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Vacation rentals in Westchester

Find and book unique accommodations on Airbnb

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
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 Miami
4.85 out of 5 average rating, 200 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!

Guest favourite
Guesthouse in Miami
4.83 out of 5 average rating, 249 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!

Guest favourite
A wraparound balcony offers panoramic views of Biscayne Bay and the Miami skyline. The scenic vista is complemented by lush greenery below and various buildings in the foreground. The sky is bright with scattered clouds, enhancing the sense of openness and tranquility.
Apartment in Coconut Grove
4.9 out of 5 average rating, 223 reviews

Stunning Studio w/Bay & City View Free Park/Pool

INCREDIBLE VALUE! First, a $30 gift card to our restaurant GreenStreet and a bottle of champagne will be awaiting you in your room! in Coconut Grove, this privately owned & renovated deluxe bright studio on the 15th floor of a luxurious waterfront property offers breathtaking bay & city views, is equipped for 2 guests w/king size bed, full kitchen, full bath & balcony. Enjoy all the luxury amenities we offer, pool & hot-tub w/ incredible bay views, penthouse gym, sauna, business center, squash.

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
4.89 out of 5 average rating, 245 reviews

Quiet Guest Suite, 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.

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, 389 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.

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
5 out of 5 average rating, 413 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, 141 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!

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, 180 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
A two-story house features a modern exterior with light-colored walls and a balcony on the second floor. Bright pink bougainvillea adorns a large planter near the entrance, while the welcoming front door is flanked by large windows.
Home in Flagami
4.87 out of 5 average rating, 115 reviews

Elegant Casita, Heart of Miami

Enjoy our beautiful and central house in the heart of the 305! With two bedrooms with queen-sized beds, 1.5 bathrooms, fully equipped kitchen, washer and dryer and custom laundry area, it is the ideal spot for your next trip to Miami. Conveniently located 10mn away from the airport and down the street from the entrance to the Palmetto Expressway leading to the junction with the Dolphin expressway, it is quite literally in the beating heart of the City!

Top guest favourite
Guest suite in Flagami
4.96 out of 5 average rating, 191 reviews

Independent apartment in downtown Miami

We are ready to make your stay a quiet and pleasant experience. We are located 8 minutes from Miami International Airport, close to universities and specialized clinics, nearby shopping places, and a 20-minute drive to the beaches of Miami Beach, Key Biscayne and other interesting sites. Enjoy a space in the middle of the city, private, quiet, independent, safe, equipped with the basic implements necessary for your comfort. Welcome!

Top guest favourite
Tiny homes in Coconut Grove
4.96 out of 5 average rating, 127 reviews

Private Gated VERY Tiny House • Coconut Grove

Quiet, respectful solo guests only. Owner onsite. No visitors. ULTRA small Tiny House (10x10) in walkable Coconut Grove with AC, fast WiFi, tiny kitchen, fridge & private outdoor shower. Gated, peaceful setting near cafés, parks, bayfront paths & the Village. Eco-focused urban glamping in Miami for minimal luggage, early nights & guests who value calm, safety, nature & a no-TV, no-frills stay.

Guest favourite
A cozy living area is featured with a light gray sofa positioned beside a circular coffee table. An accent wall displays a decorative sign, while shelves are neatly arranged with books and decorative items. A soft glow is provided by a floor lamp in the corner.
Guest suite in Miami
4.91 out of 5 average rating, 257 reviews

Private Guest Suite with Private Entry

Private GUEST SUITE within host home with PIVATE access: The whole group will enjoy easy access to everything from this centrally located guest suite. Private updated shower bathroom. Queen sized bed with 55” tv. Living area / breakfast nook. Coffee maker, microwave and Small mini fridge included. Private patio space included. No smoking on premises. No events or parties.

Popular amenities for Westchester vacation rentals

When is the best time to visit Westchester?

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Avg. price$189 CAD$216 CAD$216 CAD$187 CAD$193 CAD$200 CAD$198 CAD$217 CAD$202 CAD$227 CAD$224 CAD$280 CAD
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Frequently Asked Questions

  • Are there family-friendly vacation rentals in Westchester?

    Westchester has more than 90 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in house rentals in Westchester?

    Experience the best of Westchester with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • 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 vacation rentals with a dedicated workspace in Westchester?

    Yes! Work meets play with ease at over 100 vacation rentals in Westchester featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there Westchester house rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 50 house rentals with pools in Westchester, available on Airbnb. Make a splash and soak up the sun in style!

  • 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.

  • Do house rentals in Westchester have air conditioning?

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

  • Do apartment rentals in Westchester have a kitchen?

    Absolutely! We offer over 20 apartment 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.

  • 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 170 vacation rentals in Westchester

  • Nightly prices starting at

    Westchester vacation rentals start at $41 CAD per night before taxes and fees

  • Verified guest reviews

    Over 10,300 verified reviews to help you choose

  • Family-friendly vacation rentals

    90 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

    100 properties have a dedicated workspace

  • Wifi availability

    170 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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