Winter Park Holiday Rentals

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Check prices for these dates

In two weeks
5 Dec - 7 Dec
In two months
16 Jan - 18 Jan
In three months
13 Feb - 15 Feb
In four months
13 Mar - 15 Mar

Holiday Rentals in Winter Park

Interior
Near Disney King Bed Condo Unit - Pool & Hot Tub!

Apartment in International Drive District

3.0 star property
The price is S$217
includes taxes & fees
3 Dec - 4 Dec
Near Disney King Bed Condo Unit - Pool & Hot Tub!
Exterior
The Blue Aztec

Apartment in Sanford

3.0 star property
9.6 out of 10, Exceptional, (13)
"Great location! Great Dining! "
United States
Lisa
The Blue Aztec
Exterior
The Cabins at Disney's Fort Wilderness Resort

Aparthotel in Bay Lake

4.5 star property
9.2 out of 10, Wonderful, (559)
"What an awesome place to stay I will definitely be coming back "
United States
Larry
The Cabins at Disney's Fort Wilderness Resort
Outdoor pool, open 7:00 AM to 11:00 PM, pool umbrellas, pool loungers
Marriott's Sabal Palms

Holiday Home in Orlando

4.0 star property
9.6 out of 10, Exceptional, (202)
"Easy check in, pool was awesome "
United States
Lisa
The price is S$315
includes taxes & fees
10 Dec - 11 Dec
Marriott's Sabal Palms
Terrace/patio
The Front Porch

Apartment in Sanford

3.0 star property
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
Living area
The Contemporary

Apartment in Sanford

3.0 star property
The Contemporary
2 bedrooms, Internet
Upstay 2BR Family Condo Ventura Golf Country Club

Apartment in Ventura

2.0 star property
The price is S$342
includes taxes & fees
24 Nov - 25 Nov
Upstay 2BR Family Condo Ventura Golf Country Club
Mini-fridge, microwave, cookware/dishes/utensils
Bella Breeze

Apartment in Sanford

2.5 star property
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
Interior
Deltona Lake House, Day Trip to Disney & Universal

Cottage in Deltona Lakes

3.0 star property
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$480
includes taxes & fees
24 Nov - 25 Nov
Deltona Lake House, Day Trip to Disney & Universal
3 outdoor pools
Disney's Beach Club Villas

Condo resort in Bay Lake

5.0 star property
9.2 out of 10, Wonderful, (39)
"Clean and great location"
United States
Anonymous traveller
Disney's Beach Club Villas
Outdoor pool, a heated pool, pool umbrellas, pool loungers
Marriott's Imperial Palm Villas

Holiday Home in Orlando

4.0 star property
9.2 out of 10, Wonderful, (59)
"Amazing property definitely worth it "
United States
Yves
The price is S$619
includes taxes & fees
11 Dec - 12 Dec
Marriott's Imperial Palm Villas
Exterior
Totally 80's

Apartment in Sanford

3.0 star property
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$204
includes taxes & fees
3 Dec - 4 Dec
Totally 80's
Pool
Storey Lake Resort 2bd Condo Overlooking Water #840 2 Bedroom Condo

Condo in Kissimmee

3.0 star property
10.0 out of 10, Exceptional, (1)
"we had a great time and enjoyed the condo for the short time we were there."
United States
Sherri Ann
Storey Lake Resort 2bd Condo Overlooking Water #840 2 Bedroom Condo
Private kitchen
Century Millenia

Apartment in Florida Center

3.0 star property
9.0 out of 10, Wonderful, (100)
" Kitchen was fully equipped, staff was available and informative, clean, and parking was available. "
United States
Elizabeth
Century Millenia
Interior
Enclave Swanky

Apartment in International Drive District

4.0 star property
8.0 out of 10, Very good, (1)
"Clean, comfortable, but compact and looking worn / tired. Price point was right."
United Kingdom
Matthew
Enclave Swanky
Terrace/patio
The Point by Edge

Aparthotel in Florida Center

4.0 star property
8.4 out of 10, Very good, (808)
"Great accommodations!"
United States
Champayne
The price is S$108
includes taxes & fees
24 Nov - 25 Nov
The Point by Edge
Living area
Boho Nights

Apartment in Sanford

3.0 star property
8.8 out of 10, Excellent, (6)
"Wonderful spot, and excellent hosts!"
United States
Thomas
Boho Nights
8 bedrooms
Super Blue- Sleeps 24 w Pool Movie Loft

Holiday Home in Kissimmee

2.0 star property
Super Blue- Sleeps 24 w Pool Movie Loft
Lobby sitting area
The View Studio Suites and Event Venue

Aparthotel in Orlando

3.0 star property
8.4 out of 10, Very good, (1394)
"Nice breakfast, friendly staff, great location "
United States
Yessica
The price is S$99
includes taxes & fees
21 Dec - 22 Dec
The View Studio Suites and Event Venue
Outdoor pool
Stylish and New! 3br, Steps fr. Universal Drive

Apartment in Orlando

3.0 star property
10.0 out of 10, Exceptional, (1)
"The owners were very responsive and attentive. Loved the kids room and we don't have kids because we are kids, lol."
United States
Dianne
Stylish and New! 3br, Steps fr. Universal Drive
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
"I really enjoyed my stay here. Truly a safe,clean and family friendly resort. This is my 3rd or 4th time staying here and everytime its a treat. I hate the 10am checkout and the 4pm checkin but I guess thats the same at all hotels/resorts. I requested a late checkout but was denied although the resort looked like it was pretty empty. That was disappointing but they did offer to hold my luggage. I was more interested in sleeping in at least until 11am. Great resort! I highly recommend."
Tiffany 4-night trip
Posted 2 days ago
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

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 69 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 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 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.