Winter Park Vacation Rentals

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Check prices for these dates

In two weeks
Mar 13 - Mar 15
In two months
Apr 24 - Apr 26
In three months
May 22 - May 24
In four months
Jun 19 - Jun 21

Our top choices for Winter Park vacation rentals

Outdoor pool

Apartment in Orlando

1-bedroom vacation room just 12 minutes from University of Central Florida
9.4 out of 10, Exceptional, (3 reviews)
"Fantastic Host"
United States
Marek K.
$163 nightly
The price is $180
Feb 25 - Feb 26
Total with taxes and fees
1-bedroom vacation room just 12 minutes from University of Central Florida
Fridge, microwave, oven, stovetop

Apartment in Orlando

Quiet and safe neighborhood come to this great place with lots of room for relax
10.0 out of 10, Exceptional, (2 reviews)
"Pool is very inviting"
United States
Geri Lamborn M.
$242 nightly
The price is $269
Feb 25 - Feb 26
Total with taxes and fees
Quiet and safe neighborhood come to this great place with lots of room for relax
Fridge, microwave, oven, stovetop

Vacation Home in Fairview Shores

Sleek, Spacious & Central – Your Ideal Getaway
10.0 out of 10, Exceptional, (1 review)
"Great location in Winter Park! So many quality restaurants and things to do close by. The home is easily accessible with plenty of space. The host, Wendy was very hospitable. We left a toiletry bag and she was kind enough to let us know so we could come back. We enjoyed our one night stay!"
United States
Adam A.
$196 nightly
The price is $218
Feb 25 - Feb 26
Total with taxes and fees
Sleek, Spacious & Central – Your Ideal Getaway
TV, offices

Vacation Home in College Park

Cozy home w/working space & kitchen
8.0 out of 10, Very Good, (2 reviews)
"We had a wonderful stay — the house was spotless, comfortable, and offered plenty of space. The peaceful neighborhood and convenient location made it easy to explore the area."
United States
Danielle H.
$235 nightly
The price is $261
Mar 4 - Mar 5
Total with taxes and fees
Cozy home w/working space & kitchen
Property grounds

Apartment in Fairview Shores

Virbo Host Website is not working for me. Do not book this property. Thank you
$99 nightly
The price is $109
Feb 25 - Feb 26
Total with taxes and fees
Virbo Host Website is not working for me. Do not book this property. Thank you
Interior

Vacation Home in Fairview Shores

Cozy home 5min to Park Ave and Downtown Orlando
$233 nightly
The price is $260
Mar 4 - Mar 5
Total with taxes and fees
Cozy home 5min to Park Ave and Downtown Orlando
Smart TV, video games

Vacation Home in Goldenrod

Serene Mid-Century 3/2 w/Bonus Room and Huge Shaded Yard w/Fence
$341 nightly
The price is $380
Feb 25 - Feb 26
Total with taxes and fees
Serene Mid-Century 3/2 w/Bonus Room and Huge Shaded Yard w/Fence
Exterior

Vacation Home in Fairview Shores

Funky Remodeled Otown Bungalow Sleeps 8
$246 nightly
The price is $274
Mar 9 - Mar 10
Total with taxes and fees
Funky Remodeled Otown Bungalow Sleeps 8
Property grounds

Vacation Home in Fairview Shores

Charming home @wp. Patio +Gazebo. close to highwys
10.0 out of 10, Exceptional, (1 review)
"Very clean and location was great"
United States
Vicki V.
$220 nightly
The price is $245
Mar 8 - Mar 9
Total with taxes and fees
Charming home @wp. Patio +Gazebo. close to highwys
Exterior

Mobile Home in Fairview Shores

Comfy Tiny Home @WP. Large Private Deck+Queen bed
$184 nightly
The price is $204
Mar 1 - Mar 2
Total with taxes and fees
Comfy Tiny Home @WP. Large Private Deck+Queen bed
Private kitchen

Vacation Home in Winter Park

Spacious 5-bedroom house in gorgeous Winter Park
$367 nightly
The price is $406
Mar 2 - Mar 3
Total with taxes and fees
Spacious 5-bedroom house in gorgeous Winter Park
Fridge, microwave, oven, stovetop

Vacation Home in Fairview Shores

Mills House @WP. Sleeps 11 Renovated. Queen beds
6.0 out of 10, (1 review)
"The air fresheners plug ins were too powerful, we had to put them outside while we stayed in the house. Not enough power outlets. Hanging lamps on master bedroom are not practical, didn’t find the switch to turn them off. Spot light outside kept me up. The motion triggered the light to go on and off constantly. "
United States
Monica E.
$290 nightly
The price is $322
Mar 2 - Mar 3
Total with taxes and fees
Mills House @WP. Sleeps 11 Renovated. Queen beds
Private kitchen

Vacation Home in Winter Park

Cute 5-bedroom,6bed house in superb 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.
$590 nightly
The price is $653
Mar 1 - Mar 2
Total with taxes and fees
Cute 5-bedroom,6bed house in superb Winter Park.
Standard Apartment | Living area | 50-inch LCD TV with digital channels, Netflix, streaming services

Apartment in Sanford

The Blue Aztec
3.0 star property
9.6 out of 10, Exceptional, (13 reviews)
"Great location! Great Dining! "
United States
Lisa
$218 nightly
The price is $235
Mar 9 - Mar 10
Total with taxes and fees
The Blue Aztec
2 bedrooms, desk, free WiFi

Apartment in Sanford

The Front Porch
3.0 star property
9.4 out of 10, Exceptional, (3 reviews)
"Enjoyed the place. Nice and relaxing. Close to downtown and lots of options for food. "
United States
Johnny
$205 nightly
The price is $230
Mar 2 - Mar 3
Total with taxes and fees
The Front Porch
Standard Apartment | Living area | 50-inch LED TV with digital channels, Netflix, streaming services

Apartment in Sanford

Boho Nights
3.0 star property
9.4 out of 10, Exceptional, (11 reviews)
"Wonderful spot, and excellent hosts!"
United States
Thomas
$140 nightly
The price is $157
Mar 9 - Mar 10
Total with taxes and fees
Boho Nights
Pool

Vacation Home in Union Park

Spacious & Private Guest Pool House Oasis
9.8 out of 10, Exceptional, (22 reviews)
"Great location , Very enjoy , private space, would book in the future for sure "
United States
Matt B.
$242 nightly
The price is $270
Feb 25 - Feb 26
Total with taxes and fees
Spacious & Private Guest Pool House Oasis
Interior

Apartment in Sanford

Totally 80's
3.0 star property
9.4 out of 10, Exceptional, (3 reviews)
"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
$131 nightly
The price is $147
Feb 25 - Feb 26
Total with taxes and fees
Totally 80's
1 bedroom, iron/ironing board, WiFi, bed sheets

Apartment in Southchase

Cozy Apartment in S Orlando, approx. 20 minutes away from Disney and Universal.
9.8 out of 10, Exceptional, (22 reviews)
"Quiet peaceful location"
United States
joseph B.
$117 nightly
The price is $129
Feb 25 - Feb 26
Total with taxes and fees
Cozy Apartment in S Orlando, approx. 20 minutes away from Disney and Universal.
Exterior detail

Apartment in Orlando

Cozy Private Apartment - Stylish & Spotless — No sharing areas
10.0 out of 10, Exceptional, (29 reviews)
"Mercedes is an amazing host and has thought of - and provided EVERYTHING you need for a fantastic stay. Would ABSOLUTELY stay here again and HIGHLY recommend!!"
United States
Rick K.
$165 nightly
The price is $183
Mar 4 - Mar 5
Total with taxes and fees
Cozy Private Apartment - Stylish & Spotless — No sharing areas
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.
View all properties

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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
"Lovely room and hotel! Would go back!"
Brianna 4-night trip
Posted 21 hours ago
Westgate Lakes Resort & Spa Universal Studios Area

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 $93 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?

Magical Stay Near Universal Studios Florida: Visitors like this Winter Park vacation home rental. It is equipped with a garden, air-conditioning, and a Smart TV to help you feel comfortable during your stay.

How many vacation rentals are there in Winter Park?

Expedia has 43 vacation rentals for your stay in Winter Park.

What can I see and do in Winter Park?

Cultural attractions include Morse Museum of American Art and Casa Feliz Historic Home Museum, 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 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.