
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.

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.

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 🌸

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

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.

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)

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
Family-friendly home rentals with a hot tub

Beautiful Poolside Studio, Heart of Miami

SF Stunning 12th Flr. Studio in the Heart of Grove

Tropical & Private Bungalow/Pool

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

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

The Lux Paradise Miami

The Miami Tropic Suite•Private Stay+Free Parking

Quiet tropical Oasis setting with 1 bed and 1 bath
Family- and pet-friendly home rentals

Tiny House • Urban Glamping Grove Micro Retreat

Cozy Studio Near Airport | Near Beaches & Downtown

Cozy and private studio.

Miami Studio | BBQ & Laundry |Near Airport & Beach

Studio with private entrance, 2 queen beds & bath

Fully Renovated Studio Near Coral Gables & Calle 8

Cozy, Mid-Century Modern Retreat

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

Tamiami Guest House- Studio #2 with pool

Grove Casita Pool Paradise, 6min beach, Parking

Stylish 1BR with Balcony | Heart of Downtown Doral

Cozy private guest studio

Dharma |15% off Monthly| Perfect 1B | South Miami

Studio Apartment Dino's Place

One Bedroom Condo King Bed With City Views

Tropical Paradise in Miami Brickell
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 | $387 SGD | $429 SGD | $367 SGD | $402 SGD | $382 SGD | $409 SGD | $366 SGD | $335 SGD | $335 SGD | $340 SGD | $421 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
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- Miami Holiday rentals
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- House rentals Westchester
- Pet-friendly rentals Westchester
- Rentals with a patio Westchester
- Rentals with a hot tub Westchester
- Flat rentals Westchester
- Rentals with pools Westchester
- Rentals with outdoor seating Westchester
- Rentals with a washing machine and dryer 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
- Jungle Island
- Phillip and Patricia Frost Museum of Science
- Key Biscayne Beach
- Crandon Beach
- Gulfstream Park Racing and Casino
- Biscayne National Park
- Biltmore Golf Course Miami
- Miami Beach Golf Club
- Boca Dunes Golf & Country Club




