Winter Garden Vacation Rentals

Our Favorite Vacation Rentals in Winter Garden

  • Cape Coral Villa
     Villa
    Booking.com
    From
    $119
  • Waterfront Clermont Cottage on Estate, Near Disney
     Cottage
    HolidayLettings
    From
    $199
  • Westgate Lakes Resort & Spa
     Studio
    NextTrip
    From
    $103
  • holiday home for max. 12 persons in Kissimmee, Florida
     Country House
    TUIvillas
    From
    $307
  • Luxury Camping Lake Louisa
     Glamping
    Booking.com
    From
    $65
  • Newly Remodeled A-Frame Cottage close to Disney
     2br Home/Apartment
    HolidayLettings
    From
    $180
  • Residence Inn Near Universal Orlando
     Home/Apartment
    NextTrip
    From
    $169
  • holiday home for max. 6 persons in Orlando, Florida
     Country House
    TUIvillas
    From
    $396

Check prices for these upcoming dates

Winter Garden Vacation Rentals with a Pool

  • Westgate Towers Resort
     Tower
    NextTrip
    From
    $101
  • Westgate Vacation Villas Resort
     Country House
    NextTrip
    From
    $99
  • Luxury Windsor Hills Condo
    Nice10br Home/Apartment
    Booking.com
    From
    $99
  • Beautiful and peaceful private room
     Home/Apartment
    Airbnb
    From
    $79

Winter Garden Vacation Rentals with Wi-Fi

  • Private Apartment near Disney
    ExcellentHome/Apartment
    Airbnb
    From
    $102
  • 1 bed with private bath at Disney's backyard #1
    ExcellentHome/Apartment
    Airbnb
    From
    $51
  • “Love Nest" Modern comfort at it's finest.
    Excellent2br Home/Apartment
    Airbnb
    From
    $219
  • Downtown Winter Garden, Florida
    Excellent2br Home/Apartment
    Airbnb
    From
    $133

Winter Garden Pet-Friendly Vacation Rentals

  • Orange Lake Resort 15 Min to Disney
     2br Home/Apartment
    HolidayLettings
    From
    $229
  • 2589OL -Forest View Drive (S)
    Good5br Home/Apartment
    HolidayLettings
    From
    $286
  • FREE DELIVERY TO DISNEY FT WILDERNESS, SLEEPS 5
    GoodHome/Apartment
    Airbnb
    From
    $141
  • FREE DELIVERY TO DISNEY FT WILDERNESS SLEEPS 4
     Home/Apartment
    Airbnb
    From
    $88

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
89° 39°
1
83°
2
83°
2
88° 47°
0
87° 37°
0
90° 51°
1
92° 61°
8
95° 70°
3
95° 72°
1
94° 71°
3
95° 73°
3
92° 52°
2
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
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 is not only local homes for renting, and not only hotels, but everything combined. When I am about to book a place to stay, I usually spend a couple of hours looking through both hotel sites and local home sites, comparing the prices and places.

    Alli Sims
    Alli SimsAlli Sims
  • — As a mom of 5 kids who enjoy traveling, I love AllTheRooms! It is quick and easy to find the best deal on lodging that fits our family, in the area we'd like. AllTheRooms really does save you time, money, and hassle.

    Becky
    BeckyKid World Citizen
  • — 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

At AllTheRooms.com we have vacation rentals from all of your favorite providers - Airbnb, RedAwning, Priceline and others. AllTheRooms has 932 vacation rentals, hotels and other great places to stay during your time in Winter Garden, with everything from inexpensive hostels and homestays to extravagant Airbnbs and hotels. For those traveling on a budget, the cheapest place to stay in Winter Garden is available at $17 per night. An average accommodation in Winter Garden costs on average $123 per night.

Those looking to get some work done during their trip to Winter Garden can pick from 344 places to stay that include WiFi. We have 29 accommodations that include a breakfast included. Choose from 226 accommodations that provide gym options, so you don't miss a single workout. If you're planning on arriving in Winter Garden by car, be sure to choose from 355 accommodations that provide parking. 265 vacation rentals have a a pool or jacuzzi

If you're traveling with your best friend, then make sure to choose one of the 52 pet-friendly accommodations available.

333 accommodations in Winter Garden have been reviewed; 40% are rated highly. 358 accommodations allow instant booking.

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