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 160 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 $65 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
Filters are available to help you tailor your search and find a great vacation rental in Winter Park. Winter Park is the perfect destination to book a property if you can't imagine a vacation without internet or you never miss an episode of your favorite show, as the most frequently offered features are "Internet" and "TV." Not as many rentals in Winter Park are available if you like to end your days curled up by the fire or if you want a rental with a balcony or a patio as "Balcony/Patio" and "Fireplace" are not very popular 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
Fine dining and cheap local eateries
Look no further than the scenic Park Avenue district to be spoiled for choice when it comes to dining. One of the most highly reviewed restaurants in the Winter Park area remains Hillstone Restaurant. Their rotisserie chicken is particularly appealing, as is their plethora of appetizer options. Luma on Park is another fine choice for a seasonally-based menu with fine wines. If you are looking for a great steakhouse, be sure to visit Fleming's Prime Steakhouse & Wine Bar. One of the best burger joints in Winter Park is BurgerFi. Other spots of interest include the Black Bean Deli, Toasted, and the Dandelion Communitea Cafe.
Winter Park: historic and interesting sites
The Charles Hosmer Morse Museum of American Art is full of timely pieces both classic and modern. To encounter art outdoors, check out the Albin Polasek Museum & Sculpture Gardens. Cornell Fine Arts Museum offers more sophisticated art to enjoy. If you want to be immersed in Winter Park's history and culture, stop by the Winter Park Historical Museum, Casa Feliz Historic Home Museum, and the Hannibal Square Heritage Center.
Tons of fun for families, too
Kids will love the Saturday Farmer's Market in Winter Park, where you can buy vegetables directly from growers, or eat some freshly-popped popcorn. Right on Orlando's doorstep, Winter Park is also within reach of Orlando's Airheads Trampoline Arena, as well as the world-famous DIsney World. Another popular destination for families is the Petting Farm at Green Meadows Farm.
Frequently Asked Questions
How much does it cost to rent a vacation rental in Winter Park?
The price for House rental and Apartment rental in Winter Park is $65 per night.
How many vacation rentals are available to book in Winter Park?
November has the highest amount of available House rental and Apartment rental in Winter Park, so you can expect plenty of offers, even for last-minute bookings.
What amenities are most popular for vacation homes in Winter Park?
If you're looking to book a vacation rental in Winter Park, the most common amenities others search for are houses with Internet, TV, and Yard.
How many vacation rentals are in Winter Park?
Discover 160 vacation rentals available to book in Winter Park.
Are pets allowed in vacation rentals in Winter Park?
Yes, there are 46 vacation homes in Winter Park that allow pets, with an average price of $350 per night.
What's the best time of year to travel to Winter Park ?
July and August are typically the warmest months in Winter Park with temperatures around 91 °F. January and February in Winter Park are the coldest, with 54 °F on average.
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