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 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!

Superhost
A spacious living area is presented with modern furnishings, including a large gray sofa facing a sleek television mounted on the wall. Light-colored cabinetry and a dining table are visible in the background, while a fireplace adds warmth to the ambiance. Potted plants offer a touch of greenery.
Home in Miami
4.88 out of 5 average rating, 142 reviews

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!

Superhost
An outdoor dining area features a wooden table with game pieces and seating. Beyond the table, a salt pool is visible, surrounded by lounge chairs and umbrellas under a clear blue sky. Ceiling fans are installed for airflow, enhancing the space's comfort.
Home in Miami
4.89 out of 5 average rating, 201 reviews

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)

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, 447 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!

Guest favorite
The vibrant living area features a blue accent wall and a large sofa adorned with decorative pillows. A foosball table occupies one corner, while the space opens to the outdoor pool area through expansive glass doors, creating a lively atmosphere.
Home in Miami
4.93 out of 5 average rating, 99 reviews

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

Guest favorite
A studio space is presented with a spacious bed featuring a textured blanket, complemented by a cozy brown sofa. A dining table with light-colored chairs is positioned nearby, while natural light fills the room through sheer curtains, enhancing the warm atmosphere.
Home in Miami
4.86 out of 5 average rating, 100 reviews

Cozy studio in Miami with private access.

Beautiful Studio in the Sunset area, with everything you need for your next visit to Miami. This studio has a completely private access with an exterior patio area. This location is walking distance to supermarkets (Publix), restaurants and schools. It is located in a very nice and quiet neighborhood. Aproximate driving times: 5 Minutes to 826 10 Minutes to FIU 10 Minutes to UM 10 Minutes to Coral Gables 15 Minutes to Coconut Grove 20 Minutes to Downtown Miami

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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