Holiday rentals in Westchester
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Quick stats about holiday rentals in Westchester
Total holiday rentals
Explore 180 holiday rentals in Westchester
Nightly prices starting at
Westchester holiday rentals start at £22 per night before taxes and fees
Verified guest reviews
Over 11,420 verified reviews to help you choose
Family-friendly holiday rentals
100 properties offer extra space & child-friendly amenities
Pet-friendly holiday rentals
Find 80 rentals that welcome pets
Holiday rentals with a pool
70 properties feature pools
Rentals with dedicated workspaces
110 properties have a dedicated workspace
Wifi availability
180 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!
Top-rated holiday rentals in Westchester
Guests agree: these stays are highly rated for location, cleanliness and more.
Canalfront Pool • Family Escape • Near MIA
🏊♂️ Private pool + scenic canal views 🌴 Outdoor lounge, BBQ & open-air bathroom 🍳 Full kitchen + coffee, air fryer & essentials 🧺 Pool & bath towels provided 🛏️ 4 bedrooms · 2 king + 2 queen · sofa bed 📺 5 Smart TVs · fast Wi-Fi 🧳 Simplified check-out 🅿️ Parking 4 cars 🛍️ 10–15 min → Dolphin Mall & FIU ✈️ 16 min → MIA Airport 🌆 20–30 min → Brickell & Beaches 🐾 Pets welcome · Pet fee applies 🔑 Entire home · private use 🤝 Superhost - English & Spanish 🚫 No parties or indoor smoking
Modern Beach Lake-Front House in Miami !
Welcome to our stunning 5/4 beachfront lake house! This newly renovated property offers the perfect blend of modern amenities and natural beauty. Located in a central and peaceful neighborhood, guests can enjoy a range of water activities such as kayaking, paddle boarding, and swimming while taking in the views of the Blue lake. Seeking relaxation or adventure, this home has something for everyone.. ✔️15min from Miami International airport ✔️25min to Downtown Miami ✔️30min from Miami Beach
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.
Miami Sanctuary | Heated Saltwater Pool & BBQ
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!
Miami 2/1 Charmer-near airport
Located in a very central Miami neighborhood, this newly remodeled 2/1 charmer is the ideal spot. Ideal for small families traveling or professionals looking for a longer term stay. Comfy mattresses, hotel style pillows and linens for a restful sleep. Kitchen is equipped w/Instapot, Rice Cooker and all cooking essentials. Located within 10 minutes of Jackson Memorial West, Nicklaus Children’s Hospital, Baptist Kendall & South Miami Hospital it’s perfect for travel nurses.
Modern & Spacious Retreat, Near Beaches & Airport
Private guest house in the heart of Miami! This fully independent unit offers a private entrance, dedicated parking, and complete privacy with no shared interior spaces or walls. Located near Bird Road & SW 102nd Ave, less than 15 minutes from Miami International Airport and close to many plastic and cosmetic surgery clinics. Enjoy easy access to major highways, shopping, restaurants, attractions, Downtown Miami, Brickell, and beautiful beaches, all within about 25 minutes.
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.
Gorgeous 5BR • Fire Pit & Games | Pool_Hot Tub_BBQ
Welcome to our home, a haven of entertainment and enjoyment that you won't want to depart. From the serene pool and hot tub to the thrilling games, this residence is crafted to deliver an unforgettable vacation for all ages. If you seek an all-inclusive getaway, look no further. 5 Bedrooms 3.5 Bathrooms Heated Pool/Jacuzzi/Pool Table/Ping Pong Table/Mega Chess/Basketball/Mini Golf/Kids Playground/BBQ/Hammock/Mini Beach/Outdoor furniture/Fire Pit/Cornhole Game
Relaxing Tropical Miami Stay • Poolside Vibes
"Are you planning to come to Miami for tourism or surgery? Our independent space is perfect for families and recovering patients. You'll enjoy a quiet, cozy, and very homey atmosphere. Our space includes: • 2 bedrooms (1 queen bed, 3 single beds) with 60" TVs. • Fully equipped kitchen and private bathroom. • Large porch for relaxing and 2 free parking spaces. • Wi-Fi, air conditioning, and family amenities. Ideal location: 10 MIA AIRPORT "duplex house"
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
Villa Madre Pet Friendly Southwest Miami
Located in highly desirable Southwest Miami. Close to the airport, shopping malls, Florida International University, and highways. Private remodeled 2 bedroom 1 bath house with kitchenette inside. The back patio is shared with the owner who lives in the back studio. Easy check-in. Assigned parking in the driveway. All essentials are provided. MAX OCCUPANCY 3 people. NO SMOKING. NO POST SURGERY GUEST. Please read house rules prior to booking.
Popular amenities for Westchester holiday rentals
Other great holiday rentals in Westchester
oasis/2ppl/pet/bbq/park/terrace
Private Guest Suite w/ Patio in Miami
Elegant Casita, Heart of Miami
Miami Studio Free Parking & Private Entrance
Cozy Miami Rental: Near Parks & University
Casa Mimosa Family Tropical Oasis with Pool
Close to Airport, Perfect for Family & Big Groups!
Tuscany Vibes • King Beds • Recliner Chair • FIU
When is the best time to visit Westchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £139 | £152 | £149 | £137 | £128 | £146 | £107 | £117 | £109 | £122 | £121 | £151 |
| 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
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.
Destinations to explore
- Miami Holiday rentals
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- Miami Beach Holiday rentals
- Orlando Holiday rentals
- Fort Lauderdale Holiday rentals
- Tampa Holiday rentals
- Hollywood Holiday rentals
- Kissimmee Holiday rentals
- Key West Holiday rentals
- St. Augustine Holiday rentals
- Cape Coral Holiday rentals
- Nassau Holiday rentals
- Fort Lauderdale Beach
- South Beach
- Hard Rock Stadium
- Brickell City Centre
- Everglades National Park
- Bayfront Park
- Haulover Beach
- Miami Beach Convention Center
- Dolphin Mall
- University of Miami
- Midtown
- Las Olas Beach
- Bayside Marketplace
- Sawgrass Mills
- LoanDepot Park
- The Tides on Hollywood Beach
- Bal Harbour Beach
- Greater Fort Lauderdale Broward County Convention Center
- CG Cosmetic Surgery
- Aventura Mall
- John Pennekamp Coral Reef State Park
- Porsche Design Tower
- Amerant Bank Arena
- Lauderdale-By-The-Sea Beach