Winter Park Holiday Rentals

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Winter Park

The View Studio Suites and Event Venue
Property entrance

The View Studio Suites and Event Venue

3.5 star property
8.4 out of 10, Very good, (667)
"Good days "
The price is S$117
includes taxes & fees
12 Jan - 13 Jan,2025
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, (8227)
"Love very nice the place "
The price is S$319
includes taxes & fees
7 Jan - 8 Jan,2025
Lake Buena Vista Resort Village & Spa
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, (11134)
"Good stay"
The price is S$306
includes taxes & fees
12 Jan - 13 Jan,2025
Floridays Resort Orlando
Florida Hotel & Conference Center in the Florida Mall
Reception

Florida Hotel & Conference Center in the Florida Mall

3.5 star property
9.0 out of 10, Wonderful, (1660)
"It’s a great hotel for both business and pleasure especially if you are traveling with your family "
The price is S$293
includes taxes & fees
2 Jan - 3 Jan,2025
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, (3116)
"Not clean"
The price is S$182
includes taxes & fees
15 Jan - 16 Jan,2025
The Point Hotel & Suites
Sonder at The Point
Outdoor pool, pool umbrellas, pool loungers

Sonder at The Point

4.0 star property
8.4 out of 10, Very good, (604)
"Location fantastic. Property perfect size. Disney 20mins in car. Universal 30min walk . Great shopping nearby . The prime outlets , Florida mall , the Millenia. "
The price is S$161
includes taxes & fees
13 Jan - 14 Jan,2025
Sonder at The Point
WorldQuest Orlando Resort
Exterior

WorldQuest Orlando Resort

4.0 star property
8.4 out of 10, Very good, (3881)
"Excellent option to stay in Orlando and visit the Disney´s parks."
The price is S$316
includes taxes & fees
28 Jan - 29 Jan,2025
WorldQuest Orlando Resort
Orlando Lakefront Tiny House Community
Individually decorated, individually furnished, laptop workspace

Orlando Lakefront Tiny House Community

3.0 star property
9.4 out of 10, Exceptional, (238)
"Beautiful, quiet and peaceful. Lots of local wildlife to observe. Simple check in. Hosts were very accommodating and helpful. Would stay here again in the future"
The price is S$280
includes taxes & fees
3 Jan - 4 Jan,2025
Orlando Lakefront Tiny House Community
Parc Corniche Condominium Suite Hotel
Exterior

Parc Corniche Condominium Suite Hotel

3.0 star property
7.8 out of 10, Good, (2105)
"I was asked if I wanted to upgrade to a newer improved room. The only issue is it wasn’t and the TV in the second room didn’t work. I asked on the morning of our last day for someone to fix it and to bring us towels and sheets at 8:30 in the morning it was never done so at 9:30 at night when I got back I had to ask again for those supplies"
The price is S$212
includes taxes & fees
14 Jan - 15 Jan,2025
Parc Corniche Condominium Suite Hotel
Sonder Wellborn
Property grounds

Sonder Wellborn

4.0 star property
8.4 out of 10, Very good, (193)
"Never spoke to or interact with anyone from Sonder while we were there. Never even saw an employee…water took forever to heat up in the shower. Like 10 minutes..so long that at first I thought we were going to have to take cold showers for 2 days but after like 10 minutes it does heat enough to take a warm shower not hot though. Place is clean and pictures were accurate. I would use their brand again. Even though we didn’t see any employees we had no real issues since we could eventually...
The price is S$162
includes taxes & fees
13 Jan - 14 Jan,2025
Sonder Wellborn
Sonder Vista Cay
Outdoor pool

Sonder Vista Cay

3.5 star property
9.0 out of 10, Wonderful, (158)
"Liked everything the apartments were very nice apart from when I got stuck in the lift for a while. But it is a very nice place. I would definitely stay again. "
The price is S$233
includes taxes & fees
6 Jan - 7 Jan,2025
Sonder Vista Cay
Blue Heron Beach Resort
Exterior

Blue Heron Beach Resort

3.5 star property
8.4 out of 10, Very good, (2908)
"Great place to stay at very clean spaces. Only thing is I wish the toaster and the coffee maker worked besides that I have no complaints. Definitely will stay again."
Blue Heron Beach Resort
Vacation Villas 2, a Ramada by Wyndham
Outdoor pool, pool umbrellas, pool loungers

Vacation Villas 2, a Ramada by Wyndham

3.5 star property
8.6 out of 10, Excellent, (1245)
"Good property, got us in at last minute as replacement. Convenient. Shower heads need to be cleaned, Orlando water is horrible. Coffee maker needs instructions."
Vacation Villas 2, a Ramada by Wyndham
Vista Cay Resort by Millenium at Universal Blvd
2 outdoor pools, pool umbrellas, pool loungers

Vista Cay Resort by Millenium at Universal Blvd

3.5 star property
8.6 out of 10, Excellent, (1522)
"All good as expected, nice area, Publix on the corner and new units."
Vista Cay Resort by Millenium at Universal Blvd
Blue Tree Resort at Lake Buena Vista
BBQ/picnic Area

Blue Tree Resort at Lake Buena Vista

3.0 star property
8.6 out of 10, Excellent, (1652)
"2nd time around for us and enjoyed our stay once again"
Blue Tree Resort at Lake Buena Vista
staySky Suites - I Drive Orlando
Outdoor pool, pool loungers

staySky Suites - I Drive Orlando

3.0 star property
7.8 out of 10, Good, (1192)
"maria i believe was her name at the desk, she was amazing!"
The price is S$145
includes taxes & fees
8 Jan - 9 Jan,2025
staySky Suites - I Drive Orlando
Bluegreen Vacations Orlando's Sunshine Resort
BBQ/picnic Area

Bluegreen Vacations Orlando's Sunshine Resort

3.5 star property
9.2 out of 10, Wonderful, (218)
"Rooms are big ,clean , have everything you need nice pool area you can uber ever where if you don’t want to drive. "
Bluegreen Vacations Orlando's Sunshine Resort
Marriott's Sabal Palms
Outdoor pool, open 6:00 AM to 11:00 PM, pool umbrellas, pool loungers

Marriott's Sabal Palms

4.0 star property
9.6 out of 10, Exceptional, (184)
"Great place. Home away from home. Fully equiped kitchen. Villa spacious. Shuttle to marriott world center where you can have multiple dinning options. Close to parks. Nice and quiet after a busy day come to a relaxing place. No resort and parking fees is a plus. Staff very nice. You have access to activities and pool at Marriot Wotld center. "
The price is S$475
includes taxes & fees
20 Jan - 21 Jan,2025
Marriott's Sabal Palms
Executive 3 Br Villa @Universal / Vista Cay/Conv.Center
2 outdoor pools

Executive 3 Br Villa @Universal / Vista Cay/Conv.Center

3.5 star property
9.2 out of 10, Wonderful, (42)
"Very clean and quiet. Plenty of room for the 5 of us. Thank you!!"
The price is S$839
includes taxes & fees
2 Jan - 3 Jan,2025
Executive 3 Br Villa @Universal / Vista Cay/Conv.Center
Vista Cay Resort by Your Vista Cay
Exterior

Vista Cay Resort by Your Vista Cay

3.5 star property
9.8 out of 10, Exceptional, (12)
"This place was so wonderful. We had to evacuate due to hurricane Milton and we felt so safe and at home staying here. The bed was great and the amenities were wonderful. We will be back!"
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.
Don't see what you're looking for?
See all available properties in Winter Park
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other types of properties in Winter Park you may be interested in

Hyatt Regency Orlando International Airport
Meeting facility

Hyatt Regency Orlando International Airport

4.0 star property
9.4 out of 10, Exceptional, (3117)
"Stay there every year. Great place."
The price is S$304
includes taxes & fees
1 Jan - 2 Jan,2025
Hyatt Regency Orlando International Airport
Holiday Inn Resort Orlando Suites - Waterpark, an IHG Hotel
Exterior

Holiday Inn Resort Orlando Suites - Waterpark, an IHG Hotel

3.5 star property
7.2 out of 10, Good, (1684)
"We enjoyed our stay here.."
The price is S$189
includes taxes & fees
1 Jan - 2 Jan,2025
Holiday Inn Resort Orlando Suites - Waterpark, an IHG Hotel
Rosen Inn Lake Buena Vista
View from room

Rosen Inn Lake Buena Vista

3.5 star property
8.4 out of 10, Very good, (4481)
"The property is close to Disney World. "
The price is S$93
includes taxes & fees
5 Jan - 6 Jan,2025
Rosen Inn 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.

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. You and your friends and family can relax into your holiday with amenities such as 1 hot tub.

How many holiday rentals are there in Winter Park?

Expedia has 62 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 Lake Virginia and Mead Garden 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.