Winter Park, FL Cabins & Vacation Rentals

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Our Favorite Vacation Rentals in Winter Park

  • New Listing! New & Contemporary Downtown Condo Condo
  • Live like a Local, 2/1 in the Heart of Orlando!
     2br Home/Apartment
  • Business Travelers Home -- Orlando Sleeps 4 -- Welcome Nurses!
     Country House
  • Fern Park House w/Pool - New Patio & Fire Pit!
  • Downtown Orlando Apartments by NUOVO
  • Orlando Group Cottage Sleep 14 Guests
     5br Home/Apartment
  • Orlando Lakefront Tiny Houses
    GoodCountry House
  • The Cottage at Oviedo

Check prices for these upcoming dates

Winter Park Vacation Rentals with a Pool

  • King James Cottage
  • Simple and Cozy Apartment
  • Tropical paradise Private pool & Master Suite
  • Luxury Living At It’s Best

Winter Park Vacation Rentals with Wi-Fi

  • Bright and Airy Winter Park Apartment
  • *Orlando Parks* I-4 Fairbanks exit *Superhost* 3/1
    Excellent3br Home/Apartment
  • Groovy Apt in great location Winter Park Orlando
  • Cozy Home Just Off N. Park Avenue
    Excellent2br Home/Apartment

Winter Park Pet-Friendly Vacation Rentals

  • Downtown Orlando apartment for rent
  • The Lake House (Tiny House)
  • Bermuda
  • 6/3 - Pool, Trampoline, Movie Theater close 2 UCF, Beaches, Disney & More!
     5br Home/Apartment

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
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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
96 º74
93 º56
87 º39
86 º40
84 º28
88 º49
88 º43
90 º53
94 º64
95 º71
95 º72
95 º73
Rainy days

This climate histogram shows you the weather patterns in Winter Park. The warmest months in Winter Park are April and July, when temperatures reach 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

  • — 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
  • — Packed full of information, from the best time of year to visit (I love NYC in Spring) to top tips from locals, All The Rooms provides the best accommodation, whether you are looking to enjoy your first time visit to New York or want to experience a new location

    JazThe Life of a Social Butterfly
  • — 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

Vacation Rentals in Winter Park

At we have vacation rentals from all of the best providers - Airbnb, Priceline, RedAwning and others. Winter Park has 452 hotels, vacation rentals and other special 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 Park is only $10 a night. In general, a place to stay in Winter Park will cost you $118 per night.

If you need an internet connection during your stay in Winter Park, then you can choose from over 338 accommodations that have WiFi internet. 40 places to stay include a breakfast. Choose from 39 accommodations that provide gym facilities, so you won't miss a single workout. If you're planning on getting to Winter Park by car, be sure to choose from 327 accommodations that provide parking. 113 places to stay come with a pool or jacuzzi

Those traveling with a cat, dog or some other animal can stay in one of 80 accommodations that are designated as pet-friendly.

336 of the accommodations in Winter Park have been reviewed and rated. 68% are rated great. You can instantly book any of 189 places to stay right now.

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