
Vacation rentals with a pool in Westchester
Find and book unique homes with a pool on Airbnb
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 ﺩ.ﺇ 147 per night before taxes and fees

Verified guest reviews
Over 3,880 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!
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.

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

Modern Studio | Downtown & Bay Views
Guest verdict: "Overall had a great time in a clean place with excellent amenities, superb walkability, and a very responsive owner. Would definitely visit again." Our studio offers a stylish space with city and bay views. It's just a 2-minute walk to Bayfront Park. This residence is perfect for any traveler seeking convenience and relaxation in the heart of Miami. Enjoy an unbeatable location close to dining, shopping, and entertainment, especially Bayside Marketplace.

The Miracle Cottage & Pool on Acre Miami Florida
Beautiful, brand new PRIVATE cottage on an acre property situated in million dollar neighborhood. Perfect place to relax and enjoy the Miami sun. This is a little piece of heaven in the heart of a magical city. Come & enjoy your best vacation. Charming , peaceful & comfortable . Cottage is a completely separate building from the main house. It’s 900 sf of living area. Cleaning & Decontamination as per CDC guidelines before every check in.

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.

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

Spanish House 3 Bedroom Pool House

Family Oasis Retreat• Heated Pool, Jacuzzi & Grill

Encanto Family/Heated pool/center of Miami/BBQ

Miami Oasis: Charming home with private pool

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

Miami Fun Oasis - Heated Pool & Private Mini Golf

EPIC Escape/Pool Access Near Malls Airport Hospita

Magnolia House Heated Pool with Slide/Pergola/ BBQ
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

Cali King 1 BedRoom: Pool Gym Balcony Jacuzzi

Luxury Miami Condo | Pool, Gym & Parking

Upscale Designer 1 Bdrm Condo - Miami Design Dist

SF Beautiful Blue & Gold Studio with Ocean View

Bay Views, Pool & Gym Access in Coconut Grove
Other vacation rentals with a pool

Blue Diamond | 7 PPL| Pool | 5 mins NU Stadium|BBQ

The Sunflower Inn

3/2 Home with Pool & Bbq near Dadeland Mall

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

Retro Chic Retreat-Heated Pool- PingPong Table

Waterfront Retreat + Heated Pool + Sand Court

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

Guesthome w/ Heated Pool 5 mins from Miami Airport
When is the best time to visit Westchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 1,733 | ﺩ.ﺇ 1,642 | ﺩ.ﺇ 1,737 | ﺩ.ﺇ 1,263 | ﺩ.ﺇ 1,476 | ﺩ.ﺇ 1,359 | ﺩ.ﺇ 1,374 | ﺩ.ﺇ 1,399 | ﺩ.ﺇ 1,146 | ﺩ.ﺇ 1,263 | ﺩ.ﺇ 1,329 | ﺩ.ﺇ 1,829 |
| 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 Vacation rentals
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- 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 washer 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
- Miami 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





