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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Guest favourite
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 Miami
4.84 out of 5 average rating, 188 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!

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
4.82 out of 5 average rating, 244 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!

Top guest favourite
An inviting living space features a comfortable couch, a plush blue armchair, and a wooden coffee table. A wall-mounted television is visible, and natural light filters through gridded windows. The area seamlessly flows into a sleeping space, enhanced by white bedding and decorative accents.
Guest suite in Miami
4.99 out of 5 average rating, 363 reviews

Cozy Farmhouse Paradise

This cozy studio is nestled in the heart of Miami, directly next to the Palmetto Expressway and Tropical Park in the highly sought after neighborhood of Glenvar Heights. This is a private guest suite with its own private entrance and a private outdoor patio area. There is a fully equipped kitchen with electric range, microwave, refrigerator, Keurig coffee maker and wines for purchase. Only a 20 min drive to Miami International Airport, Downtown & Brickell, Wynwood and 25 mins from South Beach.

Top 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 Miami
4.92 out of 5 average rating, 378 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.

Guest favourite
A compact living area is presented, featuring a full-size bed covered with a patterned duvet and a couch adorned with cushions. A window-mounted air conditioning unit is also visible. Light-colored walls enhance the sense of space, complemented by a small television above a storage unit.
Campervan/Motorhome in Coral Way
4.89 out of 5 average rating, 149 reviews

Camper for the Solo Traveler

Mini Camper for the solo traveler. Private for your use only. Camper is located on my property. Cozy with all the basic necessitates. Quiet and safe residential area. Centrally located close to Downtown Miami, and Little Havana. It's totally private, clean, and has free parking available on the street. Near to everything in Miami, 33145 zip code. It will take you little time to get anywhere. Close to supermarkets, shopping, nightlife, attractions, pharmacy, beaches, and many other places.

Guest favourite
A serene bedroom features a full-sized bed dressed in floral patterns, accompanied by a nightstand and a small lamp. A colorful artwork adorns the wall above the bed, while a ceiling fan provides gentle airflow. Natural light enters through the window, partially draped with sheer curtains.
Flat in Miami
4.75 out of 5 average rating, 268 reviews

Private Place Kendall - Near Zoo & Miami D College

My efficiency is part of our home but is private and has a separate entrance. In the main bedroom, we offer one full-sized bed. The second room serves as a small living room and offers a full-sized sofa bed. The efficiency also has several amenities including WiFi and cable TV. The listing is located in southwest Miami in a region called Kendall, about 25 minutes from Miami International Airport. We are close to Florida's Turnpike for rapid transit to get to several great destinations.

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
4.96 out of 5 average rating, 139 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 well-furnished bedroom features a wooden bedframe adorned with patterned bedding. A ceiling fan circulates air, while a decorative lamp stands to one side. Artwork depicting flowers and a black-and-white cityscape adorns the walls, adding character to the serene environment.
Guest house in Miami
4.99 out of 5 average rating, 140 reviews

Tranquil Corner Studio with many Trees!

Your stay here will be one you will truly treasure. And will certainly be on your back to visit list when visiting Miami again. Large studio apt is COMPLETELY PRIVATE! /private entrance/private bathroom. Extra commodities to make you feel even more at home. Close to most tourists sites while main essential are provided for your beach enjoyment. I am not an ordinary host. My main purpose is to go that extra mile to make you as comfortable as possible. When you are HAPPY I am HAPPIER 🌸

Guest favourite
Flat in Flagami
4.79 out of 5 average rating, 869 reviews

2PPL/Top Location/Parking/10 min Airport #3

Brand-new private studio with free parking just minutes from Miami Airport, Coral Gables, and South Beach. Enjoy premium mattresses and a smart TV with Netflix. We maintain exceptional cleanliness for a comfortable, worry-free stay. No animals of any kind are allowed, including service animals, due to an Airbnb-approved health exemption. We cannot store luggage. Early check-in at 1 p.m. is available for a $15 fee, with advance notice. Thanks for choosing our place!

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
4.95 out of 5 average rating, 170 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.

Superhost
A cozy studio features a queen bed with white linens and decorative pillows. A side table with a lamp is positioned next to the bed. A light-colored dresser is visible, along with a compact dining area in the background.
Guest house in Flagami
4.84 out of 5 average rating, 124 reviews

Cute and Cozy Miami Studio

Cozy remodeled studio for your Miami getaway. This remodeled unit features a queen-bedroom set that can sleep two guests. A fully equipped kitchen, private entrance, a smart tv and a starter supply of toiletries to help you settle in comfortably. Centrally located just 25 minutes from South Beach, 10 minutes from Coral Gables, 25 minutes from the Miami Seaquarium, and less than a 10 drive to Brickell City Centre.

Guest favourite
The sleeping area features a compact bed adorned with a white quilted cover and several plush pillows, including a heart-shaped accent pillow. A light wood paneling creates a cozy backdrop, while natural light enters through a window covered by dark blinds.
Campervan/Motorhome in Flagami
4.94 out of 5 average rating, 206 reviews

Delightful One Bedroom Camper with parking

3pm check-in time and 11am check-out time, you will enjoy Miami's beautiful sunny day in this exquisite 22" Camper/Mobil home. It has a full bathroom but SMALL, especially for someone that is recovering from a medical treatment. Please let us be aware of who will be joining the property. And remember this is a Camper and not a house room, so some functions are different. Enjoy the Camper moment

Popular amenities for Westchester family-friendly rentals

When is the best time to visit Westchester?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$346 SGD$386 SGD$428 SGD$367 SGD$402 SGD$381 SGD$408 SGD$365 SGD$334 SGD$334 SGD$339 SGD$420 SGD
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Quick stats about holiday rentals that are family-friendly in Westchester

  • Total holiday rentals

    Explore 100 holiday rentals in Westchester

  • Nightly prices starting at

    Westchester holiday rentals start at $91 SGD per night before taxes and fees

  • Verified guest reviews

    Over 5,440 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 50 rentals that welcome pets

  • Holiday rentals with a pool

    60 properties feature pools

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

  • Wifi availability

    100 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!