Compare best Airbnb in Winter Garden, FL from 100+ providers!
97 available vacation rental offers
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating
Best Vacation rentals and Airbnb offers in Winter Garden, FL
9.6 7 reviews
Winter Garden, FL
07/29 – 08/31
$89/nighttotal: $2937 (33 )
Chic Studio Apartment In Near Downtown Winter Garden
1 2
studio , Winter Garden
This Winter Garden studio apartment is conveniently located a short walk from downtown Winter Garden, offering easy access to boutiques, cafes, and the farmers market, and is 20 minutes from Walt Disney World and 15 minutes from Universal Orlando Resort. The unit sleeps three guests, includes one bathroom, high-speed Wi-Fi, air conditioning, and off-street parking; nearby attractions include Orlando International Premium Outlets and Mall at Millenia.
9.8 60 reviews
Winter Garden, FL
07/29 – 08/31
$159/nighttotal: $5247 (33 )
1921 Winter Garden Home 22 Min From Magic Kingdom
1 2
apartment , Winter Garden
This renovated 1921 bungalow in Winter Garden, Florida, is located less than a 15-minute walk from Plant Street's farmers market, breweries, restaurants, and shops. This two-bedroom, two-bathroom house offers a fully equipped kitchen with modern appliances, a private backyard, and sleeps up to five guests, boasting a blend of historic details and updated amenities.
9.7 37 reviews
Winter Garden, FL
07/29 – 08/31
$134/nighttotal: $4422 (33 )
The Swift House
1 2
apartment , Winter Garden
This Plant Street cottage in Winter Garden, Florida, is steps from Plant Street's shops and restaurants, a short walk to the lake, and 20 minutes from Disney World. This pet-friendly one-bedroom, one-bathroom house sleeps three, boasts a full kitchen with dishwasher and French door fridge, a private fenced 0.25-acre backyard, designated off-street parking, and a Taylor Swift-inspired theme.
10 2 reviews
Winter Garden, FL
07/29 – 08/31
$195/nighttotal: $6435 (33 )
Luxury Stay | Pool + Gym + Fast Wi-fi
1 2
apartment , Winter Garden
This Orlando condo is located 12-13 miles from Camping World Stadium, The Wizarding World of Harry Potter, Universal Studios Orlando, and Church Street Station, with Orlando International Airport 21 miles away. This 890 sq ft apartment accommodates up to 7 guests and features a private pool, a full kitchen, complimentary Wi-Fi, and a fitness center, offering a non-smoking environment with a strict policy against bachelor(ette) parties.
9.8 17 reviews
Winter Garden, FL
07/29 – 08/31
$132/nighttotal: $4356 (33 )
Modern Luxury Unit In Beautiful Down Town Winter Garden With Wifi, Cable & Pool
1 2
apartment , Winter Garden
This ground-floor condo offers easy access in downtown Winter Garden, located two blocks from restaurants, entertainment, the farmers market, and the West Orange Trail, and two minutes from the 429 highway. This 910 sq ft furnished residence features one bedroom, one bathroom, and can accommodate up to four guests, with a king bed and an additional queen mattress, plus on-site amenities including a fitness room and swimming pool.
8.8 5 reviews
Winter Garden, FL
07/29 – 08/31
$178/nighttotal: $5874 (33 )
Stylish 2br • Pool & Gym • Minutes To Disney
1 2
apartment , Winter Garden
This 2-bedroom, 2-bathroom condo is located in the central Downtown Winter Garden district, offering a 0.2-mile walk to the West Orange Trail and close proximity to the historic Winter Garden Farmers Market. This apartment provides internet, air conditioning, a swimming pool, a fitness center, and parking for up to 5 guests, with a stylish interior and a welcoming atmosphere for exploring Winter Garden.
9.9 25 reviews
Winter Garden, FL
07/29 – 08/31
$121/nighttotal: $3993 (33 )
Winter Garden Butterfly Retreat
1 2
apartment , Winter Garden
This Winter Garden private suite is located one block from the 22-mile West Orange Trail, offering direct access to downtown Winter Garden's historic district, coffee shops, restaurants, and farmer's market. This 1-bedroom, 1-bathroom apartment accommodates 2 guests and features a private living area, kitchenette with fridge, freezer, and microwave, air conditioning, Wi-Fi, a garden, and parking for 2 cars, with Disney World and Universal Studios approximately 30 and 35 miles away, respectively.
Winter Garden, FL
07/29 – 08/31
$176/nighttotal: $5808 (33 )
Stylish 2br • Pool & Gym • Minutes To Disney
2 2
apartment , Winter Garden
This Orlando condo is located 12-13 miles from Camping World Stadium, Universal Studios' Islands of Adventure, and The Wizarding World of Harry Potter, with Orlando International Airport 21 miles away. This 1120 sq ft residence offers 2 bedrooms, 2 bathrooms, and accommodates up to 8 guests, featuring a private garden with a playground and outdoor fireplace, a year-round outdoor pool, a gym, and a terrace with an outdoor dining area.
10 4 reviews
Winter Garden, FL
07/29 – 08/31
$233/nighttotal: $7689 (33 )
The Garden Luxe Retreat
1 2
apartment , Winter Garden
This Winter Garden vacation rental is centrally located, offering easy access to Universal Studios Florida™, the Wizarding World of Harry Potter™, Orlando International Premium Outlets, and Mall at Millenia. This two-bedroom, two-bathroom apartment sleeps four guests and features an on-site water park, plus proximity to the Florida Citrus Bowl Stadium and Kia Center.
9.5 107 reviews
Winter Garden, FL
07/29 – 08/31
$103/nighttotal: $3399 (33 )
3407 Luxury Option For Your Visit
1 2
studio , Orlando
This one-bedroom apartment is located in a residential area of Orlando, just 2 miles from Universal Studios' Islands of Adventure and 3 miles from the Orange County Convention Center. The apartment features a private terrace, a fully equipped kitchenette, and a swimming pool, making it a comfortable and convenient option for families and couples visiting Orlando.
9.2 10 reviews
Winter Garden, FL
07/29 – 08/31
$102/nighttotal: $3366 (33 )
All-you-need Studio Apartment Near Downtown
1 2
apartment , Winter Garden
This studio apartment is situated in Historic Downtown Winter Garden, a short walk to shops, cafes, the Winter Garden Farmers Market, and the bike trail, offering convenient access to highways and attractions. This accommodation for two features a Queen bed, a compact kitchenette, a modern bathroom, complimentary WiFi, and off-street parking for one vehicle, ideal for exploring Winter Garden's amenities and nearby recreational paths.
9.4 26 reviews
Winter Garden, FL
07/29 – 08/31
$185/nighttotal: $6105 (33 )
Dtwn Winter Garden Home: 12 Mi To Disney!
3 2
apartment , Winter Garden
This charming cottage is located just half a mile from Winter Garden's downtown area, offering easy access to the farmers market, restaurants, and shops. The property has received excellent user ratings, with very good scores for location and cleanliness. This 3-bedroom, 2-bathroom home comfortably accommodates up to 7 guests. The cottage features a well-equipped kitchen with stainless steel appliances, a private yard, and modern amenities like a Smart TV, free Wi-Fi, and complimentary toiletries.
Discover Family-Friendly Vacation Rentals in Winter Garden, FL
The right family vacation rental in Winter Garden, FL makes all the difference, keeping you close to top city attractions.
9.2 73 reviews
Winter Garden, FL
07/29 – 08/31
$179/nighttotal: $5907 (33 )
Updated Condo Near Conv Ctr, I-drive & Universal
3 2
apartment , Williamsburg
This apartment is located just 1.7 miles from the Orange County Convention Center and 2 miles from The Wheel at ICON Park Orlando, making it a convenient base for exploring Orlando's attractions. It has received excellent ratings for location, cleanliness, and overall user experience. The apartment has three bedrooms and covers 1410 square feet of space. It includes amenities like a swimming pool, Jacuzzi, fitness center, and a tennis court, providing plenty of opportunities for relaxation and recreation.
9.4 136 reviews
Winter Garden, FL
07/29 – 08/31
$187/nighttotal: $6171 (33 )
Newly Renovated Lakeview Vista Cay Condo
3 2
apartment , Williamsburg
This waterfront apartment in Williamsburg offers stunning views and is within 3 miles of major tourist attractions. It has excellent user, location, and cleanliness ratings. The apartment has a floor area of 2060 square feet and features a family-friendly layout with a sofa bed and a fully equipped kitchen. It also boasts a fitness center, a spa tub, and an arcade/game room for entertainment.
9.3 149 reviews
Winter Garden, FL
07/29 – 08/31
$175/nighttotal: $5775 (33 )
Lovely Third-floor Vista Cay Resort Condo
3 2
apartment , Williamsburg
This Lovely Third-floor Vista Cay Resort Condo! offers a peaceful setting on a lake with stunning views. Located within easy reach of major attractions like Shingle Creek Golf Course, Orange County Convention Center, and Aquatica, this family-friendly resort has excellent user, location, and cleanliness ratings. The spacious 3-bedroom condo features a fully equipped kitchen, a balcony, and covers an area of 2100 square feet. Guests can enjoy amenities such as a fitness center, a spa tub, an arcade/game room, and barbecue grills.
9.8 172 reviews
Winter Garden, FL
07/29 – 08/31
$130/nighttotal: $4290 (33 )
Walkable Winter Garden Bungalow: 3 Blocks To Dtwn
1 2
house , Winter Garden
This Winter Garden vacation home is within walking distance of the Winter Garden Art Association, Central Florida Railroad Museum, and Winter Garden Heritage Museum. The house has excellent user, location, and cleanliness ratings. The 640-square-foot house has 1 bedroom, 1 bathroom, and can accommodate up to 4 guests. It features a fully equipped kitchen, air conditioning, a terrace, a garden, a spa, parking, and a sofa bed for additional sleeping arrangements.
Best Winter Garden, FL vacation rentals with parking
8.8 3 reviews
Winter Garden, FL
07/29 – 08/31
$233/nighttotal: $7689 (33 )
Winter Garden Charm, Near Disney
1 2
apartment , Winter Garden
This Winter Garden apartment rental is centrally located on Plant Street in historic downtown Winter Garden, steps from restaurants and boutiques, and 20 minutes from Walt Disney World. The 1,184 square-foot unit features two bedrooms, two bathrooms, a terrace, and accommodates four guests, boasting amenities such as a swimming pool, parking, and a kitchen with a fridge, microwave, and dishwasher.
10 6 reviews
Winter Garden, FL
07/29 – 08/31
$185/nighttotal: $6105 (33 )
Cozy 2 Bedroom Apartment In Winter Garden With Fast Wifi, Pool & Fitness Room
2 2
apartment , Winter Garden
This 2-bedroom rental is located downtown Winter Garden, offering direct access to the West Orange Trail and a 12-minute drive to Highway 429, AdventHealth Hospital, and Orlando Health Hospital. This 1170 sq ft condo accommodates up to 6 guests and features a microwave, dishwasher, air conditioning, parking, and an on-site fitness room with a yoga studio, perfect for exploring Winter Garden Village and Orlando attractions.
10 2 reviews
Winter Garden, FL
07/29 – 08/31
$254/nighttotal: $8382 (33 )
Emerald Grove - Close To Disney
1 2
apartment , Winter Garden
This Winter Garden apartment rental, located in the Emerald Grove community, offers convenient access to Universal Orlando Resort, Disney World, Orlando International Premium Outlets, and Mall at Millenia, though precise distances aren't specified. The 1,184 square-foot condo features two bedrooms, two bathrooms, accommodates four guests, and includes a fully equipped kitchen with a refrigerator, microwave, dishwasher, and in-unit laundry, plus a refreshing swimming pool and parking.
9.0 7 reviews
Winter Garden, FL
07/29 – 08/31
$170/nighttotal: $5610 (33 )
House 2 Bedrooms /2 Full Bathrooms Downtown Winter Garden
2 2
apartment , Winter Garden
This fully renovated Winter Garden house is located in downtown, a short walk from Winter Garden's shops and restaurants, and a 25-minute drive from Walt Disney World Resort and Orlando International Airport. This two-bedroom, two-bathroom home sleeps four guests comfortably and features a fully equipped kitchen, laundry facilities, and is steps away from the West Orange Trail.
Frequently Asked Questions about vacation rentals in Winter Garden, FL
What should a first-time visitor not miss in Winter Garden, FL?
You should definitely check out the Winter Garden Village, a charming outdoor shopping center with unique stores and restaurants. Also, the historic downtown area is a must-see with its beautiful brick buildings and antique shops. And don't forget to visit the Winter Garden Heritage Museum to learn about the city's rich history.
What are the best Airbnb and vacation rentals in Winter Garden, FL?
Which neighborhood in Winter Garden, FL should you consider for a vacation rental?
The area around Plant Street is a popular choice for vacation rentals. It's a vibrant area with lots of restaurants, shops, and a lively atmosphere. You can find a variety of rental options, from cozy cottages to spacious apartments.
What are the most popular Airbnbs in Winter Garden, FL?
What are the top family-friendly attractions in Winter Garden, FL?
The Winter Garden Village is a great place for families, with a playground and a carousel. The West Orange Trail is a great place for a family bike ride or walk. And the Winter Garden Farmers Market is a fun way to spend a Saturday morning, with live music and fresh produce.
What are the best vacation rentals with a pool in Winter Garden, FL?
When is the best time to book a vacation rental in Winter Garden, FL?
The best time to book a vacation rental in Winter Garden is during the shoulder seasons, from April to May or September to October. You'll avoid the crowds and the prices will be lower than during peak season.
What are the best rentals for families and kids in Winter Garden, FL?
What events or festivals should visitors check out in and around Winter Garden, FL?
The Winter Garden Farmers Market is a popular event, held every Saturday morning. The Plant Street Market is another great option, with a variety of food trucks and vendors. And the annual Winter Garden Heritage Festival is a fun celebration of the city's history.
What are the best rentals or Airbnbs with a jacuzzi in Winter Garden, FL?
What are the best budget-friendly activities in Winter Garden, FL?
The West Orange Trail is a great option for a free walk or bike ride. You can also explore the historic downtown area and enjoy the free events at the Winter Garden Village.
What are the best restaurants with local dishes in Winter Garden, FL?
The Winter Garden Farmers Market is a great place to try local produce and food. For a sit-down meal, try The Crooked Spoon or The Ravenous Pig, both known for their fresh, seasonal dishes.
What are the best walking or cycling routes in Winter Garden, FL?
The West Orange Trail is a popular option for both walking and cycling. It's a paved, 22-mile trail that runs through Winter Garden and several other cities. The Winter Garden Heritage Trail is a shorter, 2-mile loop that goes through the historic downtown area.
Are there pet-friendly attractions in Winter Garden, FL?
Yes, many of the parks and trails in Winter Garden are pet-friendly. The West Orange Trail is a great option for a walk with your dog. The Winter Garden Village also has a few pet-friendly restaurants and shops.
What are the benefits of choosing a vacation rental in Winter Garden, FL?
Vacation rentals offer more space and privacy than a hotel room. They also often come with amenities like a kitchen and laundry facilities, which can be helpful for families or longer stays.
What are the top sports attractions and facilities in Winter Garden, FL?
Winter Garden is home to the National Training Center, a world-class athletic facility that hosts a variety of sports events. There are also several public parks with sports fields and courts, such as Winter Garden Village Park and Plant Street Park.
Destinations nearby
Top Vacation Rentals with Balconies in Winter Garden, FL
Wake up to breathtaking views at these Winter Garden, FL vacation rentals with balconies, perfect for your morning coffee.
9.2 186 reviews
Winter Garden, FL
07/29 – 08/31
$196/nighttotal: $6468 (33 )
4012 Vista Cay
3 2
house , Williamsburg
This Williamsburg vacation home is conveniently located near popular attractions like SeaWorld's Discovery Cove, The Wheel at ICON Park Orlando, and SeaWorld Orlando, all within a short drive. The house has consistently received excellent user ratings for location and overall experience, as well as a very good rating for cleanliness. This 3-bedroom house provides comfortable accommodations for families or groups. Guests can enjoy amenities like a swimming pool, jacuzzi, spa, fitness center, and a fully equipped kitchen, as well as a terrace/balcony, garden, and free parking.
Winter Garden, FL
07/29 – 08/31
$99/nighttotal: $3267 (33 )
Luxury 1br • Pool & Gym • Close To Downtown
1 2
apartment , Winter Garden
This apartment in Winter Garden is 12 miles from The Wizarding World of Harry Potter and Universal Studios' Islands of Adventure, and 12 miles from Camping World Stadium. This 910 sq ft condo accommodates up to 7 guests with 1 bedroom, 1 bathroom, a fully equipped kitchen, a private terrace with a fireplace, an outdoor pool, a fitness center, and free WiFi, offering convenient access to Orlando's theme parks and downtown amenities.
9.8 262 reviews
Winter Garden, FL
07/29 – 08/31
$118/nighttotal: $3894 (33 )
Deluxe Studio W/ Lakeview - Free Parking/pool
1 2
studio , Orlando
This 1-bedroom, 1-bathroom apartment is located in Orlando, within walking distance of Pirate's Dinner Adventure and CoCo Key Water Resort, and a short drive to Universal Orlando Resort and The Wheel at ICON Park. The apartment has an excellent user rating, location rating, and cleanliness rating. The apartment has a fully equipped kitchen with a refrigerator, stovetop, microwave, and dishwasher, as well as a private balcony, indoor and outdoor pools, a fitness center, and free WiFi. The apartment is 480 square feet and has a washer and dryer for added convenience.
9.4 144 reviews
Winter Garden, FL
07/29 – 08/31
$191/nighttotal: $6303 (33 )
Ground-floor Vista Cay Condo Near Clubhouse Pool
3 2
apartment , Williamsburg
This ground-floor condo is located in Orlando, Florida, just 1.2 miles from the Orange County Convention Center and close to major attractions. It’s rated excellent for location, cleanliness, and user experience. The apartment has three bedrooms and is 1410 square feet. You’ll enjoy a swimming pool, a jacuzzi, a terrace, a garden, a fitness center, a tennis court, and more.
Find the Best Dog-Friendly Vacation Rentals in Winter Garden, FL
Travel with ease to Winter Garden, FL with pet-friendly rentals located near local dog parks and scenic city walks.
9.9 140 reviews
Winter Garden, FL
07/29 – 08/31
$438/nighttotal: $14454 (33 )
Waterfrontwntrgdnpoolhse Views Dock Wildl Nr Disn
1 2
apartment , Winter Garden
This Winter Garden vacation home offers stunning Lake Apopka sunrise views, a private fishing pier, and is a five-minute drive from Historic Downtown Winter Garden, home to the Central Florida Railroad Museum and Garden Theatre, with major theme parks like Universal Studios (20 minutes away) and Disney World (25 minutes away) also easily accessible. The newly refurbished 4-bedroom, 3-bathroom house sleeps 8, features a well-appointed kitchen with dishwasher, multiple smart TVs, a screened porch, outdoor patios, a fire pit, and is close to the West Orange Trail and weekly events at Plant Street Market.
8.0 1 review
Winter Garden, FL
07/29 – 08/31
$136/nighttotal: $4488 (33 )
Dog-friendly Condo With A Kitchenette, Ac, Pools, Hot Tubs, Tennis, & Gym
2 2
apartment , Orlando
This 2-bedroom, 2-bathroom condo is located in Orlando's International Drive District, offering convenient proximity to Walt Disney World, Universal Orlando Resort, and SeaWorld, all within 5 miles. This 580 square foot unit accommodates up to 4 guests and features a furnished balcony with pool and lake views, a full kitchenette, central air conditioning, and access to on-site amenities including heated pools and lighted tennis courts.
9.2 78 reviews
Winter Garden, FL
07/29 – 08/31
$151/nighttotal: $4983 (33 )
Beautiful Studio At Westgate Lakes Resort & Spa Near Disney Universal Sea World
1 2
studio , Doctor Phillips
This waterfront studio in Orlando's Doctor Phillips district offers lake views and is located within minutes of the Orange County Convention Center, CoCo Key Water Resort, Arnold Palmer's Bay Hill Golf Club, and Mystic Dunes Golf Club. This 500 sq ft studio accommodates up to 4 guests and features a kitchenette, a private balcony, a jetted tub, and access to seven outdoor pools, a jacuzzi, spa, sauna, tennis court, and concierge services.
9.4 239 reviews
Winter Garden, FL
07/29 – 08/31
$186/nighttotal: $6138 (33 )
Luxury Pet Friendly Condo, Near Clubhouse & Pool
3 2
apartment , Williamsburg
This eco-friendly apartment is located in Orlando, Florida, just 1.2 miles from the Orange County Convention Center and within a 2-mile radius of the Wheel at ICON Park Orlando and SeaWorld Orlando. Guests rave about the apartment's excellent location, cleanliness, and overall experience. The apartment features 3 bedrooms and 2 bathrooms, offering 1410 square feet of space. Guests can enjoy a variety of amenities including a swimming pool, jacuzzi, fitness center, and a tennis court.
