Holiday houses in Westchester

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Top-rated holiday rentals in Westchester

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

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Guest favourite
Tiny home in Coconut Grove
4.97 out of 5 average rating, 121 reviews

Private Gated Tiny House • C Grove Micro Retreat

Quiet, respectful guests only. Owner onsite. No visitors allowed. Ultra-tiny 10×10 Tiny House micro-retreat in walkable Coconut Grove with AC, fast WiFi, small kitchen, mini fridge & private outdoor shower. Ideal for solo travelers seeking safety, simplicity, nature & the outdoors within a gated, peaceful setting near cafés, parks, bayfront paths and the Village—an eco-focused, secure urban glamping stay in Miami. Designed for minimal luggage, early nights & guests who value calm over nightlife

Guest favourite
A light-filled bedroom features a spacious bed with crisp white linens and a built-in headboard. French doors lead to an outdoor space, while a flat-screen TV is mounted on the wall. Soft gray curtains frame the windows, complementing the neutral decor.
Guesthouse in Miami
4.82 out of 5 average rating, 245 reviews

Kusikuy Private Guesthouse

This wonderful Cottage has a private entrance in the side, surrounded by a garden with a pond in a peaceful environment located in a quiet residential neighborhood. Centrally located at only 12 minutes to the airport, fast access to the main highways to get in 20-25min to South Beach (12miles), 15min to Dolphin Mall, 15min to Dadeland Mall and 25min to the redland farms in Homestead or the Everglades. A fridge with free beverages, Wi-fi, silent cold Ac split and a Smart TV are waiting for you!

Top Guest favourite
A cozy bedroom features a queen-size bed with fresh linens and decorative pillows. Natural light enters through a window adorned with light curtains. Wooden flooring complements the space, which includes bedside tables and lamps for additional lighting.
Guesthouse in Flagami
4.97 out of 5 average rating, 205 reviews

Cosy Guesthouse Central Located

Welcome to our centrally located Miami guesthouse! This cozy retreat is perfect for solo travelers or couples. Complete renovated with free private gated parking, your own entrance and outdoor patio to enjoy a comfortable stay with modern amenities and easy access to the city's top attractions. Just minutes away from Miami Airport, Downtown, Coral Gables and the Beaches. Convenient located to explore nearby restaurants, shops, and nightlife. Book your stay now for a memorable Miami experience!

Guest favourite
A spacious bedroom features a comfortable bed with a light-colored quilt, complemented by wooden accents. Natural light filters through, illuminating the room's earthy tones. A small nightstand and artwork depicting a bird add character, while a private bathroom entrance is visible in the background.
Guest suite in Coral Way
4.9 out of 5 average rating, 229 reviews

Guest Studio apt, Private entrance, Patio, Parking

Take it easy at this unique and tranquil getaway in our 1930's Spanish Villa in the center of Little Havana and Coral Gables in the heart of Shenandoah. Your Guest Suite is equipped with a private entrance, private garden, and parking. Casita Amorcita is designed to give you the feeling of 'home' and 'love,' with the guest experience in mind. All linens are 100% cotton. Here you will have all that you need to rest, recover, recharge, and enjoy. We look forward to welcoming you home.

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, 383 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, 398 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, 397 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
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
4.96 out of 5 average rating, 140 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!

Top Guest favourite
The outdoor area features vibrant green synthetic grass and a large shade tree. A playground set with swings is visible alongside a colorful slide. A chess set on the lawn adds a playful touch, while various seating options are arranged nearby in a spacious backyard.
Home in Flagami
4.96 out of 5 average rating, 139 reviews

Tropical Getaway | Jacuzzi | King| 10 mins Airport

⭐️Relax in a vibrant city with full access to top attractions, dining, nightlife and unforgettable adventures. Self check in (SMART LOCK)🔐 DEDICATED WORKSPACE 💻 EV 2 CHARGER 🚗🔌 HOT TUB🛁 BLUETOOTH SPEAKER🎵 BLACKOUT CURTAINS🌅 Bluetooth Victrola 🎼 Smart TVs in every room📺 Backyard 🏡 Piano 🎹 Fast WIFI📶 KARAOKE 🎤 Fully equipped kitchen🍽️ Pool Table and Games🎱 FREE AMPLE parking🅿️ Wood Pellet Smoker / Outside dining table😋 FREE Washer & Dryer👚 Kids👶/Pets 🐶 Friendly

Guest favourite
Apartment in Flagami
4.79 out of 5 average rating, 882 reviews

2PPL/Top Location/Parking/10 min Airport #3

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
4.93 out of 5 average rating, 177 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.

Top 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, 847 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.

Popular amenities for Westchester holiday rentals

When is the best time to visit Westchester?

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Avg. price$205 AUD$235 AUD$235 AUD$204 AUD$209 AUD$217 AUD$215 AUD$236 AUD$220 AUD$196 AUD$187 AUD$242 AUD
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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 1,250 vacation rentals in Westchester, and over 1,250 vacation rentals in University Park.

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

    Enhance your stay in our Private Suite Rentals with the most popular amenities: over 10 homes with free parking, over 10 homes with air conditioning, over 10 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 house rentals in Westchester have wifi?

    Absolutely! We offer over 120 house 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 house rentals in Westchester have free parking?

    Absolutely! We offer over 120 house rentals with free parking in Westchester. Enjoy a tailored experience with all the comforts you desire.

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 $45 AUD per night before taxes and fees

  • Verified guest reviews

    Over 10,300 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

    100 properties have a dedicated workspace

  • Wi-Fi availability

    170 of Westchester holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi 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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