
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 $187 NZD per night before taxes and fees

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

Pet-friendly accommodation
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

Wi-Fi availability
90 of Westchester holiday rentals include Wi-Fi 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

Kusikuy Private Guesthouse
This wonderful Cottage has a private entrance in the side, surrounded by a garden with a pond in a peaceful environment located in a quiet residential neighborhood. Centrally located at only 12 minutes to the airport, fast access to the main highways to get in 20-25min to South Beach (12miles), 15min to Dolphin Mall, 15min to Dadeland Mall and 25min to the redland farms in Homestead or the Everglades. A fridge with free beverages, Wi-fi, silent cold Ac split and a Smart TV are waiting for you!

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.

[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!

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!

Home Sweet Home Family & Friends getaway with Pool
Welcome to our charming 4-bedroom family home nestled in the heart of vibrant Miami! The home is perfect for families, couples, or friends looking for a comfortable getaway. Minutes away from Miami International Airport, Miami Beach, Downtown Miami, Brickell, and Doral. ✔ Fully Equipped Kitchen ✔ Comfortable Bedrooms with King/Queen/Full beds/bunk beds ✔ Open Concept Living Area ✔ Office Desk ✔ High-Speed Wi-Fi ✔ Free parking on premises ✔ Large Patio and yard with pool

Gorgeous 5BR/Games/Fire Pit/BBQ/H. Pool & Hot Tub
5 Bedrooms 3.5 Bathrooms Heated Pool/Jacuzzi/Pool Table/Ping Pong Table/Mega Chess/Basketball/Mini Golf/Kids Playground/BBQ/Hammock/Mini Beach/Outdoor furniture/Fire Pit/Cornhole Game Welcome to our home, a haven of entertainment and enjoyment that you won't want to depart. From the serene pool and hot tub to the thrilling games, this residence is crafted to deliver an unforgettable vacation for all ages. If you seek an all-inclusive getaway, look no further.

Sleek Studio at Elser | Resort Pool & Downtown
Guest verdict: "The best place to stay in Miami close to everything." This Elser studio offers a modern base for your Miami adventures. Enjoy vibrant downtown views and easy access to Bayfront Park (2 min walk) and Kaseya Center (3 min walk). April brings event energy with eMerge Americas (April 23-24) just a short Metromover ride away. Our residence is built for the standard Miami traveler seeking a dynamic stay with all the city's best within reach.

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

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

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!

Bay Views, Pool & Gym Access in Coconut Grove
Family- and pet-friendly home rentals

Immaculate spacious 3/2 in the heart of Miami, FL

Suite close to Kendall Hospital and FIU

Retro Chic Retreat-Heated Pool- PingPong Table

The Salsa Queen’s Pearl| Top Location | Hot tub

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

3 BR Cozy Miami Home with Pool

Pool home 7 miles from Airport & near FIFA Stadium

Private Bungalow FIU & Tropical Park Wifi&Parking
Family-friendly home rentals with a pool

World Cup Lakefront Hub | 5BR | Heated Pool

Spanish House 3 Bedroom Pool House

3/2 Home with Pool & Bbq near Dadeland Mall

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

Private Pool CasaMia • 15 min to MIA & Wynwood

Waterfront Retreat + Heated Pool + Sand Court

Terramar Villa- World Cup Luxury near Doral & MIA

Studio Apartment Dino's Place
When is the best time to visit Westchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $666 NZD | $617 NZD | $676 NZD | $479 NZD | $525 NZD | $497 NZD | $533 NZD | $477 NZD | $436 NZD | $463 NZD | $508 NZD | $644 NZD |
| 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
- 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
- Fort Lauderdale Holiday rentals
- Havana Holiday rentals
- Tampa Holiday rentals
- Four Corners Holiday rentals
- Kissimmee Holiday rentals
- House rentals Westchester
- Apartment rentals Westchester
- Pet-friendly rentals Westchester
- Rentals with a washing machine and dryer Westchester
- Rentals with pools Westchester
- Rentals with outdoor seating Westchester
- Rentals with a hot tub Westchester
- Rentals with a patio 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
- Las Olas Beach
- LoanDepot Park
- Lauderdale-By-The-Sea Beach
- Dolphin Mall
- Seminole Hard Rock Hotel and Casino
- Bal Harbour Beach
- Fort Lauderdale Beach
- Sawgrass Mills
- John Pennekamp Coral Reef State Park
- Zoo Miami





