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Holiday houses 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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Guest favourite
A wooden side table is adorned with a decorative tray holding candles and pebbles. Above, a framed artwork showcases a cityscape, while a wall clock displays the time. A framed certificate and a ceramic figure add character to the space.
Home in East Dubuque
4.88 out of 5 average rating, 369 reviews

Cozy Oasis/DBQ/FieldDreams/Galena-Fenced for Pets

As natives to Dubuque and Galena , we wanted a place we could come home to when visiting that is also PET friendly!! Plenty of indoor/outdoor space. Make this your FIELD of DREAMS home base - just 20 minute drive to field and then you are 2 miles from Dubuque Casino and 14 mile scenic drive to Galena Main Street.Outdoor patio with plenty of seating , fire pit for late night snacks w camping chairs, Grill for your outdoor cooking. We have it all and if we don’t we will find it!! Fenced backyard!

Top Guest favourite
Guest suite in Dubuque
4.95 out of 5 average rating, 350 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.

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
4.96 out of 5 average rating, 139 reviews

Deer Trail Cabin

🌿 Cozy cabin nestled in the peaceful Wisconsin woods—your perfect getaway. Relax in the outdoor hot tub under the stars, explore private forest trails, gather around the fire pit,  and enjoy watching our free-range goats, ducks and chickens. note that our home is across the driveway, so you may occasionally see us caring for the animals, but your cabin and outdoor space are all your own and we respect the privacy of all our guests. Our goal is to provide a comfortable relaxing stay for you!🌿

Guest favourite
A cozy living room features exposed brick walls, a comfortable sectional sofa, and a round coffee table. A flat-screen TV is mounted above a wooden console, while natural light enters through the window with wooden blinds. Decorative wall art enhances the space.
Apartment in Downtown Dubuque
4.91 out of 5 average rating, 429 reviews

Drake House: Fleur de Lis with Private Hot Tub

No expenses were spared on this beautifully decorated suite! The Fleur de Lis is located in the downtown Millwork District on the second floor. It is ideal for one couple but can sleep up to 4. Perfect for a romantic get-away or business. The unit has 1 bedroom, 2 full baths, a ready to cook-in kitchen, a fireplace, a spacious living room and a private hot tub on the deck. The unit is within walking distance of downtown Dubuque. We hope you enjoy, relax and rejuvenate during your stay!

Top Guest favourite
An inviting firepit area features two black Adirondack chairs positioned around a circular stone firepit. The A-frame cabin is seen in the background, softly illuminated by decorative lights, surrounded by trees at dusk.
Cabin in Elizabeth
4.98 out of 5 average rating, 131 reviews

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.

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.
Apartment in Downtown Dubuque
5 out of 5 average rating, 143 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 positioned on a private deck, surrounded by scenic views of the Mississippi River backwaters. The calm water reflects greenery from the banks, while a seating area with dark outdoor furniture is visible nearby.
Place to stay in East Dubuque
4.96 out of 5 average rating, 221 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
A rustic cabin is presented, featuring a sloped metal roof and wooden exterior. Snow covers the ground, while a stone pathway leads to the porch. Two rocking chairs are positioned on the deck, inviting relaxation amid the natural surroundings.
Cabin in Hazel Green
4.99 out of 5 average rating, 168 reviews

Romantic one bedroom cabin with indoor fireplace

Relax and unwind at this getaway on a private 8 acres. Quaint decor yet newly updated amenities in this cabin only 7 miles away from the historic and charming Galena, Illinois. Convenient access to renowned fine dining and shopping in Galena and Dubuque and surrounding tri-state area, casinos, river life with boating and fishing, museums, cafes, vineyards/wineries, located on ATV/UTV trails and much more. You will find a guidebook in the cabin outlining these attractions and many more.

Top Guest favourite
The exterior of a charming red barn is framed by blossoming trees, providing a vibrant contrast to the greenery. Multiple windows allow natural light to enter, and warm light from a nearby lamp adds to the welcoming atmosphere of the property.
Barn in Dubuque
5 out of 5 average rating, 78 reviews

Annabel Lee Barn ~ A Getaway of Warmth & Charm!

Whether you're looking for a romantic or family get-away, the rustic, elegant Annabel Lee Barn is the place for YOU! The 1907 restored Iowa barn offers the warmth of two, wood-burning fireplaces, a cozy loft suite, state-of-the-art kitchen, and a wrap around deck. Enjoy a glass of wine or warm cup of coffee while enjoying the country views of the surrounding valley. A morning stroll along the Catfish Creek will definitely start your day off just right! A getaway you'll never forget.

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, 226 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 large jetted tub is surrounded by tiled walls and natural light filtering through textured window coverings. A wooden tray rests across the tub, holding a glass of water, a bowl, and a book, inviting relaxation.
Home in Dubuque
4.86 out of 5 average rating, 343 reviews

JACUZZI SUITE 2 Queen Beds Private and Romantic!

This hidden gem is located in the heart of Dubuque, IA in a park like setting. This home is perfect for a little getaway. Featuring 2 bedrooms with queen beds, elegant open floor plan, and the most amazing jetted tub you will ever see. Not only does this home have all hardwood flooring but it is also a single level home. Smart TV's in each bedroom and living room. The garage is used as storage at the moment and is not accessible to guests.

Guest favourite
Townhouse in Dubuque
4.95 out of 5 average rating, 191 reviews

2 Bedroom-Open-layout Townhouse

Our home is nested in the Washington Neighborhood, blocks from coffee shops, a grocery store, micro breweries, restaurants, and walking and biking paths. Right across the street from a park where kids can play and community garden! Enjoy the kitchen, living space, yoga/meditation room, and outdoor patio along with access to Wifi and netflix!

Popular amenities for Key West holiday rentals