Winter Park Vacation Rentals

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Check prices for these dates

In two weeks
Jun 19 - Jun 21
In two months
Jul 31 - Aug 2
In three months
Aug 28 - Aug 30
In four months
Sep 25 - Sep 27

Our top choices for Winter Park vacation rentals

Exterior

Hilton Vacation Club Grand Beach Orlando

Hilton Vacation Club Grand Beach Orlando
3.0 star property
Orlando
9.4 out of 10, Exceptional, (1,535 reviews)
"Great resort!!"
United States
Nathaniel
The price is P6,174
P8,682 total
includes taxes & fees
Jun 9 - Jun 10
Hilton Vacation Club Grand Beach Orlando
Exterior

The Jazz Loft

The Jazz Loft
3.0 star property
Sanford
8.6 out of 10, Excellent, (8 reviews)
"Location, location, location!!! What a cute and fun space. I thoroughly enjoyed my entire Jazz Loft experience. Look fwd to next trip! "
United States
Deborah
The price is P4,445
P9,127 total
includes taxes & fees
Jun 8 - Jun 9
The Jazz Loft
Interior

Bella Breeze

Bella Breeze
2.5 star property
Sanford
9.8 out of 10, Exceptional, (15 reviews)
"Great location for restaurants and river trail. Very well stocked so it is an easy and comfortable stay."
United States
Nancy
The price is P4,441
P9,118 total
includes taxes & fees
Jun 7 - Jun 8
Bella Breeze
Living area

Boho Nights

Boho Nights
3.0 star property
Sanford
9.6 out of 10, Exceptional, (15 reviews)
"Great location very clean awesome decor "
United States
Heather
The price is P4,445
P9,127 total
includes taxes & fees
Jun 5 - Jun 6
Boho Nights
Living area

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 price is P4,723
P14,069 total
includes taxes & fees
Jun 27 - Jun 28
The Blue Aztec
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

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

10/10 Excellent
"We had a deluxe villa and it had everything we needed for a comfortable stay. The staff was very attentive and the location was great. Wholefoods and Walmart was a short drive away from the resort. Would definitely stay there again in the future."
Gregoria 3-night trip
Posted less than an hour ago
Westgate Lakes Resort & Spa Universal Studios Area

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 54 vacation rentals for your stay in Winter Park.

What can I see and do in Winter Park?

Cultural attractions include Rollins Museum of Art and Morse Museum of American Art, whereas Lake Virginia and Mead Garden are a couple of picturesque spots to enjoy the outdoors. Kia Center and Universal Studios Florida 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.