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

Winter Park Vacation Rentals

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Check prices for these dates

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

Our top choices for Winter Park vacation 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, (5,142 reviews)
"Good location, many activities, good breakfast."
United States
Laura
$96 nightly
The price is $108
Oct 30 - Oct 31
Total with taxes and fees
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, (336 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
$86 nightly
The price is $96
Oct 15 - Oct 16
Total with taxes and fees
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, (1,395 reviews)
"Enjoyed our stay and felt it was a great price for the location."
United States
Lisa
$83 nightly
The price is $93
Oct 26 - Oct 27
Total with taxes and fees
The Point Hotel & Suites Orlando
A modern kitchen with a central island, bar stools, and a dining area with a sofa and table.

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
$367 nightly
The price is $413
Nov 3 - Nov 4
Total with taxes and fees
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, (2,178 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
$82 nightly
The price is $92
Oct 12 - Oct 13
Total with taxes and fees
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
$309 nightly
The price is $347
Oct 11 - Oct 12
Total with taxes and fees
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, (12,190 reviews)
"Awesome place wish I knew about this place before looking forward to staying there in future visits"
United States
Richard
$179 nightly
The price is $201
Oct 11 - Oct 12
Total with taxes and fees
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
$141 nightly
The price is $158
Oct 16 - Oct 17
Total with taxes and fees
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, (154 reviews)
"Easy booking. Great price. When I arrived the code wasn't working so I called in and got a new code quickly and easily. The unit was beautiful, clean, comfortable and fully stocked with necessities. The onsite laundry machines was a bonus while traveling."
United States
Jessica
$200 nightly
The price is $216
Oct 26 - Oct 27
Total with taxes and fees
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, (4,146 reviews)
"Great place to stay with the family."
United States
Vanessa
$96 nightly
The price is $108
Nov 2 - Nov 3
Total with taxes and fees
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, (240 reviews)
"Good place to stay."
United States
Geronimo
$603 nightly
The price is $678
Oct 25 - Oct 26
Total with taxes and fees
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
$264 nightly
The price is $297
Oct 14 - Oct 15
Total with taxes and fees
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
$197 nightly
The price is $221
Nov 3 - Nov 4
Total with taxes and fees
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, (281 reviews)
"Everything was good"
United States
Ghansham
$154 nightly
The price is $174
Nov 3 - Nov 4
Total with taxes and fees
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, (326 reviews)
"Place is minutes from away from Disney Springs and major attractions, clean and modern, with a wonderful golf course."
United States
Ernie
$176 nightly
The price is $198
Nov 9 - Nov 10
Total with taxes and fees
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, (2,093 reviews)
"It was clean nice property, easy access"
United States
Mohammad
$122 nightly
The price is $137
Nov 1 - Nov 2
Total with taxes and fees
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
$590 nightly
The price is $664
Oct 25 - Oct 26
Total with taxes and fees
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
$222 nightly
The price is $250
Oct 12 - Oct 13
Total with taxes and fees
Upstay Condo Near MCO Airport w Golf Pool
A modern kitchen with white cabinets, a granite countertop, and a central island with bar stools.

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
$495 nightly
The price is $557
Oct 15 - Oct 16
Total with taxes and fees
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

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

10/10 Excellent
"Amazing"
Michelle 3-night trip
Posted 1 hour ago
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Find out more about Winter Park

Everything you need to know about Winter Park vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winter Park vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winter Park vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winter Park vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winter Park. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winter Park in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $92 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winter Park rentals

At Expedia, we put the best Winter Park vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winter Park rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winter Park vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winter Park. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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?

Beautiful 9-bedroom house with AC in serene Kissimmee , Bring the whole Family !: Visitors like this Winter Park vacation home rental. It has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

How many vacation rentals are there in Winter Park?

Expedia has 55 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 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 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.