
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.

Cozy private guest studio
Welcome! This is a private guesthouse located in a quiet neighborhood. Accommodations are with a private entrance and parking space to make you feel at home. We are located near a major expressway. We have a pool; The POOL is a SWIM AT YOUR OWN RISK. It is shared with Owner. Enjoy a smoke free cottage. Ashtrays are provided outside for those guest that do smoke. We provide a queen size bed and a couch/bed. This space is perfect and comfortable for two guest.Please NO children and NO animals.

"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

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

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

Feels Like Summer ~ Panoramic Water Views! 2BR
Bluewater Realty Miami welcomes you to The Grand, located in Downtown Miami on Biscayne Bay. Our 2 bedroom Feels Like Summer! is the ultimate retreat. Enjoy incredible panoramic water Biscayne Bay views that will leave you in awe. With South Miami Beach 3 miles away you can take in the sun of Miami Beach, while still feeling the energy of downtown Miami. It's the best of both worlds, giving you the ultimate Miami experience. Your Airbnb Superhosts, Rachel and Mia Bluewater Realty Miami

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 Miami’s international airport, 15-min drive to Miami Beach.

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! 🌴✨

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.

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.
Popular amenities for Westchester rentals with a pool
House rentals with a pool

Private Pool and Tropical Garden Oasis

Encanto Family/Heated pool/center of Miami/BBQ

Luxury Oasis in Brickell - Only 3 min to Ocean

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

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

Centrally Located Resort Style Miami home

Cozy Oasis Pool Home-1 Min from Baptist Hospital

Sunny Getaway: Relaxing Miami Home
Condo rentals with a pool

Modern and Comfortable Suite

*Coconut Grove Retreat: Balcony Pool, Free Parking

Ocean View Balcony. Pool & Hot tub. Fast Wi-Fi

Fontainebleau Jr. Suite King Bed with Ocean Views.

Beautiful NEW Studio condo in the heart of Doral

Miami Design District Luxury Unit Stunning Views

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

5350 Park Doral Downtown luxury apartment.

Miami Getaway

Stylish Miami • Studio Weekly Discount • Pool+Gym

Waterfront Retreat + Heated Pool + Sand Court

Terramar Villa- Luxury near Doral & MIA

3 BR Cozy Miami Home w/ Pool

LuxeParadise:Tropical StylePost-OpEdition Zip33165
When is the best time to visit Westchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $609 NZD | $686 NZD | $726 NZD | $599 NZD | $700 NZD | $644 NZD | $651 NZD | $663 NZD | $543 NZD | $594 NZD | $583 NZD | $726 NZD |
| 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 $70 NZD 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 and kid-friendly amenities

Pet-friendly accommodation
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
60 of Westchester holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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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