Winter Park Vacation Rentals

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Our top choices for Winter Park vacation rentals

1-bedroom vacation room just 12 minutes from University of Central Florida

1-bedroom vacation room just 12 minutes from University of Central Florida
Orlando
9.6 out of 10, Exceptional, (4 reviews)
"Great location close to lots of things to do. Very clean and cozy. Quiet neighborhood, very friendly owners. Will definitely go back."
United States
jamie l.
$159 nightly
The price is $176
Jul 21 - Jul 22
Total with taxes and fees
1-bedroom vacation room just 12 minutes from University of Central Florida

Quiet and safe neighborhood come to this great place with lots of room for relax

Quiet and safe neighborhood come to this great place with lots of room for relax
Orlando
9.4 out of 10, Exceptional, (3 reviews)
"Pool is very inviting"
United States
Geri Lamborn M.
$265 nightly
The price is $294
Jun 28 - Jun 29
Total with taxes and fees
Quiet and safe neighborhood come to this great place with lots of room for relax

Charming home @wp. Patio +Gazebo. close to highwys

Charming home @wp. Patio +Gazebo. close to highwys
Fairview Shores
5.4 out of 10, (3 reviews)
"Very clean and location was great"
United States
Vicki V.
$201 nightly
The price is $224
Jun 25 - Jun 26
Total with taxes and fees
Charming home @wp. Patio +Gazebo. close to highwys

Cute 5-bedroom house in peaceful Winter Park

Cute 5-bedroom house in peaceful Winter Park
Winter Park
10.0 out of 10, Exceptional, (1 review)
"This property is perfect for a family get together. Very clean and close to so many restaurants and entertainment. The communication the host was great. I would definely stay there again."
United States
Mary Ellen R.
$281 nightly
The price is $311
Jun 24 - Jun 25
Total with taxes and fees
Cute 5-bedroom house in peaceful Winter Park

Funky Remodeled Otown Bungalow Sleeps 8

Funky Remodeled Otown Bungalow Sleeps 8
Fairview Shores
10.0 out of 10, Exceptional, (1 review)
"Easy booking/check-in process, great location"
United States
Julia K.
$233 nightly
The price is $259
Jul 21 - Jul 22
Total with taxes and fees
Funky Remodeled Otown Bungalow Sleeps 8

Comfy Tiny Home @WP. Large Private Deck+Queen bed

Comfy Tiny Home @WP. Large Private Deck+Queen bed
Fairview Shores
$201 nightly
The price is $223
Jul 1 - Jul 2
Total with taxes and fees
Comfy Tiny Home @WP. Large Private Deck+Queen bed

Cozy home 5min to Park Ave and Downtown Orlando

Cozy home 5min to Park Ave and Downtown Orlando
Fairview Shores
$271 nightly
The price is $301
Jul 1 - Jul 2
Total with taxes and fees
Cozy home 5min to Park Ave and Downtown Orlando

Serene Mid-Century 3/2 w/Bonus Room and Huge Shaded Yard w/Fence

Serene Mid-Century 3/2 w/Bonus Room and Huge Shaded Yard w/Fence
Goldenrod
10.0 out of 10, Exceptional, (4 reviews)
"Nice and roomy!"
United States
Ashley C.
$481 nightly
The price is $534
Jul 1 - Jul 2
Total with taxes and fees
Serene Mid-Century 3/2 w/Bonus Room and Huge Shaded Yard w/Fence

Spacious 5-bedroom house in gorgeous Winter Park

Spacious 5-bedroom house in gorgeous Winter Park
Winter Park
10.0 out of 10, Exceptional, (2 reviews)
"Rented this property for a friend's engagement party and it worked super well. Host was super nice and great with communication"
United States
Hannah F.
$277 nightly
The price is $306
Jul 6 - Jul 7
Total with taxes and fees
Spacious 5-bedroom house in gorgeous Winter Park

The Canopy on Periwinkle- A Home Away From Home

The Canopy on Periwinkle- A Home Away From Home
Goldenrod
10.0 out of 10, Exceptional, (2 reviews)
"Our stay here was excellent! We were able to have a birthday party for our one-year-old grandson, turning 2 and it was an awesome day. Everything was perfect, and the host was very generous about giving us a late check out on the day we left. Would LOVE to stay here again in the future! Thank you, Glen!"
United States
t z.
$369 nightly
The price is $410
Jun 24 - Jun 25
Total with taxes and fees
The Canopy on Periwinkle- A Home Away From Home

Mills House @WP. Sleeps 11 Renovated. Queen beds

Mills House @WP. Sleeps 11 Renovated. Queen beds
Fairview Shores
8.0 out of 10, Very Good, (2 reviews)
"Comfortable beds and plentiful TV screens. Nice central location to shopping and dining. Lights are bright without dimming options, and some fixtures not working. "
United States
Larry S.
$301 nightly
The price is $334
Jul 14 - Jul 15
Total with taxes and fees
Mills House @WP. Sleeps 11 Renovated. Queen beds

5/4 King bed LUX Arcade near WP/CP & DT Orlando ‼️

5/4 King bed LUX Arcade near WP/CP & DT Orlando ‼️
College Park
10.0 out of 10, Exceptional, (1 review)
$3,695 nightly
The price is $4,101
Jun 24 - Jun 25
Total with taxes and fees
5/4 King bed LUX Arcade near WP/CP & DT Orlando ‼️

Cute 5-bedroom,6bed house in superb Winter Park.

Cute 5-bedroom,6bed house in superb Winter Park.
Winter Park
4.0 out of 10, (1 review)
"We checked in late and were surprised to find half eaten food in the fridge and freezer. Both were very dirty with a noticeable odor. The dishwasher was full of dirty dishes. The oven was full of dirty pans. Most of the dishes in the cupboards had little bits in them as well. There was a fire alarm battery beeping in one of the bedrooms. There was no coffee maker or wine opener or wine glasses or hand soap. There were very few dishes in general, it would have been challenging to cook and serve...
United States
Nyssa S.
$343 nightly
The price is $379
Jul 1 - Jul 2
Total with taxes and fees
Cute 5-bedroom,6bed house in superb Winter Park.

The Blue Aztec

The Blue Aztec
3.0 star property
Sanford
9.6 out of 10, Exceptional, (13 reviews)
"Great location! Great Dining! "
United States
Lisa
$205 nightly
The price is $221
Jun 28 - Jun 29
Total with taxes and fees
The Blue Aztec

The Blue Aztec

The Blue Aztec
Sanford
10.0 out of 10, Exceptional, (14 reviews)
"Perfect location within walking distance of all the fun yet nice and quiet. Place was squeaky clean. Will stay again"
United States
Min O.
$150 nightly
The price is $158
Jun 28 - Jun 29
Total with taxes and fees
The Blue Aztec

Boho Nights

Boho Nights
3.0 star property
Sanford
9.6 out of 10, Exceptional, (16 reviews)
"Great stay!"
United States
Nicholas
$135 nightly
The price is $151
Jun 28 - Jun 29
Total with taxes and fees
Boho Nights

Cozy Apartment in S Orlando, approx. 20 minutes away from Disney and Universal.

Cozy Apartment in S Orlando, approx. 20 minutes away from Disney and Universal.
Southchase
9.8 out of 10, Exceptional, (30 reviews)
"Made our stay in Orlando convenient and easy. "
United States
Mark M.
$122 nightly
The price is $135
Jun 28 - Jun 29
Total with taxes and fees
Cozy Apartment in S Orlando, approx. 20 minutes away from Disney and Universal.

Eastpark. Pet friendly! Lake Nona

Eastpark. Pet friendly! Lake Nona
East Park
9.2 out of 10, Wonderful, (99 reviews)
"Very nice accommodations. Great stay!!"
United States
John G.
$252 nightly
The price is $280
Jun 24 - Jun 25
Total with taxes and fees
Eastpark. Pet friendly! Lake Nona

Mi Casa Es Su Casa!!🏡 4 Bdrm home with pool

Mi Casa Es Su Casa!!🏡 4 Bdrm home with pool
Orlando
8.6 out of 10, Excellent, (114 reviews)
"Easy check, great location. Very quiet neighborhood, no complaints . Host did very well. Really enjoyed our stay"
United States
Matthew J.
$415 nightly
The price is $461
Jun 30 - Jul 1
Total with taxes and fees
Mi Casa Es Su Casa!!🏡 4 Bdrm home with pool

Charming 2-bedroom apartment with WiFi, AC in lovely Orlando

Charming 2-bedroom apartment with WiFi, AC in lovely Orlando
Orlando
9.8 out of 10, Exceptional, (12 reviews)
"Very clean and hospitable. Recommend staying here for sure!"
United States
Kyle Y.
$231 nightly
The price is $257
Jun 24 - Jun 25
Total with taxes and fees
Charming 2-bedroom apartment with WiFi, AC in lovely Orlando
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

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 $88 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?

Grand Luxury Lakes 3BR Townhouse near Disney: Visitors like this Winter Park vacation home rental. It is equipped with a garden, air-conditioning, and laundry facilities to help you feel comfortable during your stay. It has 3 bedrooms and a kitchen with a dishwasher.

How many vacation rentals are there in Winter Park?

Expedia has 53 vacation rentals for your stay in Winter Park.

What can I see and do in Winter Park?

Cultural attractions include Rollins Museum of Art and Morse Museum of American Art, whereas Lake Virginia and Mead Garden are a couple of picturesque spots to enjoy the outdoors. Kia Center and Universal Studios Florida 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.