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.

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Guest favorite
The living area features a spacious blue tufted sofa complemented by a sleek glass coffee table. A modern accent chair adds contrast, while large sliding glass doors provide ample natural light and stunning views of the surrounding skyline.
Condo in Downtown Miami
4.92 out of 5 average rating, 124 reviews

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

Top guest favorite
The exterior of a private guesthouse is showcased, surrounded by lush greenery and tropical plants. Screened windows provide a view of the outdoors while offering a sense of openness. The building is designed with a light-colored façade, blending harmoniously with the natural setting.
Guesthouse in Miami
4.98 out of 5 average rating, 206 reviews

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.

Top guest favorite
A serene outdoor space includes a swimming pool surrounded by terracotta tiles and lush tropical vegetation. A tiki hut is positioned in the background, with an evening sky showcasing warm tones of orange and yellow. Soft furnishings and a relaxed seating area are visible nearby.
Tiny home in Cutler Bay
4.98 out of 5 average rating, 255 reviews

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.

Top guest favorite
A spacious backyard is showcased with a clear pool reflecting the sky. Sun loungers are arranged nearby, accompanied by a large umbrella for shade. Paths of stepping stones lead through a pebble area, enhancing the serene outdoor setting.
Home in Miami
4.92 out of 5 average rating, 378 reviews

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 guest favorite
A spacious outdoor area features a large pool surrounded by a sun deck with colorful lounge chairs. The area is enclosed with a mesh roof, allowing for sunlight while providing shade. Vibrant inflatable floats rest in the pool, enhancing the inviting atmosphere.
Home in Miami
4.95 out of 5 average rating, 108 reviews

[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!

Top guest favorite
A modern living area features a gray sofa adorned with decorative pillows, complemented by a stylish coffee table. A flat-screen TV is mounted on the wall, while a dining area with sleek furnishings is visible in the backdrop. Soft lighting enhances the open atmosphere.
Condo in Doral
4.96 out of 5 average rating, 133 reviews

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

Top guest favorite
A spacious backyard is showcased, featuring a clean saltwater pool surrounded by lounge chairs and tropical landscaping. A covered patio area is visible, with a stone countertop and decorative plants. The bright blue sky complements the serene outdoor setting.
Home in Miami
4.99 out of 5 average rating, 390 reviews

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

Top guest favorite
An open living area features a white leather sofa, a coffee table with magazines, and two ottomans in teal. A mounted TV is positioned on a white console, while a dining area is visible in the background, showcasing a modern kitchen design.
Apartment in Brickell
4.96 out of 5 average rating, 236 reviews

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

Guest favorite
Condo in Miami Design District
4.89 out of 5 average rating, 170 reviews

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.

Superhost
The spacious room features a king-sized bed with crisp white linens. A pink and white curved accent wall adds a modern touch. Adjacent, a stylish chair and a vibrant vanity area are visible, alongside a closet with hangers and a framed window allowing natural light.
Apartment in Miami
4.8 out of 5 average rating, 601 reviews

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

Top guest favorite
A spacious pool area is surrounded by vibrant greenery and palm trees. Seating arrangements with cushions are positioned near the water, complemented by a shaded area under an umbrella. The pool features a rock formation and is accented by colorful lounge chairs.
Home in Miami
4.97 out of 5 average rating, 394 reviews

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.

Top guest favorite
A colorful hammock is suspended between two palm trees, inviting relaxation beside a sparkling pool. Lush tropical plants surround the outdoor area, creating a peaceful ambience. The inviting pool area is visible in the background, enhancing the serene outdoor setting.
Guest suite in Homestead
5 out of 5 average rating, 159 reviews

“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.

Popular amenities for Westchester rentals with a pool

When is the best time to visit Westchester?

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Avg. priceﺩ.ﺇ1,285ﺩ.ﺇ1,447ﺩ.ﺇ1,531ﺩ.ﺇ1,263ﺩ.ﺇ1,476ﺩ.ﺇ1,359ﺩ.ﺇ1,374ﺩ.ﺇ1,399ﺩ.ﺇ1,146ﺩ.ﺇ1,252ﺩ.ﺇ1,230ﺩ.ﺇ1,531
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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!