
Family-friendly holiday rentals in Westchester
Find and book unique family-friendly homes on Airbnb
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

[Kids Favourite] World Cup Family Oasis | 5BR | Ht
Welcome to our family-friendly retreat in Miami! Our renovated, spacious home at offers comfort and convenience for all ages. Enjoy nearby attractions like the thrilling Aquatica water park and the vibrant Miami Children's Museum. Or stay in and enjoy the fully equipped kitchen, a cozy living area, and a private, covered backyard, with loads of games & toys, it’s perfect for family bonding. You’re just a short drive from beautiful beaches and shopping. Make lasting memories in sunny Miami!

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

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 family-friendly rentals
Family-friendly home rentals with a hot tub

Dble Bay Studio Sleeps 4 Kitchenette Free Pkg/Pool

FIFA 2026-Guest house w/pool, hot tub, grill, golf

Miami Getaway - Heated Pool, Hot tub, BBQ

Hotel Arya Apt w/Waterfront View, Free Parking

5BR Single-Level Home | Heated Pool, Spa, Grill

Very Private 1/1 Apt w/Oasis Pool Patio Setting

Miami Modern Luxury with Pool & Spa

2-story:Luxury PH located in Coconut Grove Hotel!
Family- and pet-friendly home rentals

Cozy and Stylish Home in Miami w HotTub & Patio

Miami Oasis: Chill | Shop | Relax | Charming Home

3B/2B Tropical Oasis w Salt-Water Pool! Lake views

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

Retro Chic Retreat-Heated Pool- PingPong Table

"Casa Mia's" pool & BBQ bungalow

Aurea | 12 PPL | Pool | BBQ |Playground |Mini Golf

“Have Fun at Hacienda Paraíso” Suite 1 | pool |
Family-friendly home rentals with a pool

Spanish House 3 Bedroom Pool House

Family Oasis Retreat• Heated Pool, Jacuzzi & Grill

3/2 Home with Pool & Bbq near Dadeland Mall

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

Joy Day Off: Pool & Billiards Home

Waterfront Retreat + Heated Pool + Sand Court

Waterfront Home 3/3.5 Resort Style-Heated Pool*

Terramar Villa- World Cup Luxury near Doral & MIA
When is the best time to visit Westchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $499 SGD | $462 SGD | $507 SGD | $359 SGD | $393 SGD | $373 SGD | $400 SGD | $358 SGD | $327 SGD | $347 SGD | $381 SGD | $483 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 that are family-friendly in Westchester

Total holiday rentals
Explore 90 holiday rentals in Westchester

Nightly prices starting at
Westchester holiday rentals start at $140 SGD 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!
Destinations to explore
- Seminole Holiday rentals
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- Miami Holiday rentals
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- Miami Beach Holiday rentals
- Fort Lauderdale Holiday rentals
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- Pet-friendly rentals Westchester
- Rentals with outdoor seating Westchester
- House rentals Westchester
- Rentals with a hot tub Westchester
- Rentals with pools Westchester
- Rentals with a patio Westchester
- Rentals with a washing machine and dryer Westchester
- Flat rentals Westchester
- Family-friendly rentals Miami-Dade County
- Family-friendly rentals Florida
- Family-friendly rentals United States
- South Beach
- Fort Lauderdale Beach
- Bayfront Park
- Bayside Marketplace
- Kaseya Center
- The Tides on Hollywood Beach
- Brickell City Centre
- Miami Beach Convention Center
- Hard Rock Stadium
- Port Everglades
- Midtown
- Everglades National Park
- Haulover Beach
- University of Miami
- LoanDepot Park
- Las Olas Beach
- Lauderdale-By-The-Sea Beach
- Dolphin Mall
- Seminole Hard Rock Hotel and Casino
- Bal Harbour Beach
- Fort Lauderdale Beach
- Sawgrass Mills
- Zoo Miami
- John Pennekamp Coral Reef State Park





