- LoanDepot Park
- Las Olas Beach
- Lauderdale-By-The-Sea Beach
- Dolphin Mall
- Bal Harbour Beach
- Seminole Hard Rock Hotel and Casino
- Zoo Miami
- Fort Lauderdale Beach




