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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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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, 213 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.

Guest favorite
A spacious suite featuring a king size bed with crisp white linens. Dark accent walls provide contrast against light wooden flooring. Natural light enters through large windows adorned with sheer curtains, while a small desk and tasteful decorative elements complete the stylish environment.
Apartment in Coconut Grove
4.81 out of 5 average rating, 126 reviews

Coconut Grove Stunning City View Suite Free Park

INCREDIBLE VALUE! First, a $30 gift card to our restaurant GreenStreet and a bottle of champagne will be awaiting you in your room! In Coconut Grove, this privately owned & renovated bright suite on the 15th floor of a luxurious waterfront property offers breathtaking city views, is fully equipped for 2 w/ a king size bed & full bath. Enjoy all the luxury amenities this property has to offer, pool & hot-tub with incredible bay views, penthouse gym, sauna, business center, 24-hr security, squash

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, 386 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 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, 389 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
An outdoor dining area features a wooden table with game pieces and seating. Beyond the table, a salt pool is visible, surrounded by lounge chairs and umbrellas under a clear blue sky. Ceiling fans are installed for airflow, enhancing the space's comfort.
Home in Miami
4.9 out of 5 average rating, 187 reviews

Miami Palm House with HEATED POOL & BBQ/BAR

Bring the whole family and friends to this Tropical Miami Home with lots of room for gatherings and entertainment! Enjoy the entire house with a stunning backyard, salt pool and gazebo! FREE PARKING 12 Guests. 4 Bedrooms. 9 Beds. 2 Baths Patio: Large Salt Pool (child friendly) BBQ Grill, Fridge, Wine Cooler, Bar Counter, Outdoor Lounge Furniture, Mini Golf Area Rooms: Bedroom 1: 1 Queen Bed Bedroom 2: 1 Queen Bed 1 Twin Bed Bedroom 3: 1 Queen Bed Bedroom 4: 5 Twin beds & (Game Room)

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, 141 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
5 out of 5 average rating, 404 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 favorite
A serene outdoor space is highlighted by a saltwater pool, surrounded by lush greenery. String lights create a warm ambiance above a covered dining area with a table and chairs, while a fire pit invites gatherings in the evening.
Home in Miami
4.96 out of 5 average rating, 139 reviews

Luxe Pool & Fire Pit | 5 min to Dolphin Mall

Experience sun-soaked luxury in Miami! Dive into the refreshing saltwater pool or unwind on one of the poolside lounge chairs. Newly renovated in 2022, this 4 bed/3.5 bath home comfortably accommodates 10 guests. For endless entertainment, compete in games of ping pong, sing your heart out with the karaoke machine, enjoy board games, or shoot some hoops. Presented by SuCasa Vacay, every detail has been thoughtfully chosen for an unforgettable Miami stay. Property Name: SuCasa Palmas

Top guest favorite
An aerial view captures a refreshing pool surrounded by lush greenery. The pool features an octagonal spa and colorful floatation rings. A lounge chair is positioned nearby on the spacious deck, creating an inviting outdoor space for relaxation.
Home in Miami
4.96 out of 5 average rating, 106 reviews

Pool & BBQ - 5BR/3 BTH - Miami Vacation

🏊‍♂️ Private pool & spa (not heated) 🌴 Covered patio, BBQ & outdoor lounge 🍳 Full kitchen + air fryer, coffee & basics 🛏️ 5 bedrooms + sofa beds · up to 12 guests 📺 6 Smart TVs + fast Wi-Fi 🧳 Easy check-out — no chores 🅿️ Parking for 4 cars 🎓 10 min → FIU · ✈️ 15 min → MIA Airport 🛒 10–15 min → Restaurants & shops 🌆 20–30 min → Brickell, Wynwood & Beaches 🔑 Entire home · private use 🤝 Superhost hospitality – English & Spanish 🚫 No parties or indoor smoking

Guest favorite
Home in Miami
4.94 out of 5 average rating, 130 reviews

Your Private Miami Oasis, Heated Pool + 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 favorite
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
4.85 out of 5 average rating, 120 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 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, 398 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?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$73,192 GYDG$82,393 GYDG$87,203 GYDG$71,937 GYDG$84,066 GYDG$77,374 GYDG$78,211 GYDG$79,675 GYDG$65,245 GYDG$71,937 GYDG$75,701 GYDG$104,142 GYD
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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 G$8,365 GYD per night before taxes and fees

  • Verified guest reviews

    Over 3,740 verified reviews to help you choose

  • Family-friendly vacation rentals

    50 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!