Choose from 166 vacation rentals located in Winter Park, Florida. Top filters in Winter Park include Air conditioner, Internet / Wifi, and Kitchen or Kitchenette. Prices range from $65 to $1,424 per night. Our most popular vacation rental types near Winter Park are Hotel and RV.

Top vacation rentals in Winter Park

Smart TV, DVD player, books, offices
5.0
Outstanding(101 Reviews)
Ideal Location, Charming 4 bedroom home w Lap Pool, fenced yard, month discounts
House
 in Winter Park
10 guests · 4 bedrooms · 2 baths
Garden · Pool · Pets allowed

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Winter Park, at $251 per night for your next great vacation.

$$$$
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Property building, On site
3.9
Good(428 Reviews)
Comfort Suites Downtown
Hotel
 in Orlando
3star
1 sofa bed, 2 full beds
Pool · Kitchen or Kitchenette · Air conditioner
Most favorited

Looking for the perfect place to call home during your trip to Winter Park? This Hotel offers a comfort and style with top-notch amenities, including Air conditioner, Internet / Wifi and Laundry, and more.

$$$$
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Balcony/Terrace
4.0
Good(355 Reviews)
Park Plaza Hotel Orlando - Winter Park
Hotel
 in Orlando
3star
1 queen bed
Garden · Pets allowed · Air conditioner

The best choice in Winter Park for Hotel, for $94 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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Bed, Bedroom
4.6
Outstanding(3 Reviews)
Winter Park charm
Bed and Breakfast
 in Orlando
Kitchen or Kitchenette · Air conditioner · Internet / Wifi

Looking for a Bed and Breakfast in Winter Park, this Bed and Breakfast for $94 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.

$$$$
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Search by amenity

Vacation rentals with air conditioning in Winter Park

Outdoor pool
4.9
Outstanding(98 Reviews)
Casa Winter Park
House
 in Winter Park
8 guests · 4 bedrooms · 4 baths
Garden · Pool · Pets allowed

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Winter Park, at $395 per night for your next great vacation.

$$$$
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WFH Friendly College Park Cottage in Orlando!
House
 in Orlando
Pets allowed · Kitchen or Kitchenette · Air conditioner

Indulge in a peaceful retreat at WFH Friendly College Park Cottage in Orlando!, our elegant House in Winter Park. Enjoy amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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Outdoor dining
5.0
Outstanding(67 Reviews)
Stylish Boutique Guest house in Historic Winter Park.
Apartment
 in Winter Park
4 guests · 3 bedrooms · 1 bath
Garden · Pool · Kitchen or Kitchenette

Nestled in Winter Park, this Apartment is perfect for your next vacation. Enjoy Stylish Boutique Guest house in Historic Winter Park. 's top-rated amenities, including Air conditioner, Fireplace and Internet / Wifi, and more.

$$$$
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Florida Vacation Rental about 6 Mi to Downtown Orlando
House
 in Orlando
Pets allowed · Kitchen or Kitchenette · Air conditioner

Experience the best of Winter Park with this House available for $94. This property is equipped with amenities including Air conditioner, Internet / Wifi and Laundry, and more.

$$$$
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Winter Park

Winter Park travel guide

Let us help you plan your perfect Winter Park vacation. Our travel guide highlights things to do, places to see, favorite vacation rental amenities in Winter Park, and more.

Frequently asked questions

What is the price range for rentals in Winter Park?

Vacation rentals in Winter Park have a price range between $65-$1,424. The average price for rentals in Winter Park is $180 per night.

What are the most popular vacation rental amenities in Winter Park?

  • Air conditioner
  • Internet / Wifi
  • Kitchen or Kitchenette

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