Winter Park vacation rentals

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Best Winter Park vacation rentals

Most recommended vacation rentals in Winter Park

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KAYAK’s insights for vacation rentals in Winter Park

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Winter Park with confidence.

Which month has the cheapest vacation rental rates in Winter Park?

Vacation rentals are cheapest in Winter Park in June, with average rates of $165. In comparison, December is the most expensive month, with prices at $620.

What is the cheapest day of the week to book a vacation rental in Winter Park?

Sunday offers the lowest rates in Winter Park, with an average nightly price of $264. The highest prices are found on Wednesday, with average rates at $418.

Good to know

Low season

June

High season

December

Average price (weeknight)

$328

Average price (weekend night)

$399
Cheapest month to stay with an average 51% drop in price.
Most expensive month to stay with an average 84% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Winter Park vacation rental deals

  • If you're planning for a weekend getaway to Winter Park house rentals, you need a place with great amenities. You can book your stay at Newly-renovated retreat W/A shared hot tub & heated pool. This condo accommodates up to four guests and is near biking trails if you love outdoor activities.
  • Beaver Village & Mountain Bliss is one of the best Winter Park vacation rentals if you need a tranquil environment away from noise and distractions. Located 1.9 miles from downtown Winter Park, you can enjoy the calm winds blowing from the mountains and have a peaceful night's sleep.
  • Planning to see many attractions during your stay in Winter Park? Winter Park Condo with pool about 3MI to Ski Resort is your go-to vacation rental. You can go to Rendezvous Event Center 1.1 miles away, Capital Prize Gold Mine Tours is about 33 miles away, and The Ditch on 40 is just 1 mile from this place.
  • Looking for Winter Park vacation rentals close to the transport system? You can book your stay at Cozy, 1 Bedroom Condo, 2 blocks from downtown, on Ski Bus Route. This way, you can board the Lift Bus to help you get around the city.
  • If you need a memorable romantic getaway, you can book your stay at Fraser Crossing and Founders Pointe. This vacation rental offers on-site skiing, including skiing lessons if you and your spouse love skiing. Again, it's located in Arapaho National Forest, where you can create beautiful memories if you're newlywed or celebrating your anniversary.
  • Hot tub and pet friendly are the most popular vacation rental property amenities in Winter Park
  • Vacation rentals in Winter Park are around 61% more expensive than hotels on average. Search here to compare prices for all accommodation types in Winter Park.
  • The best vacation rental properties in Winter Park are New Luxury Loft 3 I Huge Hot Tub I Great Views I Best Price I Free Adventures Daily (10.0, 21 reviews), Winter Park Founders Pointe Slope Side Studio Steps To Base Area (9.9, 72), and New Luxury Loft #19 With Huge Hot Tub & Great Views - 500 Dollars Of Free Activities & Equipment Rentals Daily (9.9, 23), based on ratings and reviews from real travelers.
  • If you’re looking for a cheap vacation rental in Winter Park, you should consider visiting during the low season. The cheapest vacation homes in Winter Park can be found in June and May.
  • The cheapest night for renting a vacation home in Winter Park is Sunday. In contrast, the most expensive is Friday.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Winter Park for 3 days.
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FAQs when booking a vacation home in Winter Park

  • How much is a vacation rental for a week in Winter Park?

    The average price for a weekly Winter Park vacation rental found by KAYAK users in the last 2 weeks is $2,397.

  • How much is a vacation rental for a month in Winter Park?

    The average price for a monthly Winter Park vacation rental found by KAYAK users in the last 2 weeks is $10,274.

  • What types of vacation rentals are available in Winter Park?

    There are loads of different property types that you can make your vacation home in Winter Park. You’ll find apartments, cabins, condos, cottages, houses, lodges and villas.

  • Are there any pet-friendly vacation rentals in Winter Park?

    There are a number of dog and pet-friendly Winter Park vacation rentals, with around 6% allowing you to bring your pet along with you.

  • How much is a vacation rental in Winter Park for tonight?

    In the last 72 hours, users have found Winter Park vacation rentals for tonight for as low as $312. Search here for similar prices

  • How can I find vacation rentals near me in Winter Park?

    Take a look at our vacation rentals map to find the best vacation rental homes near you.

  • Where are the best vacation rentals to stay in Winter Park for families or large parties?

    Several Winter Park vacation rentals are ideal for large families. Hi Country Haus has a three-bedroom condo that can sleep up to eight guests. It has game rooms where families can have fun. Another vacation rental excellent for large families is Beautiful apartment and good value #2, which accommodates 10 guests. Again, it's near hiking trails such as Idlewild North Loop, where families can have fun.

  • Where are the best vacation rentals in Winter Park with a view?

    Booking a vacation rental with a view in Winter Park makes your stay enjoyable. Cozy Winter Park Studio with views-Walk to downtown, is one of the best choices. You can enjoy the mountain views on your balcony. Another vacation rental with a view is Zephyr Mountain Lodge, with mountain and slopeside views.

  • What are the benefits of self-catering in Winter Park Holiday Homes?

    Cooking your meals during a vacation assures you of eating clean food. You can purchase fresh ingredients from large food markets in Winter Park, such as Fireside Market & Eatery and cook what you desire after a long day.

  • Where are the best vacation rentals to stay in Winter Park for nightlife?

    Timber Run Vista 2 is located approximately 3.5 miles from downtown Winter Park. Thus, if you love the nightlife, you can have a good time at various places in the city, including Denos, Hecks Tavern at Devils Thumb Ranch, The Ditch, and The Library Sports Grille & Brewery.

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Where to stay in Winter Park?

Our map will help you find the perfect place to stay in Winter Park by showing you the exact location of each vacation rental.

Winter Park vacation rental deals. Search for vacation homes, apartments, condos, cabins, cottages, villas and more in Winter Park. Find cheap vacation homes to rent in Winter Park. KAYAK searches hundreds of travel sites to help you find and book a vacation rental in Winter Park that suits you best.

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