97 Holiday rentals and Airbnb in Winter Garden, FL
10 13 reviews
Winter Garden, FL
29/07 – 31/08
168 €/nighttotal: 5544 € (33 )
Dtwn Winter Garden Home: 12 Mi To Disney!
3 2
cottage , Winter Garden
This Winter Garden holiday home is situated less than 1km from Winter Garden's town centre, offering easy access to the farmers' market and restaurants, and within 24km of Walt Disney World Resort and 23km of Universal Studios Florida. The 111 square metre property sleeps seven guests across three bedrooms and two bathrooms, boasting a private garden, spa, Wi-Fi, and a well-equipped kitchen with dishwasher, plus off-street parking.
Winter Garden, FL
29/07 – 31/08
86 €/nighttotal: 2838 € (33 )
Luxury 1br • Pool & Gym • Close To Downtown
1 2
apartment , Winter Garden
This Orlando flat is situated 19 kilometres from Camping World Stadium and The Wizarding World of Harry Potter, and 34 kilometres from Orlando International Airport. This 85 square metre apartment accommodates up to 7 guests, featuring 1 bedroom, 1 bathroom, a fully equipped kitchen, air conditioning, a terrace, a swimming pool, a fitness centre, and a children's playground, with free Wi-Fi provided.
9.9 45 reviews
Winter Garden, FL
29/07 – 31/08
181 €/nighttotal: 5973 € (33 )
The Garden Luxe Retreat, Near Disney
1 2
apartment , Winter Garden
This Winter Garden apartment is situated on Plant Street, a short walk from Winter Garden's historic downtown area and 2km from the Plant Street Market, offering easy access to the West Orange Trail. The two-bedroom, two-bathroom flat sleeps four guests and boasts a fully equipped kitchen, a private balcony or patio (where applicable), free on-site parking, and a fitness centre and swimming pool, all within easy reach of Walt Disney World, Universal Orlando Resort and Downtown Orlando.
9.5 107 reviews
Winter Garden, FL
29/07 – 31/08
89 €/nighttotal: 2937 € (33 )
3407 Luxury Option For Your Visit
1 2
studio , Orlando
This one-bedroom apartment is situated in a residential area of Orlando, just 3 kilometres from Universal's Islands of Adventure theme park and 4.2 kilometres from the Orange County Convention Center. The self-catering apartment offers a private garden, a terrace, a fully equipped kitchenette, free Wi-Fi, air conditioning, and free parking.
9.9 56 reviews
Winter Garden, FL
29/07 – 31/08
119 €/nighttotal: 3927 € (33 )
Cozy Cottage In Winter Garden
1 2
apartment , Winter Garden
This newly renovated two-bedroom, two-bathroom house is situated near Winter Garden's downtown area, within easy reach of restaurants, cafes, the Winter Garden Farmers Market, and the West Orange Trail (approximately 6.4km from Disney World and Universal Studios). The 4-guest property boasts a fully equipped kitchen, air conditioning, parking, excellent Wi-Fi, and is a convenient base for exploring Winter Garden and Orlando's theme parks.
Winter Garden, FL
26/06 – 02/07
162 €/nighttotal: 972 € (6 )
Well-located 1br Kitchen Near Theme Parks
1 5
apartment , Orlando
This Orlando flat offers a prime location, situated just over 3 kilometres from Universal Studios Florida and approximately 3.8 kilometres from Universal Epic Universe, with The Wheel at Icon Park Orlando a 17-minute walk away. This 50 square metre accommodation, suitable for up to 10 guests, features a fully equipped kitchen with a dishwasher, air conditioning, a hot tub, and complimentary WiFi, with an elevator providing easy access.
9.8 44 reviews
Winter Garden, FL
29/07 – 31/08
181 €/nighttotal: 5973 € (33 )
Winter Garden Charm, Near Disney
1 2
apartment , Winter Garden
This Winter Garden apartment, situated on Plant Street, offers easy access to downtown Winter Garden's restaurants and boutiques, and is less than 3km from the West Orange Trail. The two-bedroom, two-bathroom flat sleeps four guests and boasts a fully equipped kitchen with stainless steel appliances, a private balcony, and access to a swimming pool, fitness centre, and parking.
9.8 60 reviews
Winter Garden, FL
29/07 – 31/08
138 €/nighttotal: 4554 € (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 17 reviews
Winter Garden, FL
29/07 – 31/08
190 €/nighttotal: 6270 € (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.
9.4 26 reviews
Winter Garden, FL
29/07 – 31/08
160 €/nighttotal: 5280 € (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.
Winter Garden, FL
26/06 – 02/07
121 €/nighttotal: 726 € (6 )
Two Queen Bed Suite W Pool, Hot Tub Near Disney
1 5
apartment , Orlando
This studio apartment is located in Sand Lake, just outside Orlando, making it a convenient base for exploring the city's theme parks, with Disney World, Universal Studios, and SeaWorld all within easy reach. The studio offers a comfortable and relaxing environment for up to 6 guests, with a spacious 50 square metres of living space. The studio comes equipped with a fully fitted kitchen, allowing guests to prepare their own meals, and offers a range of amenities including a swimming pool, hot tub, BBQ area, fitness centre, and a laundromat. Guests can also enjoy the outdoor terrace and garden, and benefit from free parking and high-speed internet access.
9.1 7015 reviews
Winter Garden, FL
26/06 – 02/07
279 €/nighttotal: 1674 € (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.
Best family friendly Winter Garden, FL holiday rentals
Among the 97 accommodations in Winter Garden, FL, here are the 4 best family friendly rentals
9.8 17 reviews
Winter Garden, FL
29/07 – 31/08
114 €/nighttotal: 3762 € (33 )
Modern Luxury Unit In Beautiful Down Town Winter Garden With Wifi, Cable & Pool
1 2
apartment , Winter Garden
This ground-floor flat is located in Winter Garden's town centre, just 320 metres from local restaurants, entertainment, and the West Orange Trail, and under 48 kilometres from Universal Studios Florida, SeaWorld, and Orlando International Premium Outlets. The 85 square metre apartment accommodates up to four guests with a king bed and a queen mattress, offering a full kitchen, fast WiFi, two televisions, air conditioning, a swimming pool, spa, fitness room, and parking.
9.6 223 reviews
Winter Garden, FL
26/06 – 02/07
317 €/nighttotal: 1902 € (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.
9.4 26 reviews
Winter Garden, FL
26/06 – 02/07
158 €/nighttotal: 948 € (6 )
88 M² House ∙ 2 Bedrooms ∙ 5 Guests
2 5
house , Clermont
This three-bedroom A-frame house in Vacation Village, Clermont, Florida, is situated approximately 32 kilometres from Walt Disney World and other major theme parks, offering deeded lakefront access. The 87-square-metre property features a fully equipped kitchen, two bathrooms, a private deck, swimming pool, spa and accommodates up to five guests, with access to community amenities including pickleball and shuffleboard courts.
9.2 914 reviews
Winter Garden, FL
29/07 – 31/08
108 €/nighttotal: 3564 € (33 )
Enclave Apartments At International Drive
2 2
apartment , Orlando
Enclave Apartments at International Drive is conveniently located on International Drive, just 2 kilometres from The Wheel at ICON Park Orlando and 3 kilometres from Universal Studios Orlando, making it easy to explore Orlando's main attractions. This apartment complex has received excellent ratings for its location, cleanliness, and overall user experience. The apartment offers a comfortable space for up to 4 guests, with 2 bedrooms and a total floor area of 60 square metres. Guests will have access to a range of amenities, including a swimming pool, jacuzzi, fitness centre, tennis court, and a restaurant and bar on-site.
Best Winter Garden, FL holiday rentals with parking
10 4 reviews
Winter Garden, FL
26/06 – 02/07
296 €/nighttotal: 1776 € (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.
9.9 19 reviews
Winter Garden, FL
26/06 – 02/07
196 €/nighttotal: 1176 € (6 )
Trailside Montverde
1 5
apartment , Montverde
This Montverde holiday home is situated near Montverde Academy and an 8-minute (approximately 13 km) drive from Bella Collina, offering easy access to Orlando's theme parks (around 64 km away). Sleeping up to six guests, the three-bedroom, one-bathroom property features a kitchen with freezer and microwave, air conditioning, Wi-Fi, parking, a spacious yard, and allows pets.
9.2 186 reviews
Winter Garden, FL
29/07 – 31/08
170 €/nighttotal: 5610 € (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.
8.4 4678 reviews
Winter Garden, FL
26/06 – 02/07
208 €/nighttotal: 1248 € (6 )
Parc Corniche Condominium Suites
2 5
resort , Williamsburg
Parc Corniche Condominium Suites is located near International Drive in Orlando, Florida, a short drive from the Orange County Convention Center and popular theme parks like SeaWorld and Walt Disney World Resort. This resort is highly rated by guests, with excellent location scores and very good ratings for cleanliness and overall experience. The suites offer a comfortable and independent stay with fully equipped kitchens and private balconies or patios. Guests can enjoy a range of amenities including a swimming pool, hot tub, fitness center, restaurant, bar, and concierge services.
Frequently asked questions about holiday rentals in Winter Garden, FL
What are the top family-friendly attractions in Winter Garden, FL?
The Winter Garden Village is a great spot for families, with shops, restaurants, and the Winter Garden Village Park. You can also check out the Winter Garden History Museum, which has activities for kids.
What are the best Airbnb and holiday rentals 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 cooler months, from November to April, when the weather is pleasant. You can also find good deals in the shoulder seasons, like spring and autumn.
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 a must-visit on Saturdays, and the annual Winter Garden Heritage Festival in October celebrates the city's history with live music, food, and crafts.
What are the best holiday rentals with a pool in Winter Garden, FL?
What are the best budget-friendly activities in Winter Garden, FL?
Take a walk or bike ride on the West Orange Trail, a paved path that runs through Winter Garden and beyond. You can also enjoy a picnic at one of the many parks, like the Winter Garden Village Park or the Plant Street Park.
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?
For a taste of local cuisine, try the Winter Garden Cafe, known for its Southern comfort food. The Crooked Can Brewing Company has a great atmosphere and offers a variety of craft beers and pub grub.
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, stretching over 22 km. You can also explore the scenic trails at the Winter Garden Village Park.
Are there pet-friendly attractions in Winter Garden, FL?
The West Orange Trail is pet-friendly, and many restaurants in Plant Street have outdoor seating where dogs are welcome. The Winter Garden Village Park also has a designated dog park.
What are the benefits of choosing a vacation rental in Winter Garden, FL?
Vacation rentals offer more space and privacy compared to hotels, and often come with amenities like a kitchen and laundry facilities. They can also be a more budget-friendly option, especially for larger groups.
What are the top sports attractions and facilities in Winter Garden, FL?
Winter Garden is home to the National Training Center, a world-class sports facility that hosts a variety of events and training camps. You can also find several public parks with sports fields and courts, like the Winter Garden Village Park.
Destinations nearby
Best Winter Garden, FL holiday rentals with a balcony
Winter Garden, FL
26/06 – 02/07
275 €/nighttotal: 1650 € (6 )
New Listing! Vacation Village Resort, 14mi To Disney & 26mi To Universal - Grh570568
2 5
resort , Clermont
New Listing! Vacation Village Resort, GRH570568, is a family-friendly villa in Clermont, Florida, located within 1.6km of Lake Louisa State Park and less than 3.2km from several golf courses including Legends Golf & Country Club and Kings Ridge Golf Club. This 465 square metre smoke-free property boasts two bedrooms, two bathrooms, sleeps five guests, and includes a private fenced yard, a fully equipped kitchen, a swimming pool, tennis court, and on-site water park access.
9.4 4873 reviews
Winter Garden, FL
26/06 – 02/07
343 €/nighttotal: 2058 € (6 )
3br 4 Bath Large Condo 5min Conv Center 1732ft
3 5
house , Williamsburg
This 3-bedroom condo is located in Orlando, Florida, just 2 miles from SeaWorld Orlando and 2.1 miles from the Orange County Convention Center, offering easy access to a variety of attractions and activities. The property has consistently received excellent ratings for its location, cleanliness, and overall user experience. The condo provides ample space for families or groups of friends, with a fully equipped kitchen, a washing machine, and free Wi-Fi. It also features a private balcony, a fitness room, concierge service, a swimming pool, a jacuzzi, a tennis court, and a restaurant and bar on site, ensuring a comfortable and enjoyable stay.
9.4 144 reviews
Winter Garden, FL
29/07 – 31/08
165 €/nighttotal: 5445 € (33 )
Ground-floor Vista Cay Condo Near Clubhouse Pool
3 2
apartment , Williamsburg
This ground-floor apartment is situated in Williamsburg, just 1.6km from the Orange County Convention Center and within 4km of popular attractions like SeaWorld Orlando and the Wheel at ICON Park Orlando. The apartment has received excellent ratings for location, cleanliness and user experience. The apartment has three bedrooms and covers 131 square metres. Guests can enjoy a range of amenities including a swimming pool, jacuzzi, terrace, garden, bar, fitness centre, tennis court, and parking.
9.4 136 reviews
Winter Garden, FL
29/07 – 31/08
162 €/nighttotal: 5346 € (33 )
Newly Renovated Lakeview Vista Cay Condo
3 2
apartment , Williamsburg
This apartment is situated in Orlando, just 2.9 kilometres from the Orange County Convention Center, offering easy access to major attractions like the Wheel at ICON Park Orlando and SeaWorld Orlando. The property has received excellent ratings for location, cleanliness, and user experience. The apartment is spacious, measuring 191 square metres, and is suitable for families and groups. Guests can enjoy a range of amenities including a swimming pool, jacuzzi, terrace, garden, bar, fitness centre, tennis court, and parking.
Best pet friendly Winter Garden, FL holiday rentals
Among the 97 accommodations in Winter Garden, FL, here are the 4 best pet friendly rentals
9.4 239 reviews
Winter Garden, FL
29/07 – 31/08
161 €/nighttotal: 5313 € (33 )
Luxury Pet Friendly Condo, Near Clubhouse & Pool
3 2
apartment , Williamsburg
This eco-friendly condo is located in Orlando, just 1.2 miles from the Orange County Convention Center, making it a convenient choice for those attending events or exploring the area. The apartment has received excellent ratings for location, cleanliness, and user experience, ensuring a comfortable and enjoyable stay. The property offers three bedrooms and two bathrooms, providing ample space for families or groups of friends, with a total floor area of 131 square metres. Guests can enjoy a range of amenities including a swimming pool, Jacuzzi, terrace, garden, restaurant, bar, fitness centre, tennis court, and parking, offering a variety of activities and comforts for a relaxing and enjoyable stay.
8.0 1 review
Winter Garden, FL
26/06 – 02/07
162 €/nighttotal: 972 € (6 )
Lilac Loft- Lake, Pool, Pickle Ball, Disney, Fun!
2 5
house , Clermont
This holiday home in Castle Hill, Clermont, is approximately 27-32 kilometres from major Disney attractions including Magic Kingdom, Walt Disney World, and the Wizarding World of Harry Potter. This 79-square-metre property offers 2 bedrooms, 2 bathrooms, a private swimming pool, a garden, tennis court, and parking, with complimentary WiFi and air conditioning.
9.8 7 reviews
Winter Garden, FL
26/06 – 02/07
194 €/nighttotal: 1164 € (6 )
Pumba's Place - Fun, Lake, Pool- No Cleaning Fees!
2 5
apartment , Clermont
This lakeside Clermont property, situated within 1.6km of Legends Golf & Country Club and Kings Ridge Driving Range, and 3.2km of Kings Ridge Golf Club and Lake Louisa State Park, offers serene views and easy access to local attractions. This 88 square metre house boasts two bedrooms, two bathrooms, sleeps six guests, and includes a fully equipped kitchen, swimming pool, spa, and free Wi-Fi; on-site BBQ facilities and a nearby water park add to the appeal.
8.1 45 reviews
Winter Garden, FL
26/06 – 02/07
221 €/nighttotal: 1326 € (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.