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.

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Superhost
An aerial view showcases a modern house situated near a tranquil canal. Lush green lawns and palm trees surround the property, with kayaks resting on a concrete area by the water's edge. The clear blue sky enhances the peaceful ambiance of the neighborhood.
Home in Sunset
4.92 out of 5 average rating, 227 reviews

Enjoy our Beautiful Home on a Fun Canal! Hot tub!

Beautiful & Modern 4/3 Canal House! completely renovated. Go Kayaking through the Canals.. Enjoy the views of the backyard and canal with jumping fish all day, House is in a centric and quiet neighborhood. Amazing backyard & terrace with a BBQ, 2 Kayaks provided for Guest. Home is near nice restaurants and close to main Highways.. ✔️15min from Miami International airport ✔️25min - Downtown Miami ✔️ 30min - Miami Beach ✔️10-15min - Dadeland Mall & Merrick Park Come Relax at our Paradise Home!

Guest favourite
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.
Guest house in Miami
4.83 out of 5 average rating, 250 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 favourite
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
4.92 out of 5 average rating, 390 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.

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, 190 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 favourite
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, 415 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 favourite
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, 143 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!

Top guest favourite
A spacious living area is surrounded by wooden walls and features a comfortable seating arrangement with a sectional sofa and accent chairs. Colorful artwork adorns the walls, while a large window allows natural light to illuminate the space, revealing a warm, inviting ambiance.
Home in Kendall
4.99 out of 5 average rating, 111 reviews

Beautiful Historic House on Gorgeous Tropical Lot

This is a 2 bedroom/2 bath historic house located on a gorgeous lot, nestled among over 50 tropical fruit trees. The house can welcome up to 5 guests , the two bathrooms have been entirely renovated, and the kitchen is fully equipped (including a Nespresso machine with free capsules). The house has a no pets, no smoking and no party policy. Guests enjoy access to the entire house and the yard. We keep access to the yard for grass cutting and regular maintenance on weekdays.

Guest favourite
A decorative vase with blue flowers is positioned on a white coffee table. In the background, a flat-screen TV is placed on a low white entertainment unit, and natural light filters through a window with contemporary blinds.
Guest suite in Westchester
4.93 out of 5 average rating, 180 reviews

Private Guest Suite w/ Patio in Miami

Cozy private suite room located in a private home, in Westchester. Great for travelers looking to stay close to the airport and popular destinations here in Miami. The suite is located on the left side of the main house with its own private entrance and side patio. Free street parking. Ideal for 2. Hermoso efficiency con excelente ubicacion en Westchester. Entrada y pequeño patio privado. Cerca de diversos destinos en Miami incluyendo Miami International Airport.

Top guest favourite
A spacious studio is showcased, featuring a queen bed and a bunk bed beside it. The sleek marble flooring reflects abundant ceiling lights. A white kitchenette with dark cabinets and a potted plant complement the modern design. A mounted TV and shelves add functionality.
Guest house in Miami
4.96 out of 5 average rating, 187 reviews

Lovely and private studio centrally located.

Look no further. This lovely studio is located in a peaceful neighborhood. Just 18 min from Miami International Airport, 10 min from the famous Dolphin Mall and International Mall, 3 min from FIU (Florida International University) and expressway. Approximately 30 min from the Port of Miami, Downtown Miami and Miami Beach. Also close to Dadeland Mall, Restaurants, Gyms, Supermarkets, Pharmacies, etc. High speed wifi that’s well-suited for working.

Guest favourite
Home in Coconut Grove
4.88 out of 5 average rating, 120 reviews

Tropical Grove Bay 1/1 | Newly Renovated Escape

Discover paradise in the heart of Coconut Grove! This charming 1-bedroom, 1-bath Key West-style cottage is fully gated with parking. Enjoy upgraded interiors featuring marble floors, granite kitchen counters, and a modern bathroom. Stay comfortable with central AC, cable, and WiFi. Walk to tennis courts, the bay, Coconut Grove Village, shops, restaurants, clubs, and parks—experience the best of Miami at your doorstep!

Guest favourite
Home in Westchester
4.94 out of 5 average rating, 129 reviews

Lux Tuscan Villa | Pool/Sauna/Gym/Spa/Basketball

🇮🇹 HOUSE OF ITALY – A Private Tuscan Escape 🇮🇹 🌟 GUEST FAVORITE with true resort-style luxury & top-rated reviews! 🌟 🎱 Pool Table • 💪 Private Gym • 😅 Sauna 🛌 4 Bedrooms • Sleeps up to 16 comfortably 🔥 Heated Pool • Hot Tub • Massage Beds • Sun Loungers 🍽 Outdoor Kitchen • BBQ • Fire Pit for unforgettable nights 🏀 Basketball Hoop & More ✨ More than a stay—an extraordinary experience from @BeyondTheBNB

Guest favourite
A cozy living area is featured with a light gray sofa positioned beside a circular coffee table. An accent wall displays a decorative sign, while shelves are neatly arranged with books and decorative items. A soft glow is provided by a floor lamp in the corner.
Guest suite in Kendall
4.91 out of 5 average rating, 259 reviews

Private Guest Suite with Private Entry

Private GUEST SUITE within host home with PIVATE access: The whole group will enjoy easy access to everything from this centrally located guest suite. Private updated shower bathroom. Queen sized bed with 55” tv. Living area / breakfast nook. Coffee maker, microwave and Small mini fridge included. Private patio space included. No smoking on premises. No events or parties.

Popular amenities for Westchester family-friendly rentals

When is the best time to visit Westchester?

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Avg. price$337 SGD$377 SGD$418 SGD$358 SGD$392 SGD$372 SGD$399 SGD$357 SGD$326 SGD$346 SGD$379 SGD$481 SGD
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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 5,560 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

    60 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!