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Vacation Rentals

Winter Park Vacation Rentals

Rentals Available: 28
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Cute Guest House In Winter Park Minutes From Downtown in Car Vacation Studio Rental
Rental PropertyRental PropertyRental PropertyRental Property
Rates - Per Rental Property (USD)
$99.00/per night
Winter Park, Studio
1 Bedrooms, Sleeps 2
1 Full Baths, 0 Half Baths
Minimum Stay: 3 Days
By: VRBO
Winter Park Home With Hints Of Florida Keys And Lovely Pool Oasis Vacation Bungalow Rental
Rental PropertyRental PropertyRental PropertyRental Property
Rates - Per Rental Property (USD)
$100.00/per night
Winter Park, Bungalow
2 Bedrooms, Sleeps 3
1 Full Baths, 0 Half Baths
Minimum Stay: 3 Days
By: VRBO
Casa Justine - Upscale Winter Park Home \ Elegant Living Room, Great Pool Vacation House Rental
Rental PropertyRental PropertyRental PropertyRental Property
Rates - Per Rental Property (USD)
$300.00/per night
Winter Park, House
3 Bedrooms, Sleeps 9
3 Full Baths, 0 Half Baths
Minimum Stay: 2 Days
By: VRBO
Charming Clean Home Vacation House Rental
Rental PropertyRental PropertyRental PropertyRental Property
Rates - Per Rental Property (USD)
$375.00/per night
Winter Park, House
0 Bedrooms, Sleeps 6
1 Full Baths, 0 Half Baths
Minimum Stay: 2 Days
By: VRBO
Gorgeous Home*Great Location*Grill*Free WiFi*AC*Baby Equipment*Pet-Friendly/dog Vacation House Rental
Rental PropertyRental PropertyRental PropertyRental Property
Rates - Per Rental Property (USD)
$309.00/per night
Maitland, House
3 Bedrooms, Sleeps 8
2 Full Baths, 0 Half Baths
Minimum Stay: 3 Days
By: VRBO
Casa Aloma - Elegant Winter Park House with Great Pool and Huge Backyard!! Vacation House Rental
Rental PropertyRental PropertyRental PropertyRental Property
Rates - Per Rental Property (USD)
$300.00/per night
Winter Park, House
3 Bedrooms, Sleeps 8
3 Full Baths, 0 Half Baths
Minimum Stay: 2 Days
By: VRBO
Beautiful home in the heart of Winter Park, Only two doors away from Park Ave. Vacation House Rental
Rental PropertyRental PropertyRental PropertyRental Property
Rates - Per Rental Property (USD)
$250.00/per night
Winter Park, House
3 Bedrooms, Sleeps 8
2 Full Baths, 0 Half Baths
Minimum Stay: 4 Days
By: VRBO
Casa Citrus - Perfect Location with Modern Luxuries !! Vacation House Rental
Rental PropertyRental PropertyRental PropertyRental Property
Rates - Per Rental Property (USD)
$300.00/per night
Orlando, House
3 Bedrooms, Sleeps 9
4 Full Baths, 1 Half Baths
Minimum Stay: 2 Days
By: VRBO
House Rental
Rates - Per Rental Property (USD)
$1,150.00/per week
Charentes Maritimes, Poitou Charentes House
4 Bedrooms, Sleeps 8
3 Full Baths, 0 Half Baths
By: VRBO
A Rare Jewel - Steps to Park Ave, Shops, Restaurants, Rollins college, Farmers m Vacation House Rental
Rental PropertyRental PropertyRental PropertyRental Property
Rates - Per Rental Property (USD)
$100.00/per night
Winter Park, House
3 Bedrooms, Sleeps 6
2 Full Baths, 0 Half Baths
Minimum Stay: 3 Days
By: VRBO
Apartment Guarujá - Pitangueiras, side view of the sea Vacation Apartment Rental
Rates - Per Rental Property (BRL)
$100.00/per night
Guarujá, Apartment
3 Bedrooms, Sleeps 10
3 Full Baths, 0 Half Baths
Minimum Stay: 2 Days
By: VRBO
House Rental
Rental PropertyRental PropertyRental PropertyRental Property
Rates - Per Rental Property (USD)
$798.00/per week
Winter Park, House
4 Bedrooms, Sleeps 6
3 Full Baths, 0 Half Baths
Minimum Stay: 3 Days
By: TripAdvisor
Guest House Rental
Rental PropertyRental PropertyRental PropertyRental Property
Rates - Per Rental Property (USD)
$553.00/per week
Winter Park, Guest House
1 Bedrooms, Sleeps 2
1 Full Baths, 0 Half Baths
Minimum Stay: 3 Days
By: TripAdvisor
Guest House Rental
Rental PropertyRental PropertyRental PropertyRental Property
Rates - Per Rental Property (USD)
$315.00/per week
Winter Park, Guest House
1 Bedrooms, Sleeps 3
1 Full Baths, 0 Half Baths
By: TripAdvisor
House Rental
Rental PropertyRental PropertyRental PropertyRental Property
Rates - Per Rental Property (USD)
$434.00/per week
Winter Park, House
1 Bedrooms, Sleeps 2
1 Full Baths, 0 Half Baths
Minimum Stay: 2 Days
By: TripAdvisor
House Rental
Rental PropertyRental PropertyRental PropertyRental Property
Rates - Per Rental Property (USD)
$434.00/per week
Winter Park, House
1 Bedrooms, Sleeps 2
1 Full Baths, 0 Half Baths
Minimum Stay: 2 Days
By: TripAdvisor
House Rental
Rental PropertyRental PropertyRental PropertyRental Property
Rates - Per Rental Property (USD)
$434.00/per week
Winter Park, House
1 Bedrooms, Sleeps 2
1 Full Baths, 0 Half Baths
Minimum Stay: 2 Days
By: TripAdvisor
House Rental
Rental PropertyRental PropertyRental PropertyRental Property
Rates - Per Rental Property (USD)
$700.00/per week
Winter Park, House
2 Bedrooms, Sleeps 5
2 Full Baths, 0 Half Baths
Minimum Stay: 7 Days
By: TripAdvisor
Condo Rental
Rental PropertyRental PropertyRental PropertyRental Property
Rates - Per Rental Property (USD)
$693.00/per week
Winter Park, Condo
1 Bedrooms, Sleeps 4
1 Full Baths, 0 Half Baths
By: TripAdvisor
Villa Rental
Rental PropertyRental PropertyRental PropertyRental Property
Rates - Per Rental Property (USD)
$3,997.00/per week
Winter Park, Villa
4 Bedrooms, Sleeps 8
4 Full Baths, 0 Half Baths
Minimum Stay: 3 Days
By: TripAdvisor
House Rental
Rental PropertyRental PropertyRental PropertyRental Property
Rates - Per Rental Property (USD)
$455.00/per week
Winter Park, House
1 Bedrooms, Sleeps 2
1 Full Baths, 0 Half Baths
Minimum Stay: 3 Days
By: TripAdvisor
Cottage Rental
Rental PropertyRental PropertyRental PropertyRental Property
Rates - Per Rental Property (USD)
$413.00/per week
Winter Park, Cottage
1 Bedrooms, Sleeps 4
1 Full Baths, 0 Half Baths
By: TripAdvisor
House Rental
Rental PropertyRental PropertyRental PropertyRental Property
Rates - Per Rental Property (USD)
$455.00/per week
Winter Park, House
1 Bedrooms, Sleeps 2
1 Full Baths, 0 Half Baths
Minimum Stay: 3 Days
By: TripAdvisor
House Rental
Rental PropertyRental PropertyRental PropertyRental Property
Rates - Per Rental Property (USD)
$2,450.00/per week
Winter Park, House
8 Bedrooms, Sleeps 18
5 Full Baths, 0 Half Baths
Minimum Stay: 5 Days
By: TripAdvisor
House Rental
Rental PropertyRental PropertyRental PropertyRental Property
Rates - Per Rental Property (USD)
$2,450.00/per week
Winter Park, House
8 Bedrooms, Sleeps 18
5 Full Baths, 0 Half Baths
Minimum Stay: 5 Days
By: TripAdvisor
House Rental
Rental PropertyRental PropertyRental PropertyRental Property
Rates - Per Rental Property (USD)
$2,450.00/per week
Winter Park, House
8 Bedrooms, Sleeps 17
5 Full Baths, 0 Half Baths
Minimum Stay: 5 Days
By: TripAdvisor
House Rental
Rental PropertyRental PropertyRental PropertyRental Property
Rates - Per Rental Property (USD)
$2,450.00/per week
Winter Park, House
3 Bedrooms, Sleeps 6
1 Full Baths, 0 Half Baths
Minimum Stay: 3 Days
By: TripAdvisor
Apartment Rental
Rental PropertyRental PropertyRental PropertyRental Property
Rates - Per Rental Property (USD)
$840.00/per month
Winter Park, Apartment
1 Bedrooms, Sleeps 4
1 Full Baths, 0 Half Baths
Minimum Stay: 30 Days
By: TripAdvisor
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Winter Park Vacation Rentals

Winter Park Vacation Rentals


Are you searching for an exciting escape from everyday life? Winter Park is the perfect vacation destination for you and your significant other. There are many rentals ranging from homes to cabins that are available for your trip to Winter Park. As one of the most sought-after vacation destinations, it's no wonder that Winter Park has some of the most fantastic rental properties available.

Winter Park Local Activities

The local activities will change depending on the Winter Park rental property you choose, but there is never short of something fun or relaxing to do here! Be sure to check your Winter Park rental property details to make sure they have the things that you like to do. You will have so much fun taking part in all of these activities that you won't want to leave!

Winter Park Nearby Activities

Depending on the season that you travel to Winter Park, you will most likely be able to take advantage of many of the most popular nearby attractions as well as other nearby activities. Whether you are renting a home, cabin or condo, all of these different events will tempt you to extend your stay!

How To Choose A Winter Park Vacation Rental


If you are considering Winter Park as your vacation destination of choice, below are some tips to help you get the perfect vacation rental for you.

You Started Off Right

You started off right by coming to VacaGuru.com to find your Winter Park destination. Because we are directly connected with rental owners, you are often saving 10%-40% over the price offered through a Winter Park real estate agency or property management firm.

What Amenities Do You Want

We suggest that you create a list of amenities that you desire to have in or around your Winter Park vacation rental. This will help you to determine the best place for you while you are browsing our site. We list all of the amenities for each Winter Park property so you can easily find the perfect place for you and your family. You may not always be able to find every amenity that you want in a vacation cabin, so be sure to put a priority on those amenities; this will save you time and money in your search.

Look At Multiple Photos

Each Winter Park listing contains interior and exterior photos of the specific rental. Take a close look at the pictures to make sure it is exactly what you expect of the place. Check for quality and cleanliness as well as the outside environment to ensure that everything is what you expect.

Read The Winter Park Reviews On Property

One of the main things that we suggest to people before they travel to a Winter Park location is to check available reviews. This can tell you whether prior guests had a good time or if it is somewhere they would never return. These reviews can help you to not only decide on a Winter Park vacation property, but they can also help you create a list on what to do when you get there.

Making The Decision And Planning

After you have found the perfect Winter Park rental for you and have done your research on the property, you are ready to make your decision and get ready for your vacation. Be sure to pack all of the essentials, and have a great time at Winter Park!
We have 28 Winter Park Rentals
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