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Family-friendly vacation rentals in Westchester

Find and book unique family-friendly homes on Airbnb

Quick stats about vacation rentals that are family-friendly in Westchester

  • Total vacation rentals

    Explore 100 vacation rentals in Westchester

  • Nightly prices starting at

    Westchester vacation rentals start at G$20,920 GYD per night before taxes and fees

  • Verified guest reviews

    Over 6,180 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 60 rentals that welcome pets

  • Vacation rentals with a pool

    60 properties feature pools

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

  • Wi-Fi availability

    100 of Westchester vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Westchester rentals

  • 4.9 Average rating

    Westchester stays are highly rated by guests—averaging 4.9 out of 5!

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
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 Westchester

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!

4.84 out of 5 average rating, 217 reviews
Guest favorite
The exterior of a renovated house is shown at sunset, featuring a clean white façade and a welcoming entrance. A curved driveway leads to the front door, complemented by well-maintained grass and landscaping along the pathway.
Home in Tamiami

10 ppl |Top Location | 20 Min Beach | Bar | Patio

Welcome to our newly renovated house, perfect for spending some unforgettable days with your family and friends Why booking with us? 1- Best Location in the heart of Miami. 2- 15 Min to Wynwood Art District 3- 15 Min to Downtown and Brickell 4- 20 Min to Beach 6- 4 Bedrooms | 2 Baths 7- Designed for 10 guests (1 King , 2 Queen, 2 Twins, 1 Queen Sofa Bed) 7- Free Parking (5 Cars) 8- Fully Equipped Kitchen 9- Fast Wi-Fi 10- Bar 11- Kids Playground 11- Private Patio 12- Barbecue Area 13- 4 TVs

4.94 out of 5 average rating, 127 reviews
Guest favorite
Home in Westchester

Canalfront Pool • Family Escape • Near MIA

🏊‍♂️ Private pool + scenic canal views 🌴 Outdoor lounge, BBQ & open-air bathroom 🍳 Full kitchen + coffee, air fryer & essentials 🧺 Pool & bath towels provided 🛏️ 4 bedrooms · 2 king + 2 queen · sofa bed 📺 5 Smart TVs · fast Wi-Fi 🧳 Simplified check-out 🅿️ Parking 4 cars 🛍️ 10–15 min → Dolphin Mall & FIU ✈️ 16 min → MIA Airport 🌆 20–30 min → Brickell & Beaches 🐾 Pets welcome · Pet fee applies 🔑 Entire home · private use 🤝 Superhost - English & Spanish 🚫 No parties or indoor smoking

4.94 out of 5 average rating, 107 reviews
Top guest favorite
A serene lakeside view features lounge chairs placed on sandy shores, framed by palm trees. A kayak rests nearby, with the crystal clear water reflecting shades of blue and aqua. The peaceful scene invites relaxation under the bright sky.
Home in Miami

Modern Beach Lake-Front House in Miami !

Welcome to our stunning 5/4 beachfront lake house! This newly renovated property offers the perfect blend of modern amenities and natural beauty. Located in a central and peaceful neighborhood, guests can enjoy a range of water activities such as kayaking, paddle boarding, and swimming while taking in the views of the Blue lake. Seeking relaxation or adventure, this home has something for everyone.. ✔️15min from Miami International airport ✔️25min to Downtown Miami ✔️30min from Miami Beach

4.96 out of 5 average rating, 201 reviews
Superhost
A spacious living area is presented with modern furnishings, including a large gray sofa facing a sleek television mounted on the wall. Light-colored cabinetry and a dining table are visible in the background, while a fireplace adds warmth to the ambiance. Potted plants offer a touch of greenery.
Home in Miami

The Lux Paradise Miami “Breakfast included”

Enjoy a stylish experience at this centrally-located place. Located in the heart of Miami, our property is close to all the main attractions the city has to offer. Whether you’re looking to explore vibrant neighborhoods like Little Havana and Coconut Grove, enjoy the stunning beaches of Miami Beach, or visit popular spots like the Miami Zoo, Vizcaya Museum, and the bustling Brickell area, you’ll find everything within easy reach. Perfect for those who want to experience the best of Miami!

4.89 out of 5 average rating, 151 reviews
Top guest favorite
A modern living room showcases marble accents and a large wall-mounted flat screen TV. A plush sectional sofa with bold black and white patterns is arranged around a decorative coffee table. Natural light filters through the window with minimalistic blinds.
Home in Miami

| LuxeLanding | Pool+Lounge+Chess+BBQ+Golf+Airport

Discover the magic of Miami at our stunning 4BR/3BA modern retreat in vibrant Little Havana’s west side! This spacious, open-concept home sleeps up to 11 and features a sleek living room, fully stocked kitchen with stainless steel appliances, dinnerware, wine/shot glasses, cookware, tabletop appliances & complimentary coffee. The highlight? A resort-style backyard with a pool, mini golf, life-size chess, cornhole, Connect Four, outdoor pool table, a covered gazebo & deluxe grill/hibachi!

4.95 out of 5 average rating, 119 reviews
Top guest favorite
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

Miami Sanctuary | Heated Saltwater Pool & BBQ

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

5.0 out of 5 average rating, 486 reviews
Top guest favorite
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

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!

4.97 out of 5 average rating, 169 reviews
Top guest favorite
Home in Miami

Cheerful, peaceful 3-Bedroom house with pool

This cozy and peaceful house is perfect for group vacations. Your stay will never be a bore with a private heated swimming pool in the backyard and a BBQ grill, great for a chilling afternoon outside! Central location that is 20 mins from Brickell, 25 from the beaches and close to the airport! Close to hospitals 10 Minutes From UM 13 Minutes from Coral Gables 14 Minutes from Dolphin Mall 15 Minutes from Miami International Airport 20 from Downtown Miami 26 Minutes from South Beach

4.92 out of 5 average rating, 112 reviews
Superhost
Home in Miami

Gorgeous 5BR • Fire Pit & Games | Pool_Hot Tub_BBQ

Welcome to our home, a haven of entertainment and enjoyment that you won't want to depart. From the serene pool and hot tub to the thrilling games, this residence is crafted to deliver an unforgettable vacation for all ages. If you seek an all-inclusive getaway, look no further. 5 Bedrooms 3.5 Bathrooms Heated Pool/Jacuzzi/Pool Table/Ping Pong Table/Mega Chess/Basketball/Mini Golf/Kids Playground/BBQ/Hammock/Mini Beach/Outdoor furniture/Fire Pit/Cornhole Game

4.86 out of 5 average rating, 138 reviews
Top guest favorite
Guesthouse in Miami

Stylish Studio Retreat – Private Entry + Parking.

Look no further—this cozy, stylish studio is in a quiet neighborhood, perfect for relaxing or working. Just 18 min from the airport, 10 min from Dolphin & International Mall, and 3 min from Florida International University and major expressways. About 30 min to Downtown, Miami Beach, and Port of Miami. Close to restaurants, gyms, and shops. Fast WiFi included for work or streaming. Private entrance and free parking included for your convenience.

4.96 out of 5 average rating, 206 reviews
Top guest favorite
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 Kendall

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.

4.97 out of 5 average rating, 428 reviews

Popular amenities for Westchester family-friendly rentals

When is the best time to visit Westchester?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$81,799 GYDG$75,732 GYDG$83,054 GYDG$74,058 GYDG$72,385 GYDG$82,008 GYDG$65,481 GYDG$58,577 GYDG$53,556 GYDG$56,903 GYDG$62,343 GYDG$79,079 GYD
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