Holiday rentals in Key West

Cozy Charming Getaway with Modern Comforts

Discover the heart of Dubuque from this clean, cozy second-floor apartment near eateries, hospitals, bars, and cafés. Recently renovated with high-speed internet, a 50” Smart TV, and in-unit laundry. Just 5 minutes from downtown, 20 minutes from Galena, close to Loras, UD, and Clarke, and within 30 minutes of ski resorts and the Field of Dreams. Note: second-floor unit accessed by stairs. Ideal for work trips, weekend escapes, or longer stays with comfort, privacy, and convenience. Book today.!!

Fun custom waterfront floating cabin-HOT TUB!

This newly built floating cabin sits on the backwaters of the Mississippi River. It’s 1970s mod design is unique and fun! This rental has 2 bedrooms with queen beds and a queen pull out couch. There is a full bathroom and a stocked kitchen. Soak in the hot tub and take in the waterfront views all around. While there are other cabins around, you have your own walkway and no one connected to you! Enjoy a kayak ride, fish, or just relax on your floating deck. This is located at Millennium Marina.

Private entrance/space. Peaceful. Close to events.

Private entrance. You have a completely updated/ remodeled private space on the walk-out level of my home. Open floor plan, a carpeted bedroom with KING bed, a full-size memory foam sleeper sofa, a living room, mini-kitchen, laundry and bath. The mini-kitchen has a mini-fridge, microwave, coffee maker, crock pot, toaster, table/chairs. The desk, with woods view, is a perfect place to reflect, read, and write. Many extras. Snacks. Quiet residential area of Dubuque. I live upstairs with my dog.

Drake House: The Loft with Private Hot Tub

No expenses were spared on this beautifully decorated suite! Newly renovated in fall 2019 and located in the famous Millwork District. The Loft is ideal for 1 couple but can sleep up to 4. It’s the perfect romantic getaway or business destination. The unit has 1 king size bed, 2 full baths, a kitchen, gas fireplace and 2 spacious living areas. There is a private hot tub on the deck and is within walking distance of downtown Dubuque. We hope you enjoy, relax and rejuvenate during your stay.

Cozy Cabin by the Pond

Primary guest must be 21+ Quiet country location to relax & enjoy. Just 9 miles west of Dubuque, near Wineries, Heritage Trail, Sundown Mountain Resort. Primary guest must be 21+ to book. Cozy cabin & 1/4 acre pond. We're sure you’ll love this space as much as we do. Not suitable for children under 12, we strictly enforce no children or pets, and must be 21+ to book. Outdoor space, gas grill, gas fire pit. Fully stocked cabin, with breakfast items included for you to enjoy at your leisure.

Hot Tub+ Firepit+ "Tiny"house+ Views+ Near Galena

Tucked away in the countryside of Galena, our charming A-frame cabin is the perfect escape for those seeking peace, nature, and a touch of nostalgia. This intimate retreat blends mid-century modern charm with cozy modern comforts, creating an unforgettable getaway. Whether you’re sipping coffee on the deck at sunrise, soaking in the brand-new hot tub under a canopy of stars, or unwinding by the fire with a vinyl record spinning in the background, every moment here is designed for relaxation.

Off-grid Tiny House farm stay

The perfect place for 1-2 guests to unplug and relax in this beautiful, natural setting. It's a short distance (less than 2 min. walk) from the parking area to this quiet, private, 12'x14' one-room cedar cabin set on a pasture with picture-window view of wooded bluffs and stream, birds and other wildlife. Writing table and chair, glider rocker, woodstove, and gas cookstove. Solar-powered desk lamp. Port-a-potty and solar shower outside (summer only). Fire pit and outdoor seating.

Swiss Valley Getaway - Dubuque / Tri-State Area

Nestled in the hills of Dubuque County and overlooking the Swiss Valley, this 5 bedroom, 2 bath, 2 car garage home is just the place for your quiet get away! Enjoy all of the beauty , peace and quiet of nature. Located directly across from the Swiss Valley Nature Center, streams and trails. Whether you're looking to get out of the city or gather with friends and family, this is your perfect place. Just minutes from Dubuque, Galena, Sundown Ski Resort and so much more!

Deer Trail Cabin

🌿 Cozy cabin tucked in the quiet Wisconsin woods—your perfect spring retreat. Enjoy fresh air, blooming trees, and peaceful forest trails right outside your door. Relax in the outdoor hot tub under the stars, gather around the fire pit in the evening (bring your own wood or collect from the property), and watch the free-range goats and chickens roaming the property. A peaceful, private getaway for couples, small families, or anyone looking to unwind in nature. 🌿

Pet Friendly Home by UD & Finley

Centrally located & steps from University of Dubuque and Finley Hospital. In-between downtown and central city. 4 bedroom home with a formal dining room, full kitchen, bathroom with a tub/shower and plenty of space to relax. Start your morning with Bob& Lou's or Charlotte's (Hartigs) across the street. Well behaved pets welcome with a fully fenced in backyard. Galena is a short 20 minute drive *Please book with total guest count including pets if applicable

1157#5/Cozy Downtown Dubuque 1BR •Walk to Millwork

Enjoy a comfortable stay in the heart of downtown Dubuque, just steps from the Millwork District, restaurants, breweries, coffee shops, and the seasonal Farmers Market. This bright 1-bedroom apartment features a cozy queen bed, full kitchen, smart TV, and fast Wi-Fi for relaxing after a day exploring the city. Easy self check-in and a reserved off-street parking space make arrival simple. A great home base for couples, solo travelers, or business visits.

Home by the River

Situated alongside the Mississippi River, wildlife abounds in every season. With eagles nesting nearby, there is always something new to see from the beautiful sunrises, cruise ships passing by, and watching the commerce of the barges and railroad right out the front window! This home has been recently refurbished and sits at the edge of our 15 acres. You can see us and visit with us if you like, or you can maintain privacy 10 acres away!