Winter Park, FL Cabins & Vacation Rentals

Our Favorite Vacation Rentals in Winter Park

  • Orlando Mid Century Modern
     Country House
    Booking.com
    From
    $144
  • Orlando Group Cottage Sleep 14 Guests
     5br Home/Apartment
    HolidayLettings
    From
    $314
  • Guest Suite located on Lake Barton
     Villa
    Booking.com
    From
    $219
  • The Cottage at Oviedo
    ExcellentCottage
    HolidayLettings
    From
    $241
  • NUOVO - Downtown Orlando
     Home/Apartment
    Booking.com
    From
    $119
  • Bay Lake Tower at Disney's Contempoy Resort (DVC)
     -1br Studio
    HolidayLettings
    From
    $603
  • Orlando Lakefront Tiny Houses
     Country House
    Booking.com
    From
    $94
  • Oviedo Charmer
     3br Home/Apartment
    HolidayLettings
    From
    $241

Check prices for these upcoming dates

Winter Park Vacation Rentals with a Pool

  • Simple and Cozy Apartment
     Home/Apartment
    Airbnb
    From
    $225
  • Spacious apartment near lake with a car garage
    GoodHome/Apartment
    Airbnb
    From
    $124
  • Entire Cozy Beautiful 3 Bedroom Orlando Townhouse
    Excellent3br Home/Apartment
    Airbnb
    From
    $128
  • Warm and cozy one bedroom apartment winter park
    ExcellentHome/Apartment
    Airbnb
    From
    $113

Winter Park Vacation Rentals with Wi-Fi

  • Chez Bienvenu
    ExcellentHome/Apartment
    Airbnb
    From
    $98
  • *3 bedroom*Fairbanks off I4*Close2Parks*Superhost*
    Excellent3br Home/Apartment
    Airbnb
    From
    $205
  • Lounge on Blue Velvet Couches at a Charming Hideaway
    Excellent4br Home/Apartment
    Airbnb
    From
    $337
  • Winter Park Pearl 5 minutes from historic Park Ave
    Excellent3br Home/Apartment
    Airbnb
    From
    $175

Winter Park Pet-Friendly Vacation Rentals

  • ORLANDO ESCAPE STARTS HERE! KING SUITE, POOL, BBQ
     Home/Apartment
    HolidayLettings
    From
    $191
  • IMMEDIATE BOOKING Available!
     2br Home/Apartment
    HolidayLettings
    From
    $165
  • MillsPark@Orlando
     Home/Apartment
    Airbnb
    From
    $678
  • Charming Cottage in College Park
    ExcellentHome/Apartment
    Airbnb
    From
    $93

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
83° 38°
3
88° 48°
2
88° 42°
2
91° 56°
2
98° 66°
4
98° 71°
12
98° 72°
6
97° 73°
13
95° 69°
3
92° 68°
6
89° 49°
1
85° 42°
4
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Rainy days

This climate histogram shows you the weather patterns in Winter Park. The hottest month in Winter Park is July, when temperatures peak at 98 ˚F. The coolest month is December, when temperatures drop to 38 ˚F. The wettest month in Winter Park is May with 13.03 inches of rain, while the driest month is February with 1.33 inches of rain.

What Expert Travelers Think

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    Laurelle McVicker
    Laurelle McVickerLaurelle McVicker
  • — 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 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

Vacation Rentals in Winter Park

Pick the perfect vacation rental for your trip at AllTheRooms.com. We compare Airbnb, Priceline, RedAwning and more. We have 452 vacation rentals, hotels and other accommodation types in Winter Park ranging from budget options to luxury places to stay. When traveling on a budget, the cheapest place to stay in Winter Park is available at $10 per night. A typical accommodation in Winter Park costs on average $113 a night.

If you need internet access during your time in Winter Park, then you can choose from over 322 accommodations that have WiFi internet. We have 36 accommodations that come with breakfast included. You can keep up with your workout regime by staying at one of 43 accommodations that provide gym facilities. If you are driving to Winter Park, you'll want to pick from 313 places to stay that provide parking. We have 121 hotels and vacation rentals that have a pool or jacuzzi.

Those traveling with a cat, dog or some other animal can stay in one of 64 accommodations that are designated as pet-friendly.

352 of the rentals in Winter Park have been reviewed by previous guests. They rated 69% as great. 182 places to stay in are instantly bookable.

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