Winter Park Vacation Rentals

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Check prices for these dates

In two weeks
Jan 30 - Feb 1
In two months
Mar 13 - Mar 15
In three months
Apr 10 - Apr 12
In four months
May 8 - May 10

Our top choices for Winter Park vacation rentals

Terrace/patio

Aparthotel in Florida Center

The Point by Edge
4.0 star property
8.4 out of 10, Very Good, (848 reviews)
"Awesome and clean place to stay for the holidays"
United States
Moses
The price is NT$1,595
NT$2,185 total
includes taxes & fees
Jan 28 - Jan 29
The Point by Edge
Restaurant

Aparthotel in Orlando

The View Studio Suites and Event Venue
3.0 star property
8.4 out of 10, Very Good, (1,549 reviews)
"Clean and spacious rooms and the breakfast was great."
United States
Karen
The price is NT$2,705
NT$3,043 total
includes taxes & fees
Jan 18 - Jan 19
The View Studio Suites and Event Venue
Suite, 2 Bedrooms | Balcony view

Condo resort in International Drive District

Floridays Resort Orlando
3.5 star property
8.6 out of 10, Excellent, (11,677 reviews)
"Great place to stay"
United States
Ana
Floridays Resort Orlando
Exterior

Aparthotel in Orlando

WorldQuest Orlando Resort
4.0 star property
8.4 out of 10, Very Good, (4,036 reviews)
"No complaints, wonderful resort. "
United States
Nigel
WorldQuest Orlando Resort
Standard Apartment | Living area | 50-inch LCD TV with digital channels, Netflix, streaming services

Apartment in Sanford

The Blue Aztec
3.0 star property
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

Apartment in Sanford

Boho Nights
3.0 star property
9.0 out of 10, Wonderful, (8 reviews)
"Wonderful spot, and excellent hosts!"
United States
Thomas
Boho Nights
Reception

Aparthotel in Orlando

Florida Hotel & Conference Center in the Florida Mall
3.5 star property
9.2 out of 10, Wonderful, (2,434 reviews)
"Friendly staff and great accommodations "
United States
jose
Florida Hotel & Conference Center in the Florida Mall
Interior

Apartment in Sanford

Bella Breeze
2.5 star property
9.6 out of 10, Exceptional, (5 reviews)
"The place was clean, cozy, and well decorated, and the amenities were wonderful! The hosts have done a great job here."
United States
Courteny
Bella Breeze
Exterior

Apartment in Sanford

The Jazz Loft
3.0 star property
8.0 out of 10, Very Good, (6 reviews)
"The loft was very cool and unique. Loved it. I will definitely book this again."
United States
sherri
The Jazz Loft
50-inch Smart TV with digital channels

Aparthotel in Kissimmee

Enchanted Dreams
3.5 star property
7.0 out of 10, Good, (8 reviews)
"Very relaxing space. Clean environment. Coming back very soon "
United States
Tanish
The price is NT$1,883
NT$4,291 total
includes taxes & fees
Jan 15 - Jan 16
Enchanted Dreams
Bar (on property)

Condo resort in Florida Center

Premier Resort Condos Near Universal
3.0 star property
9.0 out of 10, Wonderful, (4 reviews)
"Great"
United States
Russell
The price is NT$2,819
NT$5,841 total
includes taxes & fees
Jan 28 - Jan 29
Premier Resort Condos Near Universal
2 bedrooms, desk, free WiFi

Apartment in Sanford

The Front Porch
3.0 star property
10.0 out of 10, Exceptional, (2 reviews)
"What a great space. 2 big bedrooms, and a great front porch apace with a hammock to watch the sunrise. Quite street just blocks from the center of downtown Sanford. I've used their properties 8-10 tines and ive never been disappointed. "
United States
Patrick
The Front Porch
Interior

Apartment in Sanford

Totally 80's
3.0 star property
9.4 out of 10, Exceptional, (3 reviews)
"Cute, clean, and comfortable. Located in a safe neighborhood, the house had everything we needed for a great stay. Communication was timely and smooth—highly recommend."
United States
Serge
The price is NT$2,531
NT$4,961 total
includes taxes & fees
Jan 15 - Jan 16
Totally 80's
House (2 Bedrooms) | Interior

Cottage in Deltona Lakes

Deltona Lake House, Day Trip to Disney & Universal
3.0 star property
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$4,303
NT$10,719 total
includes taxes & fees
Jan 19 - Jan 20
Deltona Lake House, Day Trip to Disney & Universal
Outdoor pool, open 7:00 AM to 11:00 PM, pool umbrellas, sun loungers

Vacation Home in Orlando

Marriott's Sabal Palms
4.0 star property
9.6 out of 10, Exceptional, (211 reviews)
"Room was great, staff friendly and grounds are clean. "
United States
DENNIS
The price is NT$10,327
NT$11,618 total
includes taxes & fees
Jan 24 - Jan 25
Marriott's Sabal Palms
Fountain

Vacation Home in Orlando

Vista Cay Resort by Casiola Vacation Homes
3.5 star property
8.8 out of 10, Excellent, (183 reviews)
"Nice place, comfortable. "
United States
John
The price is NT$5,301
NT$13,549 total
includes taxes & fees
Feb 10 - Feb 11
Vista Cay Resort by Casiola Vacation Homes
Apartment, 3 Bedrooms | Private kitchen | Toaster

Apartment in Florida Center

Century Millenia
3.0 star property
9.0 out of 10, Wonderful, (107 reviews)
"Beautiful place to stay and loved that it had washer and dryer on site. Super helpful for a longer stay. Definitely recommend staying here! "
United States
Collin
Century Millenia
Hallway

Aparthotel in Kissimmee

Enchanted Fantasy
3.5 star property
6.0 out of 10, (2 reviews)
"That’s very good"
United States
Shamsuddin
The price is NT$1,708
NT$4,093 total
includes taxes & fees
Jan 22 - Jan 23
Enchanted Fantasy
Deluxe Condo, 2 Bedrooms, Non Smoking | Balcony view

Aparthotel in International Drive District

Parc Corniche Condominium Suite Hotel
3.0 star property
8.0 out of 10, Very Good, (2,207 reviews)
"Beautiful property in a great location. I was there for a trade show at the convention center and this place was very close to that and right next door to sea world."
United States
Melissa
The price is NT$2,393
NT$4,295 total
includes taxes & fees
Jan 15 - Jan 16
Parc Corniche Condominium Suite Hotel
Outdoor spa tub

Aparthotel in Orlando

Blue Tree Resort at Lake Buena Vista
3.0 star property
8.6 out of 10, Excellent, (1,870 reviews)
"Had a great time"
United States
michael
Blue Tree Resort at Lake Buena Vista
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
"Beautiful rooms"
Natalie 1-night trip
Posted 18 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.

What's the top vacation rental that Winter Park has to offer?

Marriott's Sabal Palms: Visitors like this Winter Park vacation home rental. It is located near the airport and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Kick off your shoes and enjoy yourself with an outdoor tennis court and a hot tub.

How many vacation rentals are there in Winter Park?

Expedia has 36 vacation rentals for your stay in Winter Park.

What can I see and do in Winter Park?

Cultural attractions include Casa Feliz Historic Home Museum and Morse Museum of American Art, 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.