
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.

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.

Artistic Design District Stay, Parking, Pool, Gym
Modern, boutique condo with outstanding amenities located steps from the famous Miami Design District. Your unit includes: a washer/dryer, full kitchen (with stove, oven, microwave, fridge, dishwasher, Keurig coffee maker, toaster, blender, tupperware, utensils, plates and cookware). Building amenities feature a beautiful gym with virtual spin studio, common work space, pool and parking garage. Your unit has a relaxing private balcony. Safe, secure building with 24/7 security and front desk.

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)

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

Pool & BBQ - 5BR/3 BTH - Miami Vacation
🏊♂️ Private pool & spa (not heated) 🌴 Covered patio, BBQ & outdoor lounge 🍳 Full kitchen + air fryer, coffee & basics 🛏️ 5 bedrooms + sofa beds · up to 12 guests 📺 6 Smart TVs + fast Wi-Fi 🧳 Easy check-out — no chores 🅿️ Parking for 4 cars 🎓 10 min → FIU · ✈️ 15 min → MIA Airport 🛒 10–15 min → Restaurants & shops 🌆 20–30 min → Brickell, Wynwood & Beaches 🔑 Entire home · private use 🤝 Superhost hospitality – English & Spanish 🚫 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, kids’ playroom, and business center, it’s 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! 🌴✨

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.

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

Spanish House 3 Bedroom Pool House

Encanto Family/Heated pool/center of Miami/BBQ

Luxury Oasis in Brickell - Only 3 min to Ocean

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

LuxuryPH at Brickell Bay-Amazing MIAMI City VIEWS

*Coconut Grove Retreat: Balcony Pool, Free Parking

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

Stylish designer condo in the heart of Brickell

Fontainebleau Jr. Suite King Bed with Ocean Views.

Front Facing Top Floor Penthouse with Ocean Views

Stunning 2 bedroom+17 foot ceilings & heated pool

W Icon Brickell 40th Floor High Ceiling Ocean View
Other holiday rentals with a pool

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

The Sunflower Inn

Charming Studio Suites at Downtown Doral.

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

Studios in Coconut Grove Hotel with Free Parking

Waterfront Retreat + Heated Pool + Sand Court

Terramar Villa- Luxury near Doral & MIA

3 BR Cozy Miami Home w/ 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 $51 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 – averaging 4.8 out of 5!
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