Winter Park, FL Cabins & Vacation Rentals

Our Favorite Vacation Rentals in Winter Park

  • NUOVO - Downtown Orlando
     Home/Apartment
    Booking.com
    From
    $119
  • Orlando Group Cottage Sleep 14 Guests
     5br Home/Apartment
    HolidayLettings
    From
    $314
  • Reunion Dory, 5 Bedrooms, Sleeps 10, Encore Club, Private Pool
     Country House
    Booking.com
    From
    $809
  • Lakefront Florida Home w/Dock - 10 Mi. to Orlando!
     3br Home/Apartment
    HolidayLettings
    From
    $370
  • Luxury high rise condo near all themes parks
     Home/Apartment
    Booking.com
    From
    $171
  • Bay Lake Tower at Disney's Contempoy Resort (DVC)
     -1br Studio
    HolidayLettings
    From
    $603
  • B Private Bedroom
     Family Stay
    Booking.com
    From
    $40
  • NEW! Altamonte Springs Home w/Canoe on Lake Marion
     Home/Apartment
    HolidayLettings
    From
    $163

Check prices for these upcoming dates

Winter Park Vacation Rentals with a Pool

  • King James Cottage
    ExcellentCottage
    Airbnb
    From
    $168
  • Simple and Cozy Apartment
     Home/Apartment
    Airbnb
    From
    $225
  • Townhouse bedroom in Baldwin Park
    ExcellentHome/Apartment
    Airbnb
    From
    $96
  • Warm and cozy one bedroom apartment winter park
    ExcellentHome/Apartment
    Airbnb
    From
    $2,288

Winter Park Vacation Rentals with Wi-Fi

  • Winter Park Pearl 5 minutes from historic Park Ave
    Excellent3br Home/Apartment
    Airbnb
    From
    $182
  • Casa Winter Park
     4br Home/Apartment
    Airbnb
    From
    $552
  • Cozy, private studio, near Downtown and Disney!!
    GoodHome/Apartment
    Airbnb
    From
    $115
  • Winter Park Bamboo Loft
    ExcellentHome/Apartment
    Airbnb
    From
    $166

Winter Park Pet-Friendly Vacation Rentals

  • Lake View Winter Park Pool Home
    Good2br Home/Apartment
    Airbnb
    From
    $101
  • Clean, cozy and simple in-law suite
    OkayHome/Apartment
    Airbnb
    From
    $130
  • Charming Farmhouse Bungalow
     3br Home/Apartment
    Airbnb
    From
    $366
  • Modern Pool Studio Suite in Orlando!
    GoodHome/Apartment
    Airbnb
    From
    $104

Winter Park Travel Guide

Contrary to its name, Winter Park is a ray of sunshine with lots to offer tourists with different interests. This historic and quaint town is family-friendly, with opportunity to enjoy arts, culture and nature all in one. There are famous museums and festivals held throughout the year, with over 70 green spaces for nature-lovers to explore. You'll also find a lot of cafes and coffee spots for the health-conscious travelers, as well as weekly farmer’s markets. It isn’t hard to see how Winter Park has become a favourite retreat in the Sunshine State for many families and couples on vacation.

Things to Do in Winter Park

You'll find one of the oldest attractions in Florida in Winter Park -- Scenic Boat Tours. A guide takes you out onto Lake Osceola to admire the flora and see if you can spot any 'gators. Winter Park Sidewalk Art Festival attracts visitors annually since it is one of the oldest and largest outdoor art festivals in the country. You can wander around Olde Winter Park and explore the traditional, brick streets and unwind in the Mead Botanical Garden, with over 48 acres of greenery. The Charles Hosmer Morse Museum of American Art also showcases the best works of artist, Louis Comfort Tiffany in the world.

Best Time to Visit Winter Park

The best time to visit Winter Park is from January to April when it's still warm but there is less rain and humidity to make it comfortable. While a lot of tourists visit this city in the Sunshine State during the summer months, Winter Park is at its hottest and most humid from May to the end of August. This is hurricane season and means the potential for storms that could affect your plans.

Cabins in Winter Park

The town of Winter Park is the perfect base village for a skiing adventure. The continental divide cuts right through Grand County, giving a stunning backdrop to all slopes in Winter Park Colorado. Winter Park Resort features 3,000 acres of award-winning terrain, with runs suitable for all abilities, as well as a large number of vacation rentals.

The fun doesn't stop in summer, and the Winter Park area becomes crowded with mountain bike enthusiasts, meaning rentals in Winter Park and nearby Fraser Valley tend to fill up during this season. The valley is surrounded by the Arapaho National Forest which is criss-crossed with a number of hiking trails -- the idea setting for any outdoor enthusiast!

Winter Park lodging fits a range of budgets. For something a little more luxurious, book a rental with a hot tub where you can soak up the surrounding mountain views. The majority of Winter Park cabin rentals have full kitchens, and many are ski-in ski-out condos, meaning you have immediate access to world-class skiing. Trailhead Lodge offers a number of 1-3 bedroom accomodations close to all of the action, or there are a number of other management companies visitors can book through.

Price and Availability in Winter Park

Most expensive
Most availability
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The cheapest day to stay at a vacation rental in Winter Park tends to be Monday, while the most expensive day tends to be Friday. Vacation homes in Winter Park tend to be busiest on Saturdays, while it tends to be much quieter on Mondays.
The most expensive month to stay in a vacation rental in Winter Park is in July, while the cheapest month is in April. The most popular time to book a vacation rental in Winter Park is in the high season in March. Winter Park has its low season in September, when less people are visiting and the vacation home occupancy rate drops.

The Weather in Winter Park

Rainy days
87° 39°
1
86° 40°
3
84° 28°
2
88° 49°
0
88° 43°
2
90° 53°
3
94° 64°
8
95° 71°
4
95° 72°
6
95° 73°
10
96° 74°
3
93° 56°
3
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Rainy days

This climate histogram shows you the weather patterns in Winter Park. The hottest month in Winter Park is April, when temperatures peak at 96 ˚F. The coolest month is December, when temperatures drop to 28 ˚F. The wettest month in Winter Park is May with 10.3 inches of rain, while the driest month is November with 0.33 inches of rain.

What Expert Travelers Think

  • — AllTheRooms.com makes travel easier, enjoyable and inexpensive through its provision of ample information, data and every possible accommodation available to choose from

    ArtMatters.Info
    ArtMatters.InfoArtMatters.Info
  • — 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 Park

Browse accommodations from all the leading providers including Airbnb, Priceline, RedAwning and many more at AllTheRooms.com. Winter Park has 482 hotels, vacation rentals and other unique places to stay, with prices to suit budget travelers, extravagant travelers and everything in between. A vacation in Winter Park can be affordable - the lowest price vacation rental is available at $10 a night. On average, an accommodation in Winter Park will cost you $115 per night.

Those looking to get some work finished during their trip to Winter Park can choose from 335 places to stay that include WiFi. We have 42 accommodations that include a breakfast included. Fitness addicts can get a workout in during their stay by choosing from 42 accommodations that have gyms. If you are driving to Winter Park, you'll want to pick from 324 places to stay that provide parking. We have 123 accommodations that have a pool or jacuzzi.

AllTheRooms has 69 pet-friendly places to stay in Winter Park, so if you're traveling with your cat or dog you won't have any trouble.

359 of our accommodations in Winter Park have been reviewed by previous guests. They rated 67% as excellent or good. You can instantly book any of 201 places to stay right now.

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