
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.

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

Stunning Studio w/Bay & City View Free Park/Pool
INCREDIBLE VALUE! First, a $30 gift card to our restaurant GreenStreet and a bottle of champagne will be awaiting you in your room! in Coconut Grove, this privately owned & renovated deluxe bright studio on the 15th floor of a luxurious waterfront property offers breathtaking bay & city views, is equipped for 2 guests w/king size bed, full kitchen, full bath & balcony. Enjoy all the luxury amenities we offer, pool & hot-tub w/ incredible bay views, penthouse gym, sauna, business center, squash.

"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

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.

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.

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

Encanto Family/Heated pool/center of Miami/BBQ

Miami Fun Oasis, Heated Pool & Private Mini Golf

EPIC Escape/Pool Access Near Malls Airport Hospita

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

The Lux Paradise Miami

Miami Modern Luxury with Pool & Spa

Centrally Located Resort Style Miami home

Cozy Oasis Pool Home-1 Min from Baptist Hospital
Condo rentals with a pool

*Coconut Grove Retreat: Balcony Pool, Free Parking

Four Seasons private studio in Brickell

Fontainebleau Jr. Suite King Bed with Ocean Views.

Gorgeous Beachy Chic Condo in Key Biscayne

Relaxing Apartment in Midtown

Modern and comfortable Studio In Downtown Doral

Stunning 2 bedroom+17 foot ceilings & heated pool

Lux 2BR • Water View • Pool • Spa • FREE Parking
Other holiday rentals with a pool

Beautiful Modern Apartment Downtown Doral

Modern Grove Studio | Parking & Washer/Dryer Incl.

Resort Style Condo in Downtown with Pool & Gym

5350 Park Doral Downtown luxury apartment.

Stylish Miami • Studio Weekly Discount • Pool+Gym

Waterfront Retreat + Heated Pool + Sand Court

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 | $512 AUD | $576 AUD | $610 AUD | $503 AUD | $588 AUD | $541 AUD | $547 AUD | $557 AUD | $456 AUD | $499 AUD | $490 AUD | $610 AUD |
| 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 $58 AUD 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!
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
- Rentals with a hot tub Westchester
- Rentals with a patio Westchester
- Family-friendly rentals Westchester
- Pet-friendly rentals Westchester
- Apartment rentals Westchester
- Rentals with outdoor seating Westchester
- House rentals Westchester
- Rentals with a washing machine and dryer Westchester
- Rentals with pools Miami-Dade County
- Rentals with pools Florida
- Rentals with pools 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
- Haulover Beach
- Ocean Reserve Condominium
- Sawgrass Mills
- Las Olas Beach
- Lauderdale-By-The-Sea Beach
- LoanDepot Park




