Winter Park Vacation Rentals

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Check prices for these dates

In two weeks
Mar 20 - Mar 22
In two months
May 1 - May 3
In three months
May 29 - May 31
In four months
Jun 26 - Jun 28

Our top choices for Winter Park vacation rentals

2 bedrooms, desk, free WiFi

The Front Porch

The Front Porch
3.0 star property
Sanford
9.4 out of 10, Exceptional, (3 reviews)
"Enjoyed the place. Nice and relaxing. Close to downtown and lots of options for food. "
United States
Johnny
The Front Porch
2 outdoor pools, open 8:00 AM to 10:00 PM, pool umbrellas, sun loungers

The Village Resort Suite and Spa

The Village Resort Suite and Spa
2.5 star property
Orlando
10.0 out of 10, Exceptional, (1 review)
"Everything was great. "
United States
Kelly
The price is NT$1,820
NT$13,213 total
includes taxes & fees
Mar 3 - Mar 4
The Village Resort Suite and Spa
6 outdoor pools, free cabanas, pool umbrellas

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
4.0 star property
Orlando
9.2 out of 10, Wonderful, (4,745 reviews)
"Beautiful property, clean and well maintained rooms, very nice staff."
United States
Debra
The price is NT$4,110
NT$4,623 total
includes taxes & fees
Mar 24 - Mar 25
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Standard Apartment | Living area | 50-inch LCD TV with digital channels, Netflix, streaming services

The Blue Aztec

The Blue Aztec
3.0 star property
Sanford
9.6 out of 10, Exceptional, (13 reviews)
"Great location! Great Dining! "
United States
Lisa
The Blue Aztec
Standard Apartment | Living area | 50-inch LED TV with digital channels, Netflix, streaming services

Boho Nights

Boho Nights
3.0 star property
Sanford
9.4 out of 10, Exceptional, (11 reviews)
"Wonderful spot, and excellent hosts!"
United States
Thomas
Boho Nights
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winter Park Hotel Reviews

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

10/10 Excellent
"Nice and complete amenities. Very clean and well taken care of property! Would definitely return!"
Dan 5-night trip
Posted 3 hours ago
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Find out more about Winter Park

Search for holiday rentals in Winter Park on Expedia! You can easily find your home rentals, villas, holiday apartments in Winter Park using one of the methods below:

  • View our selection of featured holiday rentals in Winter Park
  • Use the map to find apartments and other holiday homes in the Winter Park neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winter Park while they last

Look no further and take a look at our great range of rental properties in Winter Park!

Frequently asked questions

Can I find vacation rentals in Winter Park?

Yes, we offer vacation rentals in Winter Park close to Kraft Azalea Gardens, or you can choose a more secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and shops in Winter Park. Make sure you have time to check out the university setting and gardens during your trip.

How many vacation rentals are there in Winter Park?

Expedia has 44 vacation rentals for your stay in Winter Park.

What can I see and do in Winter Park?

Cultural attractions include Morse Museum of American Art and Casa Feliz Historic Home Museum, whereas Kraft Azalea Gardens and Lake Virginia are a couple of picturesque spots to enjoy the outdoors. Universal Studios Florida and Universal Orlando Resort are other popular places to visit in the area.

What are vacation rentals like in Winter Park?

Vacation rentals are privately owned accommodations you can stay in for several days or more in Winter Park. Vacation rentals offer extras such as patios, hot tubs, and fire pits to help you enjoy your stay. If you're concerned about cleanliness, vacation rentals can provide a sense of safety away from public hotel elevators and lobbies packed with people while still allowing you to travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great option for a small group gathering.