Family-friendly vacation rentals in Sister Bay

4.86 out of 5 average rating, 307 reviews

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.

Condo in Fish Creek

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.

4.98 out of 5 average rating, 283 reviews

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.

Apartment in Fish Creek

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).

4.97 out of 5 average rating, 258 reviews

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.

Guesthouse in Fish Creek

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.

4.92 out of 5 average rating, 103 reviews

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

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

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.

4.93 out of 5 average rating, 193 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%).

4.99 out of 5 average rating, 174 reviews

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

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.

The entrance features a bright red door set against a gray wooden wall. A small window with white trim is visible nearby. A snow shovel, a bucket, and two wooden sleds are arranged neatly next to the door, along with a cozy blanket and a pair of boots.

4.89 out of 5 average rating, 283 reviews

Sister Bay Eclectic Cottage

Stunning fresh + modern cottage ready for your visit NEW as of August 2018! Less than 1 mile walk or drive to Sister Bay Downtown + just minutes from the Beach! 3 Bedrooms: 1 king w/ on-suite bath, 1 queen w/ on-suite bath, twin trundle bed 3 full bathrooms: 1 on the main floor, 2 on-suite on 2nd floor Great cooks kitchen, fully stocked w/ open concept living space, w/ Sonos in kitchen! BBQ gas grille + awesome fire pit, expansive deck w/ dining space & lounge chairs

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.

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!

5 out of 5 average rating, 106 reviews

Condo in Sister Bay

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"

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.

5 out of 5 average rating, 203 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.

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.

4.99 out of 5 average rating, 149 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.

A cozy living room features a light grey couch adorned with navy blue pillows, paired with two beige armchairs. A round wooden coffee table is centered on a soft area rug, while large windows provide natural light and views of the surrounding greenery.

4.99 out of 5 average rating, 134 reviews

Cottage in Sister Bay

Beautiful + modern cottage ready for your visit! Cozy up in this private cottage during your Door County stay! Just three miles from downtown Sister Bay, Pineview Cottage is located on a serene lot nestled in the woods. A perfect place for you to unwind after your Door County adventures. If you would rather stay back, relax on our beautiful covered front and back porch or gather around the campfire with friends and family!

Popular amenities for Sister Bay family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.87 out of 5 average rating, 189 reviews

A spacious farmhouse exterior is highlighted by its rustic wooden siding and multiple gabled roofs. The porch spans the front, framed by large windows. Lush greenery surrounds the home, with a well-maintained lawn leading towards the entrance, providing a serene country setting.

Home in Ellison Bay

Northern Lights Farmhouse with Hot Tub

4.86 out of 5 average rating, 92 reviews

A well-lit A-Frame cabin is viewed at night, with a bright blue hot tub in the foreground. The cabin features large windows and a door that lead to an outdoor seating area with multiple chairs. Soft lighting accentuates the cabin's exterior.

Tiny home in Stephenson

Natureside A-Frame Cabin: Cozy.Sauna.Hot Tub

4.97 out of 5 average rating, 135 reviews

The exterior of a house is set against a backdrop of tall trees, showcasing a spacious lawn. A selection of wooden chairs surrounds a fire pit area, providing an inviting space for outdoor gatherings. The house features multiple levels, with a large deck visible.

Home in Sturgeon Bay

Modern Door County Waterfront House + Hot Tub

4.92 out of 5 average rating, 158 reviews

The lodge's exterior is characterized by a classic log cabin style, featuring large windows that allow ample natural light. Surrounding greenery includes well-kept shrubs and trees, with a vibrant red maple adding a burst of color against the serene backdrop.

Cabin in Egg Harbor

Green Apple Lodge (w/hot tub & hi-speed wifi!)

A modern kitchen is equipped with stainless steel appliances, including a refrigerator and microwave. Light wood cabinetry surrounds a spacious island with a white countertop. Large windows provide abundant natural light, while a decorative farmhouse-style planter adds a touch of greenery to the space.

4.88 out of 5 average rating, 17 reviews

Group Stay • Hot Tub, Arcades, Family/Dog Friendly

5 out of 5 average rating, 85 reviews

A covered outdoor area features a relaxing hot tub, surrounded by a serene natural landscape. A cozy seat with plush cushions is positioned nearby, inviting relaxation while enjoying the tranquil surroundings. The space is divided by a sturdy pergola, offering shade and comfort.

Home in Egg Harbor

Egg Harbor Fall & Winter Escape| Sauna| Hot Tub.

4.96 out of 5 average rating, 53 reviews

Home in Fish Creek

Gorgeous home close to Fish Creek & Hot Tub!

5 out of 5 average rating, 75 reviews

A contemporary living area features a cozy fireplace surrounded by a natural wood accent wall. Large windows allow sunlight to illuminate the plush seating area, complemented by a modern coffee table and an open kitchen space, enhancing the inviting atmosphere.

Home in Egg Harbor

RetreatAzure-Outdoor Wood Burning HotTub-EggHarbor

Family- and pet-friendly home rentals

4.82 out of 5 average rating, 191 reviews

A spacious kitchen and dining area features modern appliances and wooden cabinetry. A wooden dining table is accompanied by comfortable chairs. Natural light floods the room through large windows, revealing a view of the greenery outside, enhancing the connection to nature.

Home in Egg Harbor

The Hein Cottage-Beautiful hideaway in the ❤️of DC

4.95 out of 5 average rating, 174 reviews

Cabin in Sister Bay

Wismar Cabin Waterfront- Private Sand Beach

Apartment in Sturgeon Bay

A charming two-story blue house is surrounded by well-maintained greenery and colorful landscaping. A paved driveway leads up to the entrance, while a side path provides access to the backyard. Tall trees offer shade and a sense of privacy to the property.

4.9 out of 5 average rating, 146 reviews

Cozy Loft | Dog Friendly + Off-Street Boat Parking

4.96 out of 5 average rating, 113 reviews

A spacious living room is featured, designed with a comfortable sectional sofa and accent chairs around a circular coffee table. Natural light floods through large windows, complemented by a stylish fireplace and wall-mounted artwork showcasing sunset views.

Apartment in Egg Harbor

The Loft | Walkable Egg Harbor Retreat w/ Style

4.93 out of 5 average rating, 103 reviews

An aerial view of a quaint blue cottage surrounded by lush greenery and tall trees. A spacious lawn extends around the cottage, with a few seating options visible. In the background, a serene waterway is nestled among the trees, enhancing the peaceful atmosphere.

Cottage in Stephenson

Charming Cabin Perfect for Relaxing!

The remodeled farmhouse is showcased with a welcoming front porch and manicured landscaping. A large tree provides shade in the front yard, while a flag flutters gently. A rustic barn is visible in the background, surrounded by lush greenery and blooming orchards.

4.88 out of 5 average rating, 106 reviews

Swedish Orchard Farm

4.86 out of 5 average rating, 481 reviews

A bright living area features hardwood floors and warm yellow walls. A comfortable sofa faces a TV, complemented by two chairs positioned near large windows that offer views of the outdoors. A plush area rug adds texture beneath a coffee table.

Apartment in Egg Harbor

Downtown Sunset View Apartment

4.92 out of 5 average rating, 143 reviews

A serene landscape features a tranquil inlet surrounded by lush greenery. A wooden dock extends over the clear water, and a large tree provides shade. Wildflowers bloom in the foreground, adding a natural charm to the peaceful setting.

Cabin in Sturgeon Bay

Tranquility Cabin

Family-friendly home rentals with a pool

4.84 out of 5 average rating, 70 reviews

A living area features a comfortable red sofa facing a large window that offers views of green outdoors. A gas fireplace is positioned beside a light wood shelf with decorative items. A TV is mounted on the wall, and a patterned chair and coffee table complete the setting.

Apartment in Fish Creek

1 Bedroom Suite in a World-Class Swedish Resort

4.88 out of 5 average rating, 178 reviews

The living area is furnished with a gray sectional sofa adorned with blue and patterned cushions. A wooden coffee table sits on a textured blue area rug, with a small plant placed on top. The open kitchen is visible in the background, featuring modern appliances and a dining island with seating.

Condo in Egg Harbor

Condo Indoor Pool Meadow Ridge #23 Egg Harbor, WI

4.9 out of 5 average rating, 187 reviews

A spacious living area is highlighted by a large sectional sofa, accented with decorative pillows. A flat-screen TV is mounted above a stone fireplace. Natural light pours in through two large windows, enhancing the welcoming ambiance of the space.

Townhouse in Egg Harbor

Indoor pool and hottub Egg Harbor condo #51

4.93 out of 5 average rating, 198 reviews

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.

Condo in Egg Harbor

DoorCo Happy Place @Landmark Resort

4.96 out of 5 average rating, 25 reviews

A hot tub is positioned on the patio, featuring jets that create a soothing water surface. Surrounding greenery adds natural beauty, while privacy is ensured by a barrier. Nearby, lounge chairs and vibrant pool toys are visible, enhancing the outdoor relaxation space.

Cabin in Sturgeon Bay

Waterfront/Pool/Hot Tub/Firepit/Game Room

4.93 out of 5 average rating, 164 reviews

A spacious living area is presented, featuring a large sectional sofa and an accent chair. Natural light filters through multiple windows. The adjoining dining area includes a long table surrounded by several chairs. A view of the modern kitchen with dark cabinetry is visible in the background.

Townhouse in Egg Harbor

Beautifully Updated Egg Harbor Townhouse in town!

4.91 out of 5 average rating, 112 reviews

The entrance to Meadow Ridge is marked by a stone facade featuring two blue signs. Surrounding greenery is complemented by pumpkins arranged on a stone outcrop, creating a seasonal display. Soft light illuminates the scene, highlighting the welcoming aspect of the property.

Condo in Egg Harbor

Entire Townhouse -Escape to Door County