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Family-friendly vacation rentals in Westchester

Find and book unique family-friendly homes on Airbnb

Quick stats about vacation rentals that are family-friendly in Westchester

  • Total vacation rentals

    Explore 90 vacation rentals in Westchester

  • Nightly prices starting at

    Westchester vacation rentals start at ﺩ.ﺇ 404 per night before taxes and fees

  • Verified guest reviews

    Over 5,550 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 50 rentals that welcome pets

  • Vacation rentals with a pool

    50 properties feature pools

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

  • Wi-Fi availability

    90 of Westchester vacation 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.

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Superhost
The entrance features a welcoming door adorned with a floral wreath. A small, wooden porch is complemented by two folding chairs and a table, with vibrant greenery framing the entry. Sunlight casts a warm glow on the inviting space.
Home in Westchester
4.85 out of 5 average rating, 207 reviews

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!

Superhost
The exterior of a renovated house is shown at sunset, featuring a clean white façade and a welcoming entrance. A curved driveway leads to the front door, complemented by well-maintained grass and landscaping along the pathway.
Home in Tamiami
4.93 out of 5 average rating, 118 reviews

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

Guest favorite
A light-filled bedroom features a spacious bed with crisp white linens and a built-in headboard. French doors lead to an outdoor space, while a flat-screen TV is mounted on the wall. Soft gray curtains frame the windows, complementing the neutral decor.
Guesthouse in Miami
4.83 out of 5 average rating, 257 reviews

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!

Guest favorite
A spacious backyard is showcased with a clear pool reflecting the sky. Sun loungers are arranged nearby, accompanied by a large umbrella for shade. Paths of stepping stones lead through a pebble area, enhancing the serene outdoor setting.
Home in Westchester
4.91 out of 5 average rating, 400 reviews

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.

Top guest favorite
Home in Westchester
4.96 out of 5 average rating, 138 reviews

[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!

Top guest favorite
A spacious backyard is showcased, featuring a clean saltwater pool surrounded by lounge chairs and tropical landscaping. A covered patio area is visible, with a stone countertop and decorative plants. The bright blue sky complements the serene outdoor setting.
Home in Fountainebleau
5 out of 5 average rating, 448 reviews

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

Top guest favorite
A welcoming entrance is highlighted by two chairs positioned on a patterned rug. Potted plants are arranged around the space, accompanied by a decorative light fixture. A ceiling fan is visible above, and a door leads into the private room, creating an inviting atmosphere.
Guest suite in Miami
4.97 out of 5 average rating, 159 reviews

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!

Superhost
An inviting outdoor space features a large pool surrounded by a spacious patio. Comfortable lounge chairs and a shaded dining area provide relaxation options, while sheer curtains frame the area. The clear sky adds to the serene atmosphere of this well-appointed outdoor setting.
Home in Fountainebleau
4.88 out of 5 average rating, 115 reviews

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

Superhost
Home in Miami
4.86 out of 5 average rating, 134 reviews

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.

Guest favorite
Apartment in Downtown Miami
4.88 out of 5 average rating, 391 reviews

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.

Top guest favorite
Guesthouse in Miami
4.96 out of 5 average rating, 196 reviews

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.

Guest favorite
Bungalow in Miami
4.95 out of 5 average rating, 103 reviews

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

When is the best time to visit Westchester?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ 1,436ﺩ.ﺇ 1,329ﺩ.ﺇ 1,458ﺩ.ﺇ 1,032ﺩ.ﺇ 1,131ﺩ.ﺇ 1,072ﺩ.ﺇ 1,149ﺩ.ﺇ 1,028ﺩ.ﺇ 940ﺩ.ﺇ 999ﺩ.ﺇ 1,094ﺩ.ﺇ 1,388
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