Choose from 125 vacation rentals located in Winter Garden, Florida. Top filters in Winter Garden include Air conditioner, Kitchen or Kitchenette, and TV. Prices range from $116 to $1,681 per night. Our most popular vacation rental types near Winter Garden are Hotel and RV.

Top vacation rentals in Winter Garden

Winter, Living room, Lobby or reception, Decorative detail
9.5
Outstanding(213 Reviews)
The Edgewater Hotel
Bed and Breakfast
 in Orlando
1 full bed
Garden · Kitchen or 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 or Patio, and more.

$$$$
booking logo
View deal
Exterior
9.8
Outstanding(41 Reviews)
Downtown Winter Garden Cottage ~ 12 Mi to Disney!
Cottage
 in Winter Garden
4 guests · 3 bedrooms · 1 bath
Garden · Kitchen or Kitchenette · Air conditioner

This attractive Cottage in Winter Garden, $359 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
vrbo logo
View deal
Fridge, microwave, stovetop, dishwasher
10.0
Outstanding(50 Reviews)
Winter Garden Bungalow w/ Gas Grill, Walk to Dtwn!
House
 in Winter Garden
4 guests · 2 bedrooms · 1 bath
Garden · Kitchen or 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 Laundry, and more.

$$$$
vrbo logo
View deal
Property view
9.2
Outstanding(8 Reviews)
Walk to Dtwn Winter Garden Home with Patio
House
 in Orlando
Kitchen or Kitchenette · Air conditioner · Internet / Wifi

Soak up the beauty of Winter Garden in our House, Walk to Dtwn Winter Garden Home with Patio. With a range of amenities such as Air conditioner, Dishwasher and Internet / Wifi, you'll feel right at home.

$$$$
booking logo
View deal

Search by amenity

Vacation rentals with air conditioning in Winter Garden

Fridge, microwave, stovetop, dishwasher
9.9
Outstanding(38 Reviews)
Spacious Winter Garden Home w/ BBQ, Walk to Dwtn!
House
 in Winter Garden
4 guests · 3 bedrooms · 1 bath
Garden · Kitchen or Kitchenette · Air conditioner

Experience the best of Winter Garden with this House available for $350. This property is equipped with amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
vrbo logo
View deal
Smart TV, computer monitors, printers
9.6
Outstanding(21 Reviews)
House with large deck, walking distance to Historic Downtown Winter Garden
House
 in Winter Garden
4 guests · 2 bedrooms · 2 baths
Garden · Pets allowed · Kitchen or Kitchenette

This attractive House in Winter Garden, $414 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
vrbo logo
View deal
Property view
8.5
Outstanding(4 Reviews)
16 Mi to Disney Cottage with Deck in Winter Garden
House
 in Orlando
Kitchen or Kitchenette · Air conditioner · Internet / Wifi

Enjoy the best of Winter Garden in our House, 16 Mi to Disney Cottage with Deck in Winter Garden. A stunning property with amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
booking logo
View deal
Property view
Downtown Winter Garden Home about 12 Mi to Disney!
House
 in Orlando
Pets allowed · Kitchen or Kitchenette · Air conditioner

House in Winter Garden, for $157 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)

$$$$
booking logo
View deal
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 $116-$1,681. 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?

  • Air conditioner
  • Kitchen or Kitchenette
  • TV

Explore near Winter Garden

Rentals near top attractions

Related vacation destinations

Nearby vacation destinations

Travel inspiration