
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

Cozy private guest studio
Welcome! This is a private guesthouse located in a quiet neighborhood. Accommodations are with a private entrance and parking space to make you feel at home. We are located near a major expressway. We have a pool; The POOL is a SWIM AT YOUR OWN RISK. It is shared with Owner. Enjoy a smoke free cottage. Ashtrays are provided outside for those guest that do smoke. We provide a queen size bed and a couch/bed. This space is perfect and comfortable for two guest.Please NO children and NO animals.

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.

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.

[Top Pick] Stunning Family Fun Oasis With Heated P
Welcome to our family-friendly retreat in Miami! Our renovated, spacious home at offers comfort and convenience for all ages. Enjoy nearby attractions like the thrilling Aquatica water park and the vibrant Miami Children's Museum. Or stay in and enjoy the fully equipped kitchen, a cozy living area, and a private, covered backyard, with loads of games & toys, it’s perfect for family bonding. You’re just a short drive from beautiful beaches and shopping. Make lasting memories in sunny Miami!

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

Condo in Brickell Business District
Stunning one bedroom condo located in the best area of Brickell just minutes away from Brickell City Centre and Mary Brickell Village with restaurants, bars, shops and entertainment. About this Space -Approx.818 sqft of natural light filled space with gorgeous bay and city views and a large private balcony with dining table and large patio couch -High-speed Wi-Fi -1 free assigned parking spot -Pool, hot tub, jacuzzi, steam room, game room, state of the art gym, and business center

One Bedroom Condo King Bed With 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.

Super cool unit with a pool in a quiet location
Super cool boutique hotel unit with a pool on Biscayne Boulevard, just a short drive to South Beach and the Design District. This unit offers a private and stylish accommodation for vacationers and business travelers. The room features a comfortable king-sized bed, hangers, a Smart TV and AC. This is a historic MiMo building, charming and nicely renovated. On site parking is available for just $15/day. Street Parking is unavailable. The unit is about 300 SQ/FT

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.

“Have Fun at Hacienda Paraíso” Suite 1 | pool |
Welcome to Room 1, the first addition at Hacienda Paraíso. This suite is conveniently located next to another Airbnb suite, providing flexibility for your stay. It features a private entrance, bathroom, kitchenette, and dining table, ensuring a comfortable and self-contained experience. Enjoy the convenience of hotel-like amenities paired with the added bonus of access to our stunning pool and lush yard, creating a truly relaxing retreat.
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Welcome To Miami

Luxury lakefront Modern mansion in Miami

Luxury Villa • Racket Court • Gym • Grand Garden

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Cozy Apartment in Downtown Doral

Modern 1 Bed in Downtown Doral With Free Parking

Grand Villa Resort B 2BR, Heated pool and sleeps 6

BellaMoon Oasis Miami
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.ﺇ1,374 | ﺩ.ﺇ1,399 | ﺩ.ﺇ1,146 | ﺩ.ﺇ1,252 | 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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- South Beach
- Fort Lauderdale Beach
- Bayfront Park
- Miami Design District
- Miami Beach Convention Center
- Hard Rock Stadium
- Everglades National Park
- Haulover Beach
- Port Everglades
- Bal Harbour Beach
- Zoo Miami
- John Pennekamp Coral Reef State Park
- Dania Beach
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- Broward Center for the Performing Arts
- Biscayne National Park
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- Phillip and Patricia Frost Museum of Science
- Key Biscayne Beach
- Gulfstream Park Racing and Casino
- Miami Beach Golf Club
- Biltmore Golf Course Miami
- Coral Castle




