
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

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

Condo in Brickell Business District
Stunning one bedroom condo located in the best area of Brickell just minutes away from Brickell City Centre and Mary Brickell Village with restaurants, bars, shops and entertainment. About this Space -Approx.818 sqft of natural light filled space with gorgeous bay and city views and a large private balcony with dining table and large patio couch -High-speed Wi-Fi -1 free assigned parking spot -Pool, hot tub, jacuzzi, steam room, game room, state of the art gym, and business center

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.

Beautiful Poolside Studio, Heart of Miami
All are welcome to enjoy this beautiful studio apartment located in Miami's Historic Grove Park . The studio is private but is attached to the main house where we live. The bed is a super comfortable pillow top queen mattress. The kitchenette is fully outfitted. You'll find everything from a salad spinner to hot sauce. The pool and spa are amazing. (Please see the house rules for details on the pool and spa use.) Free gated parking, and keyless self check-in.

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.

Spanish House 3 Bedroom Pool House
If you are planning a vacation in Miami, this is the place to stay, You can enjoy all day at the pool no matter the exterior temperature the water will be perfect for a swim or go out to the existing Miami. 5 minutes away from the Miami International Airport located in one of the most safe and peaceful neighborhoods in Dade County. 15 minutes from the beach. Located at the heart of Miami close to all major entertainment districts
Popular amenities for Westchester rentals with a pool
House rentals with a pool

Encanto Family/Heated pool/center of Miami/BBQ

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

EPIC Escape/Pool Access Near Malls Airport Hospita

Ily's House

Centrally Located Resort Style Miami home

Miami Palm House with HEATED POOL & BBQ/BAR

Cozy Oasis Pool Home-1 Min from Baptist Hospital

Sunny Getaway: Relaxing Miami Home
Condo rentals with a pool

Modern and Comfortable Suite

Fontainebleau Jr. Suite King Bed with Ocean Views.

Modern Luxe at Brickell | Pool & Spa Access

Breathtaking Brickell Penthouse - Guest Favorite!

Beautiful apt. 1st floor 2/2. wifi and parking

Modern and comfortable Studio In Downtown Doral

Upper Penthouse Corner Unit 2B/2B | Icon Brickell

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

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

5350 Park Doral Downtown luxury apartment.

Modern 1BD Penthouse with Stunning Bay View

Miami Getaway

Studios in Coconut Grove Hotel with Free Parking

Perfect Studio for 2 Guest 20 Minute from DT Miami

LuxeParadise:Tropical StylePost-OpEdition Zip33165

Experience Design District, Pool, Gym and Parking
When is the best time to visit Westchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 301 | € 339 | € 358 | € 296 | € 345 | € 318 | € 321 | € 327 | € 268 | € 293 | € 288 | € 358 |
| 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 € 26 per night before taxes and fees

Verified guest reviews
Over 3,550 verified reviews to help you choose

Family-friendly vacation rentals
60 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!
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