
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.

Luxury Vacation House in Miami’s Center!
Luxury Property in the Center of Miami. Completely renovated with wonderful pool/patio area for your perfect vacation. 3 blocks away from Miami’s most famous bakery Karla and other restaurants. 5 min. Away from Coral Gables. 10 min. yo Intern. Airport. 10 min. away from Brickell, Downtown and Wynwood restaurant and bar areas. 10 min. away from Dolphin Mall. 20 min. away from Miami Beach. Quiet residential area NO PARTIES! NO DRUG USE ON PROPERTY! Infractions will be reported to police!

[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.

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!

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

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

Heated pool home only 7 miles from MIA Airport
A block a way from the Famous Calle OCHO . The Property is located in the heart of Miami. Property is only 6.4 miles away from Miami International Airport. ONLY 14 MILES AWAY FROM SOUTH BEACH Property is close to lots of restaurants and shopping centers. great location and property. Property Very comfortable and spacious with a private pool. You will love it because of the cleanliness & comfort, its for family, couples,friends,business travelers.Equipped kitchen for cooking.

3B/2B Tropical Oasis w Salt-Water Pool! Lake views
Enjoy a private Lakeside Paradise. 3B/2B Family Home with a Deep Salt Water Pool and Chef Garden. You've just found the perfect getaway for those seeking relaxation, privacy and nature. Come cook up a delicious meal, listen to the local birds and kick-back by the pool to enjoy a sweeping lake view. We have everything you need for that perfect stay, with easy access to MIA+FLL and a deep salt water pool, so you can relax and enjoy! >The SUNSET will leave you SPEECHLESS!<

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! 🌴✨

Magnolia House Heated Pool with Slide/Gazebo/ BBQ
Magnolia House Miami features a beautiful heated pool with slide, large Gazebo, Brazilian BBQ, Domino Table, Sunbeds & lots of outside seating & tables. This is a spacious 4 bedroom 2 bathroom home, with a large kitchen. Very Close to Miami Airport, Cruise Port, & South Beach, Little Havana, Coral Gables, all hot spots & major attractions. Large driveway with ample parking & High speed WiFi. The pool and patio is very private.
Popular amenities for Westchester rentals with a pool
House rentals with a pool

3/2 Home with Pool & Bbq near Dadeland Mall

Miami Oasis: Charming home with private pool

Joy Day Off: Pool, Billiards & Tropical Park 5 min

Luxury Glow Villa | 4K Cinema | Heated Pool & Spa

Retro Chic Retreat-Heated Pool- PingPong Table

Centrally Located Resort Style Miami home

Waterfront Retreat + Heated Pool + Sand Court

Waterfront Home 3/3.5 Resort Style-Heated Pool*
Apartment rentals with a pool

*Coconut Grove Retreat: Balcony Pool, Free Parking

Lovely 1 Bedroom apartment/Pool,Heart of Wynwood

Luxury Condo - 3B/3B with Amazing Skyline View

Modern Luxe at Brickell | Pool & Spa Access

Luxury Condo in Hotel, amenities Downtown/Brickell

Oceanfront Brickell Miami Condo Pool Free Parking

Modern Apartment in Downtown Doral

Your Bay View Escape in Coconut Grove, Pool & Gym
Other holiday rentals with a pool

Luxury Lakefront Getaway

The Sunflower Inn

Waterfront Miami Oasis w/ Kayaks | Heated Pool

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

Escape to Miami/Heather+Pool/9pl/BBQ/pool table.

Cheerful, peaceful 3-Bedroom house with pool

LuxSurgery: 1BedroomTropicalOasisResidenceZip33165

Aurea | 12 PPL | Pool | BBQ |Playground |Mini Golf
When is the best time to visit Westchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $446 SGD | $502 SGD | $531 SGD | $438 SGD | $512 SGD | $471 SGD | $476 SGD | $485 SGD | $397 SGD | $438 SGD | $461 SGD | $634 SGD |
| 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 $51 SGD 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!
Destinations to explore
- Seminole Holiday rentals
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- Family-friendly rentals Westchester
- Rentals with a patio Westchester
- Rentals with outdoor seating Westchester
- House rentals Westchester
- Pet-friendly rentals Westchester
- Rentals with a hot tub Westchester
- Rentals with a washing machine and dryer Westchester
- Flat rentals 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
- The Tides on Hollywood Beach
- Kaseya Center
- Brickell City Centre
- Miami Beach Convention Center
- Miami Beach
- Hard Rock Stadium
- Port Everglades
- Everglades National Park
- Midtown
- Haulover Beach
- University of Miami
- Calle Ocho Plaza
- Ocean Reserve Condominium
- Miami Design District
- LoanDepot Park
- Las Olas Beach
- Lauderdale-By-The-Sea Beach
- Bal Harbour Beach
- Sawgrass Mills
- Dolphin Mall




