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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.

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Guest favourite
A spacious studio features a king-sized bed and a pull-out sofa, with large windows showcasing city views. Neutral colors enhance the relaxing atmosphere. Two framed black-and-white photographs adorn the walls, complementing the contemporary furnishings.
Condo in Coconut Grove
4.94 out of 5 average rating, 298 reviews

CityView Balcony Pool& Hottub. Wi-Fi. Full Kitchen

* Professional disinfecting cleaning before each stay * Central & Convenient Studio in the heart of Coconut Grove village * Front desk staffed all night ( check in starts at 4 PM ) 100 yards/meters to Restaurants, Coffee Shops, Shopping, Marina & Park 10 min by car to the University & Hospital 15 min by car to Brickell * Fast WIFI * Top Floor Gym * Pool & Hot Tub * Laundry Room * Onsite Parking offered for $10/ night Guest must be at least 21 years of age by check in. Our private studio

Guest favourite
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, 381 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 favourite
A spacious driveway curves past vibrant tropical plants and palm trees leading to a welcoming entrance of the property. The house features a warm orange exterior with decorative elements and a large garage door, complementing the lush landscaping.
Guest suite in Miami
4.9 out of 5 average rating, 384 reviews

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

Superhost
A spacious living area is presented with modern furnishings, including a large gray sofa facing a sleek television mounted on the wall. Light-colored cabinetry and a dining table are visible in the background, while a fireplace adds warmth to the ambiance. Potted plants offer a touch of greenery.
Home in Miami
4.88 out of 5 average rating, 124 reviews

The Lux Paradise Miami

Enjoy a stylish experience at this centrally-located place. Located in the heart of Miami, our property is close to all the main attractions the city has to offer. Whether you’re looking to explore vibrant neighborhoods like Little Havana and Coconut Grove, enjoy the stunning beaches of Miami Beach, or visit popular spots like the Miami Zoo, Vizcaya Museum, and the bustling Brickell area, you’ll find everything within easy reach. Perfect for those who want to experience the best of Miami!

Guest favourite
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, 136 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 favourite
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, 396 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

Guest favourite
Condo in Miami Design District
4.89 out of 5 average rating, 167 reviews

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.

Top Guest favourite
The pool area is surrounded by palm trees, with lounge chairs and seating arranged along the water's edge. A spacious outdoor lounge is visible in the background, and the building's glass facade reflects the bright sky and clouds.
Condo in Miami Design District
5 out of 5 average rating, 107 reviews

Bay View Design District Apt, Pool, Gym & Parking

Enjoy the best of everything Miami has to offer at this centrally located Design District condo near Wynwood, Midtown, Downtown, Miami Beach and Mimo. Our condo has all the necessities of home with a fully equipped kitchen, comfy bed, cozy living space and a spacious balcony with amazing bay and sunrise views. Resort-style amenities including a rooftop pool, full gym, BBQ grills, community work space and a complimentary parking spot in our covered garage are also included.

Guest favourite
A modern studio apartment is presented with a spacious king bed adorned with decorative pillows. A round glass table and white chairs accommodate dining. A television is mounted on the wall, and large sliding doors provide abundant natural light and access to a balcony.
Apartment in Doral
4.93 out of 5 average rating, 104 reviews

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.

Guest favourite
A vibrant backyard features a heated pool surrounded by tropical landscaping. Lounge chairs are positioned near the pool, while a covered pergola with seating is visible in the background. Colorful flowers and a miniature golf area add charm to the outdoor space.
Home in Miami
4.94 out of 5 average rating, 123 reviews

Miami Fun Oasis, Heated Pool & Private Mini Golf

Family & Group Friendly Oasis in Miami! Enjoy a private tropical home with a heated pool, mini-golf, and spacious indoor areas perfect for families and group stays. Just minutes from Miami International Airport, dining, and shopping , with ample parking and all the comforts you need. Relax, gather, and create unforgettable memories. Entire home is private for your stay. Questions about amenities or nearby attractions? Feel free to reach out anytime! 🌴✨

Guest favourite
A bright living area is furnished with a light-colored sofa and a wooden coffee table, enhancing the spacious feel. A large TV sits on a console, and natural light flows in from sliding glass doors that open to a balcony, framed by greenery.
Apartment in South Miami
4.84 out of 5 average rating, 113 reviews

Dharma |15% off Monthly| Perfect 1B | South Miami

Spacious, comfortable, upscale, and ideally located, Dharma Home Suites at Red Road Commons are the furnished accommodations you’ve been looking for. Quality living is at the forefront of this apartment community and we’ve made sure its modern and cozy interior offers the perfect home away from home for all travelers. Immerse yourself in Coral Gables’ vibrant surroundings, enjoy resort-style amenities and beautiful surroundings in the heart of South Miami.

Top Guest favourite
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, 396 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.

Popular amenities for Westchester rentals with a pool

When is the best time to visit Westchester?

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Avg. price$522 AUD$587 AUD$622 AUD$513 AUD$599 AUD$552 AUD$558 AUD$568 AUD$465 AUD$508 AUD$499 AUD$622 AUD
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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 $60 AUD per night before taxes and fees

  • Verified guest reviews

    Over 3,740 verified reviews to help you choose

  • Family-friendly holiday rentals

    50 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 40 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    60 of Westchester holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Westchester rentals

  • 4.8 Average rating

    Westchester stays are highly rated by guests—averaging 4.8 out of 5!