
Holiday rentals in Westchester
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Top-rated holiday rentals in Westchester
Guests agree: these stays are highly rated for location, cleanliness and more.

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!

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!

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.

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.

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.

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

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!

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.

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!

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!

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.

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 holiday rentals
Other great holiday rentals in Westchester

Near Dolphin Mall / Airport with parking

*Luxury on the 2nd Floor*

Twin bed, short term stay.

Modern 1 bedroom apartment with parking.

Tucker at Palmer Dadeland Miami | 1 Bedroom

Luxury Room

Miami Studio near Dolphin Mall, FIU & Airport

Garden View at the Spanish Villa
When is the best time to visit Westchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $176 SGD | $202 SGD | $202 SGD | $175 SGD | $180 SGD | $186 SGD | $185 SGD | $203 SGD | $189 SGD | $212 SGD | $209 SGD | $262 SGD |
| Avg. temp | 20°C | 22°C | 23°C | 25°C | 27°C | 28°C | 29°C | 29°C | 28°C | 27°C | 24°C | 22°C |
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 holiday rentals in Westchester

Total holiday rentals
Explore 170 holiday rentals in Westchester

Nightly prices starting at
Westchester holiday rentals start at $38 SGD 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 & child-friendly amenities

Pet-friendly holiday rentals
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

Wifi availability
170 of Westchester holiday 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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- South Beach
- Fort Lauderdale Beach
- Bayfront Park
- The Tides on Hollywood Beach
- Bayside Marketplace
- Brickell City Centre
- Miami Beach Convention Center
- Miami Design District
- Miami Beach
- Kaseya Center
- Hard Rock Stadium
- Everglades National Park
- Midtown
- Port Everglades
- Haulover Beach
- University of Miami
- Ocean Reserve Condominium
- Calle Ocho Plaza
- Sawgrass Mills
- Las Olas Beach
- LoanDepot Park
- Lauderdale-By-The-Sea Beach
- Bal Harbour Beach
- Aventura Mall




