Winter Garden Vacation Rentals

Our Favorite Vacation Rentals in Winter Garden

  • Disney World Shuttle + On-Site Water Park | Spacious Condo
     Home/Apartment
    RedAwning
    From
    $244
  • CareFree Camping Lake Louisa
     Glamping
    Booking.com
    From
    $65
  • 5 - Deluxe Luxury 2 Bed/bath Suite Apartment, International Dr.
    Excellent2br Home/Apartment
    HolidayLettings
    From
    $313
  • holiday home for max. 6 persons in Clermont, Florida
     Country House
    TUIvillas
    From
    $275
  • Villa Near Walt Disney World Resort and SeaWorld with 52 Holes of Golf
     2br Villa
    RedAwning
    From
    $345
  • Casa Bella Mansion near Disney World
     Villa
    Booking.com
    From
    $1,002
  • Lake Louisa Events Resort Mansion, Reunion, Wedding, Conference, Corporate
     8br Home/Apartment
    HolidayLettings
    From
    $2,214
  • holiday home for max. 10 persons in Kissimmee, Florida
     Country House
    TUIvillas
    From
    $230

Check prices for these upcoming dates

Winter Garden Vacation Rentals with a Pool

  • Shuttle to Popular Orlando Theme Parks | BUDGET FRIENDLY Suite
     Home/Apartment
    RedAwning
    From
    $167
  • 4802 vista cay
     3br Home/Apartment
    RedAwning
    From
    $469
  • Enchanted Palms
     4br Home/Apartment
    RedAwning
    From
    $591
  • Villa Close to Disney World | 2 Pools, Hot Tub Access + 18-Hole Mini Golf
     2br Villa
    RedAwning
    From
    $208

Winter Garden Vacation Rentals with Wi-Fi

  • RENOVATED Sunny + Cozy Orlando Retreat | Minutes from Theme Parks!
     2br Home/Apartment
    RedAwning
    From
    $268
  • Vacation Vista
     3br Home/Apartment
    RedAwning
    From
    $560
  • Disney Penthouse Amazing Lake Bryan view
     2br Home/Apartment
    RedAwning
    From
    $377
  • Deluxe Tower & Suites in Kissimmee
     Home/Apartment
    RedAwning
    From
    $144

Winter Garden Pet-Friendly Vacation Rentals

  • Family-Friendly Condo w/ WiFi, Free Shuttle to Theme Parks, Resort Pool & Dining
     Home/Apartment
    HolidayLettings
    From
    $183
  • Orange Lake Resort 15 Min to Disney
     2br Home/Apartment
    HolidayLettings
    From
    $229
  • Resort Townhome w/Pool, 9 Mi. to Disney World
     5br Townhouse
    HolidayLettings
    From
    $408
  • Beautiful house 3 miles from Disney World
     4br Home/Apartment
    Airbnb
    From
    $170

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
84° 39°
2
88° 46°
1
91° 42°
1
90° 53°
1
95° 66°
2
99° 71°
2
96° 69°
3
94° 74°
4
96° 69°
2
91° 67°
1
88° 45°
0
85° 41°
2
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Rainy days

This climate histogram shows you the weather patterns in Winter Garden. The hottest month in Winter Garden is July, when temperatures peak at 99 ˚F. The coolest month is December, when temperatures drop to 39 ˚F. The wettest month in Winter Garden is May with 3.55 inches of rain, while the driest month is February with 0.44 inches of rain.

What Expert Travelers Think

  • — I love All the Rooms because instead of having to check one place for home rentals, another for hotel, another for bed and breakfasts, and yet another for a room rental in a private residence, I can finally see EVERYTHING at one site; saving me considerable time

    Jeff Campbell
    Jeff CampbellMiddle Class Dad
  • — 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
  • — Whenever I am making travel plans I always use comparison sites to find the best accommodation for us at the best price. Whether it be for hotel stays or private rentals AllTheRooms makes this so much easier and quicker as it brings all my searches into one place, with a great offering of options

    Sarah Pool
    Sarah PoolTammymum

Vacation Rentals in Winter Garden

Browse places to stay from all the leading providers including Airbnb, RedAwning, Priceline and many more at AllTheRooms.com. AllTheRooms has 796 vacation rentals, hotels and other great places to stay during your time in Winter Garden, with everything from budget hostels and homestays to extravagant Airbnbs and hotels. A vacation in Winter Garden can be affordable - our lowest price vacation rental is available at $12 a night. A typical accommodation in Winter Garden costs on average $126 per night.

If you need an internet connection during your stay in Winter Garden, then you can choose from over 339 accommodations that have WiFi internet. 28 of our accommodations come with breakfast in the price. Fitness fanatics can get a workout in during their stay by choosing from 235 accommodations that have gym facilities. If you're planning on arriving in Winter Garden by car, be sure to choose from 348 accommodations that provide parking. 266 accommodations have a a pool or jacuzzi

If you're traveling with your best friend, then be sure to choose one of the 47 pet-friendly accommodations available.

We compare vacation rentals, hotels and other bespoke accommodation types from loads of providers in Winter Garden, including 341 places to stay from Airbnb, 15 accommodations from RedAwning and 6 places to stay from Priceline

333 of our rentals in Winter Garden have been rated by previous guests. They rated 41% as great. You can instantly book any of 305 places to stay right now.

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