
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 60 holiday rentals in Westchester

Nightly prices starting at
Westchester holiday rentals start at $70 NZD per night before taxes and fees

Verified guest reviews
Over 3,880 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, 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.

Pool home 7 miles from Airport & near FIFA Stadium
Stay in the heart of Miami at this spacious pool home, just 1 block from famous Calle Ocho! Only 7 miles from Miami International Airport and 14 miles from South Beach. Enjoy a private heated pool, comfortable living spaces, and easy access to top restaurants, shopping, nightlife, and the FIFA stadium. Perfect for families and groups looking for the ideal Miami getaway. You’ll love the cleanliness, comfort, and private heated pool. Perfect for families with a fully equipped kitchen for cooking

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.

Guesthome w/ Heated Pool 5 mins from Miami Airport
This home is located just 5 minutes from the Miami Airport and is central to many attractions here in Miami. Take a walk down Calle Ocho, swim at Miami Beach, enjoy a game at Marlins baseball stadium or American Airlines Arena (home to the Miami Heat), and dine at one of the many popular restaurants such as Versailles. These are all within 15 minutes of this private comfortable home. Come enjoy a location that provides a rich experience into the vibrant hispanic culture that Miami radiates.

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.

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)

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

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

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

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! 🌴✨

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.

Wellness Retreat | 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

Sunny Getaway: Relaxing Miami Home
Welcome to our stunning Miami Airbnb home! This spacious retreat accommodates up to 10 guests with 5 bedrooms, 6 beds, and 2.5 bathrooms. Enjoy the private pool, hot tub, and safe neighborhood. Conveniently located near the Port of Miami for cruises, and close to major expressways for easy transportation. Explore Miami's beaches, nightlife, shopping, dining, and popular attractions. Book now for an amazing stay!
Popular amenities for Westchester rentals with a pool
House rentals with a pool

Family Oasis Retreat• Heated Pool, Jacuzzi & Grill

3/2 Home with Pool & Bbq near Dadeland Mall

Encanto Family/Heated pool/center of Miami/BBQ

Miami Oasis: Charming home with private pool

Charming house with private pool & large patio

EPIC Escape/Pool Access Near Malls Airport Hospita

Magnolia House Heated Pool with Slide/Pergola/ BBQ

Modern 4BR Home w/ Pool, Fast Wi-Fi & Near Airport
Condo rentals with a pool

Studio at The Ritz-Carlton Key Biscayne Miami

Beautiful apt. 1st floor 2/2. wifi and parking

Modern Apartment in Downtown Doral

Luxury Miami Condo | Pool, Gym & Parking

SF Beautiful Blue & Gold Studio with Ocean View

Penthouse 1910 Ocean and Bay View 2BD Monte Carlo

Bay Views, Pool & Gym Access in Coconut Grove

Best area of Doral with all the services!
Other holiday rentals with a pool

Tropical Retreat Miami 5BR w/Pool, BBQ & GameRoom

The Sunflower Inn

Retro Chic Retreat-Heated Pool- PingPong Table

Waterfront Retreat + Heated Pool + Sand Court

"Casa Mia's" FIFA World Cup pool & BBQ bungalow

3 BR Cozy Miami Home with Pool

“Have Fun at Hacienda Paraíso” Suite 1 | pool |

Luxury Stunning Pool | Games| 12PPL+/TOP Location
When is the best time to visit Westchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $823 NZD | $780 NZD | $825 NZD | $600 NZD | $701 NZD | $645 NZD | $652 NZD | $665 NZD | $544 NZD | $600 NZD | $631 NZD | $869 NZD |
| 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 |
Destinations to explore
- Miami Holiday rentals
- Orlando Holiday rentals
- Four Corners Holiday rentals
- Kissimmee Holiday rentals
- Miami Beach Holiday rentals
- Tampa Holiday rentals
- Fort Lauderdale Holiday rentals
- Hollywood Holiday rentals
- St. Augustine Holiday rentals
- Key West Holiday rentals
- Davenport Holiday rentals
- Sarasota Holiday rentals
- Pet-friendly rentals Westchester
- Family-friendly rentals Westchester
- Rentals with a patio Westchester
- Apartment rentals Westchester
- Rentals with a hot tub Westchester
- Rentals with a washing machine and dryer Westchester
- Rentals with outdoor seating Westchester
- House rentals Westchester
- Rentals with pools Miami-Dade County
- Rentals with pools Florida
- Rentals with pools United States
- Fort Lauderdale Beach
- South Beach
- Hard Rock Stadium
- Port Everglades
- Bayfront Park
- Miami Beach Convention Center
- Everglades National Park
- Haulover Beach
- Brickell City Centre
- University of Miami
- Dolphin Mall
- Kaseya Center
- Las Olas Beach
- LoanDepot Park
- Sawgrass Mills
- Seminole Hard Rock Hotel and Casino
- Midtown
- Bayside Marketplace
- Bal Harbour Beach
- Florida International University
- The Tides on Hollywood Beach
- Aventura Mall
- Lauderdale-By-The-Sea Beach
- John Pennekamp Coral Reef State Park





