Vacation Rentals By Owner In Sister Bay, WI

$772.97

New construction coastal farmhouse-walk to town

Sister Bay, Wisconsin, United States

Brand new farmhouse style custom built home in Sister Bay. Enjoy morning coffee in rocking chairs on wide front porch, watching the sun come up. In the evenings, relax with your favorite cocktail on the back screened in deck, enjoying a leisurely dinner you grilled on the Weber or cooked in the gourmet kitchen, and a beautiful Door County sunset through the trees. Cozy up to the indoor gas fireplace and a movie on cool nights. Perfect for 3 couples with 3 king beds or room for a family to spread out. High end appliances and gourmet kitchen with brand new kettles, utensils and a variety of dishware for all your needs. Easy to use washer/dryer on main level. Two large walk in showers and powder room right off kitchen. Walk to downtown (under 1 mile), grocery store, mini golf and Peach Barn brewery. Northern Haus wedding venue and Christkindlmarkt are both just up the road. Quiet area, close to all the action provided in Sister Bay, yet tucked away.

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Sleeps

$239.2

/ Nightly

Apartment

Door County Retreat ~ 3 Mi to Sister Bay Beach

Sister Bay, Wisconsin, United States

Venture up to Door County for a relaxing and rejuvenating retreat at this vacation rental. Situated in the quaint town of Sister Bay, this upstairs apartment boasts 1 bedroom, 1 bathroom, and an unbeatable location just 5 minutes from the area's largest beach. Additionally, the apartment offers all the comforts of home, including a full kitchen, wireless internet access, and outdoor living space. Rent a boat for a day of fun on Green Bay before dining out at a nearby waterfront restaurant!brbr-- THE PROPERTY --brbrDoor County Tourism Zone Lodging Permit #32-56-2006-00 | Free WiFi | Private Entrance | BBQ Grill | Front PorchbrbrThis lovely apartment is ideal for small groups of friends and family looking to experience the beauty of northern Wisconsin - regardless of the season! brbrBedroom: Queen Bed | Living Room: Sleeper Sofa | Additional Sleeping (Closet): Floor MattressbrbrINDOOR LIVING: Flat-screen cable TV, picture window, laptop-friendly workspace, open-concept living space, en-suite bathroom, gamesbrKITCHEN: Fully equipped, drip coffee maker, cooking essentials, tea kettle, dishware/flatwarebrPRIVATE DECK: Outdoor dining set, gas grill, forest viewsbrGENERAL: Linens/towels, complimentary toiletries, hair dryer, AC, heating, self check-in brPARKING: Driveway (2 vehicles)brbr* NOTE: The homeowner lives on-site, in a separate unit, and may be present during your stay *brbr-- THE LOCATION --brbrWATER FUN: Seaquist Bay Shore Inc (0.3 miles), Sister Bay Beach (3.7 miles), Sister Bay Marina (3.4 miles), Sister Bay Boat Rental (3.5 miles), Door County Kayak (11.2 miles)brHIKING & PARKS: Ellison Bluff Natural Area (2.8 miles), Door Bluff County Park (5.9 miles), Newport State Park (8.1 miles), Peninsula State Park (8.9 miles), Cave Point County Park (23.8 miles)br FAMILY FUN: Seaquist Orchards Farm Market (0.8 miles), Falcon Orchard (1.0 miles), Pirate’s Cove Adventure Golf (4.3 miles), Johnson’s Park (4.3 miles), Lakeshore Adventures Zipline (10.7 miles), Eagle Bluff Lighthouse (12.6 miles), Cana Island Lighthouse (14.6 miles), Lautenbach’s Orchard Country Winery & Market (14.9 miles)brFOOD & DRINK: Door County Ice Cream Factory & Sandwich Shoppe (1.8 miles), Waterfront Restaurant (2.7 miles), Mink River Basin (2.7 miles), The Viking Grill and Lounge (2.8 miles), Wickman House (3.0 miles), Shoreline Restaurant (7.6 miles)brWINTER: Cross-country skiing, ice skating, snowmobiling, ice fishing, sleddingbrEVENTS: Sister Bay Fall FestbrAIRPORT: Green Bay Austin Straubel International Airport (89.2 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: The homeowner lives on-site, in a separate unit, and may be present during your staybr- NOTE: The property requires stairs and may be difficult for guests with limited mobility

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$447.95

/ Nightly

Condo

Newly built Excecutive Condo located in heart of Sister Bay!

Sister Bay, Wisconsin, United States

Newly constructed Mill Road Place is in heart of downtown Sister Bay located a half a block up mill from Bayshore Drive. More information and pictures coming soon. The units will have LVP flooring, tiled showers, stainless steel appliances, granite countertops, shiplap in bedrooms, fireplace, 55′ TV, 40′ TV’s in bedrooms, patio with table and chairs, bike rack, and propane grill. Unit 1 is on the first floor.brbr*Turnover day is Sunday during the peak season*brbr** No Camper or Boat parking at any time. Contact the local township for information on public overnight parking **br** Parking of up to two vehicles at all times, including any visitors.**brbrAccommodationsbrbrLocated directly in the center of downtown Sister BaybrBeach and waterfront a couple hundred yards awaybr55 inch Flat Screen in living roombrFireplacebr40 inch Flat Screens in each bedroom

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$943.96

/ Nightly

Condo

Marina Views & Walkable Sister Bay Condo- Paddle Boards & Bikes Included

Sister Bay, Wisconsin, United States

Stunning Marina Views & Walkable Sister Bay RetreatbrbrDiscover one of the most sought-after Door County vacation rentals — a modern, third-floor condo with sweeping marina and sunset views, elegant finishes, and an unbeatable downtown Sister Bay location just steps from restaurants, shops, and waterfront fun. This is the place to experience the best of a Door County vacation in style and comfort..brbrTHE SPACE — Comfortable, Stylish & Full of Extrasbr- Sleeps 8 in 3 bright bedrooms — perfect for families or groupsbr- Primary Bedroom: King bed, en suite bath, water-view balcony access, Smart TVbr- Bedroom 2: King bed + twin bunkbeds (perfect for families or groups)br- Bedroom 3: Queen bed, Smart TVbr- Open-concept living area with wall of windows framing that iconic marina vistabr- Balcony with famous Sister Bay sunsets — sip your coffee or a glass of winebr- Chef’s kitchen with stainless steel appliances & granite countertopsbr- Gas fireplace sets the mood for cozy eveningsbr- Fast Wi-Fi - ideal for remote work br- In-unit washer/dryer for added conveniencebr- Smart TVs throughoutbrbrOUTDOOR PERKS — Adventures Guests Love: br- Gear for adventure in the garage:br- 4 Bikesbr- 2 Paddleboards br- 2 Beach Chairsbr- 4 Life Jacketsbr- Pickleball racketsbrbrWALKABLE LOCATION — Steps to it All:br- Directly across from Sister Bay Marina, with boat rentals and scenic strolls at your doorstep.br- Walk to Door County restaurants, ice cream, boutique shopping, and live music. br- Minutes on foot to the beach, park, and public boat launch — perfect for summer fun or autumn exploration.brbrPARKING/ELEVATORbrParking included, including one car garage for guest use, with an additional parking space in the parking lot of the building. This unit is located on the 3nd floor, and an elevator is available for access. brbrFOODIES & FUNbrAfter enjoying your relaxing base, explore exceptional Door County restaurants just outside your door — from casual bites to local favorites — as part of your unforgettable Door County vacation experience. brbrYOUR HOSTSbrWhen you stay with Northern Door Vacations, you’ll enjoy truly personalized, local service—no call centers, no robots—just a real Door County team who answers every call and text, before and during your stay. Northern Door Vacations — where vacations feel personal.brbrNOTESbr-Slip rental available for your boat, directly across the street! Contact us for more information.br-To ensure a seamless check-in experience, guests are required to review and sign our standard rental agreement and complete a quick check-in form prior to arrival. This helps us comply with local regulations and provide the best possible stay.br-Although we have a relaxed cancellation policy, we still incur the 4% cc fee. Your refund will be in full, minus the 4% cc fee. This is detailed in the guest contract.br-In an effort to keep the entire property more secure, the house is equipped with a ring doorbell camera to monitor the driveway and the front entry.br-The primary renter must be 25 years or older.

3

Bed

2

Bath

8

Sleeps

$850.77

/ Nightly

Private Vacation Home

Sister Bay Waterfront Cabin with kayaks, boathouse deck, and game room!

Sister Bay, Wisconsin, United States

Bayfront Log Cabin Escape — Best of Door County Waterfront Living!brbrExperience one of the most magical Vacation homes in Door County — a private bayfront log cabin just minutes from downtown Sister Bay. With direct access to the water, epic sunsets, kayaks, and a fun-filled game room, this standout Door County vacation rental blends relaxation, adventure, and local charm. Perfect for families, friends, and getaway seekers who want both nature + walkability near restaurants, marinas, galleries, and beaches.brbrTHE SPACE — Where Comfort Meets Waterfront Viewsbr-Sleeps 8 br-3 bedrooms + sofa bed (King, Queen, Queen)br-2 fully updated bathroomsbr-Remodeled kitchenbr-Cozy living room with a gas fireplacebr-Large windows with bay viewsbr-Fast, High-speed Wi-Fi — Ideal for working remotelybr-Washer + Dryerbr-Coffee bar — feels like homebrbrOUTDOOR FEATURES — Wake Up to the Baybr-Private shoreline on Sister Bay — paddle straight from your doorstepbr-Kayaks with life vests includedbr-Boathouse with upper deckbr-Fire pit & Gas grill — perfect for cozy evenings under the starsbrbrFUN & GAMES — Rain or Shinebr-Dedicated game room with:br-Shuffleboardbr-Dartsbr-Wall hookybr-Classic arcade games — ideal for all ages!brbrLOCATION — Close to It Allbr-3 minutes to downtown Sister Bay — shops, nightlife, and festivalsbr-Steps from live music, marinas, galleries, and local parksbr-Explore Door County restaurants and cafés — local flavors just a short drive awaybr-Minutes from Ellison Bay, state parks, boat launches, and wineriesbrbrTHE HOSTSbr-When you stay with Northern Door Vacations, you’ll enjoy truly personalized, local service—no call centers, no robots—just a real Door County team who answers every call and text, before and during your stay. NDV — where vacations feel personal.brbrReady for a memorable Door County getaway This waterfront gem delivers the best of nature, comfort, and local culture — all from your very own bayfront vacation home. brbrNOTESbr-To ensure a seamless check-in experience, guests are required to review and sign our standard rental agreement prior to arrival. This helps us comply with local regulations and provide the best possible stay.br-In an effort to keep the entire property more secure, the house is equipped with a ring camera at the front entrance and a security camera on a tree facing the waterline in the backyard.br-Although we have a relaxed cancellation policy, we still incur the 4% cc fee. Your refund will be in full, minus the 4% cc fee. This is detailed in the guest contract.br-The primary renter must be 25 years or older.

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$668.52

/ Nightly

Private Vacation Home

Family-Friendly, Historic, Renovated Sister Bay Farmhouse with Crib + Toys

Sister Bay, Wisconsin, United States

Welcome to Oak & Orchard House, a family-friendly, beautifully renovated 1923 farmhouse on a quiet street, nestled between forest and field. Full of character and modern amenities, it sits alongside an old orchard of apple and pear trees, making it the quintessential Door County setting. Designed for easy travel with babies and young kids, the home includes a crib, high chair, toys, kids’ dishes, and a backyard playset, so you can pack lighter and enjoy a peaceful getaway.brbrThe spacebrYou will feel at home in the fully equipped kitchen with granite countertops, farmhouse sink, stainless steel appliances, and handcrafted island made with reclaimed wood. Relax and gather with friends and family in the open concept living room and dining room with original built-in leaded glass china cabinet, exposed brick chimney, and one-of-a-kind antique furniture. Rainy day or not, there are plenty of things to do indoors. Stream your favorite shows and sports on the Samsung Smart TV, make a puzzle, or cozy up in the window seat with a good book. Grab a deck of cards or board games like The Game of Life, Clue, Sequence, Monopoly, and more. There is also a gorgeous bathtub downstairs to relax and unwind, or a traditional shower in the upper bath with lots of natural light. brbrWorking virtually With reliable internet, strong cell service, a built-in desk and multiple workspace-friendly areas in the house, this is the perfect place to work from home.brbrEnjoy your morning coffee out on the huge deck while listening to the birds and look for wildlife. or fire up the 5-burner gas grill and watch the sunset. The fire pit behind the garage is perfect for roasting s'mores and star-gazing. Little ones will love the swing set and tons of space to run and play. Challenge your crew to a friendly game of croquet, or toss a frisbee in the backyard.brbrPerfect for Babies & Young FamiliesbrbrTraveling with a baby or young child You can leave the bulky gear at home. This home is thoughtfully equipped to make family travel easy and comfortable.brbrFor babies & toddlers, we provide:brbr* Cribbrbr* High chairbrbr* Changing padbrbr* Baby Bjorn training pottybrbr* Children’s books, toys, coloring activitiesbrbr* Children’s silverware, dishes, and cupsbrbr* Outlet coversbrbr* Bottle warmerbrbr* Baby monitorbrbr* Baby washbrbrPlease Note: Some reviews written prior to 2026 reference long-term tenants who previously lived at the separate dwelling at the back of the home; however, they no longer reside on the premises. From time to time, our family may visit and use the separate residence on the property. Your guest space remains fully dedicated to you and your group during your stay.brbrFor guest security, an exterior Nest camera is located at the side and back doors, monitoring the entrances and driveway only.brbrABOUT THE HOUSE:brbr* Sleeps up to 6- maximum guest totalbrbr*1 dog allowed, up to 50 pounds, with prior approval. There is a pet fee of $30 per night (maximum of 1 dog). brbr* 3 Bedrooms + 2 Full BathroomsbrbrBedroom #1: Upper Level, King size bed, Ceiling fan, room darkening shades, hangersbrbrBedroom #2: Upper Level, 2 twin beds, 1 crib, room darkening shadesbrbrBedroom #3: Upper Level, Queen size bed, room darkening shades, hangersbrbrBathroom #1: Main level, Full bathroom with shower + tub, hair dryerbrbrBathroom #2: Upper level, Full bathroom with walk-in shower, hair dryerbrbrBed linens, pillows, blankets, bathroom linens, and beach towels are provided.brbrWe provide a starter pack of essentials which includes the following: 2 rolls of toilet paper per bathroom, paper towel, dish soap, dishwasher soap, hand soap and garbage bags. brbrWe also supply shampoo, conditioner, and body wash in each bathroom.brbrDue to state health and safety licensing guidelines, all pantry items must be removed between guests. Please bring cooking essentials you might need such as cooking oil/spray, salt, pepper and other spices, sugar, etc. as legally we are prohibited from providing them to guests.brbrKITCHEN AMENITIES:brbrFully equipped with a refrigerator, freezer with ice maker, stove, oven, dishwasher, microwave, blender, hand mixer, waffle maker, toaster, pots and pans, baking sheets, other basic cooking supplies, dishes, utensils, glassware, and wine glasses.brbrTraditional drip coffee pot, coffee bean grinder, Nespresso machine, electric tea kettle.brbrOTHER AMENITIES + APPLIANCES:brbr* Internet strong enough to support video meetingsbrbr*1 Smart TV in the living roombrbr* Washer + Dryerbrbr* Central Heatbrbr* A/C + 3 portable fansbrbr* Some books and games for your enjoyment!brbrOUTDOOR AREA:brbr* Firepit with 6 adult chairs + 2 child chairsbrbr* Patio table with 6 chairsbrbr* Propane grillbrbr* Croquet, football, and frisbee for outdoor fun!brbrOther things to notebrbrMust climb stairsbrbrThe master bedroom does not have a heat source other than the gravity vent. We provide a space heater for that room during the cooler months.brbrDoor County Tourism Zone Commission Permit #32-56-2659-00

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$968.87

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Private Vacation Home

Classic Door County Cottage on Lake Michigan + Great for Families

Sister Bay, Wisconsin, United States

Welcome to Tranquility Bay Getaway, our stunning waterfront retreat in Sister Bay hosted by The Simple Life Rentals! This charming home offers a perfect blend of tranquility and adventure, promising an unforgettable getaway for you and your loved ones.brbrYou'll be greeted by the cozy atmosphere and captivating views of Lake Michigan. With three beautifully appointed bedrooms and two spacious baths, this retreat comfortably accommodates families or groups of friends. The living area is designed to be a gathering space where you can unwind. The kitchen is fully stocked to ensure you have all of the comforts of home. Amenities such as a private office space, washer, dryer, games and two Smart TVs may entice you to stay even longer.brbrStep outside onto the huge deck and enjoy the breathtaking vistas that surround you. The private Lake Michigan waterfront offers a rocky shore but is suitable for swimming. With a large deck, outdoor seating, a firepit, and a private view of the sunrises and start, you may spend most of your time outside enjoying the beach, water and views.brbrThis property allows up to 2 well-behaved dogs. There is an additional fee collected at booking.br  brProperty Features:br+ Private, Lake Michigan waterfrontbr+ Large deck with plenty of seatingbr+ Grill and fire pit br+ Outdoor gamesbr+ Hammock (seasonal) br+ Dog friendly - 2 maximumbr+ Internet/ Wi-Fi (due to the rural nature of the property, Wi-Fi and cell phone coverage and service can vary)  br+ 2 Smart TV's (living area and main level bedroom) with Roku streaming device. Guests may log in using their own accounts. br+ DVD and Blu Ray players with video librarybr+ Dining area includes 2 bar stools at the kitchen counterbr+ Electric baseboard heat (No air conditioning)br+ 3 portable fans (one in each bedroom as well as ceiling fans in bedrooms)br+ Wood burning fireplace in living area (please bring local firewood)br+ Books, puzzles and guitar provided for guest’s enjoyment br+ Desk and chair in bedroombr+ Highchairbr+ Pack ‘n Play (guest need to bring linens)br+ Children's books, toys and silverwarebr+ Yoga mats br+ Washer, dryer, iron, ironing boardbr+ Fully equipped kitchen (see amenities)brbrSleeping Accommodations:brBedroom 1 (main level): Queen size bed, TV, ceiling fanbrBedroom 2 (upper level): Queen size bed, ceiling fanbrBedroom 3 (upper level): Queen size bed, ceiling fan br brBathrooms: brBathroom 1 (main level): Full bathroom with combination tub and shower, hair dryer.brBathroom 2 (upper level): Full bathroom with walk-in shower.brbrOutdoor Area:brLarge deck with patio table with 6 chairsbrLarge umbrellabr2 seat couch, 2 loungers, 1 small table brPropane grill (propane provided)brCharcoal grill (guests provide own charcoal) brFire pit with 4 chairs (please bring local firewood) brCornhole game (bean bag toss)br4 parking spots available in driveway with room for a trailer and boat, per municipal ordinancebr brWater Access:brRocky shorelinebrWater is swimmable, and is shallow for approximately 300 feet, then gradually gets deeperbr2 adult, universal life vests on site for guest use brNo dockbrClosest public boat launch is in Baileys Harbor br  brAmenity + damage protection waiver includes:br• Bed linens, pillows, blankets, and bathroom towels. (Please bring your own beach towels) br• 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. br• PEACE OF MIND Damage protection covers up to $1000 per stay for accidental damage that is reported prior to departure (excludes any pet damage). brbrHome Truths:brNo ice maker or dockbrHome does not offer air conditioning, it does provide fans (portable and ceiling fans).brThe garage is not accessible for guest use.brbrThis 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 parties at the property including bachelor or bachelorette parties, reunions, or other rowdy gatherings. br brDoor County Tourism Zone Commission Permit #32-56-3104-07 brbrPlease be aware that you must sign a terms and conditions agreement, which will be sent to you separately, to finalize your reservation.

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$1204.24

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Private Vacation Home

Luxury 4-bedroom retreat (sleeps 12) featuring a private 6–8 person barrel sauna. Walk to The Northern Haus wedding venue & downtown Sister Bay’s shops, restaurants, and waterfront. Perfect for wedding weekends, gatherings, and Door County getaways.

Sister Bay, Wisconsin, United States

4

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3

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12

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