
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.

"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 āmakeshiftā 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 Parkās a block away

Charming house with private pool & large patio
This is the classic 1950ās 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. Youāll 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

One Bedroom Condo King Bed With City Views
Entire luxury condo at Quadro in the Design District. Fully equipped - Free parking, coffee, Wi-Fi & cable. The building features amenities in the 6th floor including a fitness center, a lounge with co-working area & a game room, an outdoor dining area with BBQ's and a great pool.Enjoy guest exclusive neighborhood discounts. Walk to hundreds of designer shops, restaurants, bars, art galleries, & more! 10-min drive to Miamiās international airport, 15-min drive to Miami Beach.

Pool & BBQ - 5BR/3 BTH - Miami Vacation
šāāļø Private pool & spa (not heated) š“ Covered patio, BBQ & outdoor lounge š³ Full kitchen + air fryer, coffee & basics šļø 5 bedrooms + sofa beds Ā· up to 12 guests šŗ 6 Smart TVs + fast Wi-Fi š§³ Easy check-out ā no chores š æļø Parking for 4 cars š 10 min ā FIU Ā· āļø 15 min ā MIA Airport š 10ā15 min ā Restaurants & shops š 20ā30 min ā Brickell, Wynwood & Beaches š Entire home Ā· private use š¤ Superhost hospitality ā English & Spanish š« No parties or indoor smoking

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, kidsā playroom, and business center, itās the perfect blend of comfort and convenience.

Miami Fun Oasis, Heated Pool & Private Mini Golf
Family & Group Friendly Oasis in Miami! Enjoy a private tropical home with a heated pool, mini-golf, and spacious indoor areas perfect for families and group stays. Just minutes from Miami International Airport, dining, and shopping , with ample parking and all the comforts you need. Relax, gather, and create unforgettable memories. Entire home is private for your stay. Questions about amenities or nearby attractions? Feel free to reach out anytime! š“āØ

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. Itās 900 sf of living area. Cleaning & Decontamination as per CDC guidelines before every check in.

āHave Fun at Hacienda ParaĆsoā Suite 1 | pool |
Welcome to Room 1, the first addition at Hacienda ParaĆso. This suite is conveniently located next to another Airbnb suite, providing flexibility for your stay. It features a private entrance, bathroom, kitchenette, and dining table, ensuring a comfortable and self-contained experience. Enjoy the convenience of hotel-like amenities paired with the added bonus of access to our stunning pool and lush yard, creating a truly relaxing retreat.

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

The River House Miami

EPIC Escape/Pool Access Near Malls Airport Hospita

Luxury Villa | Spa - Pool |Top Location| Pets |BBQ

Magnolia House Heated Pool with Slide/Gazebo/ BBQ

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
Apartment rentals with a pool

LuxuryPH at Brickell Bay-Amazing MIAMI City VIEWS

*Coconut Grove Retreat: Balcony Pool, Free Parking

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

Icon Brickell (W) Huge unit with bay & river views

Fontainebleau Jr. Suite King Bed with Ocean Views.

Beautiful NEW Studio condo in the heart of Doral

Front Facing Top Floor Penthouse with Ocean Views

Modern and comfortable Studio In Downtown Doral
Other holiday rentals with a pool

Anjole Luxury Villa | 12PPL | Pool | Games | BBQ

Chic Guest house w/pool, hot tub, grill, mini golf

South Miami 2BR/2BA - Steps from Dadeland Mall

5350 Park Doral Downtown luxury apartment.

Waterfront Retreat + Heated Pool + Sand Court

Miami Chic-Heated Pool Near FIU and Coral Gables

Terramar Villa- Luxury near Doral & MIA

3 BR Cozy Miami Home with Pool
When is the best time to visit Westchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $449 SGD | $506 SGD | $535 SGD | $442 SGD | $516 SGD | $475 SGD | $480 SGD | $489 SGD | $401 SGD | $438 SGD | $430 SGD | $535 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 $51Ā SGD per night before taxes and fees

Verified guest reviews
Over 3,740 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 ā averaging 4.8 out of 5!
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- Rentals with poolsĀ Miami-Dade County
- Rentals with poolsĀ Florida
- Rentals with poolsĀ United States
- South Beach
- Fort Lauderdale Beach
- Bayfront Park
- The Tides on Hollywood Beach
- Miami Design District
- Sea Air Towers Condominium Association
- Brickell City Centre
- Bayside Marketplace
- Miami Beach
- Miami Beach Convention Center
- Ritz-Carlton
- Kaseya Center
- Hard Rock Stadium
- Midtown
- Everglades National Park
- Port Everglades
- Fortune House Hotel
- University of Miami
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- Sawgrass Mills
- Las Olas Beach
- Lauderdale-By-The-Sea Beach
- LoanDepot Park




