Winter Park Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Aug 26 - Aug 27
Tomorrow
Aug 27 - Aug 28
This weekend
Aug 29 - Aug 31
Next weekend
Sep 5 - Sep 7

Vacation Rentals in Winter Park

Our top choices for Winter Park vacation rentals

Floridays Resort Orlando
2 outdoor pools, a heated pool, open 7:00 AM to 11:00 PM, pool umbrellas

Floridays Resort Orlando

3.5 star property
8.6 out of 10, Excellent, (11483)
"Always come to this place to my orlando vacation, great spot"
The price is NT$4,066
NT$5,774 total
includes taxes & fees
Sep 1 - Sep 2
Floridays Resort Orlando
The View Studio Suites and Event Venue
Lobby sitting area

The View Studio Suites and Event Venue

3.5 star property
8.4 out of 10, Very Good, (1258)
"Good location, friendly staff"
The price is NT$2,446
NT$2,751 total
includes taxes & fees
Aug 31 - Sep 1
The View Studio Suites and Event Venue
Lake Buena Vista Resort Village & Spa
2 outdoor pools, a heated pool, open 8:00 AM to 10:00 PM, pool umbrellas

Lake Buena Vista Resort Village & Spa

4.0 star property
8.4 out of 10, Very Good, (9108)
"We enjoyed staying here, great place for family "
Lake Buena Vista Resort Village & Spa
Florida Hotel & Conference Center in the Florida Mall
Reception

Florida Hotel & Conference Center in the Florida Mall

3.5 star property
9.2 out of 10, Wonderful, (2111)
"Great access to the mall and food very well rounded nice for families."
Florida Hotel & Conference Center in the Florida Mall
The Point Hotel & Suites
Outdoor pool

The Point Hotel & Suites

3.5 star property
8.0 out of 10, Very Good, (3255)
"Good location, handy to all things…parks, shopping, dining the works. Super quite great to turn in after massive days out. Worth the stay"
The price is NT$2,446
NT$3,102 total
includes taxes & fees
Sep 11 - Sep 12
The Point Hotel & Suites
The Point by Edge
Terrace/patio

The Point by Edge

4.0 star property
8.6 out of 10, Excellent, (768)
"My stay at this place was great. I would stay here again "
The price is NT$1,948
NT$2,569 total
includes taxes & fees
Sep 2 - Sep 3
The Point by Edge
Parc Corniche Condominium Suite Hotel
Exterior

Parc Corniche Condominium Suite Hotel

3.0 star property
8.0 out of 10, Very Good, (2162)
"This is a great place to stay with a family has all the basic needs for a family there "
The price is NT$2,345
NT$4,180 total
includes taxes & fees
Aug 31 - Sep 1
Parc Corniche Condominium Suite Hotel
Blue Tree Resort at Lake Buena Vista
Outdoor spa tub

Blue Tree Resort at Lake Buena Vista

3.0 star property
8.6 out of 10, Excellent, (1780)
"Very nice resort would stay again."
Blue Tree Resort at Lake Buena Vista
Sonder by Marriott Bonvoy Vista Cay Apartments
Outdoor pool

Sonder by Marriott Bonvoy Vista Cay Apartments

3.5 star property
9.0 out of 10, Wonderful, (239)
"Great place love the stay "
The price is NT$3,468
NT$3,901 total
includes taxes & fees
Sep 14 - Sep 15
Sonder by Marriott Bonvoy Vista Cay Apartments
Vista Cay Resort by Millenium at Universal Blvd
2 outdoor pools, pool umbrellas, sun loungers

Vista Cay Resort by Millenium at Universal Blvd

3.5 star property
8.6 out of 10, Excellent, (1545)
"Wonderful place to stay for families! The split level plan is great if two groups of families are traveling together. The townhouse was clean and close to everything we needed. Will definitely stay here again! "
Vista Cay Resort by Millenium at Universal Blvd
Blue Heron Beach Resort
Front of property

Blue Heron Beach Resort

3.5 star property
8.4 out of 10, Very Good, (2957)
"I. Loved to stay"
Blue Heron Beach Resort
Enchanted Dreams
Full-size fridge, microwave, oven, stovetop

Enchanted Dreams

3.5 star property
6.0 out of 10, (2)
"Clean, comfortable home. Everything was excellent from the security to amenities. I will book again, share with friends and family. "
The price is NT$2,436
NT$4,838 total
includes taxes & fees
Aug 28 - Aug 29
Enchanted Dreams
Marriott's Sabal Palms
Outdoor pool, open 7:00 AM to 11:00 PM, pool umbrellas, sun loungers

Marriott's Sabal Palms

4.0 star property
9.6 out of 10, Exceptional, (199)
"Condo was fantastic "
The price is NT$6,942
NT$7,810 total
includes taxes & fees
Sep 16 - Sep 17
Marriott's Sabal Palms
staySky Suites - I Drive Orlando
Outdoor pool, sun loungers

staySky Suites - I Drive Orlando

3.0 star property
7.8 out of 10, Good, (1229)
"Excellent option for those visiting the park "
The price is NT$2,097
NT$2,563 total
includes taxes & fees
Sep 8 - Sep 9
staySky Suites - I Drive Orlando
Century Millenia
Apartment, 2 Bedrooms | Private kitchen | Toaster

Century Millenia

3.0 star property
9.0 out of 10, Wonderful, (79)
"Very comfortable,quite, safe and clean"
Century Millenia
WorldQuest Orlando Resort
Outdoor pool, pool umbrellas, sun loungers

WorldQuest Orlando Resort

4.0 star property
8.4 out of 10, Very Good, (4001)
"The staff is friendly and the room was clean and cozy. It is close to most Disney parks and restaurants."
WorldQuest Orlando Resort
Wellborn Hotel Downtown, Sonder by Marriott Bonvoy
Property amenity

Wellborn Hotel Downtown, Sonder by Marriott Bonvoy

4.0 star property
8.2 out of 10, Very Good, (293)
"Stayed here for a night to go to a concert at camping world stadium and really enjoyed the stay, really pretty property and felt safe, would definitely come back "
The price is NT$2,558
NT$2,877 total
includes taxes & fees
Aug 27 - Aug 28
Wellborn Hotel Downtown, Sonder by Marriott Bonvoy
Premium Condos near Universal Studios
Indoor pool, 2 outdoor pools, open 8:00 AM to 8:00 PM, pool umbrellas

Premium Condos near Universal Studios

3.5 star property
9.0 out of 10, Wonderful, (19)
"Amazing resort. "
The price is NT$2,713
NT$5,073 total
includes taxes & fees
Aug 30 - Aug 31
Premium Condos near Universal Studios
Orlando Lakefront Tiny House Community
The Club House | 2 bedrooms, individually decorated, individually furnished

Orlando Lakefront Tiny House Community

3.0 star property
9.4 out of 10, Exceptional, (328)
"We enjoyed our stay."
The price is NT$2,318
NT$4,834 total
includes taxes & fees
Aug 27 - Aug 28
Orlando Lakefront Tiny House Community
Vista Cay Resort by Your Vista Cay
Exterior

Vista Cay Resort by Your Vista Cay

3.5 star property
9.2 out of 10, Wonderful, (15)
"Great location and amenities. Host very responsive. We enjoyed our stay. "
Vista Cay Resort by Your Vista Cay
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winter Park Hotel Reviews

Hyatt Regency Orlando International Airport

Hyatt Regency Orlando International Airport

10/10 Excellent
"It was a short stay but a great experience "
Maria 1-night trip
Posted 23 hours ago
Hyatt Regency Orlando International Airport

Find out more about Winter Park

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 69 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 Albin Polasek Museum and Sculpture Gardens, 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.