6 Bedrooms - Rating 5 (26)

Our Lakeside Legacy


Bedroom 6 bedrooms
Bathroom 7 baths
Guests 14 guests
Pets Not Allowed Pets Not Allowed


Bedding Bedding
User User
Bedroom 1
Sleeps: 2
1 King

Upper level

Attached Bathroom

User User
Bedroom 2
Sleeps: 2
1 Queen

Upper level

Attached Bathroom

User User
Bedroom 3
Sleeps: 2
1 Queen

Upper level

Attached Bathroom

User User
Bedroom 4
Sleeps: 2
1 King

Upper level

Attached Bathroom

User User
Bedroom 5
Sleeps: 2
1 Queen

Upper level

Attached Bathroom

User User User User
Bedroom 6
Sleeps: 4
1 Queen
1 Sofa Bed

Level 3

Attached Bathroom


Description Description
Welcome to Our Lakeside Legacy, the house that our great grandparents built as some of the first settlers in Baileys Harbor. This loving, well cared for Brann family home has created many great memories for us and we are honored for you to make your own at this one-of-a-kind property, hosted by Simple Life Rentals. All five suites are ensuite – offering you the utmost comfort and privacy when vacationing with up to 14 of your family and friends.

Perfectly situated in the heart of town with over 150 feet of lake frontage in your backyard. The large yard offers expansive views of Baileys Harbor, the lighthouse, and Lake Michigan. Enjoy three levels of patios and decks, all lake facing, to take in the incredible views. Plus, a classic, town facing covered front porch is the perfect spot to watch the folks walking by as they move around town. This heart of town location is steps from some of Door County’s finest dining, breweries, shops, marina, kayaking, charter fishing, and beaches.

Property Features:
+ 150 feet of Lake Michigan waterfront
+ Over 5000 square feet of living space!
+ One 65" Smart TV in main level living room, streaming content via Roku and equipped with a DVD player. Guests may log in using own account.
+ 4 spacious living spaces on the first level, offering versatile areas for relaxation and socializing
+ 2 dedicated work areas (parlor on the first level and primary suite on second level)
+ 3 fireplaces for aesthetics only, not for guest use
+ T-Mobile Home Internet service is available for reliable connectivity throughout your stay
+ Hot water heat throughout the home
+ Mitsubishi cooling appliances in each of the living spaces
+ Washer, dryer, iron, ironing Board
+ Books and games for guest's enjoyment
+ Large, fully equipped chef's kitchen (see amenites) includes ice maker, Viking range, blender, crockpot, beverage center and wine chiller
+ Level two features a beverage refrigerator

Accommodations:
Suite 1 (second floor): Waterfront, King bed, ceiling fans, separate living room, wet bar area with beverage center and a workspace complete with desk and chair; private full bath with shower and double vanity sinks
Suite 2 (second floor): 2 separate bedrooms each with a queen bed; shared full bathroom in the middle has a tub shower combo
Suite 3 (second floor): Waterfront, king bed, shared waterside deck; private full bath with a tub shower combo
Suite 4 (second floor): Waterfront, queen bed, shared waterside deck; private full bath with original claw foot tub shower combo
Suite 5 (third floor): Waterfront, queen bed, living space, private deck and pullout sofa bed for additional sleeping space; private full bath with walk-in shower
Plus 2 additional bathrooms
Hair dryers are provided in each full bathroom

Dining Seating:
Kitchen island with seating for 4, morning table for 2, plus a formal dining room with seating for 6
for convenient access to refreshments

Outdoor Area:
Large, covered front porch with 2 chairs and coffee table
Multiple patios, decks and private balconies with several patio tables and plenty of seating, all lake-facing suites, offering breathtaking views
Gas grill
Parking for 2 vehicles in driveway
Plenty of nearby street and off-street parking available

Water Access:
Shelf rock shorefront
Water shoes recommended for swimming
Public dock use and water activity rentals available at nearby town marina

Extra Perks:
Walk across the street to Lakeshore Adventures for kayak, paddle board, etc rentals and to book zipline tours and charter fishing trips. Check-in instructions include details to get a discount when staying at Lakeside Legacy.

Amenity + damage protection waiver includes:
-Bed linens, pillows, blankets, and bathroom towels. (Please bring your own beach towels)
-A starter pack of essentials which includes toilet paper, paper towel, dish soap, dishwasher soap, hand soap, and garbage bags. Due to septic systems, we do not provide facial tissue. One each of travel size shampoo, conditioner, and body wash per full bathroom.
-PEACE OF MIND Damage protection covers up to $1000 per stay for accidental damage that is reported prior to departure (excludes any pet damage).

Home Truths:
Security cameras are positioned at the front entrance and in the back of the house.
No dock
Until fiber optic is available in the area, we don’t want our guests to compete for streaming services and therefore just one Smart TV is provided.
No garage access.
14 maximum guests total on the property at all times. This home is located in a quiet community with neighbors and is geared towards quiet family vacations. Due to the proximity of neighbors, we cannot accommodate bachelor or bachelorette parties, reunions, or other rowdy gatherings.

Door County Tourism Zone Commission Permit #02-56-2894-07

Please be aware that you must sign a terms and conditions agreement, which will be sent to you separately, to finalize your reservation.

Amenities 59 Amenities
  • Mini fridge
Bedrooms & Bathrooms
  • Body Soap
  • Conditioner
  • Hair Dryer
  • Hangers
  • Shampoo
Cleaning & Comfort
  • Dryer
  • Iron & Ironing Board
  • Washer
Entertainment
  • Board Games/ Puzzles
  • Books
  • DVD Player
  • Smart TV
  • Wireless Internet
Featured
  • Great For Large Groups
  • Luxury
  • Village
  • Water View
  • Waterfront
Indoors
  • Dining table
  • Living Room
Kitchen
  • Baking sheet
  • Barbecue utensils
  • Blender
  • Coffee
  • Cooking Basics
  • Crockpot
  • Dishes & Silverware
  • Dishwasher
  • Drip Coffee Maker
  • Hot water kettle
  • Kitchen Area (general)
  • Microwave
  • Oven
  • Stove
  • Toaster
  • Wine glasses
Location
  • Door County
Outside
  • Deck Patio Uncovered
  • Free Parking
  • Garden or Backyard
  • Grill
  • Parking
  • Patio or Balcony
  • Street Parking
Safety
  • Carbon Monoxide Detector
  • Fire Extinguisher
  • Private Entrance
  • Smoke Detector
Things to Do Nearby
  • Cycling
  • Fishing
  • Golf Course
  • Hiking
  • Hunting
  • Paddle Boating
  • Swimming
  • Water Tubing
  • Wind Surfing
  • Winery

Location Location

Reviews Rating 5 (26) Reviews
Rating 5
Great property. Upon arrival, there were a few things we noticed. When contacted, the host responded timely to fix necessary items.
Amanda - Posted: 10/14/2025
Hello Amanda, Thank you very much for taking the time to share your feedback and review! We truly appreciate your understanding and patience, and we’re glad our team was able to assist promptly during your stay. We hope to have the opportunity to welcome you back for an even smoother experience next time! Warm regards, The Simple Life Rentals Team
Simple Life Rentals staff
Rating 5
Fantastic time. Everything needed was provided. The only glitch was the oven which we dealt with. Location is awesome and the lawn setup made evenings wonderful. The house was very welcoming and gave us a great place to come back to after exploring the peninsula. 10/10 would stay here again.
Craig - Posted: 10/9/2025
Hello Craig, We truly appreciate your kind words and are so glad to hear you had a fantastic stay! It’s wonderful to know the home, location, and outdoor space made your visit enjoyable. Thank you for being understanding about the oven issue. We’d be delighted to welcome you back again anytime! Warm regards, The Simple Life Rentals Team
Simple Life Rentals staff
Rating 5
Cathy B. - Posted: 8/30/2025
Rating 5
Late summer road trip
The property had an amazing location and the views were exquisite. We had a wonderful time.
Paula - Posted: 8/5/2025
Hello Paula, Thank you for sharing your experience! We’re so happy you had an amazing stay and look forward to welcoming you back. Warm regards, The Simple Life Rentals Team
Simple Life Rentals staff
Rating 5
The house is beautiful and large enough for a big family that wants to vacation together under one roof. We hope to return next year.
Amy - Posted: 7/26/2025
Sounds like wonderful memories were made! We’d be thrilled to host you again next year.
Simple Life Rentals staff
Rating 5
Perfect Lake Views and Ideal Location
We had a fantastic stay! The house had amazing views of the lake and a perfect porch for relaxing and people watching. The location couldn’t have been better—walking distance to great breweries, restaurants, and everything in town. We had a couple of quick questions during our stay, and the host’s communication was prompt and helpful. Highly recommend!
Jim F. - Posted: 7/19/2025
We love hearing this, thank you! So glad you enjoyed the views, the porch, and the location. It was a pleasure hosting you. Come back anytime!
Simple Life Rentals staff
Rating 5
Responsive owner, beautiful property.
Austin - Posted: 7/7/2025
Thanks so much, we’re happy you had a great experience! 😊
Simple Life Rentals staff
Rating 5
We stayed here prior to our daughter’s wedding. The master bedroom above the garage was perfect for us to get ready! There is a very spacious bedroom and a beautiful sitting area with wet bar that was perfect for our needs for the day. We had some issues with circuit breakers blowing but it was addressed quickly and effectively.
We had an issue with a/c in the top floor bedroom on our last 2 days, but again it was taken care of quickly. Will was very friendly and helpful with whatever we needed!! We will definitely try to stay here again as a family!!
Mary - Posted: 6/23/2025
Hello Mary,
Thank you so much for your kind words! We’re honored you chose to stay with us during such a special time for your family. We're glad the space worked so well for your needs and appreciate your patience with the minor issues — we're happy to hear they were resolved quickly. We’ll be sure to pass along your kind words to Will. We’d love to welcome you and your family back anytime!
Warm regards,
The Simple Life Rentals Team
Simple Life Rentals staff
Rating 5
The place was just as advertised. The attached bathroom to each bedroom was extremely convenient. The best part of the house, besides the sunrise in the morning, was the location.
Thomas - Posted: 10/20/2024
Thank you for your kind review! We are so glad you enjoyed your time and hope we have the pleasure of hosting you again!
Simple Life Rentals staff
Rating 5
This place was great! Very impressive. Love the town it's nestled in! I would most definitely rent again!
Mark - Posted: 10/16/2024
We are so glad you enjoyed your stay! We hope you will stay with us again!
Simple Life Rentals staff
Rating 5
A beautiful home. The location was excellent. The views of the lake were spectacular. The home was well stocked with everything we needed. It was clean and meet our group’s needs very well!
Jean - Posted: 10/10/2024
We're so glad you enjoyed your time in Door County! We're so happy that Our Lakeside Legacy was just what you needed. We would be honored to host you again!
Liz and the Simple Life Team
Simple Life Rentals staff
Rating 5
Brad - Posted: 9/14/2024
Rating 5
Family getaway
Beautiful home, great location for anywhere in Door County.
Lisa - Posted: 9/5/2024
Thank you for your kind review, Lisa! Our team and the homeowners are thrilled you enjoyed your stay. We hope you will consider staying with us again.
Simple Life Rentals staff
Rating 5
Family Vacation
Beautiful home. Great vacation and would definitely stay again.
Vanessa - Posted: 8/4/2024
Thank you for the lovely review! We are delighted to hear that you had a wonderful vacation and enjoyed your stay. We look forward to welcoming you back in the future!
Simple Life Rentals staff
Rating 5
Gorgeous waterfront property
We really enjoyed staying at this house. It was large enough for our group of 7 to spread out. The house is a combination of historic and contemporary decor. It has a lot of history with a stunning view of the water. The location was perfect, we walked to nearby restaurants every night. Highly recommend!!
Kimberly - Posted: 7/28/2024
We are so grateful for your kind review, Kim! This means so much to our team and to the home owners. Happy to hear you had a wonderful stay and we hope to host you again!
Simple Life Rentals staff
Rating 5
We had a wonderful stay with 10 adults and 4 kids. The house was well appointed, clean, and a lot of fun. The location is amazing, with lots of great stuff within walking distance, and also well located for exploring the other areas of Door County. We loved being right on the water. Would absolutely stay here again.
Rob - Posted: 7/23/2024
We are so grateful for your kind review, Rob! This means so much to our team and the homeowner. We will definitely share your feedback and suggestions so we can continue to improve for future guest. Happy to hear you had a wonderful stay and we hope to host you again!
Simple Life Rentals staff
Rating 5
We loved the beautiful lake view from all throughout the home and comfortable amenities!
Callyn - Posted: 7/14/2024
We are so grateful you enjoyed your stay and this beautiful home. We hope to have the opportunity to host you again in the future!
Simple Life Rentals staff
Rating 5
Great house, great location!
This house is gorgeous and is about 12 minutes to everything. A few bars/wineries in walking distance. House had everything we needed and it was very comfortable. Definitely someplace we would stay again.
Candi - Posted: 5/11/2024
Thank you, thank you!! These genuine reviews and your happy experience in one of our homes is why we do what we do. We hope to host you again soon, Candi!
Simple Life Rentals staff
Rating 5
Great family get together location
The property is beautiful, conveniently located and with amazing indoor and outdoor space
Christiane - Posted: 10/22/2023
Thank you, Christiane! Your kind feedback means so much to our owners and team.
Simple Life Rentals staff
Rating 5
This was an amazing place to stay for a weekend away. The views of the lake and the town were perfect. Hosts were very responsive and accommodating. Just maybe be prepared to bring some extra sheets and towels.
Jane - Posted: 10/15/2023
We appreciate your feedback, Jane! Your kind review means so much to our team and owners, thank you. We are glad you enjoyed your stay and hope we may host you again sometime!
Simple Life Rentals staff
Rating 5
Lakeside loveliness!
The house was picture perfect for our extended family vacation! Being right on the water was spectacular. We found the house to be stocked with most of the items we have come to expect from renting other properties. There was no hair dryer. We found the beds and linens to be soft and comfortable. One thing that was a bit of a surprise was the layout of the two bedrooms with the shared bath. While reading the description, we did not understand that you had to walk through the first bedroom and bathroom to get to that second bedroom. It worked for us, but may not be ideal for all groups. Maybe I missread, but wanted to point it out to others. As a previous reviewer mentioned, we also had a problem with hot water and multipe showers going at once.
Jackie - Posted: 9/4/2023
Thank you for sharing your feedback with us! We are pleased to hear you and your family had a great overall stay, and hope we may host you again sometime.
Simple Life Rentals staff
Rating 5
Great location! The house is beautiful. It’s right across from the brewery which is very convenient!
No extra linens though. They count the pull out couch as a bed but provided no linens for it.
Overall a great place to stay!
Taylor - Posted: 8/20/2023
Hi Taylor, thank you for your feedback to us! We will be sure to share that with our operations team. We are so happy to hear you had a wonderful overall stay and hope we may host you again.
Simple Life Rentals staff
Rating 5
Awesome lake house
Great experience in Bailey's Harbor
Nick - Posted: 8/19/2023
Thank you, Nick! We hope to host you again sometime.
Simple Life Rentals staff
Rating 5
What a wonderful weekend in Bailey's Harbor! We had a large family group (two grandparents, eight parents, and five grandchildren) and there was truly something for everyone. The home has plenty of room to spread out, so we had cribbage and chess games in one room and Candyland in another. The house is amazingly quiet for being right in the middle of town, and the lakeside was peaceful and serene. The kids loved exploring the rocks and finding treasures, and it was an easy walk to the sandy beach in town for swimming. We also rented kayaks to enjoy the lake, took advantage of the Sunday farmer's market just down the street, and came home with Door County cherries and lots of great memories. Hope we can visit again!
Bob - Posted: 8/7/2023
This makes us so happy to hear! Thank you, Bob! We are so pleased you all had a wonderful stay and time in the area. We would be happy to host you again sometime.
Simple Life Rentals staff
Rating 5
Great home base for a trip to Door County
Located in Bailey’s Harbor so everything is within a 15 min driving distance - the view is beautiful so even if you wanted to linger at the house and stare out at the water all day you could. Our family enjoyed eating in the spacious kitchen for breakfast each morning, while most days we spent afternoons out. The grill was a little dirty from continuous use - so we needed to clean it to be able to grill on it. The fat trap needs to be emptied to ensure that there is not a hazard from flames shooting up. And the only other issue is the showers and not being able to have multiple people showering at the same time. If you’re booking a large house and expect a number of people to stay and use the numerous bathrooms at once, the distribution of the hot water needs to be remedied. Otherwise the house was ideal for our needs.
Maya - Posted: 8/6/2023
We appreciate all your feedback, Maya. Thank you! So glad that you had a great overall stay.
Simple Life Rentals staff
Rating 5
Private view of the lake and well maintained landscaping, best place for weekend getaway
Yigang - Posted: 7/3/2023
Thank you, Yiganag! We appreciate this so much.
Simple Life Rentals staff
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Have a question? Customer Questions & Answers Have a question? Customer Questions & Answers

Want to know specifics? Ask anything about this specific property that you would like to know...

Example: "Is the balcony screened in?" or "Is there a toaster oven?"

How many parking spots at this location?

Richard K - Posted: 06/30/2025

Answer:

Hi Richard,

This property includes parking for 2 vehicles in the driveway. There's also plenty of nearby street and off-street parking available if needed.

Please let us know if you have any other questions!

Warm regards,

The Simple Life Rentals Team


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