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.

Recommended vacation rentals in Winter Park
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Explore the 224 offers listed in Winter Park and find a welcoming spot for a relaxing vacation. By directly analyzing these vacation rentals, HomeToGo highlights the most economical offers and the most popular vacation homes in Winter Park.
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Popular Rental Amenities in Winter Park
Finding a rental with a pool is easy in Winter Park. One-third of the accommodations offer pools. Also, more House rental have pools than any other type of property. They are a great choice if you go in a group of 9, as that is the number of people they can accommodate on average. Among these vacation rentals, 57 of them are within 2 miles of water.
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.
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.
Information about vacation rentals in Winter Park
🏡 Vacation rentals available | 224 rentals |
---|---|
💳 Possible discounts | up to 75% |
🌙 Nightly prices starting at | $56 |
⭐ Popular amenities | Pool, Pets allowed and Internet |
🐾 Pet friendly homes | 100 homes |
🏊 Vacation rentals with pools | 72 homes |
Frequently Asked Questions
What is the average nightly price for a vacation rental in Winter Park?
The price of a night's stay in Winter Park starts at $56. $263 is the average nightly price for house rentals in Winter Park. Apartment rentals in Winter Park cost $201 per night on average.
How many vacation rentals are available for booking in Winter Park?
There are currently 224 vacation rentals to choose from for your upcoming trip.
What amenities are most popular for vacation rentals in Winter Park?
If you're looking to book a vacation rental in Winter Park, others search for homes with Pool, Pets allowed and Internet.
How many vacation rentals with pools are there in Winter Park?
Winter Park has 72 Hotel room and Apartment rental options on offer to book.
Are pets allowed in vacation homes in Winter Park?
In case if you are traveling with a pet in Winter Park - 45% of vacation homes are pet-friendly.
When is it better to travel to Winter Park ?
Winter Park has its warmest time of year around July and August, with average nightly prices being around $56.
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