
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.

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.

[Kids Favourite] World Cup Family Oasis | 5BR | Ht
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!

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

Home Sweet Home Family & Friends getaway with Pool
Welcome to our charming 4-bedroom family home nestled in the heart of vibrant Miami! The home is perfect for families, couples, or friends looking for a comfortable getaway. Minutes away from Miami International Airport, Miami Beach, Downtown Miami, Brickell, and Doral. ✔ Fully Equipped Kitchen ✔ Comfortable Bedrooms with King/Queen/Full beds/bunk beds ✔ Open Concept Living Area ✔ Office Desk ✔ High-Speed Wi-Fi ✔ Free parking on premises ✔ Large Patio and yard with pool

Gorgeous 5BR/Games/Fire Pit/BBQ/H. Pool & Hot Tub
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 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.

Sleek Studio at Elser | Resort Pool & Downtown
Guest verdict: "The best place to stay in Miami close to everything." This Elser studio offers a modern base for your Miami adventures. Enjoy vibrant downtown views and easy access to Bayfront Park (2 min walk) and Kaseya Center (3 min walk). April brings event energy with eMerge Americas (April 23-24) just a short Metromover ride away. Our residence is built for the standard Miami traveler seeking a dynamic stay with all the city's best within reach.

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.
Popular amenities for Westchester rentals with a pool
House rentals with a pool

3/2 Home with Pool & Bbq near Dadeland Mall

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

Luxury Stay w/ Heated Pool, Golf & Chess Yard

Luxury Vacation House in Miami’s Center!

Retro Chic Retreat-Heated Pool- PingPong Table

Waterfront Home 3/3.5 Resort Style-Heated Pool*

Aurea | 12 PPL | Pool | BBQ |Playground |Mini Golf

3 BR Cozy Miami Home with Pool
Apartment rentals with a pool

Hotel Arya Apt w/Waterfront View, Free Parking

Modern Apartment in Downtown Doral

Cali King 1 BedRoom: Pool Gym Balcony Jacuzzi

Guest Favorite Coconut Grove,pool, sauna,park free

Urban Boho 1 Bdrm Condo, Best Miami Location

Bay Views, Pool & Gym Access in Coconut Grove

Beautiful BAY VIEW Apt, 2/2br 1100sqf

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

Lakefront Pool Home 10 Minutes to HardRock Stadium

Joy Day Off: Pool & Billiards Home

Private Pool CasaMia • 15 min to MIA & Wynwood

Great for family gatherings / Miami Vacay

High House by Stone Bridge & Sunken Garden

Blue Breeze | 8PPL | Pool | Mini Golf | Pool Table
When is the best time to visit Westchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £352 | £333 | £352 | £256 | £299 | £276 | £279 | £284 | £232 | £256 | £270 | £371 |
| 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 |
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 £30 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 & child-friendly amenities

Pet-friendly holiday rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
60 of Westchester holiday rentals include wifi 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!
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- Rentals with a washing machine and dryer Westchester
- Rentals with outdoor seating Westchester
- Rentals with a hot tub Westchester
- Rentals with a patio Westchester
- Rentals with pools Miami-Dade County
- Rentals with pools Florida
- Rentals with pools United States
- South Beach
- Fort Lauderdale Beach
- Bayfront Park
- Bayside Marketplace
- Kaseya Center
- The Tides on Hollywood Beach
- Brickell City Centre
- Miami Beach Convention Center
- Hard Rock Stadium
- Port Everglades
- Midtown
- Everglades National Park
- Haulover Beach
- University of Miami
- Las Olas Beach
- LoanDepot Park
- Lauderdale-By-The-Sea Beach
- Dolphin Mall
- Seminole Hard Rock Hotel and Casino
- Bal Harbour Beach
- Fort Lauderdale Beach
- Sawgrass Mills
- John Pennekamp Coral Reef State Park
- Zoo Miami





