Some info has been automatically translated. Show original language

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.

%{current} / %{total}1 / 1
Guest favourite
A wraparound balcony offers panoramic views of Biscayne Bay and the Miami skyline. The scenic vista is complemented by lush greenery below and various buildings in the foreground. The sky is bright with scattered clouds, enhancing the sense of openness and tranquility.
Apartment in Coconut Grove
4.9 out of 5 average rating, 223 reviews

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.

Top guest favourite
A heated pool is surrounded by palm trees, offering a refreshing oasis. Comfortable outdoor seating arrangements include chairs and loungers, alongside a sun umbrella. The patio area is designed for relaxation and leisure, with vibrant greenery adding to the tranquil atmosphere.
Guesthouse in Miami
4.99 out of 5 average rating, 288 reviews

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.

Superhost
A spacious living area is presented with modern furnishings, including a large gray sofa facing a sleek television mounted on the wall. Light-colored cabinetry and a dining table are visible in the background, while a fireplace adds warmth to the ambiance. Potted plants offer a touch of greenery.
Home in Miami
4.89 out of 5 average rating, 139 reviews

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!

Superhost
An outdoor dining area features a wooden table with game pieces and seating. Beyond the table, a salt pool is visible, surrounded by lounge chairs and umbrellas under a clear blue sky. Ceiling fans are installed for airflow, enhancing the space's comfort.
Home in Miami
4.89 out of 5 average rating, 199 reviews

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)

Top guest favourite
A spacious backyard is showcased, featuring a clean saltwater pool surrounded by lounge chairs and tropical landscaping. A covered patio area is visible, with a stone countertop and decorative plants. The bright blue sky complements the serene outdoor setting.
Home in Miami
5 out of 5 average rating, 434 reviews

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

Top guest favourite
A serene outdoor space is highlighted by a saltwater pool, surrounded by lush greenery. String lights create a warm ambiance above a covered dining area with a table and chairs, while a fire pit invites gatherings in the evening.
Home in Miami
4.96 out of 5 average rating, 151 reviews

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

Guest favourite
Home in Flagami
4.88 out of 5 average rating, 182 reviews

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.

Guest favourite
An outdoor dining area is set under a shaded patio, featuring a glass-top table surrounded by eight metal-framed chairs. Potted plants adorn the table, while a pool glistens in the background. Neatly arranged stone tiles lead towards lush greenery, enhancing the tranquil environment.
Home in Miami
4.88 out of 5 average rating, 104 reviews

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!

Guest favourite
A modern living area features a comfortable gray sofa with patterned black and white cushions. A wooden coffee table is positioned in front, holding a small decorative arrangement. Art pieces adorn the walls, while a dining area with a wooden table and chairs is visible in the background.
Apartment in South Miami
4.89 out of 5 average rating, 127 reviews

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.

Top guest favourite
A spacious pool area is surrounded by vibrant greenery and palm trees. Seating arrangements with cushions are positioned near the water, complemented by a shaded area under an umbrella. The pool features a rock formation and is accented by colorful lounge chairs.
Home in Miami
4.97 out of 5 average rating, 407 reviews

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.

Top guest favourite
Home in Miami
4.91 out of 5 average rating, 141 reviews

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.

Guest favourite
A serene waterfront view showcases several three-story buildings framed by palm trees. The calm water reflects the bright blue sky dotted with fluffy clouds, while a fountain creates gentle ripples, enhancing the tranquil atmosphere of the resort.
Condo in Miami
4.95 out of 5 average rating, 878 reviews

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

When is the best time to visit Westchester?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
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. temp20 °C22 °C23 °C25 °C27 °C28 °C29 °C29 °C28 °C27 °C24 °C22 °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!