Winter Park Highlands holiday rentals

We found 42 holiday rentals — enter your dates for availability

Discover a selection of 26 homes and other holiday rentals in Winter Park Highlands that are perfect for your trip. Whether you’re staying in a holiday home with family or friends, you'll have the best amenities for spending time at your home away from home, which might include a pool and a washer and dryer. At the end of the day, you'll be sure to find a property to rent that has what everyone needs, including accessible or non-smoking choices.

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

What is the most popular type of holiday home accommodation in Winter Park Highlands?
Houses are the most popular kind of holiday home in Winter Park Highlands, according to our data. Even if you have something else in mind, Stayz has properties in a variety of shapes and sizes. Browse our options to find your perfect fit.
How much does it cost to rent a holiday home in Winter Park Highlands?
Several factors influence how much you'll pay for a holiday home in Winter Park Highlands, including the length of stay, season and type of property. Still, all of our holiday homes have one thing in common — exceptional value. Simply add your travel dates to find your perfect match.
How much does it cost to rent a beach house in Winter Park Highlands?
The average price for a holiday home near the beach in Winter Park Highlands depends on when you're visiting the area and the type and size of property you're looking for. Find prices quickly and easily on Stayz by entering your dates of travel. Then make use of the filter tool to pick the number of bedrooms and amenities important to you, such as WiFi, a pool and air conditioning.
Are there pet-friendly holiday homes in Winter Park Highlands?
Good news! Yes. You can pick from 24 holiday homes that cater to pets in Winter Park Highlands. Some of our pet-friendly holiday homes even come with an area outdoors for your four-legged fur baby to have fun in, special dog beds, complimentary treats and proximity to parks or green space. Apply the "Pets allowed" filter to find your pawfect holiday home on Stayz.
Can I rent a house with a pool in Winter Park Highlands?
Dig out your swimsuit and swim ring, because there are five houses with a private pool in Winter Park Highlands. Base yourself at one of these terrific holiday homes and enjoy a pool day every day. Simply enter your travel dates into Stayz, then use the "pool" filter to find the perfect place for a splashing good time!
What are popular home amenities in Winter Park Highlands?
Some of the most popular home amenities people search for in Winter Park Highlands include an electric car charging station, a nearby river and a sauna. Whether you're going on holiday with family, friends or even pets, Stayz holiday properties include the best amenities for hanging out with the people that matter most.
Are there large group holiday homes in Winter Park Highlands?
Choose from 17 holiday homes in Winter Park Highlands that can host a group of 10 or more guests. Whether you're organising a trip with the family or a celebration like a birthday, there's plenty of space to get your group together under one roof.
Are there holiday homes in Winter Park Highlands that welcome kids?
Winter Park Highlands has 24 family-friendly holiday homes. And securing a stay that welcomes kiddos is a cinch with Stayz's "Properties good for families" filter. As well as having the whole place to yourselves, you'll also enjoy access to perks and conveniences such as living rooms, kitchens and yards.
What are the top attractions for families in Winter Park Highlands?
If you're looking for something entertaining for the family near the heart of Winter Park Highlands, check out Pole Creek Golf Club.
Are there holiday homes with WiFi in Winter Park Highlands?
Whether you want to keep up with the headlines, send a few emails or surf social media, there are 11 holiday homes with WiFi in Winter Park Highlands. Check the "WiFi" box when searching on Stayz and stay connected on your holiday.
How old do you have to be to rent a holiday home in Winter Park Highlands?
The minimum required age is generally 16, 18 or 21. It can vary between properties on Stayz, so look at the rules of your preferred Winter Park Highlands holiday home before booking your stay.
How long can I rent a holiday home in Winter Park Highlands for?
It's really down to the Winter Park Highlands property. To browse available options offering extended stays, simply type your dates and number of people into Stayz. Enjoy having the property to yourself, along with home comforts such as a fully-equipped kitchen and a yard where your little ones can play. Keep your eyes open for any long-term stays that offer discounted weekly or monthly prices.

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