
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.

Make It Happen! Brand New with Amazing Water Views
Bluewater Realty Miami welcomes you to The Grand, located in Downtown Miami on Biscayne Bay. Our 2 bedroom Make It Happen! is the ultimate retreat, equipped with everything you could need. Enjoy views of Biscayne Bay and Margaret Pace Park that will leave you in awe. With South Miami Beach 3 miles away you can indulge in the sun of Miami Beach while still feeling the energy of downtown Miami, giving you the ultimate Miami experience. Your Airbnb Superhosts, Rachel and Mia Bluewater Realty Miami

"Casa Mia's" pool & BBQ bungalow
Private entrance offers bungalow experience to the one bedroom space, walk in closet en suite bathroom. Shared structural walls: sounds do travel. Exclusive access to pool (unheated), BBQ, stove top, small outdoor 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; quick access to airport and beaches. Merry Christmas Park’s a block away

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.

Best area of Doral with all the services!
Experience the best of Miami in our stunning rental property condo located in the heart of Doral. This modern 1-bedroom, 1-bathroom condo boasts spacious living areas, modern furnishings, and breathtaking city views. Enjoy access to the building's amenities, pool, fitness center, and 24-hour security and 1 parking spot. Just steps from shopping, dining, and entertainment, this condo is the perfect home base for your Miami adventure. Book your stay today and experience the best of Doral

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

Gorgeous 1 Bdrm 1 Bath - Magical City Views
Entire luxury condo at Quadro in the Design District. Fully equipped - Free parking, coffee, Wi-Fi & cable. The building features amenities in the 6th floor including a fitness center, a lounge with co-working area & a game room, an outdoor dining area with BBQ's and a great pool.Enjoy guest exclusive neighborhood discounts. Walk to hundreds of designer shops, restaurants, bars, art galleries, & more! 10-min drive to Miami’s international airport, 15-min drive to Miami Beach.

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.

Spanish House 3 Bedroom Pool House
If you are planning a vacation in Miami, this is the place to stay, You can enjoy all day at the pool no matter the exterior temperature the water will be perfect for a swim or go out to the existing Miami. 5 minutes away from the Miami International Airport located in one of the most safe and peaceful neighborhoods in Dade County. 15 minutes from the beach. Located at the heart of Miami close to all major entertainment districts

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 and 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

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

Habitat Privé The Majestic Tree

Beautiful Home HEATED SALT POOL Near Beach Airport

Miami Oasis: Charming home with private pool

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

Magnolia House Pool Slide/Gazebo/Built in BBQ

Big Pool - BBQ - Fun & Relax - Beach style

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

Luxury PH at Brickell Bay-Amazing MIAMI City VIEWS

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

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

NEW Apartment in Downtown Doral 1512

Beautiful condo with ocean view at Miami Brickell

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

Stunning 2 bedroom+17 foot ceilings & heated pool

BEAUTIFUL 2BD ★ OVERLOOKING THE OCEAN ★BRICKELL
Other vacation rentals with a pool

Waterfront Miami Oasis w/ Kayaks | Heated Pool

Modern Condo in Downtown Miami 1609

villa caleta

Dream 3BR + Pool Gables Oasis

Luxe collection home in Miami.

Pool + Fire Pit + Karaoke

Boho MIA Oasis Pool &Canal View

South Miami/Coral Gables House with Exclusive Pool
When is the best time to visit Westchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ1,285 | ﺩ.ﺇ1,447 | ﺩ.ﺇ1,531 | ﺩ.ﺇ1,263 | ﺩ.ﺇ1,476 | ﺩ.ﺇ1,359 | ﺩ.ﺇ1,451 | ﺩ.ﺇ1,293 | ﺩ.ﺇ1,098 | ﺩ.ﺇ1,282 | ﺩ.ﺇ1,230 | ﺩ.ﺇ1,531 |
| 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 ﺩ.ﺇ110 per night before taxes and fees

Verified guest reviews
Over 3,550 verified reviews to help you choose

Family-friendly vacation rentals
60 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
60 of Westchester vacation rentals include wi-fi 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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