Holiday rentals in Cana Island

4.98 out of 5 average rating, 251 reviews

Flat 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).

4.91 out of 5 average rating, 120 reviews

Cabin in Ellison Bay

Unique architect-designed home on waterfront bluff

An architect gem with a million dollar view. Located on the bay on a private drive near Ellison Bay, it’s close enough to town but far enough away to be secluded. The main house features a roomy living area with sleeper, kitchen, dining room, shower bath, and loft bedroom. The newly-finished "Garage-Mahal" features a full bathroom, two bedrooms (one full and two twins), kitchenette, and small living room with sleeper. This separate building is ideal for anyone who likes their own space.

Guest house in Fish Creek

4.97 out of 5 average rating, 226 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.

Superhost

Cottage in Sturgeon Bay

4.92 out of 5 average rating, 184 reviews

Peace of Beach, 4 season waterfront cottage

Beautiful 4 season, private 2 bedroom Knotty Pine Cottage located on the shores of Lake Michigan just 10 yards away from water in Sturgeon Bay, WI. 2 BR/1 bath cottage with beautiful stone, wood burning fireplace. A fully equipped kitchen with high bar dining which seats 8. Lots of living space with leather sectional and full size hide-away sofa sleeps 2, Main Guest Room 1 w/ queen log bed and Guest Room 2 with full size log bunk beds, Large screen tv, wifi and panoramic lake view.

Farm stay in Baileys Harbor

4.95 out of 5 average rating, 232 reviews

A True Farmhouse Experience

How would you like to get away from it all? How would you like to just kick back, relax, and take things in like the good ‘ol days? The Farmhouse might just be the place for you. Located just outside the town of Baileys Harbor, the Farmhouse is located on Gray-Aire Farms, a working farm since 1960. Nestled in the gorgeous surroundings of Northern Door County, you’ll be able to kick your feet up and take in the fresh country air, while watching the cows graze in the pasture.

4.91 out of 5 average rating, 327 reviews

Never Want to Leave Cottage

Three bedroom, lake home on the shores of Lake Michigan. Step into a beautiful, comfortable, clean environment on quiet North Bay in Door County, Wisconsin. As hosts, we have always taken great care to provide a safe and clean environment for our guests. To protect our guests, we are following the cleaning and sanitizing guidelines based on recommendations from the Centers for Disease Control and Prevention (CDC). We look forward to hosting you! Permit Number: 32-56-1996-00

5 out of 5 average rating, 188 reviews

Cottage in Sister Bay

Cozy A-Frame - Coffee Bar, 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.

4.98 out of 5 average rating, 128 reviews

Cottage in Sister Bay

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.

4.94 out of 5 average rating, 256 reviews

Waterfront on Peaceful Moonlight Bay

Located on the shore of Moonlight Bay Lake Michigan overlooking Toft and Bues Points. Private waterfront access with beach and dock. Kayaking, canoeing, SUPs, biking, swimming, and fishing (all included). Located on a bike route near Bues Point public boat ramp, Cana Island Light House, The Ridges Sanctuary, and Baileys Harbor. Conveniently located yet private a short trip to Fish Creek/Egg Harbor (15 min), Ephraim/Sister Bay (10 min).

4.97 out of 5 average rating, 358 reviews

Flat in Egg Harbor

Award Winning Modern Flat in Egg Harbor - #104

The Flats on Church Street are Door County's newest, most modern vacation rentals. The days of kitsch and lace are over! We built these rentals to give visitors to Door County something different. Each 1-bedroom/1-bathroom apartment features floor-to-ceiling windows, heated floors, a small kitchen, a king sized bed and a queen-sized sleeper sofa. They're centrally located within walking distance of all that Egg Harbor has to offer.

5 out of 5 average rating, 116 reviews

Home in Sister Bay

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!

Cottage in Baileys Harbor

4.95 out of 5 average rating, 131 reviews

20% Off! 4 BR + Coffee Bar + Firepit + Disc Golf

May & June Sale! Book now and save 20% on remaining May & June dates—perfect for families, couples, or a quiet Door County escape! Pull off the highway to the charm of a century-old, lovingly restored cottage just minutes from downtown in the heart of Door County. Stonewall Cottage blends historic character with modern comfort, offering a peaceful escape for families, couples, or friends.

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Popular amenities for Cana Island holiday rentals

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Free parking on premises

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Other great holiday rentals in Cana Island

Superhost

Tiny home in Stephenson

4.88 out of 5 average rating, 72 reviews

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

KameronRating, 5 stars2 weeks ago

Our stay was absolutely amazing! My new husband, our dog and I came here for our mini moon/ escape after our wedding and exactly what we needed with such a beautiful view. We really appreciated having all of the property questions answered before even needing it such as how to work the sauna and how to actually find the property. We fully plan on coming back here for anniversary’s. 😊

5 out of 5 average rating, 49 reviews

Lakefront cottage w/ sand beach & waterfront deck

DeborahRating, 5 stars4 days ago

Dan & Beth said they wanted us to feel at home and we certainly did! We had 7 adults in our group & we talked about the house & cost to stay there. We all agreed it was absolutely worth every cent. Dan couldn’t have been more helpful whenever we reached out with a question. Being right on the beach was magical. Fires at night with a plentiful supply of dry wood was a nice surprise! Anything you could possibly think of was at our disposal! Even the refrigerator was pristine, which in my experience, doesn’t always happen in a rental. We will miss Sandvik house!

4.95 out of 5 average rating, 44 reviews

Cottage in Ellison Bay

Waterfront cottage on Rowleys Bay!

SusanRating, 5 stars7 months ago

Door County has been a favorite spot of ours for 40 years. Joe and Kate's space was clearly the most private and the most stunningly beautiful surroundings I have experienced and yet just minutes from the "action". I would meditate on the shore of Lake Michigan while the sun came up and went to sleep with the sounds of the waves. Joe and Kate have put a great deal of care into this home and there are whimsical features that you will need to find out for yourself😉

Superhost

Cabin in Baileys Harbor

4.71 out of 5 average rating, 255 reviews

Baileys Harbor Cabin Near Kangaroo Lake-South Unit

KarenRating, 5 stars1 week ago

What a wonderful stay! We were able to relax and recharge. Such a cozy and comfortable place to stay. We’ve stayed at both North and South side now and they pretty much mirror each other. The South yard is a little more private away from the driveway. The Coyote Roadhouse across the street has wonderful food! Alyssa was wonderful to work with. This is the second time we have stayed here and we plan on it again next spring!

Guest house in Baileys Harbor

4.95 out of 5 average rating, 43 reviews

Rustic Beach House

CarleyRating, 5 stars1 week ago

We had a wonderful stay at Emily's rustic cabin for our babymoon! It was exactly what we were looking for - peaceful, private, rustic charm, right on the beach. We loved walking on the beach with our morning coffee, making a cozy fire in the fireplace each night, and being just a short drive away from all the wonderful towns around Door County. Other than some dead bugs (rather they be dead than buzzing about!) the place was clean, homey, and had everything we needed. Nice hot water for showers, a cozy bed, and stocked kitchen. Emily was so easy to communicate with and answered any questions we had right away. We would stay again in a heartbeat - you just can't beat being steps away from Lake Michigan.

4.75 out of 5 average rating, 68 reviews

Serene Lakefront Baileys Harbor Home w/ Deck!

LaimaRating, 5 stars8 months ago

We could not ask for a better backyard view that made our wedding weekend super special. The cottage itself was also very cute and homy. We will be definitely back! A must stay in Door County.

4.9 out of 5 average rating, 98 reviews

Home in Sturgeon Bay

Walden too

JessicaRating, 5 stars3 weeks ago

We had a great cozy stay at Jan’s. We were in Door County for a bachelorette weekend. Close to all things fun, but on the quiet side of the peninsula. Would love to visit again.