Vacation rentals with a pool in Westchester

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Top-rated rentals with a pool in Westchester

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Top guest favourite
A tranquil pool area is surrounded by lush greenery and tropical plants, creating a serene atmosphere. The rectangular swimming pool is framed by terracotta tiles and features potted plants on the edges, offering spaces for relaxation in the sun.
Guest suite in Coconut Grove
4.96 out of 5 average rating, 279 reviews

"Casa Mia's" pool & BBQ bungalow

Private entrance offers bungalow experience to the one bedroom space, walk in closet and en suite bathroom. Shared structural walls: sounds do travel. Exclusive access to pool (unheated), BBQ, stove top, small fridge, and “makeshift” sink. Plenty of privacy! 20 minute stroll to Coco Walk; restaurants, lush nature and historic sites. Nestled between Coral Gables ; South Miami and Brickell. Close to University of Miami, with quick access to airport and beaches. Merry Christmas Park’s a block away.

Guest favourite
A serene outdoor space includes a swimming pool surrounded by terracotta tiles and lush tropical vegetation. A tiki hut is positioned in the background, with an evening sky showcasing warm tones of orange and yellow. Soft furnishings and a relaxed seating area are visible nearby.
Tiny homes in Cutler Bay
4.98 out of 5 average rating, 248 reviews

Quiet tropical Oasis setting with 1 bed and 1 bath

Tropical oasis centrally located between Miami Beach and Key Largo. Although you may never want to leave. The cozy casita with private bath and balcony is tucked away, surrounded by lush vegetation and sounds of the waterfall. Take a dip in the pool or grotto, relax with an afternoon cocktail under the tiki hut, or snooze in the hammock. During those cooler months soak in the hot tub. We have bikes available to cruise the miles of nearby paths stretching from Coconut Grove to Black Point Marina.

Top guest favourite
Villa in Coral Way
4.98 out of 5 average rating, 181 reviews

Huge heated pool, spa & Grill.12 mins to Brickell.

Step into your stylish 3-bedroom (sleeps 12) Miami villa just minutes from Brickell’s dining & nightlife. Relax in the private heated pool & spa, sip coffee on the sunny backyard patio, then retreat to plush Queen & King beds. Superhost • Guest Favorite • 4.98-star rated in over 200 reviews Huge outdoor TV Lounge and Dining area. Fast Wi-Fi & 4K TVs Chef-ready kitchen with stainless appliances, outdoor Grill ready for your cookout or Hibachi private chef In-home washer & dryer Bathroom essent

Guest favourite
A spacious backyard is showcased with a clear pool reflecting the sky. Sun loungers are arranged nearby, accompanied by a large umbrella for shade. Paths of stepping stones lead through a pebble area, enhancing the serene outdoor setting.
Home in Miami
4.92 out of 5 average rating, 373 reviews

Charming house with private pool & large patio

This is the classic 1950’s Miami family home in the very well-known neighborhood of Westchester. Original terrazzo floors with modern, mid-century inspired decor. The best feature is the spacious and private backyard with pool an large tiki hut, bbq, and plenty of space to relax and enjoy the weather. The house is fully furnished and well equipped. Bedding and towels provided. Washer and dryer are conveniently located inside the house. Large parking space in a very quiet and charming street.

Superhost
A serene outdoor space is highlighted by a heated saltwater pool surrounded by lush palm trees. Poolside seating includes elegant iron chairs and tables. Soft lighting enhances the tranquil ambiance, creating a welcoming atmosphere for relaxation and enjoyment.
Home in Miami
4.92 out of 5 average rating, 196 reviews

Private Pool and Tropical Garden Oasis

Welcome to the Tangleleaf, a beautiful 3 bedroom 2 bath house with pool and gardens centrally located in Miami. 10-15 minutes to Miami's airports, beaches, Design District, Wynwood, and Downtown. Your stay includes two queen beds and one king, heated saltwater pool, wireless internet, Smart TV, outdoor grill, laundry, and parking for 4 cars ONLY. We also provide fresh towels, linens, and kitchen utensils. Our goal as your host is to make sure you enjoy every aspect of our beautiful city.

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
4.99 out of 5 average rating, 372 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
The entrance of the property is framed by mature palm trees and lush landscaping, showcasing vibrant greenery. A large half-circle driveway leads up to the house, highlighted by a smooth, paved surface. The warm-toned exterior of the home is visible, inviting guests into a tranquil setting.
Guest suite in Miami
4.91 out of 5 average rating, 418 reviews

Cozy Suite -Exterior Entrance, SelfCheckin

If you like Clean, New, Quiet and Great Hospitality, then this is the Perfect Room for you. We are conveniently located between Key Largo and Downtown Miami, in an upscale community. You’ll feel Safe and Welcome here! -GATEWAY to the Keys and Everglades -Private Entrance -Self Check-in -Free Parking -Fast WIFI -Bathroom with 2 sinks -SWIMMING POOL -Central A/C -HBO TV -Refrigerator -Ceiling Fan -Closet Space -Ceramic Tile Floors -Iron & Board -Towels & Bath essentials -Hair dryer

Guest favourite
A scenic view of Biscayne Bay is captured from a private balcony, highlighting the blue waters and distant boats. The image includes glimpses of the lush greenery along the shore and nearby buildings, providing a backdrop to a serene waterfront setting.
Apartment in Coconut Grove
4.89 out of 5 average rating, 211 reviews

SF Amazing Studio - Walking Distance to Cocowalk

🌴 Peaceful Bayview Condo at Hotel Arya in Coconut Grove 🌴 Large Studio • Sleeps 3 • Balcony • Pool & Gym Access • Free Parking Escape to this peaceful bayview condo in Coconut Grove, located inside the upscale Hotel Arya. Enjoy full access to premium amenities like a pool, gym, and sauna while staying steps from the Grove’s best restaurants, shops, and waterfront parks. Ideal for couples or solo travelers looking for a relaxing Miami getaway with easy access to top attractions.

Superhost
Home in Miami
4.89 out of 5 average rating, 115 reviews

Escape-5BR-HotTub-Games-FirePit-BBQ-Fun

5 Bedrooms 3.5 Bathrooms Heated Pool/Jacuzzi/Pool Table/Ping Pong Table/Mega Chess/Basketball/Mini Golf/Kids Playground/BBQ/Hammock/Mini Beach/Outdoor furniture/Fire Pit/Cornhole Game Welcome to our home, a haven of entertainment and enjoyment that you won't want to depart. From the serene pool and hot tub to the thrilling games, this residence is crafted to deliver an unforgettable vacation for all ages. If you seek an all-inclusive getaway, look no further.

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, 389 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.

Guest favourite
A private pool with clear, inviting water reflects sunlight. The pool features a gentle gradient leading to a shallow entry with stainless steel steps. Lush greenery surrounds the area, providing a natural backdrop for relaxation.
Home in Miami
4.83 out of 5 average rating, 151 reviews

Ily's House

Fabulous fully remodeled house. Private pool and covered patio. New kitchen, granite counter top, nice porcelain and hard wood floor. Fifteen minutes away from the airport. Close to many shopping plazas, restaurants and various entertainment. The University of Miami is 2.9 miles and the golf course is 3.5 miles away from the house. The house is located near several Plastic Surgery Centers and a major Hospital. High speed internet.

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, 782 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

Quick stats about vacation rentals with a pool in Westchester

  • Total rentals

    60 properties

  • Nightly prices starting at

    $42 CAD before taxes and fees

  • Total number of reviews

    3.6K reviews

  • Family-friendly rentals

    60 properties are a good fit for families

  • Pet-friendly rentals

    40 properties allow pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace