
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.

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.

"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.

Guest Suite-Exterior Entrance, SelfCheckin.
If you like Clean, New, Quiet and Great Hospitality, then this is the Perfect Place 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 -Swimming Pool -Central A/C -Ceiling fan -Kitchenette -Refrigerator -Microwave -Coffee maker -Netflix-HBO TV -Ceramic Tile Floors -Full Closet -Towels/Bath essentials -Iron & Board

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

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.

Modern & Cozy Studio | Resort-Style Amenities
This stylish Studio apartment is fully equipped for up to 2 guests, offering comfort and convenience. It features a spacious area and a stocked kitchen with stainless steel appliances, an in-unit washer/dryer, a cozy king bed, 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.

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.

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

Private Pool and Tropical Garden Oasis

Luxury Vacation House in Miami’s Center!

[Kids Favourite] Stunning Family Fun Oasis With He

Luxury Villa | Spa - Pool |Top Location| Pets |BBQ

Magnolia House Heated Pool with Slide/Gazebo/ BBQ

Biscayne Villa, with Heated Pool Oasis

Miami Paradise Westchester * Heated Pool*

Silver Bluff Private Luxury Home 3Beds 2Baths-Pool
Condo rentals with a pool

Feels Like Summer ~ Panoramic Water Views! 2BR

SUNNY ISLES GORGEOUS 15A OCEAN FRONT (+hotel fees)

Luxury Beach & City View Condo 5 min walk to beach

NEW Apartment in Downtown Doral 1512

Oceanfront Brickell Miami Condo Pool Free Parking

Front Facing Top Floor Penthouse with Ocean Views

Modern and comfortable Studio In Downtown Doral

SF Beautiful Blue & Gold Studio with Ocean View
Other vacation rentals with a pool

Habitat Privé The Majestic Tree

Cozy Apartment in Downtown Doral

Heated* Pool•Hot Tub•Sauna•Games•Prime for Groups*

Miami Oasis: Charming home with private pool

Perfect Studio for 2 Guest 20 Minute from DT Miami

Sleek Doral Retreat 1 Bed Oasis W/ Free Parking

Miami Chic-Heated Pool Near FIU and Coral Gables

LuxeParadise:Tropical StylePost-OpEdition Zip33165
When is the best time to visit Westchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $479 CAD | $539 CAD | $570 CAD | $470 CAD | $550 CAD | $506 CAD | $511 CAD | $521 CAD | $427 CAD | $466 CAD | $458 CAD | $570 CAD |
| 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 $41 CAD 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 and kid-friendly amenities

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
60 of Westchester vacation 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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