Holiday rentals in Gibraltar

Bay View Beauty on the Bluff

**Stunning home on the Bluff with Spectacular, Panoramic Bay Views** Enjoy the best of Door County at this beautiful 5-bedroom, 4.5-bath home perched on Gibraltar Bluff, offering breathtaking views of Fish Creek Harbor. This spacious retreat sits on over 2 wooded acres and is conveniently located less than 5 minutes from both downtown Fish Creek and the entrance to Peninsula State Park, making it the perfect destination for families or groups looking for an unforgettable Door County experience.

Serene, cozy cottage in the woods

Welcome to your safe Haven in the woods! Located conveniently in Sturgeon Bay one block from the lake, this cozy cottage will not disappoint! Sipping coffee on the inviting front porch, getting comfy around the grand fireplace or creating a delicious dinner in the modern kitchen will have you feeling right at home! Haven offers plenty of space for families to get together and create lasting memories. Even a bunk room above the garage gives the kids their own hang out space. Close to all the fun!

Cole's Country Cottage •In The Heart of Fish Creek

Come relax at our very comfortable, homey, quiet space located in the heart of Fish Creek, just minutes from downtown, the beach, Peninsula State Park + popular restaurants and shops. We prioritize the cleanliness of our space + the comfort of our guests. Two bedrooms, a living room, kitchen + bathroom make it perfect for families - you get plenty of backyard space too! We provide coffee + a fully equipped kitchen and bathroom. Stay with us for some relaxation + see all Door County has to offer!

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).

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.

Mid Century Lake House with private beach

Come enjoy Door County in this beautiful lake house. Completely renovated with private beach access this is the perfect place to relax. Everything in this home is brand new! Conveniently located next to Ellison Bay & Sister Bay, enjoy all the hustle and bustle of Door County and retreat back to the serenity of the house Swim in the lake, paddle board, or take one of our bicycles and enjoy the scenery. Enjoy the winter snow shoeing, cross country skiing or snowmobiling.

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!

Cedar & Glass | Fish Creek Architectural Retreat

Wake up surrounded by forest. Cedar and Glass is a custom-built architectural retreat in Fish Creek where floor-to-ceiling windows, heated polished concrete floors, and a modern fireplace bring the outside in. Set on five private wooded acres, it’s a luxury escape for those who want genuine seclusion without sacrificing a single comfort. Ideal for couples celebrating something special, small families who want space to breathe, or remote workers who need a real reset.

Pearl Of Sister Bay Luxury Downtown Condo

Welcome to the Pearl of Sister Bay,a chic downtown condo ideal for a relaxing escape! This 1-bedroom, 1-bathroom condo offers modern comforts and design. Condo , has a fully equipped kitchen with a stove and refrigerator, fireplace, deck with a partial water and village view. Located in the heart of Sister Bay, you’ll be steps from the beach, local bars and restaurants, shopping and local attractions. Relax, recharge, and enjoy the charm of this vibrant destination!

Sister Bay A-Frame, Fire Pit, Coffee Bar, 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 Bed In Fish Creek, Fire Pit, Private Trails

Escape to Orchard Ranch in Fish Creek—a newly remodeled home that sleeps 10 and offers private walking trails, a fire pit, ping pong table, and a cozy coffee bar. Just minutes from Peninsula State Park and Fish Creek dining. Great for families, friend groups, or couples' getaways. Only a few open summer dates remain—book now and save! -7 minutes to Peninsula State Park -2 minutes to Lautenbach's Orchard -5 minutes to Egg Harbor

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

HOT TUB & SAUNA! Get away from it all when you stay under the stars at Natureside! This A-Frame cabin is nestled on 40 acres of wooded terrain. The area will give you seclusion and the A-Frame will give you luxury. Completely renovated to suite your needs and then some! Enjoy a hot tub and sauna view of nature or a warm fireplace! You will love this luxury getaway!