Key West holiday rentals

We found 126 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in Key West that are perfect for your trip. Holiday homes offer the best amenities for your family, friends or furry companion, such as air conditioning and Wi-Fi. At the end of the day, you'll be sure to find a property to rent that has what everyone needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Key West

Showing deals for:15 Jan - 22 Jan

Dining
Private kitchen
Interior
Exterior
Exceptional
(7 reviews)

Spacious 4-bedroom home in a beautiful neighborhood on the edge of town

Dubuque

8% off
AU$3,408
for 7 nights, 1 home
AU$487 per night
includes taxes & fees
Spacious 4-bedroom home in a beautiful neighborhood on the edge of town
Living area
Private kitchen
Living area
Room
Exceptional
(47 reviews)

Cozy Cabin Retreat located just minutes to Galena, IL & DBQ, IA

Hazel Green

8% off
AU$2,175
for 7 nights, 1 cabin
AU$311 per night
includes taxes & fees
Cozy Cabin Retreat located just minutes to Galena, IL & DBQ, IA
Exterior
Interior
Interior
Dining
Exceptional
(36 reviews)

Spacious 7-bedroom house- unique history, modern comforts and incredible views

Dubuque

8% off
AU$7,587
for 7 nights, 1 home
AU$1,084 per night
includes taxes & fees
Spacious 7-bedroom house- unique history, modern comforts and incredible views
Interior
Living area
Interior
Living area
Exceptional
(53 reviews)

Beautiful view of the City and Mississippi River!

Dubuque

7% off
AU$2,013
for 7 nights, 1 home
AU$288 per night
includes taxes & fees
Beautiful view of the City and Mississippi River!
Outdoor sitting area.
adjustable queen bed with 800 thread count Egyptian cotton sheets
4 season room with wood burning stove
wood stove with utensils sitting area
Exceptional
(7 reviews)

Barn-dominium living experience w/ park view, adjustable bed, 4-seasons room

Dubuque

8% off
AU$2,232
for 7 nights, 1 home
AU$319 per night
includes taxes & fees
Barn-dominium living experience w/ park view, adjustable bed, 4-seasons room
Dining table. Seating up to 8.
Dishwasher, microwave, coffee pot, and toaster provided.
Shuffleboard
Fire place in 2nd living room/sitting room.
Exceptional
(127 reviews)

Entire house. Bonus Game Rm. Lg yard w/firepit/driveway/garage.

Dubuque

8% off
AU$2,500
for 7 nights, 1 home
AU$357 per night
includes taxes & fees
Entire house. Bonus Game Rm. Lg yard w/firepit/driveway/garage.
Dining
Exterior detail
Room
Private kitchen
Exceptional
(36 reviews)

Bluff Row. Historic Row Home in Cathedral Square. Downtown Dubuque.

Dubuque

7% off
AU$2,057
for 7 nights, 1 home
AU$294 per night
includes taxes & fees
Bluff Row. Historic Row Home in Cathedral Square. Downtown Dubuque.
Living area
Living area
Terrace/patio
Private kitchen
Exceptional
(162 reviews)

Drake House: The Loft (Private Hot Tub)

Dubuque

8% off
AU$2,202
for 7 nights, 1 apartment
AU$315 per night
includes taxes & fees
Drake House: The Loft (Private Hot Tub)
Living area
Exterior
Interior
Exterior detail
Exceptional
(55 reviews)

Charming Historic 4 Bedroom with Hot Tub

Dubuque

8% off
AU$3,597
for 7 nights, 1 home
AU$514 per night
includes taxes & fees
Charming Historic 4 Bedroom with Hot Tub
Room
Mainfloor Living Room. Seating for 6 comfortably
Private kitchen
Dining room. Wall dedicated to local photographer’s work
Exceptional
(41 reviews)

The Dubuque House - Historic Downtown Location

Dubuque

8% off
AU$2,121
for 7 nights, 1 home
AU$303 per night
includes taxes & fees
The Dubuque House - Historic Downtown Location
Dining room that seats 8 comfortably!
Exterior detail
Private kitchen
Room
Exceptional
(71 reviews)

Dubuque Luxury “Hot Tub” Farmers Market

Dubuque

16% off
AU$3,069
for 7 nights, 1 home
AU$438 per night
includes taxes & fees
Dubuque Luxury “Hot Tub” Farmers Market
Interior
Property grounds
Eat in kitchen.
Stackable washer and dryer inside closet.
Exceptional
(184 reviews)

Drake House- Fleur De Lis (Private hot tub)

Dubuque

8% off
AU$2,192
for 7 nights, 1 apartment
AU$313 per night
includes taxes & fees
Drake House- Fleur De Lis (Private hot tub)

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Choose a holiday rental for your Key West getaway

Learn about the unique charm of Key West with a stay in a holiday home rental. This city has something for everyone. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities and attractions in and around Key West

Do you want to find things to do while you're in town? Venture out of your holiday home and check out everything that makes Key West a fun place to get away to. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • National Mississippi River Museum and Aquarium (4.2 mi / 6.8 km)
  • Grand Harbor Resort and Waterpark (4.3 mi / 6.9 km)
  • Sundown Mountain (8.7 mi / 14 km)
  • Galena Golf Club (12 mi / 19.3 km)
  • Bellevue Golf Club (15.5 mi / 24.9 km)
  • Storybook Park & Zoo (2.9 mi / 4.6 km)

Exploring the natural features in Key West

Whether you're an outdoor enthusiast or just want to take in the scenery, Key West is a great spot to appreciate mother nature. Here are a few of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • Crystal Lake Cave (3.5 mi / 5.6 km)
  • Grant Park (13.5 mi / 21.7 km)
  • Casper Bluff Land and Water Reserve (14.8 mi / 23.8 km)
  • Upper Mississippi River Wild Life and Fish Refuge (15.5 mi / 24.9 km)
  • Swiss Valley Park (3.6 mi / 5.8 km)
  • Dubuque Arboretum and Botanical Gardens (6.5 mi / 10.5 km)

Travelling to and around Key West

Fly into Dubuque, IA (DBQ-Dubuque Regional), the closest airport, located 2.5 mi (4 km) from the city centre.

Frequently asked questions

What is the best area to stay in Key West when booking a holiday rental?
In Key West, Iowa, one of the best areas to consider for a holiday rental is the charming waterfront neighbourhood. This area offers a relaxed atmosphere and stunning views, making it superb for those looking to unwind. Here, you can find a variety of properties, from quaint cottages to larger family homes, ensuring there's something to suit every traveller's needs.Nearby, you can enjoy attractions such as the scenic waterfront park, which is ideal for leisurely strolls and picnics, and the local marina, where you can indulge in various water activities like boating and fishing. Additionally, the vibrant downtown area boasts an array of shops, cafés, and restaurants, providing plenty of options for dining and entertainment.
When is the best time to visit Key West for a holiday rental?
The best time to visit Key West for a holiday rental is during the peak season from August to October, with October being particularly popular. This month offers a delightful blend of warm weather and vibrant local events, making it an attractive option for travellers seeking both relaxation and adventure. As temperatures hover around 24 to 30 degrees Celsius, you can comfortably enjoy outdoor activities, from exploring the stunning coastline to indulging in water sports.October is also a fantastic time for those interested in local culture, as the annual Fantasy Fest takes place, showcasing a lively array of parades, parties, and artistic displays. The atmosphere is electric, with plenty of opportunities to engage with fellow visitors and locals alike, ensuring a memorable experience.If you're considering a more budget-friendly option, visiting in December can provide a quieter experience, superb for enjoying the beautiful beaches and scenic sunsets without the bustling crowds. While the weather is slightly cooler, ranging from 15 to 25 degrees Celsius, it's still pleasant enough for outdoor activities and sightseeing.
What are the top attractions in Key West?
In Key West, Iowa, visitors can enjoy a variety of attractions that highlight the area's charm and natural beauty. The quaint downtown area features unique shops and local eateries, superb for a leisurely stroll. The scenic waterfront offers opportunities for walking and enjoying the views of the Mississippi River, making it a lovely spot for both relaxation and recreation.Nearby, the Key West Park provides a great setting for outdoor activities, including picnicking and hiking along nature trails. The area's historical sites, such as the old railway bridge, add to the local character and provide a glimpse into the region's past. For those interested in birdwatching or fishing, the surrounding natural areas offer ample opportunities to engage with the local wildlife.
Are all fees included in the Key West holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Key West holiday homes with parking?
Stayz offers a wide selection of holiday homes in Key West with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Key West holiday homes?
You can find great discounts on holiday homes in Key West on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Key West holiday home booking on Stayz?
To find Key West holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Key West?
A long-stay holiday home in Key West is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Key West holiday home?
Book your Key West holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Key West?
Prices for holiday homes in Key West vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Key West to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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