Choose from 98 vacation rentals located in Winter Garden, Florida. Top filters in Winter Garden include Kitchen / Kitchenette, Air conditioner, and TV. Prices range from $93 to $694 per night. Our most popular vacation rental types near Winter Garden are Hotel and RV.

Top vacation rentals in Winter Garden

Property view
4.8
Outstanding(240 Reviews)
Bed and Breakfast
 in Orlando
The Edgewater Hotel
Garden · Kitchen / Kitchenette · Air conditioner

Discover the beauty of Winter Garden with a stay at The Edgewater Hotel, a top rated Bed and Breakfast with amenities such as Air conditioner, Internet / Wifi and Balcony / Patio, and more.

$$$$
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Winter Garden Vacation Rental | 2BR | 1BA | 3 Steps Required for Entry
4.9
Outstanding(39 Reviews)
Cottage
 in Winter Garden
Downtown Winter Garden Cottage ~ 12 Mi to Disney!
4 guests · 2 bedrooms · 1 bath
Garden · Kitchen / Kitchenette · Air conditioner

This attractive Cottage in Winter Garden, $259 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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Winter Garden Vacation Rental | 1BR | 1BA | 630 Sq Ft | Step-Free Access
5.0
Outstanding(42 Reviews)
House
 in Winter Garden
Winter Garden Bungalow w/ Gas Grill, Walk to Dtwn!
4 guests · 1 bedroom · 1 bath
Garden · Kitchen / Kitchenette · Air conditioner

Experience vacation in Winter Garden with our House, Winter Garden Bungalow w/ Gas Grill, Walk to Dtwn!. Enjoy amenities such as Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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Winter Garden Vacation Rental | 2BR | 1BA | 1,000 Sq Ft | 3 Steps to Access
5.0
Outstanding(34 Reviews)
House
 in Winter Garden
Spacious Winter Garden Home w/ BBQ, Walk to Dwtn!
4 guests · 2 bedrooms · 1 bath
Garden · Kitchen / Kitchenette · Air conditioner

Experience the best of Winter Garden with this House available for $190. This property is equipped with amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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Search by amenity

Vacation rentals with a kitchen in Winter Garden

Property view
4.8
Outstanding(4 Reviews)
House
 in Orlando
Downtown Winter Garden Cottage about 12 Mi to Disney!
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

Looking to create some memories in Winter Garden? Look no further than our House, Downtown Winter Garden Cottage about 12 Mi to Disney!. Enjoy top-rated amenities including Air conditioner, Internet / Wifi and Laundry, and more.

$$$$
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Room
4.6
Outstanding(10 Reviews)
Condo
 in Oakland
The Oak View Place..
2 guests · 1 bedroom · 1 bath
Garden · Pool · Pets allowed

Looking to create some memories in Winter Garden? Look no further than our Condo, The Oak View Place.. . Enjoy top-rated amenities including Air conditioner, Internet / Wifi and Pets allowed, and more.

$$$$
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Room
5.0
Outstanding(8 Reviews)
House
 in Winter Garden
Mid Century Hipster
6 guests · 3 bedrooms · 2 baths
Garden · Pets allowed · Kitchen / Kitchenette

Looking to create some memories in Winter Garden? Look no further than our House, Mid Century Hipster . Enjoy top-rated amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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Property view
4.8
Outstanding(15 Reviews)
House
 in Winter Garden
WATERFRONTWinterGdnHSE+VIEWS+Dock+Wildlife+Firepit
8 guests · 4 bedrooms · 3 baths
Garden · Pets allowed · Kitchen / Kitchenette

Experience the best of Winter Garden with this House available for $725. This property is equipped with amenities including Air conditioner, Dishwasher and Fireplace, and more.

$$$$
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city photo
Winter Garden

Winter Garden travel guide

Let us help you plan your perfect Winter Garden vacation. Our travel guide highlights things to do, places to see, favorite vacation rental amenities in Winter Garden, and more.

Frequently asked questions

What is the price range for rentals in Winter Garden?

Vacation rentals in Winter Garden have a price range between $93-$694. The average price for rentals in Winter Garden is $175 per night.

What are the top things to do in Winter Garden, FL?

Winter Garden, FL is a great place to visit for outdoor activities and cultural attractions. Here are the top things to do:

  • Visit the Winter Garden Heritage Museum
  • Go kayaking or canoeing on Lake Apopka
  • Explore the local farmers market
  • Take a stroll along the West Orange Trail

Whether you want to explore the outdoors or learn about the city's history, Winter Garden has something for everyone!

What are the most popular vacation rental amenities in Winter Garden, FL?

The most popular vacation rental amenities in Winter Garden, FL are:

  • Outdoor pool
  • Fitness center
  • Free WiFi
  • Air conditioning
  • Kitchen

These amenities offer guests the opportunity to relax and enjoy their stay in Winter Garden. The outdoor pool is a great way to cool off in the Florida heat, and the fitness center allows guests to stay active during their vacation. Free WiFi and air conditioning are essential for comfort and convenience. Finally, the kitchen allows guests to prepare their own meals and save money.

Where is Winter Garden, FL?

Winter Garden, FL is located in Orange County in the central part of the state. It is approximately 20 miles west of downtown Orlando and is a part of the Orlando-Kissimmee-Sanford metropolitan area. It is known for its parks, trails, and historic downtown district.

What are the best neighborhoods to visit in Winter Garden, FL?

The best neighborhoods to visit in Winter Garden, FL are:

  • Downtown Winter Garden
  • Oakland Park
  • John's Lake Landing

Downtown Winter Garden offers a vibrant atmosphere with a variety of shops and restaurants. Oakland Park has a charming historic district with a variety of recreational activities. John's Lake Landing is a great spot for outdoor activities such as fishing, boating, and kayaking.

What are the popular shopping destinations in Winter Garden, FL?

The popular shopping destinations in Winter Garden, FL are:

  • Winter Garden Village at Fowler Groves
  • Plant Street Market
  • Downtown Winter Garden

Is Winter Garden, FL safe to travel to?

Winter Garden, FL is a safe place to travel to. Here are a few reasons why:

  • Low crime rate
  • Friendly locals
  • Lots of outdoor activities

What is the culture like in Winter Garden, FL?

Winter Garden, FL is a vibrant city with a unique culture that is rooted in its history as a small farming town. Here are five points to consider when considering the culture of Winter Garden:

  • The city is known for its vibrant downtown area, which includes a variety of restaurants, shops, and entertainment options.
  • The city is home to a thriving arts and culture scene, with several galleries, museums, and performing arts venues.
  • The city is home to a variety of festivals throughout the year, from the annual Winter Garden Music Fest to the Winter Garden Art Festival.
  • The city is home to a number of historic sites, including the Winter Garden Heritage Museum and the historic Edgewater Hotel.
  • The city is home to a number of outdoor activities, including hiking, biking, and fishing.

Where can I find affordable accommodation in Winter Garden, FL?

Winter Garden, FL is a great destination for those looking for affordable accommodation. Here are some of the best options:

  • The Winter Garden Hotel: Offering comfortable rooms at budget-friendly rates.
  • The Hampton Inn & Suites: A modern hotel with a variety of amenities.
  • The Best Western Plus: An affordable option with free Wi-Fi and breakfast.
  • The Comfort Inn & Suites: Providing a convenient location and great value for money.

These accommodations are sure to provide a comfortable and pleasant stay for travelers of all budgets.

How can I get around in Winter Garden, FL?

You can get around in Winter Garden, FL by:

  • Walking
  • Biking
  • Using public transportation

Winter Garden also offers rideshare services, such as Uber and Lyft, for those who need a lift.

What are the must-visit tourist attractions in Winter Garden, FL?

Winter Garden, FL is a great place to visit for its many attractions. Here are some must-visit tourist attractions in Winter Garden, FL:

  • Garden Theatre
  • Historic Downtown Winter Garden
  • Central Park West Meadow
  • Winter Garden Farmers Market

Garden Theatre is a great place to watch a show or movie. Historic Downtown Winter Garden is a great place to explore the local culture and cuisine. Central Park West Meadow is a great spot for a picnic or a stroll. Winter Garden Farmers Market is a great place to pick up some local produce and goods.

What do I need to know before visiting Winter Garden, FL?

Before visiting Winter Garden, FL, it is important to know that the city is located in Central Florida, about 15 miles west of downtown Orlando. It is known for its historical downtown area, which is filled with restaurants and shops. Additionally, visitors should be aware of the following:
  • The city is known for its extensive bike trails.
  • Outdoor activities such as fishing, boating, and camping are popular.
  • The weather is hot and humid during the summer months.

What are the most popular vacation rental amenities in Winter Garden?

  • Kitchen / Kitchenette
  • Air conditioner
  • TV

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