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Holiday rentals in Key West

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Top-rated holiday rentals in Key West

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
Guest suite in Dubuque
4.95 out of 5 average rating, 333 reviews

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.

Top guest favourite
A serene view of a tranquil pond reflects a cozy cabin surrounded by greenery. Soft grasses frame the foreground, while the sky showcases gentle clouds. The cabin features a covered porch, enhancing the peaceful ambiance of the quiet country location.
Cabin in Durango
4.99 out of 5 average rating, 338 reviews

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.

Guest favourite
Flat in Downtown Dubuque
4.96 out of 5 average rating, 293 reviews

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

Top guest favourite
A cozy efficiency suite is shown, featuring a spacious bed with neutral bedding and decorative pillows. A subtle artwork hangs above the bed. A television is mounted on the wall, and a modern air conditioning unit is visible. A comfortable seating area adds additional space.
Flat in Downtown Dubuque
5 out of 5 average rating, 126 reviews

1st St Jewelry Box Suite.

This unique place has a style all its own. This downsized efficiency suite is a comfortable living space. Within 3 blocks; historic cable car + shopping, restaurants, casino, Cathedral, Julien Hotel, Five Flags, River Museum, spas/yoga, Mississippi Riverwalk, winery, breweries, graffiti murals. Coffee included. Awesome for 1-2 people. Sundown mountain short 20-minute drive. Traveling with buddies? Just ask! We have 3 more units next to this one. We have short-term furnished places as well.

Top guest favourite
A hot tub is situated on a spacious deck, overlooking serene waters surrounded by lush trees. Comfortable seating is arranged on the deck, providing an ideal spot for relaxation while enjoying the tranquil view.
Place to stay in East Dubuque
4.96 out of 5 average rating, 200 reviews

Retro themed floating river cabin with a HOT TUB!

Our unique floating cabin features retro vibes and beautiful views of the Mississippi River backwaters. This cabin sits DIRECTLY in the water and has amazing views of the water You can even fish right off your deck! Enjoy the nature around you while sitting on your private floating deck, or snuggle up inside in front of the electric fireplace and Smart TV. This cabin features 2 bedrooms with queen beds, and a pull out couch in the living room. Our rental is located at Millennium Marina.

Top guest favourite
The exterior of the cedar cabin is visible, showcasing a natural wood finish beneath a sloping roof. A screened porch allows for views of the surrounding greenery. A potted plant adds a pop of color along the porch, with fallen leaves on the ground and dappled sunlight filtering through the trees.
Tiny home in Dubuque
4.94 out of 5 average rating, 192 reviews

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.

Guest favourite
A modern home is set amidst vibrant autumn foliage, featuring a diverse array of trees in shades of yellow, orange, and red. A winding driveway leads to the entrance, while the surrounding landscape showcases a blend of grassy areas and natural vegetation.
Home in Peosta
4.83 out of 5 average rating, 124 reviews

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!

Top guest favourite
The living area features a high wooden ceiling with a unique chandelier. Comfortable seating is arranged around a coffee table, accompanied by a rustic design. A kitchenette is visible in the background, along with large windows allowing natural light to enhance the open space.
Cabin in Hazel Green
4.98 out of 5 average rating, 121 reviews

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. 🌿

Top guest favourite
A cozy living area features a comfortable green sofa with patterned throw pillows and two orange armchairs. Natural light filters through large windows, illuminating the space. A wooden coffee table sits on a checkered rug, with a decorative piece displayed on top.
Home in Dubuque
4.97 out of 5 average rating, 200 reviews

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

Top guest favourite
A welcoming living area features a comfortable sofa and a wooden coffee table. Large windows provide a scenic view of the landscape and river, allowing natural light to fill the space. A TV is mounted above a stone fireplace, creating a cozy atmosphere.
Home in Dubuque
4.99 out of 5 average rating, 211 reviews

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!

Superhost
A tranquil lakeside view is captured at sunset, with silhouettes of trees framing the water. A small dock and a picnic table are visible, while canoes are lined up along the shore, providing a peaceful setting for relaxation.
Home in East Dubuque
4.88 out of 5 average rating, 422 reviews

A MUST SEE! 2BR Lakefront Home w/ Boats & More!

Welcome to our cozy lakefront home located in East Dubuque, Il which is only minutes away from Galena, IL and Dubuque, IA. This two bedroom home sleeps 6. We provide canoe's, and lifejackets. This home also has a large garage, a private deck overlooking the lake, and large yard. Other amenities include central air, comfy mattresses, all kitchen appliances, washer/dryer, Smart TVs with sound bar, and cable Internet. Don't miss out book now.

Top guest favourite
A sleeping area features a spacious bed made with a white blanket and dark gray accents. Two windows are flanked by dark curtains, while a ceiling fan provides ventilation. A nightstand with a digital clock is situated beside the bed, and a dresser is visible in the corner.
Flat in Dubuque
4.95 out of 5 average rating, 137 reviews

Eagle Point, River Area Getaway 2BR 1BA

This private apartment has easy access to travel to the main attractions of the city & surrounding area. Located in the historic Mathias Ham & Eagle Point district, enjoy easy access to boat landings on the Mississippi, river walk, Q Casino, ImOn hockey ice arena, the city pool & Eagle Point Park. Easy access to Hwys 151, 20, & 61 for adventures outside the city. On-street parking is always available for easy parking for truck & trailers.

Popular amenities for Key West holiday rentals

  1. Airbnb
  2. United States
  3. Iowa
  4. Dubuque County
  5. Key West