
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.

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!

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!

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.

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.

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.

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.

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!

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 🌸

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!

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.

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.

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
Family-friendly home rentals with a hot tub

Beautiful Poolside Studio, Heart of Miami

Make It Happen! Brand New with Amazing Water Views

Tropical & Private Bungalow/Pool

Condo in Brickell Business District

Very Private 1/1 Apt w/Oasis Pool Patio Setting

The Lux Paradise Miami

Escape-5BR-HotTub-Games-FirePit-BBQ-Fun

Guesthome w/ Heated Pool 5 mins from Miami Airport
Family- and pet-friendly home rentals

Brand NEW Cottage with Gorgeous Patio! 5 mi Beach!

Cozy and private studio.

Miami Stay: 5 Mins to Everything + W/D Inside

Your Cozy Home Away from Home – 10 min to MIA

"Casa Mia's" pool & BBQ bungalow

Miami Oasis Studio | Near Airport & Downtown

Studio with private entrance, 2 queen beds & bath

Casa Bella | Unit B
Family-friendly home rentals with a pool

Tamiami Guest House- Studio #2 with pool

Stylish 1BR with Balcony | Heart of Downtown Doral

Grove Casita Pool Paradise, 6min beach, Parking

Super cool unit with a pool in a quiet location

Cozy private guest studio

Stylish 1Bdrm Penthouse In Miami Design District

Tropical Paradise in Miami Brickell

Romantic Miami Jūngalow w/ Pool & Parking
When is the best time to visit Westchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| 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 |
| Avg. temp | 20°C | 22°C | 23°C | 25°C | 27°C | 28°C | 29°C | 29°C | 28°C | 27°C | 24°C | 22°C |
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!
Destinations to explore
- Seminole Holiday rentals
- Central Florida Holiday rentals
- Miami Holiday rentals
- Saint Johns River Holiday rentals
- Orlando Holiday rentals
- Gold Coast Holiday rentals
- Miami Beach Holiday rentals
- Havana Holiday rentals
- Fort Lauderdale Holiday rentals
- Four Corners Holiday rentals
- Tampa Holiday rentals
- Kissimmee Holiday rentals
- House rentals Westchester
- Rentals with pools Westchester
- Rentals with a washing machine and dryer Westchester
- Rentals with outdoor seating Westchester
- Pet-friendly rentals Westchester
- Rentals with a hot tub Westchester
- Flat rentals Westchester
- Rentals with a patio Westchester
- Family-friendly rentals Miami-Dade County
- Family-friendly rentals Florida
- Family-friendly rentals United States
- South Beach
- Fort Lauderdale Beach
- Bayfront Park
- Miami Beach Convention Center
- Hard Rock Stadium
- Everglades National Park
- Haulover Beach
- Port Everglades
- Bal Harbour Beach
- Miami Design District
- Zoo Miami
- John Pennekamp Coral Reef State Park
- Dania Beach
- Ocean Terrace Public Beach
- Broward Center for the Performing Arts
- Phillip and Patricia Frost Museum of Science
- Jungle Island
- Crandon Beach
- Key Biscayne Beach
- Biscayne National Park
- Gulfstream Park Racing and Casino
- Biltmore Golf Course Miami
- Miami Beach Golf Club
- Boca Dunes Golf & Country Club




