97 Holiday rentals and Airbnb in Winter Garden, FL
Winter Garden, FL
26/06 – 02/07
139 €/nighttotal: 834 € (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.
Winter Garden, FL
03/07 – 04/07
168 €/nightfor 1 night
Hilton Vacation Club Cypress Pointe Orlando
1 2
resort , Lake Buena Vista
Cypress Pointe Resort By Diamond Resorts is located in the Disney Downtown Lake Buena Vista area, just a short distance from the Walt Disney World Resort and Disney Springs. This puts you right in the heart of the action, with easy access to all the attractions and entertainment Orlando has to offer. The resort has a range of comfortable rooms and suites, all equipped with modern amenities. You'll also find a variety of facilities on site, including a pool, hot tub, fitness centre, playground, mini golf course, restaurant, bar, and convenience store.
9.7 112 reviews
Winter Garden, FL
26/06 – 02/07
275 €/nighttotal: 1650 € (6 )
Orlando 1 Acre 4 Bd Home Central Near Universal
4 5
apartment , Orlovista
This house in Orlovista is located just 2.7 kilometres from the Central Florida Fairgrounds and 3.5 kilometres from the University of Central Florida Valencia West campus, making it ideal for exploring the local area. It has received excellent ratings for user experience, location, and cleanliness. The property has four bedrooms and two bathrooms, spanning 219 square metres, comfortably accommodating up to 13 guests. Amenities include a private garden, a swimming pool, a spa, and a fully equipped kitchen, offering the perfect blend of relaxation and entertainment for a memorable stay.
10 51 reviews
Winter Garden, FL
29/07 – 31/08
199 €/nighttotal: 6567 € (33 )
Emerald Grove - Close To Disney
1 2
apartment , Winter Garden
This Winter Garden apartment, situated on Plant Street, offers easy access to Winter Garden's downtown area and is approximately 32km from Walt Disney World. The two-bedroom, two-bathroom flat sleeps four guests and features a fully equipped kitchen with stainless steel appliances, a swimming pool, fitness centre, and free on-site parking; nearby attractions include the Plant Street Market and West Orange Trail.
Winter Garden, FL
03/07 – 04/07
140 €/nightfor 1 night
Beautiful 1-bedroom Apartment With Ac In Pleasant Gotha
1 2
apartment , Ocoee
This Gotha flat offers proximity to natural sites such as Tinker Field and Wekiwa Springs State Park, with Universal Orlando Resort and Universal Studios Florida approximately 15 kilometres away. This one-bedroom flat accommodates up to three guests, featuring air conditioning, Wi-Fi, parking, and a garden, ideal for exploring local attractions.
8.5 1441 reviews
Winter Garden, FL
31/08 – 01/09
92 €/nightfor 1 night
Westgate Leisure Resort
1 2
resort , Williamsburg
The Westgate Leisure Resort is located near Orlando International Airport, just a short distance from attractions like Orlando Vineland Premium Outlets, Aquatica, and the Orange County Convention Center. The resort has received very good ratings for its location, cleanliness, and overall experience. This family-friendly resort offers a range of amenities and activities, including two outdoor swimming pools, a fitness centre, a spa tub, and a restaurant. Guests can also enjoy free Wi-Fi in public areas, free self-parking, and a business centre.
8.5 25270 reviews
Winter Garden, FL
31/08 – 01/09
122 €/nightfor 1 night
Floridays Orlando Two & Three Bed Rooms Condo Resort
1 2
resort , Williamsburg
The Floridays Orlando Two & Three Bed Rooms Condo Resort is situated just 10 minutes from Walt Disney World theme parks and 5 minutes from the Orlando Premium Outlets Mall, offering easy access to major attractions and shopping. The resort has received very good user ratings, with an excellent location rating and very good cleanliness rating. The resort offers spacious two and three-bedroom apartments, providing ample space for families or groups. Each apartment comes with a full kitchen, washer and dryer, and a spa bath in the master bedroom, and the resort features a well-equipped gym, a children's activity room, two outdoor pools, and a poolside bar and grill.
10 4 reviews
Winter Garden, FL
29/07 – 31/08
202 €/nighttotal: 6666 € (33 )
The Garden Luxe Retreat
1 2
apartment , Winter Garden
The Garden Luxe Retreat apartment is situated in Winter Garden, Florida, offering convenient access to attractions such as Universal Studios Florida and the Orlando International Premium Outlets. This two-bedroom, two-bathroom self-catering property sleeps four guests and boasts on-site water park access, alongside proximity to the Florida Citrus Bowl Stadium and opportunities for exploring nearby nature reserves.
8.6 3786 reviews
Winter Garden, FL
03/07 – 04/07
160 €/nightfor 1 night
Renaissance Orlando At Seaworld®
1 2
resort , Williamsburg
The Renaissance Orlando at SeaWorld® is located near SeaWorld® aquarium park in Orlando, Florida, just 5.7 miles from Universal Orlando and 1.9 miles from the Orange County Convention Center. The hotel has consistently received very good ratings for its cleanliness and overall experience, with an excellent location rating. The hotel offers a range of amenities to suit all guests, including a swimming pool, Jacuzzi, spa, fitness centre, and restaurant. Guests can also enjoy on-site entertainment, including a sports bar and a coffee shop, as well as free shuttle service to both SeaWorld® and Aquatica Water Park.
10 2 reviews
Winter Garden, FL
29/07 – 31/08
169 €/nighttotal: 5577 € (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.
9.6 223 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.
9.7 38 reviews
Winter Garden, FL
29/07 – 31/08
116 €/nighttotal: 3828 € (33 )
The Swift House
1 2
apartment , Winter Garden
This Plant Street cottage in Winter Garden, Florida, is conveniently located a short walk from Lake Apopka and Plant Street's shops and restaurants, and a 32km drive from Walt Disney World. This one-bedroom, one-bathroom self-catering property sleeps three guests and boasts a fully equipped kitchen, private parking, a large fenced garden, smart TV, Alexa, and Swiftie-themed décor.
Best family friendly Winter Garden, FL holiday rentals
Among the 97 accommodations in Winter Garden, FL, here are the 4 best family friendly rentals
Winter Garden, FL
03/07 – 04/07
204 €/nightfor 1 night
Js Luxury Vacation
1 2
apartment , Orlando
This Orlando flat offers scenic river and potential lake views, located 1.9 kilometres from The Wheel At Icon Park and 2.4 kilometres from Universal Studios' Islands of Adventure, with Orlando International Airport 14.9 kilometres away. This two-bedroom apartment includes air conditioning, complimentary WiFi, a fully equipped kitchen with a dishwasher, oven, and microwave, as well as a balcony, patio, garden, bar, and hot tub, with complimentary private parking provided.
9.2 10 reviews
Winter Garden, FL
26/06 – 02/07
288 €/nighttotal: 1728 € (6 )
Beautiful Spacious 4 Bdrm Home
4 5
apartment , Windermere
This Windermere house, situated in a peaceful neighbourhood a short 8km drive from Windermere town centre and conveniently close to Orlando's theme parks, offers a perfect base for exploring the Lake District. Sleeping up to 10 guests across four uniquely themed bedrooms and three-and-a-half bathrooms, this property boasts a modern kitchen with granite worktops, a garden, parking, air conditioning, and Wi-Fi; enjoy the nearby Friday farmers' market in Windermere.
9.4 165 reviews
Winter Garden, FL
29/07 – 31/08
172 €/nighttotal: 5676 € (33 )
Palm Villa
3 2
house , Williamsburg
Palm Villa is a comfortable house located in Orlando, Florida, just a short distance from popular attractions like The Wheel at ICON Park Orlando and SeaWorld Orlando. The property has received excellent ratings for its location, cleanliness, and overall experience. The house offers a well-equipped kitchen with modern appliances and a bathroom, providing a comfortable and spacious stay. Guests can enjoy a range of amenities, including a swimming pool, jacuzzi, tennis court, and a restaurant and bar on site.
8.8 3 reviews
Winter Garden, FL
29/07 – 31/08
202 €/nighttotal: 6666 € (33 )
Winter Garden Charm, Near Disney
1 2
apartment , Winter Garden
This Winter Garden apartment, situated on Plant Street, offers easy access to Winter Garden's historic downtown area, with its restaurants and boutiques, and is within a 32km radius of Walt Disney World. The 1100 square metre (approx. 11840 sq ft) property features a modern two-bedroom, two-bathroom layout, accommodating up to four guests and includes a swimming pool, terrace, parking, and a fully equipped kitchen with a fridge, microwave, and dishwasher.
Best Winter Garden, FL holiday rentals with parking
9.2 187 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.
10 6 reviews
Winter Garden, FL
29/07 – 31/08
160 €/nighttotal: 5280 € (33 )
Cozy 2 Bedroom Apartment In Winter Garden With Fast Wifi, Pool & Fitness Room
2 2
apartment , Winter Garden
This 109 square metre flat in Winter Garden is situated 27 kilometres from the Kia Centre and 37 kilometres from Magic Kingdom Park, offering convenient access to local attractions. This residence accommodates up to six guests and features two bedrooms, two bathrooms, a fully equipped kitchen with a microwave and dishwasher, air conditioning, and on-site parking.
9.8 262 reviews
Winter Garden, FL
29/07 – 31/08
102 €/nighttotal: 3366 € (33 )
Deluxe Studio W/ Lakeview - Free Parking/pool
1 2
studio , Orlando
This studio apartment is located in Orlando, just under 2 kilometres from the Wheel at ICON Park Orlando and Universal Studios' Islands of Adventure, making it an ideal base for exploring the city's attractions. The property has received excellent ratings for location, cleanliness, and overall experience. The studio is a comfortable and well-equipped space, with a floor area of 45 square metres, and offers a range of amenities, including a fully equipped kitchen, air conditioning, a swimming pool, a jacuzzi, a terrace, a garden, a fitness centre, a tennis court, and free parking.
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.
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
8.9 174 reviews
Winter Garden, FL
03/07 – 04/07
638 €/nightfor 1 night
Magnificent 2 Bedroom Apartment Vista Cay Resort 107
1 2
house , Williamsburg
This apartment is conveniently located in Orlando, Florida, just a short distance from the Orange County Convention Center and SeaWorld Orlando, making it an ideal base for exploring the area. It has been highly rated for its cleanliness, location, and overall quality. The apartment has two bedrooms and two bathrooms, making it suitable for families or groups of friends. It comes equipped with a range of amenities, including a swimming pool, jacuzzi, terrace, garden, fitness centre, and parking.
Winter Garden, FL
26/06 – 02/07
277 €/nighttotal: 1662 € (6 )
Last Minute Disney Getaway! Luxury Villa With Private Patio. Book Now! #115911
5 5
house , Windermere
This Windermere holiday home is situated in southwest Orange County, Florida, 4km from Lake Butler, 0.16km from the Windermere Farmers' Market, and within 4.6km of several golf courses including the Isleworth Golf & Country Club. The five-bedroom, four-bathroom property sleeps up to 11 guests, offering a fully equipped kitchen, alfresco dining, indoor games (shuffleboard, foosball), a fireplace, covered patio, private patio with table tennis, and a balcony terrace; plus a mid-stay clean for bookings over 28 days and pet-friendly accommodation (fees apply, pets must be approved).
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.
8.9 54 reviews
Winter Garden, FL
03/07 – 04/07
598 €/nightfor 1 night
Cozy Condo Wprivate Balcony & Free Resort Access
2 2
apartment , Williamsburg
This two-bedroom apartment is located just 2.2 miles from the Orange County Convention Center and 2.3 miles from SeaWorld Orlando, offering easy access to the vibrant attractions of this popular tourist destination. The apartment has received very good user ratings and excellent location ratings, making it a popular choice for travellers. The apartment is equipped with a fully equipped kitchen, perfect for preparing meals, and offers a private balcony to enjoy the fresh air. Guests can take advantage of the resort amenities, including a swimming pool, jacuzzi, fitness centre, tennis court, and a restaurant and bar on site.
Best pet friendly Winter Garden, FL holiday rentals
Among the 97 accommodations in Winter Garden, FL, here are the 4 best pet friendly rentals
8.8 5 reviews
Winter Garden, FL
31/08 – 01/09
82 €/nightfor 1 night
Relax In Comfort W/ King Bed Near Universal Studios - Free Breakfast Included
1 2
studio , Orlando
This studio apartment is located in Orlando's International Drive district, offering a lakeside setting and proximity to Universal Orlando Resort (1.2 km) and Universal's Islands of Adventure (1.2 km), as well as Orlando International Premium Outlets (1.5 km). This accommodation for two guests features air conditioning, complimentary WiFi, a refrigerator, a microwave, and on-site access to a water park, with a complimentary breakfast served daily.
9.0 6388 reviews
Winter Garden, FL
03/07 – 04/07
175 €/nightfor 1 night
Hyatt Regency Grand Cypress Resort - Free Shuttle To Theme Parks!
1 2
resort , Lake Buena Vista
The Hyatt Regency Grand Cypress Resort is conveniently located just a short drive from Walt Disney World and other popular attractions, making it an ideal base for exploring Orlando. It has received excellent ratings for location, cleanliness and overall guest experience. The resort offers a range of accommodation options, including spacious rooms with balconies and select rooms with access to a private club lounge. Guests can enjoy a variety of amenities, such as a Jack Nicklaus golf course, a luxurious spa, a private lake and lagoon pool, and multiple dining options.
10 1 review
Winter Garden, FL
26/06 – 02/07
262 €/nighttotal: 1572 € (6 )
Metrowest Stay 2br Near Universal And Disney
2 5
apartment , Orlando
This Orlando flat is situated approximately 5.9 kilometres from the Holy Land Experience and within 7 kilometres of Universal Studios Orlando, The Wizarding World of Harry Potter, and Universal's Islands of Adventure. This 94 square metre apartment offers two bedrooms, two bathrooms, a fully equipped kitchen with a fridge and coffee machine, complimentary private parking, free Wi-Fi, a private terrace, a swimming pool, and a children's playground, accommodating up to nine guests.
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.
