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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$20,906 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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Guest favorite
Home in Flagami

Miami Family Pool Retreat | Near Airport & Stadium

Stay in the heart of Miami at this spacious pool home, just 1 block from famous Calle Ocho! Only 7 miles from Miami International Airport and 14 miles from South Beach. Enjoy a private heated pool, comfortable living spaces, and easy access to top restaurants, shopping, nightlife, and the FIFA stadium. Perfect for families and groups looking for the ideal Miami getaway. You’ll love the cleanliness, comfort, and private heated pool. Perfect for families with a fully equipped kitchen for cooking

FamilyIndoor spacesCheck-in

4.89 out of 5 average rating, 197 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

Indoor spacesFamilyHospitality

4.96 out of 5 average rating, 204 reviews
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!

KitchenFamilyPool

4.94 out of 5 average rating, 130 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

KitchenIndoor spacesSleep quality

5.0 out of 5 average rating, 494 reviews
Superhost
A beach-style pool is surrounded by lush greenery and trees. Colorful inflatable pool toys float on the water. Two bright yellow lounge chairs are positioned nearby, and a thatched-roof gazebo adds a relaxing touch to the outdoor space.
Home in Miami

Beach-Style Pool • Colorful Retreat • Near FIU

🌴 Colorful Mexican-inspired design 🇲🇽 🏊 Beach-style pool & sunny terrace 🍖 BBQ & outdoor family fun 🍳 Full kitchen + coffee & essentials 🛏️ 4 bedrooms · 3 Kings · 2 Queens · sofa beds 📺 6 Smart TVs + fast Wi-Fi 🧺 Washer/dryer + linens & toiletries 🧳 Easy check-out 🛒 10 min to Publix ·🎓 15 min to FIU ✈️ 18–20 min to MIA 🌆 25–30 min to Brickell & Miami Beach 🐾 Pets welcome · Pet fee applies 🔑 Entire home · private use 🤝 Superhost – responsive & caring 🚫 No parties allowed

FamilyKitchenValue

4.86 out of 5 average rating, 100 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!

FamilyIndoor spacesBeach

4.97 out of 5 average rating, 172 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

FamilyKitchenPets

4.92 out of 5 average rating, 114 reviews
Guest favorite
The pool area features a heated pool with gentle waterfalls, illuminated by soft lighting. Surrounded by palm trees, the outdoor dining space is visible in the background, furnished with a table and chairs, creating a serene environment for relaxation.
Home in Westchester

Tuscan Resort | Sleeps 16, Pool, Sauna, Gym, Spa

Your private Tuscan resort in Miami — heated pool, sauna, gym, pool table & room for 16 to spread out, never squeeze in. 🇮🇹 House of Italy — where Tuscany meets Miami. Resort amenities plus what hotels can't give: privacy, freedom, space to be together. 🌟 Guest Favorite — 4.95★ from 149 groups 🔥 Heated pool, hot tub, fire pit & BBQ 💪 Gym, sauna & massage beds 🎱 Pool table & basketball 📍 Minutes from Coral Gables & beaches More than a stay. An experience. @BeyondTheBNB

FamilyKitchenPets

4.93 out of 5 average rating, 161 reviews
Guest favorite
An outdoor dining area is set under a shaded patio, featuring a glass-top table surrounded by eight metal-framed chairs. Potted plants adorn the table, while a pool glistens in the background. Neatly arranged stone tiles lead towards lush greenery, enhancing the tranquil environment.
Home in Miami

Miami Tropical Villa -Pool & BBQ

Welcome to "Miami Tropical Villa" – Miami's ultimate tropical escape! Immerse in luxury with the stunning blue pool, a haven of relaxation under the Florida sun. Poolside loungers invite you to unwind. Beyond the villa, Miami's treasures await. From South Beach nightlife to the Wynwood art scene, adventure is at your doorstep. This Tropical Villa invites you to make unforgettable memories in a tropical paradise that transcends the ordinary. Your escape to luxury begins here!

Indoor spacesFamilyQuiet

4.87 out of 5 average rating, 119 reviews
Guest favorite
Home in Westchester

Miami Tropical Fun Oasis • Heated Pool & Mini Golf

Escape to your private Miami oasis! Enjoy a sparkling heated pool, mini-golf, and a covered game terrace with pool table—perfect for families & groups of up to 12. Spacious interiors offer comfort and style, just minutes from Miami International Airport, top dining, and shopping. Ample parking included. Relax, reconnect, and create unforgettable memories in this fully private home. Questions about amenities or local attractions? We’re here to help anytime! 🌴✨

Indoor spacesFamilyBathroom

4.94 out of 5 average rating, 162 reviews
Superhost
Home in Miami

Modern Home • 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

KitchenFamilyWalkability

4.86 out of 5 average rating, 139 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.

KitchenFamilySleep quality

4.96 out of 5 average rating, 207 reviews

Popular amenities for Westchester family-friendly rentals

When is the best time to visit Westchester?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$81,742 GYDG$75,679 GYDG$82,996 GYDG$74,007 GYDG$72,334 GYDG$81,951 GYDG$65,435 GYDG$58,536 GYDG$53,519 GYDG$56,864 GYDG$62,299 GYDG$79,024 GYD
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