Holiday rentals with a pool in Westchester

Find and book unique homes with a pool on Airbnb

Quick stats about holiday rentals with a pool in Westchester

  • Total holiday rentals

    Explore 70 holiday rentals in Westchester

  • Nightly prices starting at

    Westchester holiday rentals start at $52 NZD per night before taxes and fees

  • Verified guest reviews

    Over 4,310 verified reviews to help you choose

  • Family-friendly holiday rentals

    60 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 40 rentals that welcome pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wi-Fi availability

    70 of Westchester holiday 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!

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 serene outdoor area features a private pool surrounded by landscaped grass. Comfortable lounge chairs are positioned near the water, while the terrace offers a dining table and hanging chair, all framed by a vibrant tree and clear blue sky.
Home in Miami
4.88 out of 5 average rating, 121 reviews

Lake House in Miami

Relax with the whole family at this peaceful place to stay. Beautiful pool house with a lake. Master bedroom with a King Size Bed, walk in closet, spacious bathroom. Second bedroom with a Queen Size Bed, third bedroom with a twin bed, sofa bed in the living room. This house can accommodate 7 people. Full equipped kitchen. Outdoor terrace where you can enjoy the beautiful lake view, nice pool, great patio, with deck by the lake. Everything that you need to have a great vacation in Miami.

Superhost
Home in Miami
4.87 out of 5 average rating, 218 reviews

Miami Paradise Westchester * Heated Pool*

Enjoy this gem in the heart of Miami newly renovated home. This modern chic home is designed to accommodate 13 guest. Perfect for entertaining backyard equipped with a counter top bar, BBQ area, dinning room area and sofa. Layout in the Miami sun in a modern pool or choose nightlife chill in jacuzzi overlooking the stars. For our fishing lovers, this home provides a deck overlooking a lake. This home is close to all main highways, malls, Miami beach, FIU, Brickell, Wynwood, downtown Miami.

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
4.89 out of 5 average rating, 204 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 favourite
A modern living room showcases marble accents and a large wall-mounted flat screen TV. A plush sectional sofa with bold black and white patterns is arranged around a decorative coffee table. Natural light filters through the window with minimalistic blinds.
Home in Miami
4.96 out of 5 average rating, 108 reviews

| LuxeLanding | Pool+Lounge+Chess+BBQ+Golf+Airport

Discover the magic of Miami at our stunning 4BR/3BA modern retreat in vibrant Little Havana’s west side! This spacious, open-concept home sleeps up to 11 and features a sleek living room, fully stocked kitchen with stainless steel appliances, dinnerware, wine/shot glasses, cookware, tabletop appliances & complimentary coffee. The highlight? A resort-style backyard with a pool, mini golf, life-size chess, cornhole, Connect Four, outdoor pool table, a covered gazebo & deluxe grill/hibachi!

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 Fountainebleau
5.0 out of 5 average rating, 468 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
The vibrant living area features a blue accent wall and a large sofa adorned with decorative pillows. A foosball table occupies one corner, while the space opens to the outdoor pool area through expansive glass doors, creating a lively atmosphere.
Home in Miami
4.93 out of 5 average rating, 104 reviews

Greek House • Heated Pool + Game Room • Near MIA

🏊 Private Heated Pool 🌴 BBQ 🎮 Family room w/ foosball 🍳 Full kitchen + air fryer, coffee & essentials 🛏️ 3 bedrooms · 2 Kings + 2 Queens + sofa beds (12 guests) 📺 5 Smart TVs · fast Wi-Fi 🧺 Pool & bath towels provided 🧳 Easy check-out — no chores 🎓 10 min → FIU 🛍️ 15 min → Dolphin Mall ✈️ 15–20 min → MIA Airport 🌆 25–30 min → Brickell & Wynwood 🌊 35–40 min → South Beach 🐾 Pets welcome · Pet fee applies 🤝 Superhost care — English & Spanish 🚫 No parties or indoor smoking

Superhost
Home in Miami
4.9 out of 5 average rating, 102 reviews

Luxury Stay w/ Heated Pool, Golf & Chess Yard

☀️ Enjoy the perfect vacation in the City of the Sun! ☀️ This spacious 4-bedroom, 4-bathroom home is located just minutes from the airport, top restaurants, bars, shops, and Miami’s main attractions. Ideal for families and groups, the property features a large backyard designed for entertainment: refreshing pool, mini beach, fire pit, golf putting area, and giant chess. Every corner is crafted for relaxation, fun, and unforgettable memories. Come live your best Miami experience! 🌴

Top Guest favourite
An outdoor dining area is set under a shaded patio, featuring a glass-top table surrounded by eight metal-framed chairs. Potted plants adorn the table, while a pool glistens in the background. Neatly arranged stone tiles lead towards lush greenery, enhancing the tranquil environment.
Home in Miami
4.89 out of 5 average rating, 113 reviews

Miami Tropical Villa -Pool & BBQ

Welcome to "Miami Tropical Villa" – Miami's ultimate tropical escape! Immerse in luxury with the stunning blue pool, a haven of relaxation under the Florida sun. Poolside loungers invite you to unwind. Beyond the villa, Miami's treasures await. From South Beach nightlife to the Wynwood art scene, adventure is at your doorstep. This Tropical Villa invites you to make unforgettable memories in a tropical paradise that transcends the ordinary. Your escape to luxury begins here!

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 Westchester
4.95 out of 5 average rating, 157 reviews

Miami Fun Oasis - Heated Pool & Private Mini Golf

Escape to your private Miami oasis! Enjoy a sparkling heated pool, mini-golf, and a covered game terrace with pool table—perfect for families & groups of up to 12. Spacious interiors offer comfort and style, just minutes from Miami International Airport, top dining, and shopping. Ample parking included. Relax, reconnect, and create unforgettable memories in this fully private home. Questions about amenities or local attractions? We’re here to help anytime! 🌴✨

Superhost
Home in Miami
4.86 out of 5 average rating, 136 reviews

Gorgeous 5BR • Pool_BBQ_Hot Tub, Fire Pit & Games

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. 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

Top Guest favourite
Condo in Doral
4.95 out of 5 average rating, 939 reviews

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.

Guest favourite
The pool area features a heated pool with gentle waterfalls, illuminated by soft lighting. Surrounded by palm trees, the outdoor dining space is visible in the background, furnished with a table and chairs, creating a serene environment for relaxation.
Home in Westchester
4.95 out of 5 average rating, 149 reviews

FourSeasons Italy | Pool/Spa/Sauna/Gym/FirePit/BBQ

🇮🇹 HOUSE OF ITALY – A Private Tuscan Escape 🇮🇹 🌟 GUEST FAVORITE with true resort-style luxury & top-rated reviews! 🌟 🎱 Pool Table • 💪 Private Gym • 😅 Sauna 🛌 4 Bedrooms • Sleeps up to 16 comfortably 🔥 Heated Pool • Hot Tub • Massage Beds • Sun Loungers 🍽 Outdoor Kitchen • BBQ • Fire Pit for unforgettable nights 🏀 Basketball Hoop & More ✨ More than a stay—an extraordinary experience from @BeyondTheBNB

Popular amenities for Westchester rentals with a pool

When is the best time to visit Westchester?

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Avg. price$817 NZD$774 NZD$819 NZD$596 NZD$696 NZD$641 NZD$648 NZD$660 NZD$540 NZD$596 NZD$627 NZD$863 NZD
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