
Family-friendly holiday rentals in Westchester
Find and book unique family-friendly homes on Airbnb
Quick stats about holiday rentals that are family-friendly in Westchester

Total holiday rentals
Explore 90 holiday rentals in Westchester

Nightly prices starting at
Westchester holiday rentals start at £83 per night before taxes and fees

Verified guest reviews
Over 5,550 verified reviews to help you choose

Pet-friendly holiday rentals
Find 50 rentals that welcome pets

Holiday rentals with a pool
50 properties feature pools

Rentals with dedicated workspaces
70 properties have a dedicated workspace

Wifi availability
90 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!
Top-rated family-friendly rentals in Westchester
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

Peaceful 3BR Retreat in Quiet Miami Neighborhood
Welcome to your 🏡 away from 🏡! This comfortable and spacious 3-bedroom, 1-bathroom home is perfect for families and small groups looking for a relaxing stay. Location Perks: • Just 5 minutes from supermarkets, restaurants, and shopping • Easy access to Palmetto Expressway for quick trips around the city Important Notes: • This listing is for the main house only • The owner resides in the backside of the property. Book your stay and enjoy a comfortable, well-located home for your next trip!

10 ppl |Top Location | 20 Min Beach | Bar | Patio
Welcome to our newly renovated house, perfect for spending some unforgettable days with your family and friends Why booking with us? 1- Best Location in the heart of Miami. 2- 15 Min to Wynwood Art District 3- 15 Min to Downtown and Brickell 4- 20 Min to Beach 6- 4 Bedrooms | 2 Baths 7- Designed for 10 guests (1 King , 2 Queen, 2 Twins, 1 Queen Sofa Bed) 7- Free Parking (5 Cars) 8- Fully Equipped Kitchen 9- Fast Wi-Fi 10- Bar 11- Kids Playground 11- Private Patio 12- Barbecue Area 13- 4 TVs

Modern Beach Lake-Front House in Miami !
Welcome to our stunning 5/4 beachfront lake house! This newly renovated property offers the perfect blend of modern amenities and natural beauty. Located in a central and peaceful neighborhood, guests can enjoy a range of water activities such as kayaking, paddle boarding, and swimming while taking in the views of the Blue lake. Seeking relaxation or adventure, this home has something for everyone.. ✔️15min from Miami International airport ✔️25min to Downtown Miami ✔️30min from Miami Beach

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.

Guesthome w/ Heated Pool 5 mins from Miami Airport
This home is located just 5 minutes from the Miami Airport and is central to many attractions here in Miami. Take a walk down Calle Ocho, swim at Miami Beach, enjoy a game at Marlins baseball stadium or American Airlines Arena (home to the Miami Heat), and dine at one of the many popular restaurants such as Versailles. These are all within 15 minutes of this private comfortable home. Come enjoy a location that provides a rich experience into the vibrant hispanic culture that Miami radiates.

The Lux Paradise Miami
Enjoy a stylish experience at this centrally-located place. Located in the heart of Miami, our property is close to all the main attractions the city has to offer. Whether you’re looking to explore vibrant neighborhoods like Little Havana and Coconut Grove, enjoy the stunning beaches of Miami Beach, or visit popular spots like the Miami Zoo, Vizcaya Museum, and the bustling Brickell area, you’ll find everything within easy reach. Perfect for those who want to experience the best of Miami!

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

Adorable private studio
Relaxing, private, peaceful and centrally-located studio. You do not share your space with anyone. Walking distance to restaurants, supermarket, bus stop, Gym and Florida International University. Conveniently close to Miami Airport, Kendall Regional Hospital, Dolphin Mall, TopGolf, Everglades Airboat Expeditions, City Place Doral with Fresh Market, shops, Movie Theaters, Comedy Club, live music and more. Eleven miles from Bayside and Wynwood Walls. The beach? A short 15-mile drive!

Greek House • Heated Pool + Game Room • Near MIA
🏊 Private Heated Pool 🌴 BBQ 🎮 Family room w/ foosball 🍳 Full kitchen + air fryer, coffee & essentials 🛏️ 3 bedrooms · 2 Kings + 2 Queens + sofa beds (12 guests) 📺 5 Smart TVs · fast Wi-Fi 🧺 Pool & bath towels provided 🧳 Easy check-out — no chores 🎓 10 min → FIU 🛍️ 15 min → Dolphin Mall ✈️ 15–20 min → MIA Airport 🌆 25–30 min → Brickell & Wynwood 🌊 35–40 min → South Beach 🐾 Pets welcome · Pet fee applies 🤝 Superhost care — English & Spanish 🚫 No parties or indoor smoking

Stylish Studio Retreat – Private Entry + Parking.
Look no further—this cozy, stylish studio is in a quiet neighborhood, perfect for relaxing or working. Just 18 min from the airport, 10 min from Dolphin & International Mall, and 3 min from Florida International University and major expressways. About 30 min to Downtown, Miami Beach, and Port of Miami. Close to restaurants, gyms, and shops. Fast WiFi included for work or streaming. Private entrance and free parking included for your convenience.

Casita For Families, Pets, Medical Stays | Hot Tub
Welcome to your perfect stay—ideal for families, pets, or medical visits! Guests rave it's “sparkling clean and designed to perfection!” ✨ Everything you need is here: 👶 Crib, stroller & high chair for little ones 🐶 Pet-friendly w/ waste stations & big yard 🏥 Near top hospitals—great for recovery or rest Enjoy these extras: ☕ Free snacks, coffee & tea bar 🔥 BBQ, free parking & your own private hot tub! 🧴 Toiletries, beach gear & laundry
Popular amenities for Westchester family-friendly rentals
Family-friendly home rentals with a hot tub

Corner Deluxe Studio w/ City View Free Park & Pool

Chic Guest House w/Pool, Hot tub, Grill, Mini Golf

Miami Getaway - Heated Pool, Hot tub, BBQ

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

Gorgeous 5BR/Games/Fire Pit/BBQ/H. Pool & Hot Tub

Oasis&Art/ArtificialBeach/HeatedPool/MiniGolf

Biscayne Bay Studio: Resort Pool & Beach Access

Sunny Getaway: Relaxing Miami Home
Family- and pet-friendly home rentals

Family Oasis Retreat• Heated Pool, Jacuzzi & Grill

| LuxeLanding | Pool+Lounge+Chess+BBQ+Golf+Airport

Stylish Miami 3 BR Home w/ Fun Games & Huge Yard

Cheerful, peaceful 3-Bedroom house with pool

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

EPIC Escape/Pool Access Near Malls Airport Hospita

Tropical Grove Bay 1/1 | Newly Renovated Escape

Magnolia House Heated Pool with Slide/Pergola/ BBQ
Family-friendly home rentals with a pool

The Sunflower Inn

3/2 Home with Pool & Bbq near Dadeland Mall

Miami Oasis: Charming home with private pool

Cozy 2 Bedroom Modern Farmhouse in Miami

Waterfront Retreat + Heated Pool + Sand Court

Modern 4BR Home w/ Pool, Fast Wi-Fi & Near Airport

Waterfront Home 3/3.5 Resort Style-Heated Pool*

Miami Chic-Heated Pool Near FIU and Coral Gables
When is the best time to visit Westchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £295 | £273 | £300 | £212 | £232 | £220 | £236 | £211 | £193 | £205 | £225 | £285 |
| 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 |
Destinations to explore
- Miami Holiday rentals
- Four Corners Holiday rentals
- Orlando Holiday rentals
- Kissimmee Holiday rentals
- Miami Beach Holiday rentals
- Tampa Holiday rentals
- Fort Lauderdale Holiday rentals
- Hollywood Holiday rentals
- St. Augustine Holiday rentals
- Key West Holiday rentals
- Davenport Holiday rentals
- Naples Holiday rentals
- Flat rentals Westchester
- Rentals with a patio Westchester
- Pet-friendly rentals Westchester
- Rentals with a hot tub Westchester
- Rentals with pools Westchester
- Rentals with a washing machine and dryer Westchester
- Rentals with outdoor seating Westchester
- House rentals Westchester
- Family-friendly rentals Miami-Dade County
- Family-friendly rentals Florida
- Family-friendly rentals United States
- Fort Lauderdale Beach
- South Beach
- Hard Rock Stadium
- Port Everglades
- Bayfront Park
- Miami Beach Convention Center
- Everglades National Park
- Haulover Beach
- Brickell City Centre
- University of Miami
- Dolphin Mall
- Kaseya Center
- Las Olas Beach
- Sawgrass Mills
- Seminole Hard Rock Hotel and Casino
- Midtown
- LoanDepot Park
- Bayside Marketplace
- Bal Harbour Beach
- Florida International University
- The Tides on Hollywood Beach
- John Pennekamp Coral Reef State Park
- Aventura Mall
- Zoo Miami





