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

Standard Room, 1 King Bed, Non Smoking, Refrigerator & Microwave | Premium bedding, in-room safe, desk, laptop workspace

Best Western Orlando Gateway Hotel

Best Western Orlando Gateway Hotel
3.0 star property
Florida Center
8.0 out of 10, Very Good, (2,466 reviews)
"Very good hotel, very clean and affordable!!"
United States
Luz
The price is NT$2,496
NT$3,341 total
includes taxes & fees
Mar 4 - Mar 5
Best Western Orlando Gateway Hotel
Restaurant

The View Studio Suites and Event Venue

The View Studio Suites and Event Venue
3.0 star property
Orlando
8.4 out of 10, Very Good, (1,709 reviews)
"Clean and spacious rooms and the breakfast was great."
United States
Karen
The price is NT$2,678
NT$3,013 total
includes taxes & fees
Mar 10 - Mar 11
The View Studio Suites and Event Venue
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
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
House (2 Bedrooms) | Interior

Deltona Lake House, Day Trip to Disney & Universal

Deltona Lake House, Day Trip to Disney & Universal
3.0 star property
Deltona Lakes
10.0 out of 10, Exceptional, (3 reviews)
"This house was perfect! Very spacious, clean, and felt like a very safe neighborhood for a few women traveling. The ONLY improvements I would suggest would be having more towels, and extra blankets available for guests. And I would replace the pull out couch mattress as it was very uncomfortable. Still a 10/10 overall!"
United States
Anonymous traveler
The price is NT$4,287
NT$10,678 total
includes taxes & fees
Mar 8 - Mar 9
Deltona Lake House, Day Trip to Disney & Universal
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
2 outdoor pools

Storey Lake condos by UNE Homes

Storey Lake condos by UNE Homes
3.5 star property
Kissimmee
8.0 out of 10, Very Good, (5 reviews)
"Location, location, location. It was a great location. It was clean, and everything went smoothly."
United States
Carrie
The price is NT$4,791
NT$12,056 total
includes taxes & fees
Mar 4 - Mar 5
Storey Lake condos by UNE Homes
Reception

Florida Hotel & Conference Center in the Florida Mall

Florida Hotel & Conference Center in the Florida Mall
3.5 star property
Orlando
9.2 out of 10, Wonderful, (2,517 reviews)
"The whole stay was fantastic!!"
United States
Kristen
Florida Hotel & Conference Center in the Florida Mall
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

Rosen Inn Lake Buena Vista

Rosen Inn Lake Buena Vista

10/10 Excellent
"A wonderful clean affordable hotel next to Disney Springs "
Jessi 2-night trip
Posted 11 hours ago
Rosen Inn Lake Buena Vista

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.