
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.

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

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.

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!

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)

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

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

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.

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! 🌴✨

Ily's House
Fabulous fully remodeled house. Private pool and covered patio. New kitchen, granite counter top, nice porcelain and hard wood floor. Fifteen minutes away from the airport. Close to many shopping plazas, restaurants and various entertainment. The University of Miami is 2.9 miles and the golf course is 3.5 miles away from the house. The house is located near several Plastic Surgery Centers and a major Hospital. High speed internet.

Marriott Villas and 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.

Lux Tuscan Villa | Pool/Sauna/Gym/Spa/Basketball
🇮🇹 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
House rentals with a pool

World Cup Lakefront Hub | 5BR | Heated Pool

Heated* Pool•Hot Tub•Sauna•Games•Prime for Groups*

3B/2B Tropical Oasis w Salt-Water Pool! Lake views

Pool House on 4 Acres in Private Neighborhood

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

Retro Chic Retreat-Heated Pool- PingPong Table

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

Waterfront Retreat + Heated Pool + Sand Court
Condo rentals with a pool

Sunset Hideaway! Direct Water Views and Renovated!

Chic Studio 5 Icon Brickell Amazing View

Beautiful and Modern Apartment in Doral. 1B/1B

Miami Design District Luxury Unit Stunning Views

Luxury Condo in Hotel, amenities Downtown/Brickell

Modern and comfortable Studio In Downtown Doral

Luxury 5 stars ICON Brickell @46TH 2B/2B, Pool/Gym

Luxury Miami Studio 2413 Amenities,View Pool, Gym
Other vacation rentals with a pool

The Sunflower Inn

Casita Miami! Pool and pickelball home

Ocean view in Coconut Grove. 1/1 + Parking

Miami Oasis: Charming home with private pool

Cozy 2 Bedroom Modern Farmhouse in Miami

Coconut Grove Retreat,1/1 Bayview-includes Parking

Miami Gem/Heated Pool/BBQ/In-Laws Atta

Sleek Doral Retreat 1 Bed Oasis W/ Free Parking
When is the best time to visit Westchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$73,236 GYD | G$82,443 GYD | G$87,255 GYD | G$71,980 GYD | G$84,117 GYD | G$77,421 GYD | G$78,258 GYD | G$79,722 GYD | G$65,285 GYD | G$71,980 GYD | G$75,747 GYD | G$104,204 GYD |
| 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 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$8,370 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!
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- Miami Beach - South Beach
- Fort Lauderdale Beach
- Bayfront Park
- The Tides on Hollywood Beach
- Bayside Marketplace
- Kaseya Center
- Brickell City Centre
- Miami Beach Convention Center
- Miami Beach
- Hard Rock Stadium
- Port Everglades
- Midtown
- Everglades National Park
- Haulover Beach
- University of Miami
- Ocean Reserve Condominium
- Calle Ocho Plaza
- Miami Design District
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- Lauderdale-By-The-Sea Beach
- Sawgrass Mills
- Bal Harbour Beach
- Dolphin Mall




