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$20,870 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
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
4.84 out of 5 average rating, 217 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!

KitchenIndoor spacesQuiet

Superhost
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
4.94 out of 5 average rating, 124 reviews

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

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Guest favorite
An aerial view showcases a modern house situated near a tranquil canal. Lush green lawns and palm trees surround the property, with kayaks resting on a concrete area by the water's edge. The clear blue sky enhances the peaceful ambiance of the neighborhood.
Home in Miami
4.93 out of 5 average rating, 245 reviews

Enjoy our Beautiful Home on a Fun Canal! Hot tub!

Beautiful & Modern 4/3 Canal House! completely renovated. Go Kayaking through the Canals.. Enjoy the views of the backyard and canal with jumping fish all day, House is in a centric and quiet neighborhood. Amazing backyard & terrace with a BBQ, 2 Kayaks provided for Guest. Home is near nice restaurants and close to main Highways.. ✔️15min from Miami International airport ✔️25min - Downtown Miami ✔️ 30min - Miami Beach ✔️10-15min - Dadeland Mall & Merrick Park Come Relax at our Paradise Home!

FamilyIndoor spacesLong stay

Guest favorite
A private pool with clear, inviting water reflects sunlight. The pool features a gentle gradient leading to a shallow entry with stainless steel steps. Lush greenery surrounds the area, providing a natural backdrop for relaxation.
Home in Miami
4.82 out of 5 average rating, 172 reviews

Ily's House

Fabulous fully remodeled house. Stay near NU Stadium the heart of this year’s FIFA excitement. This comfortable and modern short term rental puts you close to the action while giving you a quiet private place to unwind. Private large pool and covered patio. New kitchen, fast Wi-Fi, smart tv’s. Fifteen minutes away from the airport. Close to many shopping plazas, restaurants and various entertainment. The University of Miami is 2.9 miles. The house is located near several Plastic Surgery Centers.

Indoor spacesKitchenSleep quality

Guest favorite
Home in Westchester
4.94 out of 5 average rating, 106 reviews

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

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Guest favorite
Home in Flagami
4.89 out of 5 average rating, 192 reviews

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

KitchenFamilyComfort

Guest favorite
A heated pool is surrounded by palm trees, offering a refreshing oasis. Comfortable outdoor seating arrangements include chairs and loungers, alongside a sun umbrella. The patio area is designed for relaxation and leisure, with vibrant greenery adding to the tranquil atmosphere.
Guesthouse in Miami
4.97 out of 5 average rating, 308 reviews

Guesthome w/ Heated Pool 5 mins from Miami Airport

This home is located just 5 minutes from the Miami Airport and is central to many attractions here in Miami. Take a walk down Calle Ocho, swim at Miami Beach, enjoy a game at Marlins baseball stadium or American Airlines Arena (home to the Miami Heat), and dine at one of the many popular restaurants such as Versailles. These are all within 15 minutes of this private comfortable home. Come enjoy a location that provides a rich experience into the vibrant hispanic culture that Miami radiates.

KitchenFamilyParks

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
4.89 out of 5 average rating, 150 reviews

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!

KitchenFamilyQuiet

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
4.97 out of 5 average rating, 115 reviews

| 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!

KitchenFamilyCleanliness

Top guest favorite
Home in Fountainebleau
5.0 out of 5 average rating, 477 reviews

Sanctuary Salt water heated pool BBQ Grill Oasis

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

FamilyKitchenGetting around

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
4.97 out of 5 average rating, 168 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!

FamilyKitchenGetting around

Guest favorite
Home in Miami
4.92 out of 5 average rating, 109 reviews

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

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Popular amenities for Westchester family-friendly rentals

When is the best time to visit Westchester?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$81,601 GYDG$75,549 GYDG$82,853 GYDG$73,879 GYDG$72,209 GYDG$81,810 GYDG$65,322 GYDG$58,435 GYDG$53,427 GYDG$56,766 GYDG$62,192 GYDG$78,888 GYD
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