
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.

CityView Balcony Pool& Hottub. Wi-Fi. Full Kitchen
* Professional disinfecting cleaning before each stay * Central & Convenient Studio in the heart of Coconut Grove village * Front desk staffed all night ( check in starts at 4 PM ) 100 yards/meters to Restaurants, Coffee Shops, Shopping, Marina & Park 10 min by car to the University & Hospital 15 min by car to Brickell * Fast WIFI * Top Floor Gym * Pool & Hot Tub * Laundry Room * Onsite Parking offered for $10/ night Guest must be at least 21 years of age by check in. Our private studio

"Casa Mia's" pool & BBQ bungalow
Private entrance offers bungalow experience to the one bedroom space, walk in closet en suite bathroom. Shared structural walls: sounds do travel. Exclusive access to pool (unheated), BBQ, stove top, small outdoor fridge, and “makeshift” sink. Plenty of privacy! 20 minute stroll to Coco Walk; restaurants, lush nature and historic sites. Nestled between Coral Gables ; South Miami and Brickell. Close to University of Miami; quick access to airport and beaches. Merry Christmas Park’s a block away

Very Private 1/1 Apt w/Oasis Pool Patio Setting
Private apartment-1 bedroom w/king size bed, 1 full size bathroom, separate living and dining area. Fully equipped kitchen. Free parking, beautiful oasis setting with salt water pool, hot tub & patio. Gazebo w/fire pit, Bar-be-cue, 2 TV’s, free WiFi. This is NOT a party spot but a place to relax in the pool, hot tub or relaxing dinners at home after visiting Miami venues. Set in a quiet neighborhood, 2 miles from shopping & restaurants. This is your home away from home vacation spot!

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.

Guest Suite-Exterior Entrance, SelfCheckin.
If you like Clean, New, Quiet and Great Hospitality, then this is the Perfect Place for you. We are conveniently located between Key Largo and Downtown Miami, in an upscale community. You’ll feel safe and welcome here! -GATEWAY to the Keys and Everglades -Private entrance -Self Check-in -Free Parking -Fast WIFI -Swimming Pool -Central A/C -Ceiling fan -Kitchenette -Refrigerator -Microwave -Coffee maker -Netflix-HBO TV -Ceramic Tile Floors -Full Closet -Towels/Bath essentials -Iron & Board

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

Your Bay View Escape in Coconut Grove, Pool & Gym
- Enjoy breathtaking bay views & sunsets in this fully remodeled Coconut Grove condo - Private balcony perfect for relaxing and taking in the scenic surroundings - Full access to building amenities, including a gym, pool, sauna/steam room and jacuzzi -Onsite restaurant, valet/parking and 24/7 security. - Located just steps from Coconut Grove’s best restaurants, shops, and marinas -Fully equipped kitchen, luxurious oversized shower and cozy bedroom with work desk.

Modern & Cozy Studio | Resort-Style Amenities
This stylish Studio apartment is fully equipped for up to 2 guests, offering comfort and convenience. It features a spacious area and a stocked kitchen with stainless steel appliances, an in-unit washer/dryer, a cozy king bed, and a private balcony to relax and enjoy the view. Located in a luxury building with 24/7 front desk service, gym, swimming pool, sauna, massage room, kids’ playroom, and business center, it’s the perfect blend of comfort and convenience.

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.

Miami Lux Lake Front Retreat
A destination on its own: 1. Spacious home- over 5500 sqft of living space. 2. Gym with sauna and steam shower. 3. Pool table 4. Gourmet kitchen. 5. Formal dining room. 6. Large TV room with leather sectional, all recliner. 7. Karaoke 8. Kayaks to enjoy the lake 9. Heated Pool 10. Outdoor ping pong 🏓 table 11. Gym 12. Sauna and steam Room
Popular amenities for Westchester rentals with a pool
House rentals with a pool

Family retreat oasis, heated pool, jacuzzi & grill

The River House Miami

Encanto Family/Heated pool/center of Miami/BBQ

Miami Fun Oasis, Heated Pool & Private Mini Golf

Centrally Located Resort Style Miami home

Cozy Oasis Pool Home-1 Min from Baptist Hospital

Sunny Getaway: Relaxing Miami Home

Heated pool home only 7 miles from MIA Airport
Condo rentals with a pool

Luxury Beach & City View Condo 5 min walk to beach

Beautiful NEW Studio condo in the heart of Doral

Miami Design District Luxury Unit Stunning Views

1/1, Queen Bed, free parking, City Views/Sunsets!

Front Facing Top Floor Penthouse with Ocean Views

Modern and comfortable Studio In Downtown Doral

Stunning 2 bedroom+17 foot ceilings & heated pool

One Bedroom Condo King Bed Plus Den.
Other vacation rentals with a pool

Habitat Privé The Majestic Tree

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

Cozy Apartment in Downtown Doral

Beautiful Modern Apartment Downtown Doral

Modern Grove Studio | Parking & Washer/Dryer Incl.

Miami Oasis: Charming home with private pool

5350 Park Doral Downtown luxury apartment.

Terramar Villa- Luxury near Doral & MIA
When is the best time to visit Westchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ1,285 | ﺩ.ﺇ1,447 | ﺩ.ﺇ1,531 | ﺩ.ﺇ1,263 | ﺩ.ﺇ1,476 | ﺩ.ﺇ1,359 | ﺩ.ﺇ1,374 | ﺩ.ﺇ1,399 | ﺩ.ﺇ1,146 | ﺩ.ﺇ1,252 | ﺩ.ﺇ1,230 | ﺩ.ﺇ1,531 |
| 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 ﺩ.ﺇ147 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!
Destinations to explore
- Seminole Vacation rentals
- Central Florida Vacation rentals
- Miami Vacation rentals
- St Johns River Vacation rentals
- Orlando Vacation rentals
- Gold Coast Vacation rentals
- Miami Beach Vacation rentals
- Havana Vacation rentals
- Fort Lauderdale Vacation rentals
- Four Corners Vacation rentals
- Tampa Vacation rentals
- Kissimmee Vacation rentals
- Rentals with a patio Westchester
- Pet-friendly rentals Westchester
- House rentals Westchester
- Rentals with outdoor seating Westchester
- Rentals with a washer and dryer Westchester
- Apartment rentals Westchester
- Rentals with a hot tub Westchester
- Family-friendly rentals Westchester
- Rentals with pools Miami-Dade County
- Rentals with pools Florida
- Rentals with pools United States
- Miami Beach - South Beach
- Fort Lauderdale Beach
- Bayfront Park
- The Tides on Hollywood Beach
- Miami Design District
- Brickell City Centre
- Bayside Marketplace
- Miami Beach
- Miami Beach Convention Center
- Kaseya Center
- Ritz-Carlton
- Hard Rock Stadium
- Midtown
- Everglades National Park
- Port Everglades
- University of Miami
- Haulover Beach
- Ocean Reserve Condominium
- Sawgrass Mills
- Las Olas Beach
- Lauderdale-By-The-Sea Beach
- LoanDepot Park
- Bal Harbour Beach
- Fort Lauderdale Beach




