Winter Garden Vacation Rentals

Our Favorite Vacation Rentals in Winter Garden

  • 16150EGRET- Sun Chaser (S)
     4br Country House
    RedAwning
    From
    $328
  • Private room
    ExcellentHome/Apartment
    Booking.com
    From
    $99
  • Beautiful Villa in exclusive Orlando suburb
     5br Country House
    HolidayLettings
    From
    $752
  • holiday home for max. 12 persons in Kissimmee, Florida
     Country House
    TUIvillas
    From
    $229
  • MSD1907 in Glenbrook
     5br Country House
    RedAwning
    From
    $324
  • CLOSE TO ALL ATTRACTIONS!! RESORT LIVING!
     Country House
    Booking.com
    From
    $159
  • NEW! Downtown Winter Garden Cottage w/ Yard!
     2br Cottage
    HolidayLettings
    From
    $228
  • holiday home for max. 6 persons in Orlando, Florida
     Country House
    TUIvillas
    From
    $360

Check prices for these upcoming dates

Winter Garden Vacation Rentals with a Pool

  • ACO FAMILY – 3 bd with pool (1712)
     3br Home/Apartment
    RedAwning
    From
    $298
  • On-Site Water Park + Pool | Shuttle to Disney World
     3br Home/Apartment
    RedAwning
    From
    $261
  • Villa Near Disney World and SeaWorld with Restaurants, Golf, a Lazy River + More
     2br Villa
    RedAwning
    From
    $283
  • Modern + Elegant Suite in a Great Location | Private Furnished Balcony
     Home/Apartment
    RedAwning
    From
    $194

Winter Garden Vacation Rentals with Wi-Fi

  • 4802 vista cay
     3br Home/Apartment
    RedAwning
    From
    $487
  • Bonnet Creek 4 Bedrooms
     4br Home/Apartment
    RedAwning
    From
    $534
  • 407 Summer Place loop
     5br Home/Apartment
    RedAwning
    From
    $351
  • Villa Close to Disney World | 2 Pools, Hot Tub Access + 18-Hole Mini Golf
     2br Villa
    RedAwning
    From
    $184

Winter Garden Pet-Friendly Vacation Rentals

  • TOUR BEAUTIFUL LAkE LOUISA& Chain of Lakes. NEW 2018 JETSKI & 2016 SPARK
    Excellent4br Home/Apartment
    HolidayLettings
    From
    $544
  • Cozy Winter Garden Home 20 MINUTES FROM DISNEY
    ExcellentHome/Apartment
    Airbnb
    From
    $153

Winter Garden Travel Guide

If you are dreaming about a Florida vacation, but don't want to stay in a super busy city, then Winter Garden is a great spot for you. Located just a few miles south of Orlando, this Florida Metropolitan Area city offers great activities. This small city lies alongside the beautiful Lake Apopka, and it was formerly a citrus fruit economic hub in the early 1900s. Winter Garden has that old, charming Florida feeling, with a historic downtown area and museums, galleries, live events and performing arts events. The city is easily accessible as it's less than 30 minutes from Orlando International Airport.

Things to Do in Winter Garden

Winter Garden is a charming city that's home to museums and historical landmarks, outdoor activities, lakes and golf courses.

Lake Apopka Wildlife Trail is an excellent spot for enjoying some outdoor time, as the trail features an 11-mile-long drive where you can spot alligators, birds and rare plants.

You can explore the lake on foot at Lake Apopka Loop trail, just keep an eye out for the 'gators!

Furthermore, if you want to explore the historic side of town, visit the Winter Garden Heritage Museum where you can learn all about Florida's heritage and how this particular area developed.

In addition, Winter Garden's close proximity to some of Florida's theme parks makes it a great place to base yourself. For an amazing time visit Universal Studios where you can tour various movie settings and get an insight into the movie-making business. You can also visit Walt Disney World where dozens of rides, parks, games, and fun await visitors of all ages.

Best Places to Stay in Winter Garden

The best area to stay at Winter Garden is in the northern district which is right at the shore of Apopka Lake. The area feature amazing vacation home rentals, with great lake-side views. There are also lots of restaurants and stores close by.

Best Time to Visit Winter Garden

The best time to visit Winter Garden is April, May and October, when the temperature does not go over 85 degrees, and there is only a slight chance for rainfall. In the summer months the temperature is very hot, and the air is extremely humid. In the rest of the year the average temperature is 65 degrees, do you will never be really cold here. Garden City is a great choice all year around!

Price and Availability in Winter Garden

Most expensive
Most availability
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Powered by:
The cheapest day to stay at a vacation rental in Winter Garden tends to be Tuesday, while the most expensive day tends to be Saturday. Vacation homes in Winter Garden tend to be busiest on Fridays, while it tends to be much quieter on Tuesdays.
The most expensive month to stay in a vacation rental in Winter Garden is in March, while the cheapest month is in November. The most popular time to book a vacation rental in Winter Garden is in the high season in March. Winter Garden has its low season in September, when less people are visiting and the vacation home occupancy rate drops.

The Weather in Winter Garden

Rainy days
95 º73
3
92 º52
2
89 º39
1
87 º40
2
83 º0
2
88 º47
0
87 º37
0
90 º51
1
92 º61
8
95 º70
3
95 º72
1
94 º71
3
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Rainy days

This climate histogram shows you the weather patterns in Winter Garden. The warmest months in Winter Garden are July and April, when temperatures reach 95 ˚F. The coolest month is December, when temperatures drop to 0 ˚F. The wettest month in Winter Garden is August with 7.7 inches of rain, while the driest month is November with 0.16 inches of rain.

What Expert Travelers Think

  • — I love AllTheRooms because it enables me to compare a range of providers in just one search. I'd normally spend time checking prices across a range of platforms by visiting different websites one-by-one, so this helps me to save time on my accommodation searches while planning my upcoming trips

    Kacie Morgan
    Kacie MorganThe Rare Welsh Bit
  • — I love how AllTheRooms shows a map with room price tags straight away when you search, it makes it so quick and easy to choose the right hotel, at the right price in the right location. Perfect for those with busy lifestyles! The AllTheRooms website is so user friendly. WiFi. Brilliant!

    Amanda Alston
    Amanda AlstonAmanda Alston
  • — My favorite thing about AllTheRooms is that it combines both rentals and hotels available so you can see an entire view of what is available in a certain area. I was able to see listings on AllTheRooms that I never even saw on other travel sites!

    Daniella Flores
    Daniella FloresILIKETODABBLE

Vacation Rentals in Winter Garden

Browse rentals from all your favorite providers including Airbnb, RedAwning, Priceline and more at AllTheRooms.com. Winter Garden has 859 hotels, vacation rentals and other unique places to stay, with prices to suit budget travelers, luxury travelers and everything in between. If you are trying to save money, the lowest priced place to stay in Winter Garden comes in at $16 per night. A typical vacation rental in Winter Garden costs on average $123 per night.

Those looking to get some work finished during their trip to Winter Garden can pick from 365 places to stay that provide WiFi. 27 places to stay include a breakfast. Choose from 248 accommodations that provide gym facilities, so you won't miss a single workout. Driving to Winter Garden? Then choose one of the 368 places to stay that comes with a parking spot included. 239 places to stay have a a pool or jacuzzi

AllTheRooms has 52 pet-friendly places to stay in Winter Garden, so if you're traveling with your cat or dog you won't have any problems.

317 of the accommodations in Winter Garden have been reviewed by previous guests. They rated 41% as great. You can instantly book any of 331 places to stay right now.

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