Vacation rentals in Westchester

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Top-rated vacation rentals in Westchester

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

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Top guest favourite
An inviting living space features a comfortable couch, a plush blue armchair, and a wooden coffee table. A wall-mounted television is visible, and natural light filters through gridded windows. The area seamlessly flows into a sleeping space, enhanced by white bedding and decorative accents.
Guest suite in Miami
4.99 out of 5 average rating, 363 reviews

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.

Top guest favourite
A spacious backyard is showcased with a clear pool reflecting the sky. Sun loungers are arranged nearby, accompanied by a large umbrella for shade. Paths of stepping stones lead through a pebble area, enhancing the serene outdoor setting.
Home in Miami
4.92 out of 5 average rating, 378 reviews

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.

Guest favourite
A light-filled living area features a soft beige leather couch and armchairs arranged around a wooden coffee table. A decorative wall mirror and a potted plant add to the space. A television is mounted on the wall, and light drapes cover the windows.
Home in Flagami
4.93 out of 5 average rating, 387 reviews

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.

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 Miami
4.99 out of 5 average rating, 389 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

Top guest favourite
Apartment in Flagami
4.81 out of 5 average rating, 899 reviews

2PPL/Top Location/Parking/10 min Airport #2

Brand-new private studio with free parking just minutes from Miami Airport, Coral Gables, and South Beach. Enjoy premium mattresses and a smart TV with Netflix. We maintain exceptional cleanliness for a comfortable, worry-free stay. No animals of any kind are allowed, including service animals, due to an Airbnb-approved health exemption. We cannot store luggage. Early check-in at 1 p.m. is available for a $15 fee, with advance notice. Thanks for choosing our place!

Guest favourite
A decorative vase with blue flowers is positioned on a white coffee table. In the background, a flat-screen TV is placed on a low white entertainment unit, and natural light filters through a window with contemporary blinds.
Guest suite in Miami
4.92 out of 5 average rating, 172 reviews

Private Guest Suite w/ Patio in Miami

Cozy private suite room located in a private home, in Westchester. Great for travelers looking to stay close to the airport and popular destinations here in Miami. The suite is located on the left side of the main house with its own private entrance and side patio. Free street parking. Ideal for 2. Hermoso efficiency con excelente ubicacion en Westchester. Entrada y pequeño patio privado. Cerca de diversos destinos en Miami incluyendo Miami International Airport.

Superhost
The spacious room features a king-sized bed with crisp white linens. A pink and white curved accent wall adds a modern touch. Adjacent, a stylish chair and a vibrant vanity area are visible, alongside a closet with hangers and a framed window allowing natural light.
Apartment in Miami
4.81 out of 5 average rating, 590 reviews

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

Top guest favourite
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 Miami
4.97 out of 5 average rating, 394 reviews

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.

Superhost
A spacious bed is centered in a bright room, adorned with crisp white linens and decorative pillows. Two bedside lamps sit on either side, illuminating the space. A framed cityscape artwork hangs above the bed, complementing the serene and clean aesthetic.
Home in Miami
4.93 out of 5 average rating, 195 reviews

Feels just like home

Remodeled studio featuring elegant Spanish tile, a brand-new kitchen with modern burners, and a stylish shower. You’ll feel right at home with total privacy, easy check-in, and a peaceful atmosphere on a quiet dead-end street with no traffic. Located in one of Miami’s best areas, close to golf courses, parks, shopping centers, diverse restaurants, the Miccosukee Resort, and Everglades Safari Park for exciting gator airboat tours.

Guest favourite
A serene waterfront view showcases several three-story buildings framed by palm trees. The calm water reflects the bright blue sky dotted with fluffy clouds, while a fountain creates gentle ripples, enhancing the tranquil atmosphere of the resort.
Condo in Miami
4.95 out of 5 average rating, 798 reviews

Marriott Villas at Doral 2BD sleeps 8

Located in one of the most prestigious areas of Miami, Marriott's Villas at Doral are a tranquil hideaway; only 13 miles from the sizzling excitement of Miami Beach, yet a world away. Sharing the 650-acre lush landscape is the celebrated Trump National Doral Miami, a Trump-managed resort. There, you have access to four championship courses, a classic European spa, a water recreation playground and several restaurants.

Top guest favourite
A sailboat is anchored in calm waters during sunset, with vibrant orange and purple hues reflected on the surface. The silhouette of the boat, featuring a tall mast and a shaded cockpit area, contrasts against the colorful sky. Nearby boats are visible in the distance.
Boat in Coconut Grove
4.98 out of 5 average rating, 832 reviews

Hunter 26 Sailboat

A one-of-a-kind experience for those who want to enjoy Miami from a different perspective. Can accommodate up to two people, includes a basic toilet and freshwater. The boat is anchored in Biscayne Bay, which allows you to view the Miami skyline from a distance. You'll be in the famous Coconut Grove area. I will be taking you from the dinghy dock to the boat. Two kayaks are included for guests.

Guest favourite
A cozy studio space is highlighted by a queen bed adorned with a vibrant yellow throw blanket. A wall-mounted flat-screen TV is positioned above a rustic coffee table, surrounded by framed photographs and a colorful tapestry, creating an inviting atmosphere.
Guest suite in Miami
4.92 out of 5 average rating, 137 reviews

The Gables Hideout- Charming/Cozy/Private

Welcome to @The Gables Hideout, our beautiful studio guest house sits in a quiet and safe neighborhood in the outskirts of Coral Gables. Equipped with its own private entrance, free dedicated parking spot, its own private outdoor patio with a BBQ, and a seating area, 24hr check-in, walk in closet, Flat-Screen smart TV, a fully equipped private kitchen and high-speed WiFi.

Popular amenities for Westchester vacation rentals

When is the best time to visit Westchester?

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Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Westchester?

    Yes! Work meets play with ease at over 120 vacation rentals in Westchester featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do apartment rentals in Westchester have air conditioning?

    Absolutely! We offer over 30 apartment rentals with air conditioning in Westchester. Enjoy a tailored experience with all the comforts you desire.

  • Where should I stay in Westchester?

    Make yourself at home in Westchester by choosing from our most frequently booked neighborhoods. We have over 1,230 vacation rentals in Westchester, and over 1,230 vacation rentals in University Park.

  • What are the most popular amenities for Apartment Rentals in Westchester?

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 30 homes with air conditioning, over 20 homes with a kitchen, over 20 homes with free parking, over 20 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do house rentals in Westchester have a kitchen?

    Absolutely! We offer over 110 house rentals with a kitchen in Westchester. Enjoy a tailored experience with all the comforts you desire.

  • Do private suite rentals in Westchester have wifi?

    Absolutely! We offer over 10 private suite rentals with wifi in Westchester. Enjoy a tailored experience with all the comforts you desire.

  • Are there pet-friendly vacation rentals in Westchester?

    Four-legged friends are welcome in Westchester. Choose from more than 70 vacation rentals for guests traveling with pets.

  • Are there Westchester vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 60 vacation homes with pools in Westchester, available on Airbnb. Make a splash and soak up the sun in style!

  • Are there family-friendly vacation rentals in Westchester?

    Westchester has more than 100 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do private suite rentals in Westchester have free parking?

    Absolutely! We offer over 10 private suite rentals with free parking in Westchester. Enjoy a tailored experience with all the comforts you desire.

Quick stats about vacation rentals in Westchester

  • Total vacation rentals

    Explore 190 vacation rentals in Westchester

  • Nightly prices starting at

    Westchester vacation rentals start at $28 CAD per night before taxes and fees

  • Verified guest reviews

    Over 10,360 verified reviews to help you choose

  • Family-friendly vacation rentals

    100 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 70 rentals that welcome pets

  • Vacation rentals with a pool

    60 properties feature pools

  • Rentals with dedicated workspaces

    120 properties have a dedicated workspace

  • Wifi availability

    180 of Westchester vacation 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!

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