Choose from 162 vacation rentals located in Winter Park, Florida. Top filters in Winter Park include Air conditioner, Internet / Wifi, and Kitchen / Kitchenette. Prices range from $81 to $656 per night. Our most popular vacation rental types near Winter Park are Hotel and RV.

Top vacation rentals in Winter Park

Full size lap pool well maintained. 6 ft privacy fence complete seclusion.
4.9
Outstanding(95 Reviews)
House
 in Winter Park
Ideal Location, Charming Home, Specious Full Lap Pool!
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 $544 per night for your next great vacation.

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3.9
Good(442 Reviews)
Hotel
 in Orlando
3star
Comfort Suites Downtown
Pool · Kitchen / Kitchenette · Air conditioner

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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4.0
Good(368 Reviews)
Hotel
 in Orlando
3star
Park Plaza Hotel Orlando - Winter Park
Garden · Pets allowed · Air conditioner

The best choice in Winter Park for Hotel, for $291 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

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4.6
Outstanding(8 Reviews)
Bed and Breakfast
 in Orlando
Winter Park charm
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

Looking for a Bed and Breakfast in Winter Park, this Bed and Breakfast for $144 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

Entrance to home.
4.9
Outstanding(34 Reviews)
House
 in Winter Park
Family Friendly
5 guests · 3 bedrooms · 2 baths
Garden · Pool · Kitchen / Kitchenette

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

$$$$
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Room
4.8
Outstanding(39 Reviews)
House
 in Winter Park
Winter Park charm. Close to Park Ave
4 guests · 2 bedrooms · 1 bath
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

This House for $138 in Winter Park, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

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Property grounds
4.7
Outstanding(52 Reviews)
House
 in Orlando
Private Luxury Pool / Smart-home
8 guests · 3 bedrooms · 3 baths
Pool · Pets allowed · Kitchen / Kitchenette

Discover the beauty of Winter Park with a stay at Private Luxury Pool / Smart-home, a top rated House with amenities such as Air conditioner, Dishwasher and Fireplace, and more.

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House
 in Orlando
Orlando Vacation Rental Less Than 2 Mi to Lake Ivanhoe!
Pets allowed · Kitchen / Kitchenette · Air conditioner

Indulge in a peaceful retreat at Orlando Vacation Rental Less Than 2 Mi to Lake Ivanhoe!, our elegant House in Winter Park. Enjoy amenities including Air conditioner, Dishwasher and Internet / Wifi, 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 $81-$656. The average price for rentals in Winter Park is $149 per night.

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

  • Air conditioner
  • Internet / Wifi
  • Kitchen / Kitchenette

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