Compare Vacation Rentals & Airbnb in Winter Garden, FL
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97 Rentals and Airbnb in Winter Garden, FL
9.1 11 reviews
Winter Garden, FL
26/06 – 02/07
$257/nighttotal: $1542 (6 )
Orlando Comfort Close To Top Attractions
1 5
apartment , Orlando
This Orlando apartment is situated near ICON Park, a 17-minute walk away, and within a short drive (approximately 4-7km) of Universal Studios, Islands of Adventure, SeaWorld, and Discovery Cove. This self-catering flat offers 50 square metres of space, comprising one bedroom, a living room, one bathroom, and a fully equipped kitchen with a dishwasher, accommodating up to 10 guests and including free Wi-Fi and on-site parking.
Winter Garden, FL
26/06 – 02/07
$225/nighttotal: $1350 (6 )
Orlando Comfort Close To Top Attractions
1 5
apartment , Orlando
This Orlando flat offers convenient access to major attractions, located a 17-minute walk from The Wheel At Icon Park and 3.06 kilometres from Universal Studios' Islands of Adventure. This air-conditioned one-bedroom apartment, covering 50 square metres, accommodates up to nine guests and features a fully equipped kitchen with a dishwasher, complimentary on-site parking, free Wi-Fi, and access to a shared pool.
10 2 reviews
Winter Garden, FL
29/07 – 31/08
$273/nighttotal: $9009 (33 )
Luxury Stay | Pool + Gym + Fast Wi-fi
1 2
apartment , Winter Garden
This Winter Garden flat offers convenient access, situated approximately 19-21 kilometres from major attractions such as Camping World Stadium, Universal Studios, and The Wizarding World of Harry Potter, and is 32 kilometres from Orlando International Airport. This 83 square metre apartment, accommodating up to seven guests, features a private swimming pool, an on-site fitness centre, a fully equipped kitchen, and complimentary high-speed Wi-Fi.
9.7 49 reviews
Winter Garden, FL
26/06 – 02/07
$316/nighttotal: $1896 (6 )
Hidden Paradise Near Orlando
1 5
apartment , Ocoee
This apartment is situated in a peaceful rural setting near Ocoee, Florida, offering easy access to major highways and attractions within a 1.5-hour drive. The property enjoys excellent user, location and cleanliness ratings, making it a popular choice for travellers. The three-bedroom dwelling sleeps up to six guests, providing ample space for families or groups of friends. The property offers a range of amenities, including a fully equipped kitchen, air conditioning, a garden, parking, and a shared washer and dryer.
9.1 7015 reviews
Winter Garden, FL
26/06 – 02/07
$451/nighttotal: $2706 (6 )
Hilton Vacation Club Cypress Pointe Orlando
2 5
resort , Lake Buena Vista
Cypress Pointe Resort is located in Lake Buena Vista, just a short drive from Disney Springs and Prime Outlets Orlando, making it a convenient base for exploring the area's attractions. The resort enjoys excellent ratings for its location, cleanliness, and overall guest experience. This family-friendly hotel offers a range of facilities to keep everyone entertained, including a swimming pool, Jacuzzi, and fitness centre. Guests can also enjoy on-site dining, a bar, and a tennis court, as well as a variety of activities like hot air ballooning and spa treatments nearby.
10 4 reviews
Winter Garden, FL
26/06 – 02/07
$478/nighttotal: $2868 (6 )
Updated 4-bedroom Winter Garden House In Golf Cart District 20 Min From Disney
4 5
apartment , Winter Garden
This four-bedroom, two-bathroom flat is situated in Winter Garden's golf cart district, less than 1.6 kilometres from the town centre and a 32-kilometre drive from Magic Kingdom® Park and Universal Studios. This 186 square metre residence accommodates up to eight guests, featuring a kitchen with a fridge, microwave, and dishwasher, air conditioning, a terrace, and parking, with optional golf cart hire available for exploring the area.
10 3 reviews
Winter Garden, FL
26/06 – 02/07
$467/nighttotal: $2802 (6 )
Updated 4/2 Winter Garden Home 20 Min From Disney!
1 5
apartment , Winter Garden
This Winter Garden flat is situated within the town's golf cart district, less than 1 kilometre from the town centre and a 20-minute drive from both Disney World and Universal Orlando Resort. This 4-bedroom, 2-bathroom flat accommodates up to 8 guests with a king bed, two queen beds, and a triple bunk, featuring air conditioning, internet, a fully equipped kitchen with a dishwasher, and optional golf cart hire for local exploration.
9.0 1 review
Winter Garden, FL
26/06 – 02/07
$181/nighttotal: $1086 (6 )
Two Queen Beds - Pool Hot Tub Close To Disney
1 5
apartment , Orlando
This Orlando apartment offers convenient proximity to ICON Park, a 17-minute walk away, and is located within 4km of Universal Studios and Islands of Adventure. The 50 square metre self-catering flat sleeps nine guests, boasting a fully equipped kitchen, a swimming pool, jacuzzi, fitness centre, and free Wi-Fi.
9.9 27 reviews
Winter Garden, FL
29/07 – 31/08
$138/nighttotal: $4554 (33 )
Winter Garden 1st. Floor Apartment, 1bedr - 1bath
1 2
apartment , Winter Garden
This Winter Garden apartment is conveniently located near Orlando International Airport, approximately 30km away, and a short distance from Winter Garden's town centre, offering easy access to local parks and a brewery. The self-contained flat comprises one bedroom, one bathroom, and sleeps two guests, featuring a kitchen, air conditioning, internet access, and on-site parking.
9.4 26 reviews
Winter Garden, FL
29/07 – 31/08
$259/nighttotal: $8547 (33 )
Dtwn Winter Garden Home: 12 Mi To Disney!
3 2
apartment , Winter Garden
This charming cottage is located just 800 metres from Winter Garden's bustling downtown area, offering easy access to the farmers market, restaurants, and shops. It is also less than 24 kilometres from Walt Disney World, making it ideal for those looking to explore the magic of Orlando. The cottage receives consistently excellent user ratings for its location, cleanliness, and overall experience. The cottage has three bedrooms and two bathrooms, comfortably accommodating up to seven guests. Enjoy a fully equipped kitchen, a private yard, and amenities like air conditioning, free Wi-Fi, and off-street parking for two vehicles.
9.8 60 reviews
Winter Garden, FL
29/07 – 31/08
$223/nighttotal: $7359 (33 )
1921 Winter Garden Home 22 Min From Magic Kingdom
1 2
apartment , Winter Garden
This beautifully renovated 1921 bungalow in Winter Garden is located less than 1.5 kilometres from Plant Street's farmers market, breweries, restaurants, and shops. The two-bedroom, two-bathroom house sleeps five guests and features a fully equipped kitchen with modern appliances, a private garden, and parking; nearby attractions include Winter Garden's main attractions.
10 13 reviews
Winter Garden, FL
26/06 – 02/07
$256/nighttotal: $1536 (6 )
Lilac Loft- Lake, Pool, Pickle Ball, Disney, Fun!
2 5
apartment , Clermont
This two-bedroom, two-bathroom holiday home in Clermont's Vacation Village is situated less than 1.6km from Legends Golf & Country Club and Kings Ridge Driving Range, and under 3.2km from Lake Louisa State Park. The 91 square metre property offers a private pool, free Wi-Fi, a fully equipped kitchen, and accommodates up to six guests, with in-house games and books provided.
Best family friendly Winter Garden, FL vacation rentals
Among the 97 accommodations in Winter Garden, FL, here are the 4 best family friendly rentals
Winter Garden, FL
26/06 – 02/07
$195/nighttotal: $1170 (6 )
Condo W Hot Tub & Pool To Near Universal Studio
1 5
studio , Orlando
This Orlando self-catering apartment is conveniently located around 5-21km from Universal Studios Florida and Walt Disney World Resort, offering easy access to major theme parks, shopping, and golf courses. The 50 square metre studio sleeps up to six guests, featuring two queen beds and a sofa bed, a fully equipped kitchenette (excluding oven), and access to a swimming pool, jacuzzi, and other on-site amenities including a fitness centre, games room and BBQ area.
9.7 210 reviews
Winter Garden, FL
29/07 – 31/08
$276/nighttotal: $9108 (33 )
Beautiful Condo W Private Balcony Near Universal
3 2
apartment , Williamsburg
This apartment is conveniently located in Williamsburg, just a short distance from Universal Studios, the Orange County Convention Center and SeaWorld Orlando, making it ideal for exploring the city's attractions. The apartment has consistently received excellent ratings from previous guests for its cleanliness, location and overall experience. This three-bedroom apartment offers 1 square metre of living space. It comes with a range of amenities including a private balcony, a fully equipped kitchen, air conditioning, a swimming pool, a Jacuzzi, a fitness centre and a tennis court.
9.8 172 reviews
Winter Garden, FL
29/07 – 31/08
$181/nighttotal: $5973 (33 )
Walkable Winter Garden Bungalow: 3 Blocks To Dtwn
1 2
house , Winter Garden
This modern bungalow is situated in Orlando, just a short drive from Winter Garden, making it ideal for exploring both the vibrant city centre and the charming town. The property has received excellent ratings for its location, cleanliness, and overall user experience. This one-bedroom holiday home, spanning 59 square metres, comfortably accommodates up to four guests. The property features a fully equipped kitchen, a private patio, a gas barbecue, and free Wi-Fi, ensuring a relaxing and enjoyable stay.
9.8 168 reviews
Winter Garden, FL
29/07 – 31/08
$146/nighttotal: $4818 (33 )
Stay A While
1 2
apartment , Winter Garden
This one-bedroom flat in Winter Garden is located just 40 kilometres from Orlando International Airport and a 25-minute drive from theme parks and nightlife. The apartment is rated excellent for location, cleanliness, and user experience. The flat has a spacious, open layout and comfortably accommodates up to five guests. Amenities include a shared swimming pool, a garden, dedicated parking, and a kitchen with a fridge and microwave.
Best Winter Garden, FL vacation rentals with parking
9.2 186 reviews
Winter Garden, FL
29/07 – 31/08
$274/nighttotal: $9042 (33 )
4012 Vista Cay
3 2
house , Williamsburg
This house is located in Orlando, Florida, just 3.8 km from The Wheel at ICON Park Orlando and 4 km from SeaWorld's Discovery Cove. It has received excellent ratings for user experience, location, and cleanliness. The property is a 3-bedroom house with a private bathroom and a spacious layout. It offers a range of amenities, including free Wi-Fi, a satellite TV, a washing machine, a fully equipped kitchen, a comfortable seating area, a swimming pool, a Jacuzzi, a terrace, a garden, a spa, a fitness centre, and parking.
10 4 reviews
Winter Garden, FL
26/06 – 02/07
$243/nighttotal: $1458 (6 )
Clermont Home Just 18 Minutes From Walt Disney World® Resort
3 5
apartment , Horizon West
This three-bedroom, two-bathroom holiday home, offered as 'Clermont Home Just 18 Minutes From Walt Disney World® Resort', is situated in Horizon West, Florida, approximately 3 km from Lake Louisa State Park and within 10 km of Northeast Regional Park and Lake Davenport. The 8-guest property boasts a fully equipped kitchen, in-house laundry, barbecue facilities, a swimming pool, and terrace, alongside convenient amenities such as a Smart TV and coffee maker, making it ideal for families seeking a self-catering base for exploring the local parks and attractions.
Winter Garden, FL
26/06 – 02/07
$195/nighttotal: $1170 (6 )
Inviting Condo W Hot Tub & Pool Near Universal
1 5
apartment , Orlando
This Orlando apartment is conveniently located within a 4.8km radius of Universal Orlando Resort and the Orange County Convention Center, also a 15-minute walk from Pirate's Dinner Adventure and CoCo Key Water Resort. This 50-square-metre one-bedroom flat sleeps six guests and boasts a fully equipped kitchen, private balcony, on-site fitness centre, swimming pool, and Jacuzzi, plus nearby access to an arcade and barbecue grills.
10 17 reviews
Winter Garden, FL
29/07 – 31/08
$306/nighttotal: $10098 (33 )
1921 Bungalow In Historic Downtown Winter Garden
2 2
apartment , Winter Garden
This 1920s bungalow offers accommodation in downtown Winter Garden, situated one block from Plant Street and approximately 19 kilometres from Walt Disney World. This pet-friendly dwelling accommodates up to six guests and includes a kitchen with a fridge, freezer, microwave, and dishwasher, alongside air conditioning, Wi-Fi, and parking, with outdoor amenities such as a sunroom, large garden, and firepit.
Frequently Asked Questions about vacation rentals in Winter Garden, FL
What are the top family-friendly attractions in Winter Garden, FL?
The Winter Garden Village is great for families, with the train depot and the Winter Garden Farmers Market. The nearby West Orange Trail is also a great option for a family bike ride.
What are the best Airbnb and vacation rentals in Winter Garden, FL?
When is the best time to book a vacation rental in Winter Garden, FL?
It really depends on your preference. Winter Garden is a popular destination during the spring and autumn months, so booking in advance is recommended. If you prefer warmer weather, summer is a good option, but you might find it more crowded.
What are the most popular Airbnbs in Winter Garden, FL?
What events or festivals should visitors check out in and around Winter Garden, FL?
The Winter Garden Farmers Market is held every Saturday morning, and there are many other events throughout the year, such as the Winter Garden Art Festival and the Winter Garden Wine & Food Festival.
What are the best vacation rentals with a pool 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 check out the Winter Garden Heritage Museum, which offers free admission on the first Saturday of each month.
What are the best rentals for families and kids in Winter Garden, FL?
What are the best restaurants with local dishes in Winter Garden, FL?
There are many great restaurants in Winter Garden, but some local favourites include The Crooked Spoon, which serves up delicious Southern comfort food, and The Ravenous Pig, which offers a more upscale dining experience with a focus on fresh, local ingredients.
What are the best rentals or Airbnbs with a jacuzzi in Winter Garden, FL?
What are the best walking or cycling routes in Winter Garden, FL?
The West Orange Trail is a popular choice for walking and cycling, and it runs for 21 miles through Winter Garden and other nearby towns. You can also explore the many parks and green spaces in Winter Garden, such as the Winter Garden Village Park and the Plant Street Market.
Are there pet-friendly attractions in Winter Garden, FL?
Many of the parks and green spaces in Winter Garden are pet-friendly, including the Winter Garden Village Park and the Plant Street Market. You can also find pet-friendly restaurants and shops in the area.
What are the benefits of choosing a vacation rental in Winter Garden, FL?
Vacation rentals offer more space and privacy than a hotel room, and they are often located in more residential areas. They can also be a more affordable option for families or groups.
What are the top sports attractions and facilities in Winter Garden, FL?
Winter Garden is home to the National Training Center, which is used by professional athletes from all over the world. The city also has a number of other sports facilities, including the Winter Garden Recreation Complex and the West Orange Trail.
Destinations nearby
Best Winter Garden, FL vacation rentals with a balcony
10 155 reviews
Winter Garden, FL
29/07 – 31/08
$271/nighttotal: $8943 (33 )
Vista Cay 3 Bed 2 Bt Huge Upscale King Wow
3 2
apartment , Williamsburg
This 3-bedroom apartment is located just 1.4 kilometres from the heart of Williamsburg, offering easy access to the area's attractions and vibrant atmosphere. It has received excellent ratings for location, cleanliness, and overall user experience. The apartment spans 195 square metres and comfortably accommodates up to 6 guests. It includes a fully equipped kitchen, a balcony, a swimming pool, a fitness centre, and other amenities to ensure a relaxing and enjoyable stay.
9.7 170 reviews
Winter Garden, FL
29/07 – 31/08
$165/nighttotal: $5445 (33 )
Studio Near Universal Studios With Great View
2 2
studio , Orlando
This Orlando studio apartment, near Universal Studios Florida, is conveniently located 2.4 kilometres from Universal Studios Florida and 2.6 kilometres from ICON Park. The 45-square-metre self-catering apartment sleeps two, boasting a fully equipped kitchen, private balcony, and access to a swimming pool, jacuzzi, fitness centre, and tennis court; free parking and Wi-Fi are also included.
9.7 500 reviews
Winter Garden, FL
29/07 – 31/08
$268/nighttotal: $8844 (33 )
Is1-110 - Orlando 3br Condo Near Disney | Sleeps 8
4 2
apartment , Williamsburg
This family-friendly apartment is located in Williamsburg, within easy reach of the Orange County Convention Center, Shingle Creek Golf Course, Aquatica and The Wheel at ICON Park™. The property has received excellent ratings for location, cleanliness, and overall user experience. This three-bedroom apartment offers ample space for families or groups. Guests can enjoy a range of amenities, including a swimming pool, jacuzzi, fitness centre, and barbecue grills.
Winter Garden, FL
26/06 – 02/07
$453/nighttotal: $2718 (6 )
Landing | Amazing 3bd, Clubhouse, Gym
3 5
apartment , Apopka
This fully-furnished apartment in Apopka, Florida, offers convenient access to natural attractions such as Wekiwa Springs State Park and Kelly Park, and is a short drive from entertainment venues including Camping World Stadium and Kia Center. This 136 square metre residence accommodates up to six guests with three bedrooms and two bathrooms, featuring in-unit laundry, fast WiFi, a resort-style saltwater pool, outdoor lounge area with firepit, and a 24/7 fitness centre.
Best pet friendly Winter Garden, FL vacation rentals
Among the 97 accommodations in Winter Garden, FL, here are the 4 best pet friendly rentals
9.2 78 reviews
Winter Garden, FL
29/07 – 31/08
$211/nighttotal: $6963 (33 )
Beautiful Studio At Westgate Lakes Resort & Spa Near Disney Universal Sea World
1 2
studio , Doctor Phillips
This studio apartment is located in Doctor Phillips, Orlando, offering lakeside views and immediate water access, just minutes from major Orlando theme parks and the Orange County Convention Centre. This 46 square meter villa accommodates up to four guests, featuring a kitchenette with a microwave and fridge, a full bathroom with a separate jetted tub and shower, and access to seven outdoor swimming pools and on-site dining at Westgate Lakes.
Winter Garden, FL
29/07 – 31/08
$211/nighttotal: $6963 (33 )
Dog-friendly Condo With A Kitchenette, Ac, Pools, Hot Tubs, Tennis, & Gym
2 2
house , Orlando
This dog-friendly apartment is located in Orlando, within 2 kilometres of The Wheel At Icon Park, Universal Studios' Islands of Adventure and Universal Studios Orlando. This 54 square metre accommodation offers 2 bedrooms, 2 bathrooms, a kitchenette with a dishwasher and oven, and can sleep up to 7 guests, with on-site amenities including swimming pools, hot tubs, tennis courts and a gym.
9.6 223 reviews
Winter Garden, FL
26/06 – 02/07
$512/nighttotal: $3072 (6 )
4 Bedroom Plus, Lake View Condo, Vista Cay | 1008
4 5
apartment , Williamsburg
This Williamsburg apartment, ideal for families, is excellently located near Shingle Creek, a 15-minute walk from the Shingle Creek Conference Centre and Golf Course, and under 5 kilometres from the Orange County Convention Center and ICON Park™. This spacious 214-square-metre property boasts four bedrooms, two bathrooms, and sleeps eight, offering a swimming pool, jacuzzi, spa, fitness centre, tennis court, and parking, alongside a fully equipped kitchen and free Wi-Fi.
8.1 45 reviews
Winter Garden, FL
26/06 – 02/07
$357/nighttotal: $2142 (6 )
Rustic Hideaway - Modern Estate - Great Location + Pet Friendly!
5 5
house , Windermere
This Windermere estate, located near Winter Garden Village (approximately 13km away), offers easy access to major theme parks (32km), golf courses (16km), and various lakes within a 5-32km radius. This 264 square metre property sleeps up to 11 guests in five bedrooms with smart TVs, boasts a spa, private garden with fire pit and BBQ, plus ample indoor games including ping-pong and shuffleboard; nearby Windermere Recreational Park is just 3 minutes away.
