Winter Park Vacation Rentals

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Check prices for these dates

In two weeks
Mar 6 - Mar 8
In two months
Apr 17 - Apr 19
In three months
May 15 - May 17
In four months
Jun 12 - Jun 14

Our top choices for Winter Park vacation rentals

Outdoor pool

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
9.4 out of 10, Exceptional, (3 reviews)
"Fantastic Host"
United States
Marek K.
$164 nightly
The price is $181
Feb 23 - Feb 24
Total with taxes and fees
1-bedroom vacation room just 12 minutes from University of Central Florida
Fridge, microwave, oven, stovetop

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
10.0 out of 10, Exceptional, (1 review)
"Pool is very inviting"
United States
Geri Lamborn M.
$242 nightly
The price is $269
Feb 24 - Feb 25
Total with taxes and fees
Quiet and safe neighborhood come to this great place with lots of room for relax
Fridge, microwave, oven, stovetop

Stylish Boutique Guest house in Winter Park

Stylish Boutique Guest house in Winter Park
Winter Park
10.0 out of 10, Exceptional, (103 reviews)
"Beautiful house and such sweet hosts! Would highly recommend! The cabinets were well stocked! "
United States
Amber V.
Stylish Boutique Guest house in Winter Park
Interior

Cozy home 5min to Park Ave and Downtown Orlando

Cozy home 5min to Park Ave and Downtown Orlando
Fairview Shores
$305 nightly
The price is $338
Feb 22 - Feb 23
Total with taxes and fees
Cozy home 5min to Park Ave and Downtown Orlando
Fridge, microwave, oven, stovetop

Sleek, Spacious & Central – Your Ideal Getaway

Sleek, Spacious & Central – Your Ideal Getaway
Fairview Shores
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 23 - Feb 24
Total with taxes and fees
Sleek, Spacious & Central – Your Ideal Getaway
Property grounds

Virbo Host Website is not working for me. Do not book this property. Thank you

Virbo Host Website is not working for me. Do not book this property. Thank you
Fairview Shores
$99 nightly
The price is $109
Feb 20 - Feb 21
Total with taxes and fees
Virbo Host Website is not working for me. Do not book this property. Thank you
TV, offices

Cozy home w/working space & kitchen

Cozy home w/working space & kitchen
College Park
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.
$228 nightly
The price is $254
Feb 25 - Feb 26
Total with taxes and fees
Cozy home w/working space & kitchen
Property grounds

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

Charming home @wp. Patio +Gazebo. close to highwys
Fairview Shores
10.0 out of 10, Exceptional, (1 review)
"Very clean and location was great"
United States
Vicki V.
$233 nightly
The price is $259
Feb 22 - Feb 23
Total with taxes and fees
Charming home @wp. Patio +Gazebo. close to highwys
Private kitchen

Spacious 5-bedroom house in gorgeous Winter Park

Spacious 5-bedroom house in gorgeous Winter Park
Winter Park
$294 nightly
The price is $325
Feb 24 - Feb 25
Total with taxes and fees
Spacious 5-bedroom house in gorgeous Winter Park
Smart TV, video games

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
$395 nightly
The price is $440
Feb 23 - Feb 24
Total with taxes and fees
Serene Mid-Century 3/2 w/Bonus Room and Huge Shaded Yard w/Fence
Exterior

Funky Remodeled Otown Bungalow Sleeps 8

Funky Remodeled Otown Bungalow Sleeps 8
Fairview Shores
$259 nightly
The price is $288
Feb 22 - Feb 23
Total with taxes and fees
Funky Remodeled Otown Bungalow Sleeps 8
Pool

Cozy RV with AC and fitness room in brilliant Winter Park

Cozy RV with AC and fitness room in brilliant Winter Park
Goldenrod
$142 nightly
The price is $157
Mar 4 - Mar 5
Total with taxes and fees
Cozy RV with AC and fitness room in brilliant Winter Park
Exterior

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

Comfy Tiny Home @WP. Large Private Deck+Queen bed
Fairview Shores
$234 nightly
The price is $260
Feb 23 - Feb 24
Total with taxes and fees
Comfy Tiny Home @WP. Large Private Deck+Queen bed
Fridge, microwave, oven, stovetop

Mills House @WP. Sleeps 11 Renovated. Queen beds

Mills House @WP. Sleeps 11 Renovated. Queen beds
Fairview Shores
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.
$296 nightly
The price is $329
Feb 22 - Feb 23
Total with taxes and fees
Mills House @WP. Sleeps 11 Renovated. Queen beds
Private kitchen

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.
$582 nightly
The price is $643
Feb 24 - Feb 25
Total with taxes and fees
Cute 5-bedroom,6bed house in superb Winter Park.
Pool

Spacious & Private Guest Pool House Oasis

Spacious & Private Guest Pool House Oasis
Union Park
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.
$240 nightly
The price is $268
Feb 22 - Feb 23
Total with taxes and fees
Spacious & Private Guest Pool House Oasis
2 bedrooms, desk, free WiFi

The Front Porch

The Front Porch
3.0 star property
Sanford
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 LCD TV with digital channels, Netflix, streaming services

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
$219 nightly
The price is $236
Mar 16 - Mar 17
Total with taxes and fees
The Blue Aztec
Standard Apartment | Living area | 50-inch LED TV with digital channels, Netflix, streaming services

Boho Nights

Boho Nights
3.0 star property
Sanford
9.2 out of 10, Wonderful, (10 reviews)
"Wonderful spot, and excellent hosts!"
United States
Thomas
$140 nightly
The price is $157
Feb 23 - Feb 24
Total with taxes and fees
Boho Nights
Exterior detail

Cozy Private Apartment - Stylish & Spotless — No sharing areas

Cozy Private Apartment - Stylish & Spotless — No sharing areas
Orlando
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 3 - Mar 4
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.
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Top Winter Park Hotel Reviews

Holiday Inn Resort Orlando Suites - Waterpark by IHG

Holiday Inn Resort Orlando Suites - Waterpark by IHG

10/10 Excellent
"Amenities 10/10"
Stephanie 3-night trip
Posted 4 hours ago
Holiday Inn Resort Orlando Suites - Waterpark by IHG

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?

Marriott's Sabal Palms: You might want to consider this vacation home rental near Winter Park, which is located near the airport and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Kick off your shoes and enjoy yourself with an outdoor tennis court and a hot tub.

How many vacation rentals are there in Winter Park?

Expedia has 45 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.