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Holiday houses in Westchester

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Westchester

Guests agree: these stays are highly rated for location, cleanliness and more.

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Superhost
The image showcases a modern living room featuring a spacious sectional sofa, a decorative area rug, and a sleek media console with a large wall-mounted TV. A vibrant piece of artwork adorns the wall, adding color to the space.
Home in Miami
4.86 out of 5 average rating, 66 reviews

Cozy Modern Home w/ Arcade MIAMI

Welcome to our vibrant Miami home, a few blocks from FIU! Immerse yourself in the heart of the city with our stylish, centrally located space. This 2-bedroom gem boasts modern decor, a fully equipped kitchen, a cozy living area, and a wonderful guava fruit tree! The highlight? An arcade game for endless entertainment! Minutes away from Miami's hotspots, beaches and nightlife, this is the perfect base for your Miami adventure. Book now and experience the ultimate blend of comfort and excitement!

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Top Guest favourite
Home in Westchester
5 out of 5 average rating, 8 reviews

Modern 4BR Home w/ Pool, Fast Wi-Fi & Near Airport

Welcome to your perfect Miami getaway—a stylish, newly renovated 2,600 sq ft home designed for comfort and relaxation. Featuring 4 bedrooms, modern furnishings, a spacious living room, dining area, private office, and fully equipped kitchen. Enjoy a private outdoor oasis with a pool, fountain, and BBQ—perfect for sunny days and warm nights. Conveniently located near the airport and Inter Miami stadium, 20–25 minutes from beaches, dining, shopping, and nightlife. Ideal for families and groups.

LocationFamilyCleanliness

Guest favourite
A bright bedroom features a spacious bed with a blue and gold headboard. Natural light enters through a large window, complemented by modern bedside lamps. A decorative wall piece adds a touch of elegance, while the grey flooring provides a contemporary look.
Home in Tamiami
4.94 out of 5 average rating, 119 reviews

Villa Chrishell “secluded & perfect for relaxing

New apartment, very clean, with 2 private bathrooms, new kitchen with an island covered in remon stone quartz, private work space. The apartment is renovated with new high-end finished floors, both rooms are new with modern and efficient furniture, located in the best area of ​​Kendall, 4 blocks from a shopping center with several stores, restaurants, markets, gym, sports bike rental and much more, close to the dolphin mall, Dadeland mall and international mall 0.8 miles from the turnpike.

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Top Guest favourite
An aerial view showcases the lakefront villa with a well-manicured lawn leading to a sandy beach. Palms gently sway in the breeze, and outdoor seating is positioned beside the water. The villa's modern architecture is complemented by its proximity to crystal-clear blue waters.
Home in Miami
5 out of 5 average rating, 51 reviews

Miami Blue Lake Beach House w/Theater & Mini Golf!

Welcome to your dream Lakefront Villa on stunning Blue Lake! This fully renovated home features crystal-clear water, a private sandy beach, theater room, pool table, and mini golf for endless fun. Enjoy lake adventures with 3 kayaks and 2 paddle boards included. Unwind and take in the views from the spacious patio. Whether you’re relaxing indoors or playing outside, this getaway offers the perfect blend of comfort, luxury, and adventure for families and friends. 30 minutes from Miami Beach!

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Superhost
Home in Miami
4.87 out of 5 average rating, 213 reviews

Miami Paradise Westchester * Heated Pool*

Enjoy this gem in the heart of Miami newly renovated home. This modern chic home is designed to accommodate 13 guest. Perfect for entertaining backyard equipped with a counter top bar, BBQ area, dinning room area and sofa. Layout in the Miami sun in a modern pool or choose nightlife chill in jacuzzi overlooking the stars. For our fishing lovers, this home provides a deck overlooking a lake. This home is close to all main highways, malls, Miami beach, FIU, Brickell, Wynwood, downtown Miami.

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Superhost
An outdoor dining area features a wooden table with game pieces and seating. Beyond the table, a salt pool is visible, surrounded by lounge chairs and umbrellas under a clear blue sky. Ceiling fans are installed for airflow, enhancing the space's comfort.
Home in Miami
4.89 out of 5 average rating, 201 reviews

Miami Palm House with HEATED POOL & BBQ/BAR

Bring the whole family and friends to this Tropical Miami Home with lots of room for gatherings and entertainment! Enjoy the entire house with a stunning backyard, salt pool and gazebo! FREE PARKING 12 Guests. 4 Bedrooms. 9 Beds. 2 Baths Patio: Large Salt Pool (child friendly) BBQ Grill, Fridge, Wine Cooler, Bar Counter, Outdoor Lounge Furniture, Mini Golf Area Rooms: Bedroom 1: 1 Queen Bed Bedroom 2: 1 Queen Bed 1 Twin Bed Bedroom 3: 1 Queen Bed Bedroom 4: 5 Twin beds & (Game Room)

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Top Guest favourite
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
5 out of 5 average rating, 454 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

LocationFamilyLaundry

Top Guest favourite
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, 160 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!

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Guest favourite
Home in Miami
5 out of 5 average rating, 12 reviews

3/2 Home with Pool & Bbq near Dadeland Mall

Relax with the entire family at this beautiful 3/2 home in Kendall, Miami, that accommodates from 6 to 7 guests, near Dadeland Mall, Flanningans, Turnpike expressway, and many other restaurants and shopping centers in the area. It has a Pool, a Bbq grill and outdoors dinning area, with nice gazebo for get togethers and a hammock. It offers a spacious, open concept and beautifully decored living room, dinning area with a full equiped kitchen, WiFi and parking space for up to 5 cars.

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Superhost
An outdoor area features vibrant green grass with two picnic tables shaded by large umbrellas. A contemporary pool glistens under the sun, while palm trees line the perimeter, creating a relaxed atmosphere. The space encourages enjoyment and comfort for outdoor gatherings.
Home in Westchester
4.86 out of 5 average rating, 73 reviews

Retro Chic Retreat-Heated Pool- PingPong Table

Hey there, welcome to "Retro Chic Retreat"! It's a wonderful mix of contemporary design and nostalgic charm that will make you feel right at home. Come on in, stay a while, and let this unique blend take you on a journey where the past meets the present! If you have any questions about our amenities or need some tips on local attractions, please don't hesitate to reach out and ask! NOTE🖋 You speak, we listen! the double bedroom that used to get a bit warm now has brand‑new AC❄️

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Top Guest favourite
A spacious living area is presented with natural light flowing through large windows. The design features a warm-toned leather sofa and two green armchairs. A dining table for six is visible in the background, complemented by light wooden flooring and decorative plants.
Home in Westchester
5 out of 5 average rating, 45 reviews

Miami Oasis: Charming home with private pool

Welcome to your Miami oasis at our 3 bedroom, 2 bathroom home! This home features a private pool and backyard with a bar, TV and plenty of seating. The pool can be heated for an additional charge. Inside is a well-equipped kitchen and ample living space for families or groups of friends. Many child friendly amenities provided. Located in a desirable and central neighborhood. 10-20 mins to Coral Gables, Little Havanna, Coconut Grove and Brickell. 25 mins to South Beach.

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Top Guest favourite
Apartment in Sweetwater
5 out of 5 average rating, 37 reviews

Modern Studio | 5 Min from FIU

Welcome to our cozy private room with separate entrance and no contact, perfect for travelers looking for comfort, privacy and a great location in Miami The space includes: Queen size bed Private bathroom Air conditioning High-speed Wi-Fi Refrigerator, coffee maker and microwave 📍Excellent location: Only 5 minutes from FIU (Florida International University) 10 minutes from International Mall and Dolphin Mall 15 minutes from Miami International Airport

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Popular amenities for Westchester holiday rentals

When is the best time to visit Westchester?

MonthJanFebMarAprMayJuneJulyAugSeptOctNovDec
Avg. price$270 AUD$294 AUD$288 AUD$195 AUD$201 AUD$208 AUD$207 AUD$227 AUD$211 AUD$237 AUD$234 AUD$292 AUD
Avg. temp20°C22°C23°C25°C27°C28°C29°C29°C28°C27°C24°C22°C

Frequently Asked Questions

  • What are the best places to stay in Westchester?

    Westchester’s residential neighborhoods have a mix of single-family homes and apartments, with many stays appealing to travelers seeking a local experience. Areas near parks or main streets are often chosen for convenience and access to amenities.

  • What are the best things to do in Westchester with kids?

    Kids can enjoy time in local parks with playgrounds, interactive spaces in nearby museums, or community workshops tailored for young visitors. Family-friendly cafes and outdoor sports fields add variety to a day out.

  • What are some of the best things to do in Westchester?

    Explore neighborhood parks, sample Cuban cafés, and discover public art murals reflecting local culture. Residents and visitors also enjoy community gatherings, food markets, and spending time in relaxed green spaces.

  • How is the weather in Westchester?

    Westchester has warm, tropical weather most of the year, with average highs from 76°F–91°F (25°C–33°C) and mild winters. Rain is more common from late spring through early fall; packing a light rain jacket is useful.

  • When is the best time to visit Westchester?

    Late fall to early spring is often recommended for pleasant temperatures around 76°F–81°F (25°C–27°C) and lighter rainfall. Visitors in summer can expect warmer, humid days and short afternoon showers.

  • What are the best places to visit in Westchester?

    Explore locally beloved parks, public art, and family-friendly spaces in Westchester. Those interested in culture can seek out nearby museums or community centers that highlight Miami’s diverse heritage.

  • What are some hiking trails in Westchester?

    Westchester has a selection of community parks with paved walking paths and shaded trails for leisurely strolls. Those looking for longer hikes often explore natural reserves in the wider Miami area.

  • What are some family activities we can do in Westchester?

    Families can enjoy playgrounds, public parks, and nearby museums with interactive exhibits. Community centers sometimes host workshops, while local sports fields welcome active play for all ages.

  • What are some of the best day trip ideas from Westchester?

    Plan a day exploring Miami’s vibrant neighborhoods, walking the sandy beaches nearby, or visiting a local nature reserve for birdwatching and fresh air. The Everglades and Coral Gables’ botanical spots are also frequently suggested options.

  • Are there any pet friendly accommodations available in Westchester?

    Many accommodations in Westchester are pet friendly and may provide outdoor spaces or easy access to parks. Always check each listing’s policy for details on bringing pets along.

  • What are some local tips for visiting Westchester?

    Locals often suggest sampling bakery cafés for Cuban pastries and coffee, and exploring smaller, family-run eateries. Wearing light, breathable clothing and packing sunscreen helps with the sunny, humid weather.

  • What is Westchester known for?

    Westchester is known for its locally rooted Cuban-American culture, vibrant dining, and proximity to Miami’s arts and entertainment. The area has parks, casual eateries, and family-focused spaces, creating a welcoming neighborhood atmosphere.

  • What are the best hidden gems to explore in Westchester?

    Seek out small neighborhood parks, independently owned bakeries, and local art murals that reflect the community’s character. Less crowded eateries tucked in side streets are frequently suggested by locals for a genuine experience.

  • What are the best foods to try in Westchester?

    Try Cuban sandwiches, croquetas, pastelitos, and fresh tropical fruit juices, which are staples in Westchester’s dining scene. Local taquerías, Latin American bakeries, and ventanitas are frequently suggested for an authentic taste.

  • What should I bring for a trip to Westchester?

    Bring light, breathable clothing, sunscreen, and comfortable shoes for exploring. A reusable water bottle and a compact umbrella or rain jacket are helpful, especially during summer’s wetter months.

  • What is the nightlife in Westchester like?

    Westchester’s nightlife centers on casual dining spots, family gatherings, and cafés that stay open into the evening. For those seeking more vibrant scenes, nearby Miami neighborhoods are known for live music and diverse bars.

  • What are the most popular events or festivals in Westchester?

    Cultural festivals celebrating Latin American heritage, food fairs, and community parades are frequently suggested events, especially during spring and around major U.S. holidays. Art shows and family events often take place at local parks or community centers.

  • Are there family friendly vacation rentals in Westchester?

    Many vacation rentals in Westchester are family friendly, with amenities like kitchens, outdoor space, and comfortable living areas. Listings often highlight features such as cribs or play areas, so check for details based on your needs.

Quick stats about holiday rentals in Westchester

  • Total holiday rentals

    Explore 170 holiday rentals in Westchester

  • Nightly prices starting at

    Westchester holiday rentals start at $43 AUD per night before taxes and fees

  • Verified guest reviews

    Over 10,510 verified reviews to help you choose

  • Family-friendly holiday rentals

    90 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 70 rentals that welcome pets

  • Holiday rentals with a pool

    60 properties feature pools

  • Rentals with dedicated workspaces

    110 properties have a dedicated workspace

  • Wi-Fi availability

    170 of Westchester holiday rentals include Wi-Fi 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!

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