
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.

"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.

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.

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

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.

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.

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

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

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.

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.

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.

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.

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

Blissful Villa Eco Pool 4B/4B

Habitat Privé The Majestic Tree

Luxury Oasis in Brickell - Only 3 min to Ocean

3B/2B Tropical Oasis w Salt-Water Pool! Lake views

The Finest Pool Jacuzzi Amenities BBQ

Centrally Located Resort Style Miami home

Private tropical oasis - Mimo Bungalow

Cozy Oasis Pool Home-1 Min from Baptist Hospital
Condo rentals with a pool

*Heart of Coconut Grove, terrace, pool, park free

Make It Happen! Brand New with Amazing Water Views

Beautiful and Modern Apartment in Doral. 1B/1B

Icon Brickell (W) Huge unit with bay & river views

Luxury Condo in Hotel, amenities Downtown/Brickell

Modern and comfortable Studio In Downtown Doral

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

Luxury 2BR Condo, Spectacular Views, Icon, W Miami
Other vacation rentals with a pool

Anjole Luxury Villa | 12PPL | Pool | Games | BBQ

Las Palmas

Miami Oasis: Charming home with private pool

5350 Park Doral Downtown luxury apartment.

Super cool unit with a pool in a quiet location

Dharma |15% off Monthly| Perfect 1B | South Miami

Luxe collection home in Miami.

Big Pool - BBQ - Fun & Relax - Beach style
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
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