Compare Vacation Rentals & Airbnb in Winter Garden, FL

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Winter Garden, FL vacation rentals
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97 Rentals and Airbnb in Winter Garden, FL

Best family friendly Winter Garden, FL vacation rentals

Among the 97 accommodations in Winter Garden, FL, here are the 4 best family friendly rentals

Gorgeous Top-floor Condo W Private Balcony - Winter Garden, FL
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.
Studio Near Universal Studios With Great View - Winter Garden, FL
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.
4br 2bath Condo Balcony 5min Conv Center 2020ft - Winter Garden, FL
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.
4012 Vista Cay - Winter Garden, FL
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

Modern Luxury Unit In Beautiful Down Town Winter Garden With Wifi, Cable & Pool - Winter Garden, FL
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.
The Garden Luxe Retreat - Winter Garden, FL
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.
1921 2bd/1bth Bungalow - Historic Winter Garden, Steps To Plant St, Dogs Welcome - Winter Garden, FL
10 4 reviews
Winter Garden, FL
29/07 – 31/08
$314/nighttotal: $10362 (33 )

1921 2bd/1bth Bungalow - Historic Winter Garden, Steps To Plant St, Dogs Welcome

2 2
apartment , Winter Garden
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.
House 2 Bedrooms /2 Full Bathrooms Downtown Winter Garden - Winter Garden, FL
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?

    The Secret Garden Apartment, Paradise Nook Near Orlando's Theme Parks and Lakeview Garden Studio are the most popular Airbnb and vacation rentals in Winter Garden, FL among travelers.

  • 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?

    Among the Airbnbs in Winter Garden, FL, The Secret Garden Apartment, Paradise Nook Near Orlando's Theme Parks and Lakeview Garden Studio are the most popular ones.

  • 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

Superb Renovated Suite, Amazing Water View Best Location To Disney And Universal - Winter Garden, FL
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.
Modern Studio On I-drive: Parking + Pool Included - Winter Garden, FL
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.
Deluxe Studio W/ Lakeview - Free Parking/pool - Winter Garden, FL
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.
Newly Renovated Lakeview Vista Cay Condo - Winter Garden, FL
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

Dog-friendly Condo With A Kitchenette, Ac, Pools, Hot Tubs, Tennis, & Gym - Winter Garden, FL
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.
Executive 3 Bedroom Villa At Universal,convention Center, Vista Cay - Winter Garden, FL
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.
Clermont 2 Bedroom Bungalow - Winter Garden, FL
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.
Luxury Pet Friendly Condo, Near Clubhouse & Pool - Winter Garden, FL
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.
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