
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

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.

“Have Fun at Hacienda Paraíso” Suite 1 | pool |
Welcome to Room 1, the first addition at Hacienda Paraíso. 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.

SF Stunning 12th Flr. Studio in the Heart of Grove
You will be in walking distance to everywhere in Coconut grove. Ditch the craziness of south beach and downtown Miami and enjoy a calmer night stay here at the Arya. This is a condo hotel which means there is no daily cleaning service but you will be able to enjoy all the amenities that hotel guest uses. Wake up in the morning and see sail boats from your Balcony! Amazing restaurants and bars are just a few minute walk away!

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

Encanto Family/Heated pool/center of Miami/BBQ

[Top Pick] Stunning Family Fun Oasis With Heated P

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

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
Apartment rentals with a pool

Luxury PH at Brickell Bay-Amazing MIAMI City VIEWS

*Coconut Grove Retreat: Balcony Pool, Free Parking

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

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

Fontainebleau Jr. Suite King Bed with Ocean Views.

Beautiful NEW Studio condo in the heart of Doral

Relaxing Apartment in Midtown

Stunning 2 bedroom+17 foot ceilings & heated pool
Other holiday rentals with a pool

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

Studio Unit at Doral

The Sunflower Inn

5350 Park Doral Downtown luxury apartment.

Studios in Coconut Grove Hotel with Free Parking

Stylish Miami • Studio Weekly Discount • Pool+Gym

Waterfront Retreat + Heated Pool + Sand Court

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 | £261 | £294 | £311 | £257 | £300 | £276 | £279 | £284 | £233 | £254 | £250 | £311 |
| 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 £30 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 – averaging 4.8 out of 5!
Destinations to explore
- Seminole Holiday rentals
- Central Florida Holiday rentals
- Miami Holiday rentals
- St Johns River Holiday rentals
- Orlando Holiday rentals
- Gold Coast Holiday rentals
- Miami Beach Holiday rentals
- Havana Holiday rentals
- Fort Lauderdale Holiday rentals
- Four Corners Holiday rentals
- Tampa Holiday rentals
- Kissimmee Holiday rentals
- Pet-friendly rentals Westchester
- Rentals with a patio Westchester
- Family-friendly rentals Westchester
- Flat rentals Westchester
- Rentals with a washing machine and dryer Westchester
- Rentals with outdoor seating Westchester
- House rentals Westchester
- Rentals with a hot tub Westchester
- Rentals with pools Miami-Dade County
- Rentals with pools Florida
- Rentals with pools United States
- South Beach
- Fort Lauderdale Beach
- Miami Design District
- Bayfront Park
- The Tides on Hollywood Beach
- 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
- Fortune House Hotel
- Port Everglades
- Lummus Park
- University of Miami
- Haulover Beach
- Ocean Reserve Condominium
- Sawgrass Mills
- Las Olas Beach
- Lauderdale-By-The-Sea Beach




