Winter Park vacation rentals

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Recommended by KAYAK

Best Winter Park vacation rentals

Most recommended vacation rentals in Winter Park

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Charming Winter Park Fully Furnished & Pet Friendly Farmhouse Bungalow - Winter Park - Living room
Charming Winter Park Fully Furnished & Pet Friendly Farmhouse Bungalow
Winter Park, FL
Pet friendly
$203+
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Stylish Boutique Guest house in Winter Park - Winter Park - Kitchen
Stylish Boutique Guest house in Winter Park
Winter Park, FL
Free Wi-Fi
$339+
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Luxury Lakeside Condo with Sunroom and Pool - King Bed - Winter Park - Living room
Luxury Lakeside Condo with Sunroom and Pool - King Bed
Winter Park, FL
Pool
$141+
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Upscale 3/2 Townhome | King Bed | Patio | Wifi - Winter Park - Patio
Upscale 3/2 Townhome | King Bed | Patio | Wifi
Winter Park, FL
$315+
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Winter Park Oasis - Winter Park - Kitchen
Winter Park Oasis
Winter Park, FL
Free Wi-Fi
$181+
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Casa Winter Park - Winter Park - Kitchen
Casa Winter Park
Winter Park, FL
Free Wi-Fi
Pool
Pet friendly
$384+
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Private Luxury Pool / Smart-home - Winter Park - Patio
Private Luxury Pool / Smart-home
Winter Park, FL
9.3Wonderful(30)
Free Wi-Fi
Spa
$342+
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Cute Guest House In Winter Park Minutes From Downtown in Car - Winter Park - Bedroom
Cute Guest House In Winter Park Minutes From Downtown in Car
Winter Park, FL
Free Wi-Fi
$153+
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Charming 2BR/2BA Winter Park Cottage, steps from Park Ave - Winter Park - Living room
Charming 2BR/2BA Winter Park Cottage, steps from Park Ave
Winter Park, FL
$140+
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Ideal Location, Charming 4 bedroom home w Pool, fenced yard, 40% off thirty days - Winter Park - Living room
Ideal Location, Charming 4 bedroom home w Pool, fenced yard, 40% off thirty days
Winter Park, FL
Free Wi-Fi
Pool
Pet friendly
$382+
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Stylish Winter Park Flat: Minutes from Park Avenue\n\n - Winter Park
Stylish Winter Park Flat: Minutes from Park Avenue\n\n
Winter Park, FL
Pool
$187+
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Chic 3br Home With Big Yard In Winter Pa - Winter Park
Chic 3br Home With Big Yard In Winter Pa
Winter Park, FL
10Wonderful(10)
Free Wi-Fi
$293+
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Spacious Condo Close To Ucf, Full Sail & Rollins - Winter Park
Spacious Condo Close To Ucf, Full Sail & Rollins
Winter Park, FL
$123+
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Modern and Romantiv Villa - Winter Park
Modern and Romantiv Villa
Winter Park, FL
Free Wi-Fi
$93+
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Pondside Retreat with Koi in Charming Winter Park, FL - Winter Park
Pondside Retreat with Koi in Charming Winter Park, FL
Winter Park, FL
Pet friendly
$256+
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Luxury Townhouse In The Heart Of Winter Park, Florida - Winter Park
Luxury Townhouse In The Heart Of Winter Park, Florida
Winter Park, FL
Free Wi-Fi
$216+
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Good to know

Low season

May

High season

February

Average price (weeknight)

$268

Average price (weekend night)

$402
Cheapest month to stay with an average 57% drop in price.
Most expensive month to stay with an average 151% 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

  • Vacation rentals in Winter Park are around 13% 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 A curated stay in the Historic College Quarter (10.0, 35 reviews), Ideal Location, Charming 4 bedroom home w Pool, fenced yard, 40% off thirty days (9.9, 29), and Casa Winter Park (9.7, 67), 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 May and November.
  • 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 7 days.

FAQs when booking a vacation home in Winter Park

  • 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, condos, cottages, houses, homestays, recreational vehicles and villas.

  • What are some of the most-loved vacation rentals available in Winter Park?

    There are many types of properties available for Winter Park vacation rentals. If you’re looking for something special, vacation rentals most loved by KAYAK users are Orlando Lakefront Tiny Houses and Formosa Valley By Une Homes.

  • 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 21% allowing you to bring your pet along with you.

  • 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 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.

Everything you need to know for your stay in Winter Park

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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