Winter Park Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
23 Jan - 25 Jan
In two months
6 Mar - 8 Mar
In three months
3 Apr - 5 Apr
In four months
1 May - 3 May

Our top choices for Winter Park holiday 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, (843)
"Awesome and clean place to stay for the holidays"
United States
Moses
The price is S$99
includes taxes & fees
27 Jan - 28 Jan
The Point by Edge
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, (1528)
"Good sized room, nice staff, good breakfast "
United States
Catherine
The price is S$110
includes taxes & fees
3 Feb - 4 Feb
The View Studio Suites and Event Venue
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, (2415)
"Friendly staff and great accommodations "
United States
jose
Florida Hotel & Conference Center in the Florida Mall
Outdoor pool, pool umbrellas, pool loungers
WorldQuest Orlando Resort

WorldQuest Orlando Resort

WorldQuest Orlando Resort
4.0 star property
Orlando
8.4 out of 10, Very good, (4034)
"Clean room and amenities, helpful staff members. "
United States
Maydelin
WorldQuest Orlando Resort
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, (11662)
"Great place to stay"
United States
Ana
Floridays Resort Orlando
Living area
Boho Nights

Boho Nights

Boho Nights
3.0 star property
Sanford
9.0 out of 10, Wonderful, (7)
"Wonderful spot, and excellent hosts!"
United States
Thomas
Boho Nights
Terrace/patio
The Front Porch

The Front Porch

The Front Porch
3.0 star property
Sanford
10.0 out of 10, Exceptional, (2)
"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
Deltona Lake House, Day Trip to Disney & Universal

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)
"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 traveller
The price is S$436
includes taxes & fees
7 Jan - 8 Jan
Deltona Lake House, Day Trip to Disney & Universal
Full-sized fridge, microwave, oven, stovetop
Enchanted Dreams

Enchanted Dreams

Enchanted Dreams
3.5 star property
Kissimmee
7.8 out of 10, Good, (7)
"Very relaxing space. Clean environment. Coming back very soon "
United States
Tanish
The price is S$177
includes taxes & fees
8 Jan - 9 Jan
Enchanted Dreams
Mini-fridge, microwave, cookware/dishes/utensils
Bella Breeze

Bella Breeze

Bella Breeze
2.5 star property
Sanford
9.6 out of 10, Exceptional, (5)
"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
The Blue Aztec

The Blue Aztec

The Blue Aztec
3.0 star property
Sanford
9.6 out of 10, Exceptional, (13)
"Great location! Great Dining! "
United States
Lisa
The Blue Aztec
Bar (on property)
Premier Resort Condos Near Universal

Premier Resort Condos Near Universal

Premier Resort Condos Near Universal
3.0 star property
Florida Center
9.0 out of 10, Wonderful, (4)
"Great"
United States
Russell
The price is S$219
includes taxes & fees
4 Feb - 5 Feb
Premier Resort Condos Near Universal
Exterior
The Jazz Loft

The Jazz Loft

The Jazz Loft
3.0 star property
Sanford
8.0 out of 10, Very good, (6)
"The loft was very cool and unique. Loved it. I will definitely book this again."
United States
sherri
The Jazz Loft
Exterior
Totally 80's

Totally 80's

Totally 80's
3.0 star property
Sanford
9.4 out of 10, Exceptional, (3)
"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 S$201
includes taxes & fees
8 Jan - 9 Jan
Totally 80's
Outdoor pool, open 7:00 AM to 11:00 PM, pool umbrellas, pool loungers
Marriott's Sabal Palms

Marriott's Sabal Palms

Marriott's Sabal Palms
4.0 star property
Orlando
9.6 out of 10, Exceptional, (210)
"Room was great, staff friendly and grounds are clean. "
United States
DENNIS
The price is S$531
includes taxes & fees
28 Jan - 29 Jan
Marriott's Sabal Palms
Indoor pool, 2 outdoor pools, open 8:00 AM to 8:00 PM, pool umbrellas
Premium Condos near Universal Studios

Premium Condos near Universal Studios

Premium Condos near Universal Studios
3.5 star property
International Drive District
9.4 out of 10, Exceptional, (28)
"Awesome place. "
United States
Ryan
The price is S$198
includes taxes & fees
26 Jan - 27 Jan
Premium Condos near Universal Studios
Private kitchen
Century Millenia

Century Millenia

Century Millenia
3.0 star property
Florida Center
9.0 out of 10, Wonderful, (107)
"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
Outdoor spa tub
Blue Tree Resort at Lake Buena Vista

Blue Tree Resort at Lake Buena Vista

Blue Tree Resort at Lake Buena Vista
3.0 star property
Orlando
8.6 out of 10, Excellent, (1863)
"We had a great stay."
United States
K Little Lady Baby Bug
The price is S$216
includes taxes & fees
7 Jan - 8 Jan
Blue Tree Resort at Lake Buena Vista
3 outdoor pools, a heated pool, pool umbrellas, pool loungers
Vista Cay Resort by Casiola Vacation Homes

Vista Cay Resort by Casiola Vacation Homes

Vista Cay Resort by Casiola Vacation Homes
3.5 star property
Orlando
8.8 out of 10, Excellent, (183)
"Nice place, comfortable. "
United States
John
The price is S$549
includes taxes & fees
7 Jan - 8 Jan
Vista Cay Resort by Casiola Vacation Homes
Terrace/patio
Enchanted Fantasy

Enchanted Fantasy

Enchanted Fantasy
3.5 star property
Kissimmee
6.0 out of 10, (2)
"That’s very good"
United States
Shamsuddin
The price is S$166
includes taxes & fees
17 Jan - 18 Jan
Enchanted Fantasy
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.
View all properties
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
"Nice clean hotel in the middle of the airport, good place to relax and stay on a layover, rather than finding a place off property. Plenty of places to eat within walking distance."
Daniel 1-night trip
Posted 11 hours ago
Hyatt Regency Orlando International Airport

Frequently asked questions

Can I find holiday rentals in Winter Park?

Yes, there are holiday rentals in Winter Park close to Kraft Azalea Gardens, or you can select 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 are some of the best holiday rentals that Winter Park has to offer?

Marriott's Sabal Palms: This holiday home rental outside of Winter Park is located near the airport, and has an outdoor pool, a balcony and a BBQ 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 1 hot tub.

How many holiday rentals are there in Winter Park?

Expedia has 35 holiday 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 holiday rentals like in Winter Park?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winter Park. Holiday rentals offer amenities such as kitchens and laundry facilities so you'll have a home away from home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of privacy away from public hotel lifts and busy lobbies while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for families.