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, 377 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 light-filled living area features a soft beige leather couch and armchairs arranged around a wooden coffee table. A decorative wall mirror and a potted plant add to the space. A television is mounted on the wall, and light drapes cover the windows.
Home in Flagami
4.93 out of 5 average rating, 385 reviews

Private duplex in the center of Miami.

1 bed/1bath Duplex located in the heart of Miami. Outdoor space is communal with free street parking. 2 minute WALK to Magic City Casino, 5 minutes away from Miami international airport, 5 minutes from restaurants and nightlife in Coral Gables & calle ocho, 10 minutes from downtown Miami, bayside, etc. Perfect for anyone with long layover at Miami Int Airport, or awaiting a cruise departure from port of Miami (Port of Miami is 10 minutes away). FREE wifi & cable included during your stay.

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
The spacious room features a king-sized bed with crisp white linens. A pink and white curved accent wall adds a modern touch. Adjacent, a stylish chair and a vibrant vanity area are visible, alongside a closet with hangers and a framed window allowing natural light.
Flat in Miami
4.82 out of 5 average rating, 570 reviews

Super cool unit with a pool in a quiet location

Super cool boutique hotel unit with a pool on Biscayne Boulevard, just a short drive to South Beach and the Design District. This unit offers a private and stylish accommodation for vacationers and business travelers. The room features a comfortable king-sized bed, hangers, a Smart TV and AC. This is a historic MiMo building, charming and nicely renovated. On site parking is available for just $15/day. Street Parking is unavailable. The unit is about 300 SQ/FT

Top guest favourite
A spacious pool area is surrounded by vibrant greenery and palm trees. Seating arrangements with cushions are positioned near the water, complemented by a shaded area under an umbrella. The pool features a rock formation and is accented by colorful lounge chairs.
Home in Miami
4.97 out of 5 average rating, 393 reviews

The Miracle Cottage & Pool on Acre Miami Florida

Beautiful, brand new PRIVATE cottage on an acre property situated in million dollar neighborhood. Perfect place to relax and enjoy the Miami sun. This is a little piece of heaven in the heart of a magical city. Come & enjoy your best vacation. Charming , peaceful & comfortable . Cottage is a completely separate building from the main house. It’s 900 sf of living area. Cleaning & Decontamination as per CDC guidelines before every check in.

Superhost
A compact room features a full-size bed with a patterned blanket. A small desk and a chair are positioned near the bed. The kitchenette contains a microwave and a mini fridge. A mirror and a doorway to the bathroom are visible, enhancing the room's functionality.
Guest suite in Miami
4.82 out of 5 average rating, 163 reviews

Cozy Studio Near MIA Airport

A small comfortable and cozy room for two in a quiet neighborhood near MIA airport. Perfect for a busy schedule. The room has a private entrance, AC unit, fully fenced and it's own bathroom. Free parking on site and 15 minutes away from all the local attractions. Strongly suggest a car to get around, nearest bus stop 3 blocks away. Fans and extra blankets are avalible in the room. NO SMOKING inside the room (fees will apply)

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.

Popular amenities for Westchester family-friendly rentals

When is the best time to visit Westchester?

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Avg. price$346 SGD$387 SGD$429 SGD$367 SGD$402 SGD$382 SGD$409 SGD$366 SGD$335 SGD$335 SGD$340 SGD$421 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!