Compare Vacation Rentals & Airbnb in Winter Garden, FL
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97 Rentals and Airbnb in Winter Garden, FL
9.8 44 reviews
Winter Garden, FL
29/07 – 31/08
$292/nighttotal: $9636 (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.
9.7 37 reviews
Winter Garden, FL
29/07 – 31/08
$187/nighttotal: $6171 (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.
8.8 3 reviews
Winter Garden, FL
29/07 – 31/08
$326/nighttotal: $10758 (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.
9.2 10 reviews
Winter Garden, FL
29/07 – 31/08
$143/nighttotal: $4719 (33 )
All-you-need Studio Apartment Near Downtown
1 2
apartment , Winter Garden
This flat is located in Historic Downtown Winter Garden, within 100 metres of local businesses, the popular farmers market, and the Winter Garden bike trail, with easy access to major motorways. This accommodation sleeps two guests and offers a Queen bed, a compact kitchenette, a modern bathroom, complimentary WiFi, and free off-street parking for one vehicle.
9.5 31 reviews
Winter Garden, FL
29/07 – 31/08
$220/nighttotal: $7260 (33 )
Winter Garden 2 Bedrooms/2 Bath Home (Downtown)
1 2
apartment , Winter Garden
This fully renovated two-bedroom, two-bathroom house in Winter Garden's downtown area is a 48km drive from Walt Disney World Resort and Orlando International Airport, and within walking distance of Lake Jennie Jewel. The 4-person property boasts a fully equipped kitchen, air conditioning, parking, and internet access, offering easy access to shops, restaurants and Winter Garden's historic district.
9.6 37 reviews
Winter Garden, FL
29/07 – 31/08
$350/nighttotal: $11550 (33 )
Fire Pit & Yard: Updated Winter Garden Home!
2 2
apartment , Winter Garden
This Winter Garden holiday home is conveniently located near Winter Garden's town centre, offering easy access to Walt Disney World (around 30km away) and Lake Apopka. The spacious 155 sq m property boasts two bedrooms, two bathrooms, a fully equipped kitchen with a fridge, microwave, and dishwasher, and an outdoor area with a gas grill; it comfortably sleeps four guests.
9.6 7 reviews
Winter Garden, FL
29/07 – 31/08
$125/nighttotal: $4125 (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 the downtown area, approximately 32km from Walt Disney World Resort and 24km from Universal Orlando Resort. The self-contained apartment sleeps three guests, features free Wi-Fi, air conditioning, off-street parking, and is within easy reach of the Orlando International Premium Outlets and Millenia Mall.
9.9 25 reviews
Winter Garden, FL
29/07 – 31/08
$169/nighttotal: $5577 (33 )
Winter Garden Butterfly Retreat
1 2
apartment , Winter Garden
This Winter Garden flat is located just 160 metres from the West Orange Trail and a short walk to the historic downtown area, offering independent access and parking for two cars. This private two-room suite accommodates two guests and features a bedroom, a full bathroom, a living area with a kitchenette and pullout sofa, air conditioning, and is cleaned with fragrance-free products.
9.9 56 reviews
Winter Garden, FL
29/07 – 31/08
$192/nighttotal: $6336 (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
29/07 – 31/08
$247/nighttotal: $8151 (33 )
Stylish 2br • Pool & Gym • Minutes To Disney
2 2
apartment , Winter Garden
This two-bedroom flat is situated in Orlando, approximately 19-21 kilometres from prominent attractions such as Camping World Stadium, Universal Studios' Islands of Adventure, and The Wizarding World of Harry Potter. This 104 square metre apartment accommodates up to eight guests and features a fully equipped kitchen with a dishwasher, air conditioning, free WiFi, a garden with a children's playground and outdoor fireplace, a year-round outdoor pool, a gym, and direct access to a terrace and balcony.
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.
10 6 reviews
Winter Garden, FL
29/07 – 31/08
$259/nighttotal: $8547 (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.
Best family friendly Winter Garden, FL vacation rentals
Among the 97 accommodations in Winter Garden, FL, here are the 4 best family friendly rentals
9.3 134 reviews
Winter Garden, FL
29/07 – 31/08
$237/nighttotal: $7821 (33 )
Gorgeous Top-floor Condo W Private Balcony
2 2
apartment , Williamsburg
This apartment is located in Orlando, Florida, just 2 kilometres from the Orange County Convention Center, making it a convenient base for exploring the city's attractions. It has received excellent ratings for user experience, location and cleanliness, ensuring a comfortable and enjoyable stay. The apartment is spacious at 103 square meters and offers a range of amenities including a fully equipped kitchen, a private balcony, a swimming pool, a jacuzzi, a fitness centre, a tennis court and a children's playground.
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.
9.4 4872 reviews
Winter Garden, FL
29/07 – 31/08
$234/nighttotal: $7722 (33 )
4br 2bath Condo Balcony 5min Conv Center 2020ft
2 2
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.
9.2 186 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.
Best Winter Garden, FL vacation rentals with parking
9.8 17 reviews
Winter Garden, FL
29/07 – 31/08
$184/nighttotal: $6072 (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.
10 4 reviews
Winter Garden, FL
29/07 – 31/08
$326/nighttotal: $10758 (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.
This restored 1921 bungalow, offering self-catering accommodation, is located in Winter Garden's Historic District, just 160 metres from Plant Street's shops and restaurants, and within walking distance of the Farmer's Market and Splash Pad. This 125 square metre property sleeps six guests across two bedrooms and a sofa bed, featuring a well-equipped kitchen with a dishwasher and microwave, air conditioning, off-street parking for vehicles, RVs or boats, and a spacious backyard with a firepit, with dogs welcome for a small fee.
9.0 7 reviews
Winter Garden, FL
29/07 – 31/08
$238/nighttotal: $7854 (33 )
House 2 Bedrooms /2 Full Bathrooms Downtown Winter Garden
2 2
apartment , Winter Garden
This fully renovated two-bedroom house is situated in downtown Winter Garden, Florida, a short walk from the town centre and approximately 40km from Walt Disney World Resort and Orlando International Airport. The self-catering property sleeps four guests, offering two queen-sized beds, two bathrooms, a fully equipped kitchen including a fridge, microwave, and dishwasher, in-house laundry facilities, and parking; nearby attractions include the West Orange Trail for outdoor activities and the Orlando International Premium Outlets and Mall at Millenia are within driving distance.
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
9.3 389 reviews
Winter Garden, FL
29/07 – 31/08
$143/nighttotal: $4719 (33 )
Superb Renovated Suite, Amazing Water View Best Location To Disney And Universal
1 2
apartment , Orlando
This waterfront flat is ideally situated in Orlando, within a short walk of Pirate's Dinner Adventure and CoCo Key Water Resort, and just a mile from Universal Orlando Resort and The Wheel at ICON Park™. It has consistently received excellent ratings for location, cleanliness, and user experience. This self-catering property can accommodate up to four guests and comes with a fully equipped kitchen, a balcony, and a washing machine. Enjoy the on-site swimming pool, Jacuzzi, and fitness centre, as well as the nearby attractions and family-friendly atmosphere.
9.8 192 reviews
Winter Garden, FL
29/07 – 31/08
$165/nighttotal: $5445 (33 )
Modern Studio On I-drive: Parking + Pool Included
1 2
studio , Orlando
This modern apartment is located in the Universal Orlando Resort Area district of Orlando, just 2 kilometres from the Wheel at ICON Park Orlando and 3 kilometres from Universal Studios Orlando. The property has excellent user, location, and cleanliness ratings, making it a popular choice for travellers. This self-catering apartment is 45 square metres and can accommodate up to four guests. Amenities include a private pool, hot tub, balcony, fully equipped kitchen, free Wi-Fi, and free parking.
9.8 262 reviews
Winter Garden, FL
29/07 – 31/08
$165/nighttotal: $5445 (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.
9.4 136 reviews
Winter Garden, FL
29/07 – 31/08
$261/nighttotal: $8613 (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 vacation rentals
Among the 97 accommodations in Winter Garden, FL, here are the 4 best pet friendly rentals
8.0 1 review
Winter Garden, FL
29/07 – 31/08
$190/nighttotal: $6270 (33 )
Dog-friendly Condo With A Kitchenette, Ac, Pools, Hot Tubs, Tennis, & Gym
2 2
apartment , Orlando
This sixth-floor flat in Orlando's International Drive District offers convenient access, being a short drive from Walt Disney World Resort, Universal Orlando Resort, and SeaWorld Orlando, with Orlando International Premium Outlets and Florida Mall also nearby. This 54 square metre apartment accommodates up to four guests with two bedrooms and two bathrooms, featuring a furnished balcony with pool and lake views, a kitchenette, air conditioning, and access to on-site amenities including heated swimming pools, hot tubs, a fitness room, and tennis courts.
9.5 370 reviews
Winter Garden, FL
29/07 – 31/08
$322/nighttotal: $10626 (33 )
Executive 3 Bedroom Villa At Universal,convention Center, Vista Cay
3 2
apartment , Williamsburg
This three-bedroom apartment is conveniently located in Williamsburg, just a short distance from the city's main attractions. It has consistently received excellent ratings for its location, user experience, and cleanliness. The apartment offers 186 square metres of space, comfortably accommodating up to eight guests. Amenities include a swimming pool, jacuzzi, terrace, garden, fitness centre, tennis court, and parking, as well as a fully equipped kitchen, a restaurant, and a bar.
9.6 10 reviews
Winter Garden, FL
29/07 – 31/08
$166/nighttotal: $5478 (33 )
Clermont 2 Bedroom Bungalow
2 2
apartment , Clermont
This Clermont vacation home, part of the Vacation Village, lies within 1.6km of Legends Golf & Country Club and Kings Ridge Driving Range, and within 3.2km of Kings Ridge Golf Club and Lake Louisa State Park. This two-bedroom, one-bathroom property sleeps four, offering a fully equipped kitchen with dishwasher, in-house laundry, a Smart TV, and proximity to Clermont's amenities.
9.4 239 reviews
Winter Garden, FL
29/07 – 31/08
$260/nighttotal: $8580 (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.