Winter Park Vacation Rentals

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Check prices for these dates

In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Winter Park vacation rentals

Terrace/patio
The Point by Edge

The Point by Edge

The Point by Edge
4.0 star property
Florida Center
8.4 out of 10, Very Good, (833)
"It was great really recommend this place"
United States
Sharam
The price is P2,960
P4,057 total
includes taxes & fees
Jan 7 - Jan 8, 2026
The Point by Edge
Reception
Florida Hotel & Conference Center in the Florida Mall

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, (2358)
"Great location and staff!"
United States
Laura
Florida Hotel & Conference Center in the Florida Mall
Lobby sitting area
The View Studio Suites and Event Venue

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, (1490)
"Good sized room, nice staff, good breakfast "
United States
Catherine
The price is P5,022
P5,649 total
includes taxes & fees
Dec 28 - Dec 29
The View Studio Suites and Event Venue
2 outdoor pools, a heated pool, open 7:00 AM to 11:00 PM, pool umbrellas
Floridays Resort Orlando

Floridays Resort Orlando

Floridays Resort Orlando
3.5 star property
International Drive District
8.6 out of 10, Excellent, (11633)
"Great place to stay"
United States
Ana
Floridays Resort Orlando
Outdoor pool, open 7:00 AM to 11:00 PM, pool umbrellas, sun loungers
Marriott's Sabal Palms

Marriott's Sabal Palms

Marriott's Sabal Palms
4.0 star property
Orlando
9.6 out of 10, Exceptional, (208)
"Room was great, staff friendly and grounds are clean. "
United States
DENNIS
The price is P18,736
P21,077 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Marriott's Sabal Palms
Outdoor pool, pool umbrellas, sun loungers
WorldQuest Orlando Resort

WorldQuest Orlando Resort

WorldQuest Orlando Resort
4.0 star property
Orlando
8.4 out of 10, Very Good, (4027)
"Clean room, active and friendly staff. Nice accommodations "
United States
Filippo
WorldQuest Orlando Resort
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

SPOT X Hotel Orlando/Intl Dr by The Red Collection

SPOT X Hotel Orlando/Intl Dr by The Red Collection

10/10 Excellent
"It is clean and great staff"
Thuy 4-night trip
Posted 2 days ago
SPOT X Hotel Orlando/Intl Dr by The Red Collection

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: You might want to consider this vacation home rental near Winter Park, which 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 34 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.