
Holiday 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 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.

1BR in the Heart of Doral Steps from Dining &Shops
This stylish 1-bedroom apartment is fully equipped for up to 4 guests, offering comfort and convenience. It features a spacious living area with a sleeper sofa, a stocked kitchen with stainless steel appliances, an in-unit washer/dryer, a cozy king bedroom, and a private balcony to relax and enjoy the view. Located in a luxury building with 24/7 front desk service, gym, swimming pool, sauna, massage room, kids’ playroom, and business center, it’s the perfect blend of comfort and convenience.

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.

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

Beautiful Poolside Studio, Heart of Miami
All are welcome to enjoy this beautiful studio apartment located in Miami's Historic Grove Park . The studio is private but is attached to the main house where we live. The bed is a super comfortable pillow top queen mattress. The kitchenette is fully outfitted. You'll find everything from a salad spinner to hot sauce. The pool and spa are amazing. (Please see the house rules for details on the pool and spa use.) Free gated parking, and keyless self check-in.

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.

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.

Beautiful and Modern Apartment in Doral. 1B/1B
5350 PARK, is a new condominium (built in 2019) with an excellent location (Downtown Doral), a few steps from a supermarket, shops, parks, restaurants, night bars. The building has all the luxury comforts.....sauna, swimming pool, academy, spa, meeting room, parking with manobrista or sem manobrista, reception and security 24 hours. A few minutes from Miami International Airport, Dolphin Mall and International Mall.

Oasis Tropical Miami- Fun Mini Golf & Heated Pool
Welcome to Miami Casa Tropical – your ideal haven for an unforgettable family retreat or get-together with friends, in the heart of the vibrant Miami atmosphere! Immerse yourself in the perfect blend of style, space, and luxury, designed to make you feel right at home. The entire space is yours for private enjoyment. Curious about our amenities or local attractions? Don't hesitate to reach out and ask!
Popular amenities for Westchester rentals with a pool
House rentals with a pool

*POOL* |Sleeps 8|Near Coral Gables | Dadeland Mall

Habitat Privé The Majestic Tree

Encanto Family, cozy heated pool, center of Miami

Luxury Vacation House in Miami’s Center!

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

Ily's House

Cozy Oasis Pool Home-1 Min from Baptist Hospital

Pro Gym • Putting Green • Luxury Design• 3 Kings
Apartment rentals with a pool

Luxury PH at Brickell Bay-Amazing MIAMI City VIEWS

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

Front Facing Top Floor Penthouse with Ocean Views

Oceanview Brickell Miami Condo Pool/Free Parking

Beautiful condo with ocean view at Miami Brickell

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

BRAND NEW APARTMENT IN THE HEART OF DOWNTOWN

W Icon Brickell 40th Floor High Ceiling Ocean View
Other holiday rentals with a pool

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

lugar de paz en plena ciudad

Miami Oasis: Charming home with private pool

5350 Park Doral Downtown luxury apartment.

Guest House on BIG property in Miami Neighborhood

Miami Chic -Heated Pool & BBQ, Near Coral Gables

LuxeParadise:Tropical StylePost-OpEdition Zip33165

Big Pool - BBQ - Fun & Relax - Beach style
Quick stats about holiday rentals with a pool in Westchester
Total holiday rentals
Explore 60 holiday rentals in Westchester
Nightly prices starting at
Westchester holiday rentals start at € 26 per night before taxes and fees
Verified guest reviews
Over 3,550 verified reviews to help you choose
Family-friendly holiday rentals
60 properties offer extra space & child-friendly amenities
Pet-friendly holiday rentals
Find 40 rentals that welcome pets
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Wifi availability
60 of Westchester holiday 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!
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