Entire home

Mid Century Modern Cottage in The Heart of Winter Park

Cottage in Winter Park with kitchen and patio

Overview
Amenities
Policies
Location

Exceptional

2 bedrooms1 bathroomSleeps 51000 sq ft

Popular amenities

Parking available
Dryer
Washer
Kitchen
Outdoor space

Explore the area

Winter Park, FL

Place, Rollins College
‪3 min drive‬
Place, Full Sail University
‪4 min drive‬
Place, AdventHealth Orlando
‪8 min drive‬
Airport, Orlando, FL (MCO-Orlando Intl.)
‪23 min drive‬

Rooms & beds

2 bedrooms (sleeps 5)

1 bathroom

Bathroom 1

Spaces

Deck or patio

Kitchen

Garden

Dining area

About this property

Mid Century Modern Cottage in The Heart of Winter Park

Furnished Mid Century Modern Short/Long term rental located in charming Olde Winter Park. Two bedrooms and one and half baths. Steps from shopping and restaurants and less than a mile from Park Ave with it's famous museums, parks, shops and dining. This home is complete with authentic mid century modern furnishings, comfortable bedding, mid century couches and chairs, new linens, two televisions (includes cable tv), central heat and air, new landscaping, irrigation and yard maintenance provided, fenced back yard, dishwasher, disposal, washer, dryer, and a fully stocked kitchen, including appliances and dishes. Power, internet, water, sewer and trash pick up included.
Queen bed in Master, two twin beds in Guest room, sleeper sofa in Sun Room. Sleeps 5 comfortably.
Rates vary with length of stay.
Just bring your toothbrush.
Pets upon approval.
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Amenities

Kitchen

Washing machine

Dryer

Pet-friendly

Free WiFi

Air conditioning

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Kitchen
Washer
Dryer
Pet-friendly

House Rules

Check in after 4:00 PM

Minimum age to rent: 25

Check out before 11:00 AM

Children

Children allowed: ages 0–17

Children welcome

Events

No events allowed

Pets

Pets allowed

Please add a $100 pet fee

Smoking

Smoking is not permitted

Non smoking only

Important information

You need to know

Extra-person charges may apply and vary depending on property policy

Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges

Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed

On-site parties or group events are strictly prohibited

Host has indicated that there is a carbon monoxide detector on the property

Host has indicated that there is a smoke detector on the property

Safety features at this property include a fire extinguisher and a deadlock

We should mention

A car is recommended for transport to and from this property

About the area

Winter Park

Located in Winter Park, this cottage is in the city centre. Florida Mall and Orlando International Premium Outlets are worth checking out if shopping is on the agenda, while those wishing to experience the area's popular attractions can visit The Wizarding World of Harry Potter™ and Universal Studios Florida. Looking to enjoy an event or a game? See what's going on at Kia Center or Camping World Stadium. Make sure you get close to the area's animals with activities such as game walks and birdwatching.

View more Cottages in Orlando

Winter Park, FL

What's nearby

Rollins College - 3 min drive - 2.0 km
Full Sail University - 4 min drive - 3.0 km
AdventHealth Orlando - 8 min drive - 5.9 km
Orlando Science Center - 9 min drive - 6.3 km
Kia Center - 12 min drive - 10.4 km

Getting around

Winter Park Station - 6 min drive
Maitland Station - 9 min drive
Orlando International Airport (MCO) - 27 min drive

Restaurants

‪McDonald's - ‬13 min walk
‪Bolay - ‬7 min walk
‪Tijuana Flats - ‬6 min walk
‪Starbucks - ‬15 min walk
‪Aloma Bowl - ‬16 min walk

Frequently asked questions

Is Mid Century Modern Cottage in The Heart of Winter Park pet-friendly?

Yes, pets are allowed at this property.

What time is check-in at Mid Century Modern Cottage in The Heart of Winter Park?

Check-in begins at 4:00 PM.

What time is check-out at Mid Century Modern Cottage in The Heart of Winter Park?

Checkout is at 11:00 AM.

Where is Mid Century Modern Cottage in The Heart of Winter Park located?

Located in the heart of Winter Park, this cottage is within 1 mile (2 km) of Winter Park Hospital and Albin Polasek Museum and Sculpture Gardens. Rollins College and Kraft Azalea Gardens are also within 2 miles (3 km).

9.8

Exceptional

9.8/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

10/10 Excellent

Joseph P.

2 Sept, 2025

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great neighborhood and location. Clean house

Stayed 58 nights in Apr 2025

10/10 Excellent

Joseph P.

2 Sept, 2025

Liked: Cleanliness, check-in, communication, location, listing accuracy

Very clean and well built house. Perfect location!Host was attentive and easy to deal with. The neighborhood was peaceful. The furniture in the living room was uncomfortable but livable.

Stayed 88 nights in Jun 2025

10/10 Excellent

Shannon R.

30 Mar, 2020

Liked: Cleanliness, check-in, communication, location, listing accuracy

Peaceful

This was my second stay at this property. It felt like coming home. Clean, cozy and safe area.

Stayed 7 nights in Mar 2020

10/10 Excellent

Kathyrn P.

31 Oct, 2021

Liked: Cleanliness, check-in, communication, location, listing accuracy

Tons of Room and Charm

The only thing that is better than the property is the host. Amazing home in convenient and safe neighborhood. Custom touches and attention to detail make this sweet bungalow an experience in itself. The host is attentive and supper responsive. No doubt we would stay here again if ever in the area!!

Stayed 30 nights in Oct 2021

10/10 Excellent

Becky R., Boerne, Texas

3 Aug, 2020

Liked: Cleanliness, check-in, communication, location, listing accuracy

Authentic mid century with great location

Every detail of this bungalow is so authentic to a mid-century vibe. We loved the location of this bungalow and loved all the conveniences that allowed us to settle in. Kathy was an amazing host who went out of her way to accommodate every request. I loved all the details and the beautiful touches; a little history lesson on design.

Stayed 12 nights in Jul 2020

10/10 Excellent

Alexander H.

2 Mar, 2024

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful stay!

Cannot say enough good things about this house and Kathy! It's beautiful, well-located, well-maintained, and great for a good visit. This was our third trip here, and we will be back! Kathy is super-responsive even with minor things and was patient with me and my family. It's a small house, but well-furnished, and the price/value ratio is off the charts. My wife, toddler daughter, and I had a great visit. (I hesitate to let people know what a gem this place is because I don't want more competition, but truly, the best place I've ever rented, and there's a reason we keep coming back!)

Stayed 41 nights in Jan 2024

10/10 Excellent

me m.

10 Mar, 2019

Cute, clean and comfortable!

Our stay in Winter Park was great. Three of our adult kids joined us for part of the week and there was plenty of room for all of us. The house was very clean, the beds were comfortable and the location was convenient (less that two miles) to “downtown” Winter Park. We enjoyed the front porch, back yard grilling and our meals in the screen porch were fun. There are grocery stores nearby, beautiful neighborhoods to walk and it is close to Rollins college if you have kids there. Kathy was helpful and responded to any questions regarding booking, etc. in a timely manner......PLUS she left a nice basket of treats on the counter as a greeting for us.

Stayed 7 nights in Feb 2019

10/10 Excellent

Herb and Deb M.

2 Apr, 2023

Liked: Cleanliness, check-in, communication, location, listing accuracy

A comfortable dog-friendly home in a great neighborhood.

We really enjoyed our 6 week stay in Winter Park. The house is on a quiet side street, in a neighborhood great for walking. The fenced back yard was perfect for our dog. Two blocks away are some convenient shops and restaurants including some with outdoor seating. Park Avenue is a 30 minute walk, and is a mecca for shopping and dining. Rollins College is a 30 minute walk. We especially liked walking in the lakeside areas very close to the house. We enjoy mid-century furnishings, and this house is a virtual museum of mid-century. There are some minor things need attention, like the worn bathtub and the side screened room furniture, but the overall feel of the house is comfortable, peaceful, and quiet.

Stayed 41 nights in Feb 2023

10/10 Excellent

Sue W., Ottawa, Canada

7 Mar, 2018

Bright, fresh and well located

We spent four weeks in this lovely little bungalow and enjoyed it very much. The house is bright and fresh-feeling. It's furnished in a fun 1950s style and while retro, nothing seems old. The house is well laid out and offers several different areas for relaxing. We spent most of our 'at home' time either in the screened room or the indoor sun room - both were very comfortable. The bed in the master bedroom is very comfortable. We didn't use the twin beds in the second bedroom but the room was nice and the extra closet space was handy. The kitchen and bathroom are small, clean and functional. The back yard (fenced all around) is sunny and has a lovely large tree offering shade. The neighbourhood was very pleasant for walking in - lots of tree lined streets and interesting houses. The main centre of Winter Park offers lots of nice restaurants and shops and is within walking distance or a short drive, as is beautiful Rollins College. There are also several restaurants within a few minutes of the house. The owner was very easy to work with and quick to respond to any questions. We're looking forward to a return visit.

10/10 Excellent

Sandy R.

13 Jul, 2021

Liked: Cleanliness, check-in, communication, location, listing accuracy

Winter Park hideaway

My husband and I had a wonderful stay at this location. No problems and would stay again. Thanks

Stayed 38 nights in May 2021

10/10 Excellent

Patricia A., Richmond

19 May, 2021

Liked: Cleanliness, check-in, communication, location, listing accuracy

Midcentury Gem

wonderful location, lovely enclosed back yard, comfortable beds, attentive host,

Stayed 32 nights in Apr 2021

10/10 Excellent

Laurie N., Louisa, VA

19 Aug, 2020

Liked: Cleanliness, check-in, communication, location, listing accuracy

Cute and Clean`

This property suited perfectly. It was cute, clean and well equipped. The back yard was fenced, so Shiloh, my German Shepherd did not have to stay on a leash the entire time. The neighborhood was quiet and it was the perfect place to get away after a busy day visiting family.

Stayed 7 nights in Aug 2020

10/10 Excellent

Shannon R., Navarre, Florida

14 Jul, 2019

Liked: Cleanliness, check-in, communication, location, listing accuracy

Winter Park Gem

This house is a gem in the heart of Winter Park. Our family of 4 and our dog loved this property. It is close to everything you could need. And you really only do need to bring your toothbrush! The linens and the beds are very comfortable and the house is decorated very nice. The owner is very easy to work with and left us a welcome basket of goodies. We look forward to another weeks stay in this sweet home.

Stayed 7 nights in Jun 2019

10/10 Excellent

Sue W.

7 Mar, 2019

Great house, great location

It was a pleasure to stay in the well located bungalow again. It’s clean, nicely decorated in a 1950s style, and bright. The large backyard is fenced and is ideal for letting the dog have a little off leash time. All the appliances function as they should and the owner is very quick to respond to any issues. We look forward to a return visit in the future!

10/10 Excellent

Bryan G., Cincinnati

1 Feb, 2019

mid century cottage

Is lovely cottage in a great location. Owner was excellent at communicating check in and out. Home nicely appointed with WIFI, cable, cooking items, and laundry room. Owner had provided a variety of nice snack items and soaps, lotions, etc. Location close to central winter park restaurants and shops. walking distance to nearby shopping center. nearby.

Stayed 7 nights in Jan 2019

10/10 Excellent

Paula M., Los Angeles

20 Jan, 2019

Felt right at home!

First, Kathy is a wonderful host. She left us a very thoughtful welcome basket and checked in with us to make sure we had arrived safely and answer any questions. The house itself was just as shown in the photos and had everything we needed, all clean and in working order. The beds were super comfortable, the linens soft, the shower hot, good wifi, and a nice quiet neighborhood. We had family over for dinner and even though the house is small it never felt cramped. The layout is really nice, open and bright with plenty of room. We had a wonderful stay and would love to have Kathy as our host again. Thanks again Kathy!

Stayed 7 nights in Jan 2019

10/10 Excellent

Sarah C.

17 Nov, 2018

Beautiful home in perfect location!

Throughly enjoyed my stay! The house is super cute and comfy and is stocked with everything you would need. The area is perfect. Its quiet but is still close to everything. Winter Park has so many restaurants and things to do. Also, super close to downtown Orlando. Would definetely stay again!

Stayed 11 nights in Nov 2018

8/10 Good

James B.

23 Oct, 2018

Nice & Neat

Neat home, good proximity to downtown Winter Park, and nice size fenced backyard.

Stayed 16 nights in Sep 2018

10/10 Excellent

Jacob A.

21 Oct, 2018

Great return - Feels like home.

This was our second stay in this cozy house in beautiful Winter Park. Feels like home.

Stayed 8 nights in Oct 2018

10/10 Excellent

Amy R.

23 Sept, 2018

Charming, comfortable, perfect.

The house is in a great location, easy to get where you want to go and especially close to Park Ave shops and restaurants. The neighborhood is nice and I felt very safe staying in the house alone. The decor is amazing mid century modern pieces that I would love for my home. I stayed 10 days and the house functions very well; the bed is super comfy. The owner is wonderful and always responded promptly, offered extra nights if I needed due to NC hurricane, and left delicious goodies for my arrival. I will definitely stay again!

Stayed 10 nights in Sep 2018

8/10 Good

LIZA A.

8 Sept, 2018

Great experience!

Great experience and owners were extremely helpful and responsive!

Stayed 30 nights in Aug 2018

10/10 Excellent

grace f.

7 May, 2018

Great stay!

Cheery and comfortable house close to Rollins which was important to us. Lovely host. Beds were comfy and kitchen had all we needed. Highly recommend!!

Stayed 31 nights in Apr 2018

This review was submitted before 2018 and has not been verified.

10/10 Excellent

Jacob A.

20 Nov, 2017

Charming house - Great location

We enjoyed our 2week stay in this charming little house. Conveniently located in beautiful Winter Park. House is clean and well equipped. Host was excellent to deal with.

Stayed 14 nights in Nov 2017

This review was submitted before 2018 and has not been verified.

8/10 Good

Deborah F.

14 Mar, 2017

Very cute house and walking distance to Park Ave and all the restaurants, shops and museums.

We enjoyed our stay in this conveniently located, charming home. Furnishings had an attractive retro vibe, beds were comfortable and there were a nice variety of rooms/floor plan. Could be a few more easily accessible outlets for plugging in our electronic devices.

Stayed 7 nights in Mar 2017

This review was submitted before 2018 and has not been verified.

10/10 Excellent

Kristina A.

31 Oct, 2016

Perfect get away

The house was comfy and cozy, kitchen well equipped, great backyard for our dogs. Great location near restaurants. Owner was great to deal with, very professional!

About the host

Hosted by Kathy Black

Kathy first moved to Winter Park in 1971 when her father retired from a career in the Air Force. She and her husband Bill graduated from both Winter Park High School and Rollins College, also located in Winter Park. Growing up in military families, both Kathy and Bill traveled extensively with stays in Japan, Hawaii and Guam. They are happy to call Winter Park their home and enjoy all it has to offer year round. They enjoy triathlons, marathons, hiking and boating and Winter Park provides the perfect playground year round. They would love to share all the amenities and beauty of this small town with you.

Why they chose this property

The location of this bungalow is perfect for shopping, dining, traveling and simply taking a walk around the beautiful neighborhood. Stately oak trees, gracious homes, brick streets, and even peacocks roam the streets nearby.