Family-friendly holiday rentals in Sister Bay

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Sister Bay

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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The living area features large windows, allowing natural light to filter in, illuminating the comfortable seating area. A wooden dining table is set with placemats, and a chandelier hangs above. A small balcony is visible through the sliding glass doors.
Apartment in Egg Harbor
4.91 out of 5 average rating, 199 reviews

DoorCo Happy Place @Landmark Resort

Welcome to this wonderful, full of positive energy and relaxing resort! The condo is a great place to relax, explore and rejuvenate! 1 bedroom with a queen size bed and queen sleeper sofa in the living room and fully equipped kitchen make enough room for 4 guests. The resort is a great place to enjoy- 1 indoor pool, exercise room and a game room located in the main building, hot tub, sauna in each building, 3 HEATED outdoor pools open seasonally (May- August), tennis court, playground, a trail.

Guest favourite
A tri-level condo complex is nestled among lush greenery, showcasing multiple balconies and staircases leading to the main entrance. A pool area is visible in the foreground, where lounge chairs are arranged around a covered pool. The serene landscape adds to the peaceful ambiance.
Apartment in Fish Creek
4.86 out of 5 average rating, 309 reviews

Evergreen Hill B Whirlpool Condo by Pen State Park

It’s all about location and this is the perfect central location for your Door County adventure! All 4 B rental condos are set on a lovely, peaceful street in Fish Creek. On warm days, enjoy hiking, swimming, biking, boating, camping, picnicking, fishing, and golf. When snow is on the ground, spend time cross-country skiing, snow shoeing, snowmobiling, and sledding. Daily housekeeping is not included. You can add it for $24 per day if you would like, just let us know when you pick up your key.

Top guest favourite
A cozy studio bedroom features a spacious bed with stylish bedding and decorative pillows. Light streams through a window covered with plantation blinds. Two lamps illuminate the space beside the bed, while a gray upholstered bench sits at the foot, complementing the wood-look flooring.
Flat in Fish Creek
4.98 out of 5 average rating, 284 reviews

Night Cap Studio Loft in Downtown Fish Creek

In the heart of Fish Creek, above our bustling Hat Head shop, enjoy your stay in our newly remodeled second story studio loft. Complete with studio bedroom, bath, kitchen with new appliances, sitting room, and private balcony deck. Enjoy walking distance to the beach, shops, restaurants, Peninsula State Park, and more. Close to the action, yet a great hideaway for privacy and relaxation. Bright and cheery, modern, simply stated, and clean. For adult single or couple. (Sorry no pets or kids).

Top guest favourite
A quaint cottage stands surrounded by snow-covered trees, with a light grey door and window accents visible. The structure features a simple white exterior, complemented by a winter landscape of freshly fallen snow, creating a serene and peaceful atmosphere.
Guest house in Fish Creek
4.97 out of 5 average rating, 260 reviews

Vintage Mod Cottage with fireplace & soaking tub!

Grandview Farm Cottage is a circa 1920s newly renovated, 420 sq. ft. private guesthouse on the grounds of a 2.5 acre Door County property built in the late 1800s. Modern, industrial and repurposed style meets vintage farmhouse charm. Central location allows for quick drive or even a bike ride to either coast of the peninsula. Enjoy nature, wildlife, your own organically grown gardens, and dark starry night skies, while being only 3 miles to nightlife and shopping and beaches and parks.

Top guest favourite
The living area features warm wooden beams and a stone fireplace, creating a cozy atmosphere. Large windows provide natural light and a view of the outdoors. Comfortable seating is arranged with a sectional couch, two chairs, and a coffee table, inviting relaxation.
Cottage in Ellison Bay
4.92 out of 5 average rating, 106 reviews

Pet-Friendly, Cozy Cottage in Northern Door County

- Pet-friendly, 2 bedroom home in Northern Door County - Indoor fireplace and outdoor bonfire pit (wood provided) - Beautiful screened porch to enjoy nature - 5 minutes from famous Curvy Road, Washington Island Ferry, Newport State Park & Europe Bay Beach - Short drive to neighboring villages - Sister Bay, Ellison Bay, Baileys Harbor, etc - Walk or bike (provided) to Hedgehog Harbor - Perfect for a family getaway or a trip with friends - Includes all amenities to make you feel at home

Top guest favourite
A charming blue cottage with yellow shutters adorns the exterior. A well-maintained stone wall and vibrant flower beds enhance the entrance. The home features a single-car garage, a front porch, and large windows that invite natural light into the living space.
Cottage in Sister Bay
4.93 out of 5 average rating, 194 reviews

The Sister Bay Getaway: Water View & Downtown!

Updated 2 bedroom home - smoke & pet free. WiFi, Smart TV and A/C. Walking distance to downtown Sister Bay shops, restaurants, beach and more! This has been a favorite Door County location for many! We sincerely hope you enjoy our vacation home, Sister Bay, and everything Door County has to offer! Accept rental agreement (House Rules) prior to your stay. Airbnb bills and remits the WI State/County Taxes (5.5%); Door County Lodging tax (8%) & Sister Bay Resort tax (0.5%).

Top guest favourite
The entrance is framed with natural wood siding and features a double glass door adorned with a festive wreath. Two wooden benches are placed on either side of a gravel pathway, complemented by greenery and decorative lighting fixtures.
Home in Baileys Harbor
4.99 out of 5 average rating, 174 reviews

Winding Down - A Retreat on the "Quiet Side"

Enjoy the fall & winter season! We still have availability for the up coming Christkindlmarket in Sister Bay & Fish Creek Winterfest in January. Get ready to relax and recharge with family & friends. Winding Down is the perfect place to enjoy the quiet side of DC. We are walking distance from the Nature Preserve & the shores of North Bay. Located in a beautiful cedar forest that provides a needed respite. Plenty of privacy but also a short drive to Ephraim & Sister Bay.

Guest favourite
A spacious living area features a dining table with six upholstered chairs surrounded by warm, red walls. A cozy seating arrangement includes a pink armchair and a black rocking chair near a fireplace, with large windows allowing natural light to fill the space.
Cottage in Sister Bay
4.96 out of 5 average rating, 121 reviews

The Key to Happiness

Sleeping 4-6 between 4 beds, Plum Retreat provides a one-of-a-kind Door County experience. With 2 large bedrooms (plus giant living room with queen sofa bed, dining area and full kitchen), the 1700 sq-feet have a charming cottage-like feel. Conveniently located with gorgeous perennial gardens, it makes a romantic, peaceful or fun space. Private lawn & patio/grill. Pretty much everything has been thought of. Last summer, all 37 groups of people gave it a 5-star rating!

Guest favourite
Apartment in Sister Bay
5 out of 5 average rating, 106 reviews

101 | Luxury | Downtown Sister Bay | Door County

Owner operated + private entrance + no shared spaces Rare opportunity to rent the developer’s unit in Sister Bay’s newest, luxury, marina view condominium development! Custom cabinetry, quartz countertops, stainless steel appliances, garage parking, and more await you in this dedicated vacation rental. Walk out your patio door to 14 plus restaurants, bars, and coffee shops, including the famous Al Johnson’s. Virtual tour in highlights on IG "@101sisterbay"

Guest favourite
The cottage showcases a distinctive A-frame design surrounded by lush greenery. A spacious wooden deck with yellow Adirondack chairs invites relaxation, while large front-facing windows allow for natural light and views of the serene wooded lot.
Cottage in Sister Bay
5 out of 5 average rating, 205 reviews

A-Frame - Coffee Bar, Gas Fireplace - Sleeps 4!

Trade the hustle and bustle for peace and quiet at our cozy retreat, just 5 minutes from the heart of Sister Bay. Tucked away on 1.6 acres of serene woods filled with beautiful beech trees, the cottage is your perfect getaway spot. Kick back on the spacious front deck, unwind on the screened-in porch, and soak in the natural beauty all around. Inside, mid-century modern vibes meet cozy comforts, with everything you need for a relaxing, stress-free stay.

Top guest favourite
A cozy cottage is nestled among tall trees, showcasing a white exterior with a stone chimney. The spacious porch features blue chairs, inviting relaxation. Lush green grass surrounds the home, complementing the peaceful rural setting.
Cottage in Sister Bay
4.99 out of 5 average rating, 151 reviews

Lofted Pines Cottage

Settle in at Lofted Pines Cottage for your Door County stay! Located off the beaten path, but only a few minutes from downtown Sister Bay or Lake Michigan, Lofted Pines is elegantly situated among mature cedar and fir trees, yet open and airy. Whether you're relaxing on the wrap around porch, cozied up in front of the fireplace or enjoying the wood burning fire pit, Lofted Pines is the perfect spot to unwind after exploring the Door County Peninsula.

Top guest favourite
A log cabin exterior is showcased, featuring a steeply pitched roof and a large porch area. Two seating chairs are positioned near the entrance, with seasonal pumpkins placed along the front. The surrounding trees display autumn foliage against a clear blue sky.
Cabin in Sister Bay
4.96 out of 5 average rating, 124 reviews

3 Bed, 2 bath log cabin in Sister Bay w/ fire pit

Door County at its finest! Located minutes away from Sister Bay's main attractions. You can enjoy the privacy of the cabin a wooded lot with quick access to many activities in the surrounding area. 1 mile away from Northern Haus wedding venue 10 minutes drive from Peninsula State Park 20 minutes drive from Newport State Park 25 min from Whitefish Dunes State Park 20 min from ferry to Washington Island

Popular amenities for Sister Bay family-friendly rentals

When is the best time to visit Sister Bay?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$325 SGD$312 SGD$344 SGD$329 SGD$400 SGD$554 SGD$761 SGD$675 SGD$501 SGD$470 SGD$364 SGD$400 SGD
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Quick stats about holiday rentals that are family-friendly in Sister Bay

  • Total holiday rentals

    Explore 70 holiday rentals in Sister Bay

  • Nightly prices starting at

    Sister Bay holiday rentals start at $208 SGD per night before taxes and fees

  • Verified guest reviews

    Over 3,040 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wifi availability

    70 of Sister Bay holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Sister Bay rentals

  • 4.9 Average rating

    Sister Bay stays are highly rated by guests – averaging 4.9 out of 5!