
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.

Coconut Grove Stunning City View Suite Free Park
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 bright suite on the 15th floor of a luxurious waterfront property offers breathtaking city views, is fully equipped for 2 w/ a king size bed & full bath. Enjoy all the luxury amenities this property has to offer, pool & hot-tub with incredible bay views, penthouse gym, sauna, business center, 24-hr security, squash

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

Stylish 1Bdrm Penthouse In Miami Design District
Entire luxury condo at Quadro in the Miami Design District. Fully furnished & equipped - Free parking, coffee, Wi-Fi & cable. The building features resort-style amenities in the 6th floor including a fitness center with a yoga/spinning studio, a lounge with co-working/conference areas & a game room, an outdoor dining area with a summer kitchen & BBQ's, a pool with cabanas overlooking Biscayne Bay. 10-min drive to Miami’s airport, 15-min drive to Miami Beach. Walk to Wynwood and Midtown.

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

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.

Your Private Miami Oasis, Heated Pool + 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.
Popular amenities for Westchester rentals with a pool
House rentals with a pool

Spanish House 3 Bedroom Pool House

Family retreat oasis, heated pool, jacuzzi & grill

Encanto Family/Heated pool/center of Miami/BBQ

EPIC Escape/Pool Access Near Malls Airport Hospita

Centrally Located Resort Style Miami home

Miami Modern Luxury with Pool & Spa

Miami Palm House with HEATED POOL & BBQ/BAR

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

LuxuryPH at Brickell Bay-Amazing MIAMI City VIEWS

Make It Happen! Brand New with Amazing Water Views

Breathtaking Brickell Penthouse - Guest Favorite!

Studio at Icon Brickell Luxury Waterfront Building

Beautiful condo with ocean view at Miami Brickell

Stunning 2 bedroom+17 foot ceilings & heated pool

Guest Favorite Coconut Grove,pool, sauna,park free

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

Cozy Apartment in Downtown Doral

South Miami 2BR/2BA - Steps from Dadeland Mall

5350 Park Doral Downtown luxury apartment.

Grove Casita Pool Paradise, 6min beach, Parking

Stylish Miami • Studio Weekly Discount • Pool+Gym

Miami Chic-Heated Pool Near FIU and Coral Gables

MIA Paradise: Best Brickell Location, Pool

Blank Canvas Wynwood Loft
When is the best time to visit Westchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 295 | € 332 | € 352 | € 290 | € 339 | € 312 | € 316 | € 322 | € 263 | € 290 | € 305 | € 420 |
| 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 € 34 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
- Family-friendly rentals Westchester
- Flat rentals Westchester
- Rentals with a patio Westchester
- Rentals with a washing machine and dryer Westchester
- Rentals with outdoor seating Westchester
- Rentals with a hot tub Westchester
- Pet-friendly rentals Westchester
- House rentals 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
- Bayside Marketplace
- Brickell City Centre
- Miami Beach
- Miami Beach Convention Center
- Kaseya Center
- Hard Rock Stadium
- Midtown
- Everglades National Park
- Port Everglades
- Haulover Beach
- University of Miami
- Ocean Reserve Condominium
- Sawgrass Mills
- Las Olas Beach
- Lauderdale-By-The-Sea Beach
- LoanDepot Park
- Ritz-Carlton
- Bal Harbour Beach
- Aventura Mall




