Winter Park Vacation Rentals

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Vacation Rentals in Winter Park

Winter Park charm. Close to Park Ave

Winter Park charm. Close to Park Ave

Winter Park, FL
This family-friendly Winter Park vacation home is within a 15-minute walk of Winter Park Village and Enzian Theater. Rollins College and Orlando Museum of Art ...
4.8/5 Exceptional! (29 reviews)
Lovely cottage
"This lovely cottage was perfect for our visit with family in the area. We enjoyed our stay!"

Reviewed on Nov 2, 2021

Winter Park charm. Close to Park Ave
Cozy ★ 3 Bedroom Home in the ♥ of Winter Park! ☼

Cozy ★ 3 Bedroom Home in the ♥ of Winter Park! ☼

Winter Park, FL
The price is $197 per night from Dec 16 to Dec 16
This family-friendly vacation home is located in the city center, within 2 mi (3 km) of Albin Polasek Museum and Sculpture Gardens, Rollins College, and Full ...
3/5 (1 review)
great place with a few improvements
"instructions for wifi were missing key connection point lacking basic items: corkscrew, wine glasses, coffee cups, blankets, toaster, toilet paper, 1-2 trash bags, 1-2 dishwasher pods mattress in paneled room rolls to the middle bedrooms should have mirrors"

Reviewed on Oct 26, 2021

Cozy ★ 3 Bedroom Home in the ♥ of Winter Park! ☼
Winter Park Oasis

Winter Park Oasis

Winter Park, FL
The price is $162 per night from Jan 1 to Jan 1
This family-friendly Winter Park vacation home is within 2 mi (3 km) of Kraft Azalea Gardens and Rollins College. Winter Park Village and Full Sail University ...
5/5 Exceptional! (6 reviews)
Perfect WP location, super clean!
"We really enjoyed our experience in this super private bungalow, very central to Winter Park. It was exceptionally clean and we had plenty of space to hang out. Thanks Rubi!"

Reviewed on Nov 27, 2021

Winter Park Oasis
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Cute Winter Park Master Suite!!!

Cute Winter Park Master Suite!!!

Winter Park, FL
Located in Goldenrod, this vacation home is 2 mi (3.3 km) from Full Sail University and within 6 mi (10 km) of Rollins College and Winter Park Village. Kraft ...
5/5 Exceptional! (2 reviews)
Cozy place. Clean. Will stay again
"Nice place. Clean. Super fast WiFi. Stayed for 2 weeks for work and had no WiFi issues. Little sitting area in back has a small fridge, microwave, toaster and coffee maker. A desk for work if needed. Full walk in closet and clean bathroom. Very quiet neighborhood. No noise issues. Separate entrance ..."

Reviewed on Sep 22, 2021

Cute Winter Park Master Suite!!!
Amazing location- walk to everything

Amazing location- walk to everything

Winter Park, FL
This family-friendly Winter Park condo building is located on a lake, within a 10-minute walk of Rollins College and Winter Park Playhouse. Winter Park Village ...
5/5 Exceptional! (10 reviews)
Great fun, excellent location
"Wonderfully clean and furnished near many things down town Park Avenue, farmers market and tucked almost on the beautiful Rollins College campus. Great area for walkers or joggers. 1.5 miles to the beautiful 9 hole golf course Near 4 prominent Art Gallery venues and more. Winter Park has so much ..."

Reviewed on Nov 29, 2021

Amazing location- walk to everything
LUXURY FLAT IN WINTER PARK

LUXURY FLAT IN WINTER PARK

Winter Park, FL
Situated on a lake, this condo building is 0.2 mi (0.3 km) from Full Sail University and within 6 mi (10 km) of Rollins College and Harry P. Leu Gardens. Winter ...
LUXURY FLAT IN WINTER PARK
Casa Winter Park

Casa Winter Park

Winter Park, FL
This family-friendly Winter Park vacation home is within 2 mi (3 km) of Full Sail University and Albin Polasek Museum and Sculpture Gardens. Rollins College ...
4.8/5 Exceptional! (28 reviews)
Weekend Getaway
"Overall, the property was gorgeous. The only negative is how shrill the backyard pool alarm is."

Reviewed on Nov 28, 2021

Casa Winter Park
Casa Aloma

Casa Aloma

Winter Park, FL
This family-friendly Winter Park vacation home is within 3 mi (5 km) of Full Sail University and Rollins College. Kraft Azalea Gardens and Albin Polasek Museum ...
4.8/5 Exceptional! (130 reviews)
A Little Touch of the Christmas Spirit
"I have used VRBO on numerous occasions and this was one of the best stays I have ever had. The Casa Aloma was very clean, the furniture and decor was very nice. Had the weather been a little warmer, we would have enjoyed swimming in the pool. We went to Orlando to spend Thanksgiving with family and ..."

Reviewed on Nov 28, 2021

Casa Aloma
Breezy Pool Home!

Breezy Pool Home!

Winter Park, FL
Located in Goldenrod, this vacation home is 2 mi (3.3 km) from Full Sail University and within 6 mi (10 km) of Rollins College and Winter Park Village. Kraft ...
4.7/5 Exceptional! (3 reviews)
We will be back in the spring!
"Beautiful property, very clean, everything you could need, and super fast and efficient communication! Thank you again Snow!"

Reviewed on Oct 27, 2021

Breezy Pool Home!
Just Like Home... With A Pool!

Just Like Home... With A Pool!

Winter Park, FL
This family-friendly Winter Park vacation home is within 3 mi (5 km) of Full Sail University and Red Bug Lake Park. Kraft Azalea Gardens and Lake Lily Park are ...
4.7/5 Exceptional! (45 reviews)
Great Property
"Sandra was so great to work with. Anything I had a question or concern about she would answer right away. I will definitely rent from her again."

Reviewed on Nov 12, 2021

Just Like Home... With A Pool!
Studio Blue

Studio Blue

Winter Park, FL
Located in the heart of Winter Park, this apartment building is within 1 mi (2 km) of Winter Park Playhouse and Orlando Science Center. Orlando Museum of Art ...
5/5 Exceptional! (1 review)
Cutest little place.
"We were just here for a quick, one night stay. It’s adorable, immaculately clean, and easy in & out. All communication with the owner was prompt. Thanks a bunch!"

Reviewed on May 1, 2021

Studio Blue
Cute bungalow minutes walk from Park Avenue.

Cute bungalow minutes walk from Park Avenue.

Winter Park, FL
Located in the heart of Winter Park, this vacation home is within 2 mi (3 km) of Albin Polasek Museum and Sculpture Gardens, Rollins College, and Winter Park ...
5/5 Exceptional! (6 reviews)
Great stay
"Great location, so comfortable, and wonderful host who was so accommodating, responsive and flexible! 10/10"

Reviewed on Aug 12, 2021

Cute bungalow minutes walk from Park Avenue.
3 BR Getaway w/ Private Pool near Full Sail University

3 BR Getaway w/ Private Pool near Full Sail University

Winter Park, FL
Situated in Winter Park, this vacation home is 1.4 mi (2.2 km) from Full Sail University and 2.3 mi (3.7 km) from Rollins College. Albin Polasek Museum and Sculpture ...
5/5 Exceptional! (1 review)
in town visiting son at full sail
"cute & quiet neighborhood good location close to full sail & ucf home has ample space for family accurate pics on listing thoroughly enjoyed the home"

Reviewed on Oct 25, 2021

3 BR Getaway w/ Private Pool near Full Sail University
Comfy Home in Winter Park, can accommodate up 6 guests!

Comfy Home in Winter Park, can accommodate up 6 guests!

Winter Park, FL
Situated in Winter Park, this vacation home is within 2 mi (3 km) of Winter Park Playhouse, Winter Park Village, and AdventHealth Orlando. Rollins College and ...
4.3/5 Excellent! (4 reviews)
Extra great!
"We ended up staying just ourselves for an extra precaution. The house was exceptional and very clean I would truly recommend it to anyone else."

Reviewed on Dec 14, 2020

Comfy Home in Winter Park, can accommodate up 6 guests!
Mid Century Luxury, 1 block from Park Ave (#3)

Mid Century Luxury, 1 block from Park Ave (#3)

Winter Park, FL
Located in the heart of Winter Park, this historic apartment building is within 2 mi (3 km) of Casa Feliz Historic Home Museum, Rollins College, and Winter Park ...
4.9/5 Exceptional! (19 reviews)
Location, location, location!
"We thoroughly enjoyed our stay at this adorable mid-century modern apartment. The bathroom and kitchen are updated and very nice. But the best part of this apartment is the location! We walked to Park Ave for dinner most nights. We also enjoyed walking through the gorgeous neighborhood every ..."

Reviewed on Aug 7, 2021

Mid Century Luxury, 1 block from Park Ave (#3)
Charming Winter Park Fully Furnished & Pet Friendly Farmhouse Bungalow

Charming Winter Park Fully Furnished & Pet Friendly Farmhouse Bungalow

Winter Park, FL
Located in Goldenrod, this vacation home is 1.4 mi (2.3 km) from Full Sail University and within 6 mi (10 km) of Rollins College and Winter Park Village. Albin ...
4.7/5 Exceptional! (9 reviews)
Great property
"The property was perfect, conveniently located and very clean. We would definitely stay again! Very easy to communicate with owner, who responded quickly when needed"

Reviewed on Nov 9, 2021

Charming Winter Park Fully Furnished & Pet Friendly Farmhouse Bungalow
Mid Century Luxury, 1 block from Park Ave (#2)

Mid Century Luxury, 1 block from Park Ave (#2)

Winter Park, FL
Situated in Winter Park, this historic apartment building is within 2 mi (3 km) of Casa Feliz Historic Home Museum, Rollins College, and Winter Park Village. ...
5/5 Exceptional! (17 reviews)
Return Visit
"The best compliment you can give a host and their property is to return. This is at least our third time to stay in this home. Thanks Michael, you have been so kind and gracious to our family and have been so flexible with all our spur of the moment decisions to visit our grandchildren. The location ..."

Reviewed on Jan 20, 2021

Mid Century Luxury, 1 block from Park Ave (#2)
Cozy Cove w/ Heated Pool and Hot Tub

Cozy Cove w/ Heated Pool and Hot Tub

Winter Park, FL
Situated in Winter Park, this vacation home is within 2 mi (3 km) of Casa Feliz Historic Home Museum, Winter Park Village, and Rollins College. Orlando Museum ...
Cozy Cove w/ Heated Pool and Hot Tub
Spend the Holiday Season in Winter Park<br>🌞🕶🏡

Spend the Holiday Season in Winter Park<br>🌞🕶🏡

Winter Park, FL
Situated in Winter Park, this romantic vacation home is within 3 mi (5 km) of Rollins College, Harry P. Leu Gardens, and Winter Park Village. Orlando Museum ...
5/5 Exceptional! (8 reviews)
"Owners were amazing hosts! The house is in a perfect location and so nicely furnished. We had an amazing time having my bridesmaids there and getting ready there for my wedding ❤️"

Reviewed on Nov 15, 2021

Spend the Holiday Season in Winter Park<br>🌞🕶🏡
Pondside Retreat with Koi in Charming Winter Park, FL

Pondside Retreat with Koi in Charming Winter Park, FL

Winter Park, FL
Situated in Winter Park, this vacation home is 2.1 mi (3.3 km) from Kraft Azalea Gardens and 2.1 mi (3.4 km) from Full Sail University. Winter Park Country Club ...
Pondside Retreat with Koi in Charming Winter Park, FL
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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.

Large Group Rentals Winter Park

Marriott Cypress Harbour 2BD Villa

Marriott Cypress Harbour 2BD Villa

Orlando, FL
The price is $190 per night from Jan 3 to Jan 3
Marriott Cypress Harbour 2BD Villa
Four Bedrooms w Pool Townhome 4841

Four Bedrooms w Pool Townhome 4841

4 out of 5
4841 Romeo Circle, Kissimmee, FL
The price is $142 per night from Dec 15 to Dec 15
Four Bedrooms w Pool Townhome 4841
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.

Large Group Cabins Winter Park

Riverfront Orlando Area Cabin in Wekiwa State Park

Riverfront Orlando Area Cabin in Wekiwa State Park

Apopka, FL
Riverfront Orlando Area Cabin in Wekiwa State Park
The Great Experience

The Great Experience

Orlando, FL
The Great Experience
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.

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 months, such as . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year. is the cheapest month to visit, with the most expensive. 

Your chosen location, property type, and amenities will impact the cost of your trip, too. Right now, Winter Park vacation rentals range between $142 per night and $197 per night.

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. 

Frequently asked questions