Winter Park house rentals

We found 1,036 house rentals — enter your dates for availability

Find spaces that suit your style

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  • 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

Are there any holiday home rentals in Winter Park?
Book one of our 1,036 holiday home rentals in Winter Park and you'll have the ideal base for your next adventure. Aloma, Orwin Manor and Rose Isle are some of the city's most sought-after areas.
How much does it cost to stay in a holiday rental house in Winter Park?
Whether you're booking a budget-friendly getaway or an upscale retreat, we have a range of holiday home rentals in Winter Park for you to choose from. Use our filters to narrow down your options and find the right stay to suit your needs.
When is the best time to rent a holiday house in Winter Park?
Consider visiting Winter Park in July, when the average temperature ranges between 25ºC and 33ºC. This is the most popular month for guests to get a holiday home rental in this well-known destination, which is located in North Orlando.
Where can I rent a Winter Park holiday house with great views?
When looking for your holiday home rental in Winter Park, take advantage of our "Location" filter. This will help you choose the types of areas you prefer to stay in, whether that's far from the hustle and bustle or somewhere close to the action.
Does Winter Park have any weekend house rentals?
Browse our weekend rentals and get packing for a fun-filled few days away. Our tips for booking your ideal house in Winter Park? Be flexible when searching and change your dates until you find the holiday home rental that suits your style.
Are there any pet-friendly house rentals in Winter Park?
Yes, you'll find nine holiday home rentals that welcome pets in Winter Park, so your four-legged companion won't miss out on the excitement! Use our filter tool to search for pet-friendly houses that come with perks like dog beds and complimentary treats for them, and lots of comforts for you.
What are the top things to do in Winter Park?
Universal Studios Florida, Florida Mall and Universal's Islands of Adventure are terrific attractions that'll keep the whole crew occupied in Winter Park. There's nothing like travel to bring everyone together, so browse our holiday home rentals in this vibrant destination.
Why should I book my holiday rental house with Stayz?
From houses by the oceanfront to those located downtown, Stayz has a wide variety of holiday home rentals to select from. One of the many great reasons to book with us? You'll never have to share your place with the owner or anyone else. And with flexible cancellation policies and support throughout your trip, we'll ensure everything goes smoothly.