A two-story house with a balcony, surrounded by lush greenery and trees.

Winter Park Holiday Rentals

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Winter Park holiday rentals

A resort pool area with palm trees, lounge chairs, and umbrellas.

1. Marriott's Grande Vista

Marriott's Grande Vista
4.0 star property
Orlando
9.0 out of 10, Wonderful, (5,113 reviews)
"Good location, many activities, good breakfast."
United States
Laura
The price is S$138
includes taxes & fees
27 Oct - 28 Oct
Marriott's Grande Vista
A modern bedroom with a large bed, a bedside table, a wooden dresser, and a hanging light fixture.

2. Suites by The Wellborn

Suites by The Wellborn
4.0 star property
Lake Cherokee
8.2 out of 10, Very good, (335 reviews)
"The check in process was smooth and did not require any front desk it was perfect for a quick stay! The room was pretty big for the price! and very clean. The property itself was cute and cozy they had a very cool common area! Love this stay"
United States
Dustin
The price is S$110
includes taxes & fees
11 Oct - 12 Oct
Suites by The Wellborn
A swimming pool with lounge chairs and palm trees.

3. The Point Hotel & Suites Orlando

The Point Hotel & Suites Orlando
4.0 star property
Florida Center
8.6 out of 10, Excellent, (1,382 reviews)
"Enjoyed our stay and felt it was a great price for the location."
United States
Lisa
The price is S$104
includes taxes & fees
21 Oct - 22 Oct
The Point Hotel & Suites Orlando
A swimming pool with lounge chairs and umbrellas, surrounded by a multi-story building with balconies.

4. Virelli Apartments Upscale King Suite in the Heart of Orlando w Pool

Virelli Apartments Upscale King Suite in the Heart of Orlando w Pool
4.0 star property
Downtown Orlando
10.0 out of 10, Exceptional, (1 review)
"Very nice place"
United States
John
The price is S$522
includes taxes & fees
12 Oct - 13 Oct
Virelli Apartments Upscale King Suite in the Heart of Orlando w Pool
A hotel room with a large bed, bedside lamps, a view of the city, a window with curtains, and a desk with a chair.

5. The View Hotel, Trademark Collection by Wyndham

The View Hotel, Trademark Collection by Wyndham
3.0 star property
Orlando
8.4 out of 10, Very good, (2,161 reviews)
"Everything was amazing. Easy check in and check out, great location and quiet place. Breakfast was great and the food was excellent excellent."
United States
Breila
The price is S$118
includes taxes & fees
12 Oct - 13 Oct
The View Hotel, Trademark Collection by Wyndham
A modern bedroom with a bed, a ceiling fan, and a TV on the wall.

6. Pet Friendly Modern Zen Studio Retreat W/ Hot Tub! Home by RedAwning

Pet Friendly Modern Zen Studio Retreat W/ Hot Tub! Home by RedAwning
3.5 star property
Colonialtown South
The price is S$474
includes taxes & fees
8 Oct - 9 Oct
Pet Friendly Modern Zen Studio Retreat W/ Hot Tub! Home by RedAwning
Children’s play area – outdoor

7. Floridays Resort Orlando

Floridays Resort Orlando
4.0 star property
International Drive District
8.6 out of 10, Excellent, (12,170 reviews)
"I had been there before and I was so happy to enjoy the experience these complex is family friendly for sure I would like to go back soon."
United States
Ambar
The price is S$196
includes taxes & fees
8 Oct - 9 Oct
Floridays Resort Orlando
A compact bedroom with a bed, a desk, a TV, and a ceiling fan.

8. Cozy Modern Studio

Cozy Modern Studio
2.0 star property
Casselberry
The price is S$200
includes taxes & fees
8 Oct - 9 Oct
Cozy Modern Studio
A modern kitchen with wooden cabinets, stainless steel appliances, and a large island.

9. Luxury House - Sleeps 8 Golf Disney Family Fun

Luxury House - Sleeps 8 Golf Disney Family Fun
2.0 star property
Ventura
8.0 out of 10, Very good, (2 reviews)
"Some items like the towel rail was damaged upon arrival other than that the stay was amazing !!"
United States
myron
Luxury House - Sleeps 8 Golf Disney Family Fun
A modern kitchen with dark wood cabinets, a granite countertop, and a central island. There is a dining area with a table and chairs, and a view of the outside through large windows.

10. Century Millenia

Century Millenia
3.0 star property
Florida Center
9.0 out of 10, Wonderful, (149 reviews)
"Absolutely amazing and perfect will be back here everytime!"
United States
Arianna
The price is S$260
includes taxes & fees
26 Oct - 27 Oct
Century Millenia
A resort pool with a central water feature, surrounded by palm trees and lounge chairs.

11. Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando
4.0 star property
International Drive District
9.2 out of 10, Wonderful, (4,102 reviews)
"Great place to stay with the family."
United States
Vanessa
The price is S$138
includes taxes & fees
28 Oct - 29 Oct
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando
A swimming pool with a water slide, surrounded by palm trees and lounge chairs.

12. Villatel Resort Orlando, Apartments by Marriott Bonvoy

Villatel Resort Orlando, Apartments by Marriott Bonvoy
4.0 star property
Orlando
9.2 out of 10, Wonderful, (239 reviews)
"Good place to stay."
United States
Geronimo
The price is S$868
includes taxes & fees
25 Oct - 26 Oct
Villatel Resort Orlando, Apartments by Marriott Bonvoy
A spacious living room with a large sofa, a coffee table, and a dining area with chairs and a table.

13. Solara Apartments Spacious 2BR Apartment Sleeps 6 Pet-Friendly

Solara Apartments Spacious 2BR Apartment Sleeps 6 Pet-Friendly
4.0 star property
Kirkman North
8.0 out of 10, Very good, (1 review)
"Large 2br apartment with access to a very nice pool and other amenities! Fully equipped kitchen, laundry, 2 full bedrooms and bathrooms, 3 good tvs, screened in balcony. Keep in mind that it is a third floor walk up and be sure to read the guides on check in, especially parking and trash."
United States
Kathy
The price is S$372
includes taxes & fees
12 Oct - 13 Oct
Solara Apartments Spacious 2BR Apartment Sleeps 6 Pet-Friendly
A spacious living room with a beige sofa, a television, and a balcony with a view of the outdoors.

14. Upstay Golfer's Retreat w Patio at Ventura Resort

Upstay Golfer's Retreat w Patio at Ventura Resort
3.5 star property
Ventura
The price is S$291
includes taxes & fees
3 Nov - 4 Nov
Upstay Golfer's Retreat w Patio at Ventura Resort
A patio with Adirondack chairs and a round table, surrounded by palm trees and a brick floor.

15. Bluegreen Vacations Orlando's Sunshine, Ascend Collection Resort

Bluegreen Vacations Orlando's Sunshine, Ascend Collection Resort
3.5 star property
International Drive District
9.2 out of 10, Wonderful, (280 reviews)
"Great apartments, perfect for families exploring Universal and the wider Orlando area."
United Kingdom
Niki
The price is S$222
includes taxes & fees
3 Nov - 4 Nov
Bluegreen Vacations Orlando's Sunshine, Ascend Collection Resort
A modern lobby with a wooden ceiling, a TV mounted on a wooden panel, and a seating area with blue chairs and a white sofa.

16. Marriott's Royal Palms

Marriott's Royal Palms
4.0 star property
Orlando
9.4 out of 10, Exceptional, (324 reviews)
"Place is minutes from away from Disney Springs and major attractions, clean and modern, with a wonderful golf course."
United States
Ernie
The price is S$253
includes taxes & fees
4 Nov - 5 Nov
Marriott's Royal Palms
A covered outdoor swimming pool area with lounge chairs, a clock, and a sign indicating spa rules and no diving.

17. 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, (2,080 reviews)
"It was clean nice property, easy access"
United States
Mohammad
The price is S$139
includes taxes & fees
1 Nov - 2 Nov
Blue Tree Resort at Lake Buena Vista
A water slide structure with a person at the bottom of the slide, water splashing around.

18. The Cabins at Disney's Fort Wilderness Resort

The Cabins at Disney's Fort Wilderness Resort
4.5 star property
Bay Lake
9.2 out of 10, Wonderful, (572 reviews)
"Pet friendly"
United States
Darren
The price is S$848
includes taxes & fees
20 Oct - 21 Oct
The Cabins at Disney's Fort Wilderness Resort
A residential area with a large pond, houses, and a swimming pool.

19. Upstay Condo Near MCO Airport w Golf Pool

Upstay Condo Near MCO Airport w Golf Pool
2.0 star property
Ventura
The price is S$317
includes taxes & fees
12 Oct - 13 Oct
Upstay Condo Near MCO Airport w Golf Pool
A spacious living room with a grey sectional sofa, a glass coffee table, and a patterned rug.

20. Chic Orlando Family Getaway w/ Fenced Yard!

Chic Orlando Family Getaway w/ Fenced Yard!
3.0 star property
Rosemont
10.0 out of 10, Exceptional, (2 reviews)
"The house was well supplied with amenities, family friendly and it was very fun to use the pool and games. There’s a super Walmart and other shops close by."
United States
Jennifer
The price is S$712
includes taxes & fees
15 Oct - 16 Oct
Chic Orlando Family Getaway w/ Fenced Yard!
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

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

10/10 Excellent
"Belle proximité"
Amelie 5-night trip
Posted 1 hour ago
Westgate Lakes Resort & Spa Universal Studios Area

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.

How many holiday rentals are there in Winter Park?

Expedia has 55 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 Mizell and Kraft Azalea Gardens 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.