Winter Park, Florida offers beautiful vacation homes in the greater Orlando area. The most common of these are fully equipped condos with decks, gardens, and all the amenities you could ask for. There are also lavish villas available, near the sea or within the city center. Another option for your upcoming vacation are expansive vacation homes with multiple bedrooms, bathrooms, and backyards.

Choose the perfect vacation rental
Best Vacation Home Deals in Winter Park
Discover a vacation rental that meets your criteria among the 201 beautiful accommodations from numerous partner websites in Winter Park. HomeToGo immediately features the best offers by comparing all of the listed vacation rentals in Winter Park from 5 different providers.
Top-Rated Rentals and Accommodations in Winter Park
Recommended Vacation Rentals in Winter Park
Find your perfect vacation rental in Winter Park: from $63 per night
Budget-friendly Vacation Rentals in Winter Park
Vacation rentals with Wi-Fi
Stay connected while traveling and book a Winter Park accommodation with high-speed internet.
Vacation rentals and apartments with air conditioning
Keep cool during your trip to Winter Park and book a vacation rental with air conditioning.
Apartments and vacation rentals with a kitchen
Cook up a feast on your next vacation and book a Winter Park rental with full kitchen.
Popular Rental Amenities in Winter Park
The Weather in Winter Park
Check out the climate diagram for Winter Park. July is the warmest month of the year in Winter Park with temperatures reaching a maximum average of 91°. No heat wave is expected in January, where minimum average temperatures usally hit a 54° low. The rainiest month is August while the driest month is November.
7-Day Weather Forecast in Winter Park
Accommodations for your vacation in Winter Park
Information about vacation rentals in Winter Park
🏡 Vacation rentals | 201 properties |
---|---|
💳 Possible discounts | up to 21% |
🌙 Nightly prices starting at | $63 |
⭐ Popular amenities | Internet, Air conditioning and TV |
🐾 Pet friendly accommodations | 57 properties |
🏊 Vacation rentals with pools | 69 properties |
Frequently Asked Questions
What is the average price per night for a vacation home in Winter Park?
The average accommodation in Winter Park is priced at $63 per night. If you’re interested in a house rental, the average price is $285 per night. A apartment rental Winter Park will cost $221 per night on average.
How many vacation rentals are available to book in Winter Park?
Currently there are 201 vacation rentals in Winter Park to browse and rent for your trip.
What amenities are most popular for vacation rentals in Winter Park?
Three most popular amenities for home rentals in Winter Park include accommodations with: Internet, Air conditioning, and TV.
Are dogs allowed in vacation homes in Winter Park?
Sure, there are 57 vacation rentals in Winter Park that allow pets , with an average nightly rate of $299.
What are the best months to travel to Winter Park ?
If booking a vacation rental in Winter Park, keep in mind that rainy season is usually in August or June, with November often being the driest.
We list offers from thousands of providers, including:











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