Hemingway holiday rentals

We found 88 holiday rentals — enter your dates for availability
Discover a selection of 15 homes and other holiday rentals in Hemingway that are perfect for your trip. Whether you’re travelling with friends, family or just with your pet, holiday homes have the amenities that you expect for your stay, including parking and a TV. You'll be sure to find a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

  • 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

Frequently asked questions

When is the best time to visit Hemingway for a holiday rental?
The best time to visit Hemingway, Florida, for a holiday rental is during the peak season from February to April. This period is particularly appealing for travellers seeking sunshine and pleasant temperatures, typically ranging from 18 to 27 degrees Celsius. The vibrant setting draws in many visitors keen to enjoy outdoor activities such as biking, fishing, and exploring the nearby natural parks.September is also a popular month, as it offers warm weather and fewer crowds compared to the busy winter months. This can be an excellent time for those wanting to soak up the sun on the beautiful beaches and participate in local events without feeling rushed. The warm ocean waters are superb for swimming, while the scenic surroundings provide a lovely backdrop for relaxation and exploration.For travellers looking for a more budget-conscious option, October presents a wonderful opportunity. With slightly cooler temperatures and a more tranquil environment, it's an ideal time for leisurely strolls along the coastline and enjoying the local cuisine in a less crowded atmosphere.Ultimately, your choice of when to visit Hemingway will depend on whether you prefer the lively buzz of peak season or the serene charm of the quieter months.
What are the top attractions in Hemingway, Florida, United States of America?
In Hemingway, Florida, visitors can enjoy a variety of attractions that highlight the area's natural beauty and cultural significance. The nearby Big Pine Key offers stunning views and access to the National Key Deer Refuge, where guests can observe the unique Key deer in their natural habitat.For those interested in history, a visit to the Ernest Hemingway Home and Museum in nearby Key West is a must. This historic site provides insight into the life of the renowned author and features beautiful grounds and a fascinating collection of memorabilia.Additionally, the surrounding waters are great for outdoor activities such as fishing, kayaking, and boating, with numerous spots to launch from in the area.
Are all fees included in the Hemingway 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 Hemingway holiday homes with parking?
Stayz offers a wide selection of holiday homes in Hemingway 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 Hemingway holiday homes?
You can find great discounts on holiday homes in Hemingway 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 Hemingway holiday home booking on Stayz?
To find Hemingway 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 Hemingway?
A long-stay holiday home in Hemingway 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 Hemingway holiday home?
Book your Hemingway 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 Hemingway?
Prices for holiday homes in Hemingway 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 Hemingway 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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