Key West holiday lettings

We found 2,351 holiday rentals — enter your dates for availability

Select from 1113 houses, 280 apartments and other holiday rentals to find the perfect place for your stay in Key West. Whether you’re staying in a holiday home with a group or just with your pet, you'll have the amenities that you expect and more, which might include air conditioning and a pool. No matter what you're looking for, you'll be sure to find a property to rent that has what everyone needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts - Key West

Showing deals for:6 Feb - 13 Feb

Image gallery for Springtide House at Lunara Bay

Large Outdoor Space! Great for spending time with friends and family.
9.8 out of 10, Exceptional, (43 reviews)
Exceptional
(43 reviews)

Springtide House at Lunara Bay

Key West, FL

8% off
Price is £12,780
for 7 nights, 1 home
£1,826 per night
includes taxes & fees
Springtide House at Lunara Bay

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Why visit Key West

  • Stunning beaches: Key West boasts beautiful sandy shores, perfect for relaxation and sunbathing.
  • Rich cultural heritage: Explore historic houses and museums that showcase the island's unique history.
  • Outdoor activities: Engage in a variety of adventures such as snorkelling, fishing, and kayaking in crystal-clear waters.
  • Charming neighbourhoods: Wander through vibrant streets filled with local shops, cafes, and art galleries.
  • Varied accommodation options: Choose from quaint cottages to modern condos, catering to all tastes and budgets.

Popular types of accommodation in Key West

Planning a getaway to Key West? The next step is selecting the perfect accommodation. From charming cottages to spacious private homes and modern condos, there’s a range of holiday rentals to suit every taste and budget. Discover the ideal house rental for your stay and enjoy the comforts of home while exploring the vibrant atmosphere of this tropical paradise.

  • Houses: The top choice for holidaymakers in Key West, offering spacious and comfortable living for families, couples, or groups of friends.
  • Condos: A favoured option for many, providing a blend of convenience and luxury, often with stunning views and shared amenities.
  • Cottages: Charming and quaint, these retreats offer a cosy atmosphere, perfect for a romantic getaway or a peaceful escape.
  • Apartments: Ideal for those seeking a home-from-home experience, with self-catering facilities and a central location.
  • Villas: Elegant and spacious, these upscale properties cater to those looking for a more lavish stay in Key West.**

Top attractions in Key West

Key West is an ideal destination for families, business travellers, and those seeking a city-themed holiday. With its stunning beaches, captivating national parks, and historic houses, visitors can indulge in a rich cultural experience while enjoying outdoor activities. Whether you're after relaxation or adventure, Key West offers a variety of attractions to suit every traveller's needs.

  • Duval Street: A vibrant hub of activity, Duval Street is lined with eclectic shops, lively bars, and delightful eateries. Experience the energetic atmosphere as you stroll along this historic thoroughfare, where street performers and local artists add to the charm.
  • Mallory Square: Famous for its spectacular sunsets, Mallory Square is a bustling gathering place where you can enjoy street performances, artisan stalls, and stunning views of the Gulf of Mexico. It's the perfect spot to unwind and soak in the local culture.
  • Smathers Beach: Offering a picturesque slice of paradise, Smathers Beach boasts soft sands and crystal-clear waters. Relax under a palm tree, partake in water sports, or enjoy a leisurely stroll along the shoreline, soaking up the sun and sea breeze.

Things to do recommended for couples

Seeking a romantic getaway in Key West? Enjoy a leisurely sunset sail on a catamaran or take a stroll along the picturesque Duval Street, soaking in the vibrant atmosphere. Don't forget to share a slice of key lime pie while watching the sunset at Mallory Square.

Things to do recommended for families

Families visiting Key West can have a splendid day at the MLK Community Pool & Community Center, where they can enjoy the outdoor pool and partake in various sports activities, all while soaking up the friendly family atmosphere of this vibrant local spot.

Things to do recommended for groups

Enjoy a round of golf at the Key West Golf Club, embrace the vibrant culture at the Waterfront Playhouse, and explore unique finds at The Kite House. These local experiences promise to create unforgettable memories for your group in the sunny paradise of Key West.

What do I need to keep in mind when booking a vacation in 'Key West

If you’re travelling with a group, family, pets, or planning an extended stay, it’s essential to filter your options based on your key priorities. Here are some helpful booking tips for using Vrbo.

  • Traveling to Key West with a group: Think about how many bedrooms you'll require, as well as additional features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for all these options and more on Vrbo.
  • Traveling to Key West with young kids: Travelling with young children can indeed be quite demanding. It's essential to prioritise their comfort and safety, alongside ensuring that there are suitable amenities for their age, such as a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Key West: For many families, a holiday wouldn’t feel complete without their furry companions. If this resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that every member of the family feels at home.
  • Planning for a long term stay visiting Key West: If you're in search of holiday rentals with special offers for stays of a month or more, you've come to the perfect place. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in Key West

Key West offers a delightful island getaway, perfect for families and couples alike. With its vibrant atmosphere, visitors can explore charming neighbourhoods, indulge in tropical excursions, and soak up the romantic vibe of this unique city. Whether you're seeking relaxation or adventure, Key West is a splendid destination to create unforgettable memories, making it an ideal choice for your next holiday.

  • Old Town Key West: Old Town Key West is a vibrant neighbourhood steeped in history and charm. Located in the heart of Key West, it offers a delightful blend of city-themed experiences, family-friendly activities, and business opportunities. Stroll through its picturesque streets lined with colourful architecture, explore local shops and boutiques, and relax at nearby family beaches. Notable attractions include the lively shopping area and various resorts, making it an ideal spot for both leisure and business travellers.
  • Key West Historic District: The Key West Historic District is a captivating area that draws visitors with its rich heritage and unique atmosphere. Nestled within Key West, this district is perfect for families and city explorers alike. With an array of shopping areas, malls, and charming resorts, it caters to diverse interests. Wander through historic streets, enjoy the local beach scene, and immerse yourself in the vibrant culture of the island. The district's attractions make it a must-visit for anyone seeking a blend of history and modern conveniences.
  • New Town: New Town offers a contemporary twist to the traditional Key West experience. Located close to the main attractions, it’s an excellent choice for families and business travellers. This neighbourhood features bustling shopping areas, modern malls, and comfortable resorts, ensuring visitors have all they need for a fantastic stay. The proximity to beautiful beaches and scenic streets makes it a great launchpad for exploring the rest of the island. Whether you’re seeking relaxation or adventure, New Town has something for everyone.

Booking with Vrbo is a breeze

Are you hoping to save on your upcoming holiday? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, you can enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, utilise our filters to sort by price, location, and type of holiday accommodation.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a user-friendly platform for you to plan new adventures, resume your previous arrangements, or simply manage your travel itinerary. Here, you can easily find the properties you’ve saved or booked, organised under Potential, Upcoming, or Current Trips. To begin using Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Take in the picturesque beauty of Key West

The area's live music and festivals are just some of the reasons to come on holiday to Key West. This city's bars, seaside and boating draw many visitors. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in Key West

Are you hoping to find attractions to see while you're in town? Travellers enjoy fun activities like boating and cycling. Venture out of your cosy holiday rental and experience everything that makes Key West a one-of-a-kind holiday spot. These are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Key West Golf Club (4 mi / 6.5 km)
  • Blue Hole (28.6 mi / 46.1 km)
  • The Kite House (0.3 mi / 0.5 km)
  • MLK Community Pool & Community Center (0.5 mi / 0.8 km)

Exploring the natural landscape of Key West

Travellers love Key West for its breathtaking sunsets and beautiful ocean views. Whether you're looking for adventure or just want to spend some time taking in the scenery, you'll be sure to find the perfect setting for your holiday in Key West. These are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • Audubon House and Tropical Gardens (0.3 mi / 0.6 km)
  • Key West Butterfly and Nature Conservatory (0.6 mi / 1 km)
  • Southernmost Point (0.6 mi / 1 km)
  • South Beach (0.7 mi / 1.1 km)
  • Simonton Beach (0.8 mi / 1.2 km)
  • Truman Beach (0.9 mi / 1.4 km)

Transport to and around Key West

Fly into Key West, FL (EYW-Key West Intl.), the closest airport, located 3 mi (4.8 km) from the city centre.

Frequently asked questions

What is the best area to stay in Key West when booking a holiday rental?
When planning a holiday rental in Key West, Florida, the Old Town neighbourhood stands out as a popular area to stay. This vibrant and historic section of the island is packed with charming architecture and lively streets, making it an ideal base for exploring. You'll find an abundance of properties available, ranging from quaint cottages to luxurious homes, ensuring there's something to suit every taste and budget.

Staying in Old Town places you within walking distance of some of the key attractions, including the famous Ernest Hemingway Home and Museum, where literature enthusiasts can immerse themselves in the life and works of the iconic author. Additionally, the bustling Duval Street offers an array of shops, bars, and restaurants, superb for experiencing the local culture and nightlife.

Another excellent option is the Truman Annex, a gated community adjacent to Old Town, known for its beautiful, historic homes and serene atmosphere. This area is particularly close to the picturesque Fort Zachary Taylor Historic State Park, ideal for sunbathing and enjoying the natural beauty of the Florida Keys.
How much does it cost to rent a holiday home in Key West?
Prices for holiday rentals 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Key West to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Key West holiday house rentals?
You can find great discounts on house rentals in Key West on Vrbo, 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.
Where are the best areas for renting a beach house in Key West?
For renting a beach house in Key West, Florida, travellers should focus on the picturesque neighbourhoods of Old Town and the area surrounding Smathers Beach. Old Town is known for its vibrant atmosphere and historic charm, where many rental properties offer easy access to the beach as well as local attractions. Here, visitors can expect amenities such as private pools, outdoor entertaining areas, and fully equipped kitchens, making them ideal for family gatherings or group holidays.

The properties near Smathers Beach typically feature stunning views of the Atlantic Ocean and are great for those looking to enjoy water activities. Many of these rentals come with beach gear, outdoor showers, and spacious balconies for soaking up the sun. Additionally, the proximity to beachfront bars and restaurants adds to the convenience for guests wanting to explore the local dining scene. Find your rental near the beach in Key West.
Are there any houseboat rentals in Key West?
In Key West, houseboat rentals are quite popular, with around 53 available throughout the area. These unique accommodations can be found in picturesque settings near the vibrant Old Town, close to attractions like Mallory Square and the Ernest Hemingway Home and Museum. Travellers can expect various amenities, including fully equipped kitchens, comfortable living spaces, and often outdoor decks great for soaking up the sun or enjoying the sunset over the water.
What is the most popular type of holiday rental accomodation in Key West?
In Key West, holiday houses are the most popular type of rental, with around 1,207 available across the island. These properties provide spacious living arrangements, often featuring multiple bedrooms, full kitchens, and outdoor areas like patios or decks—ideal for enjoying the warm, tropical climate. Many houses are situated in charming neighbourhoods close to points of interest such as the historic Old Town, Duval Street, and the vibrant waterfront.

Condominiums are also quite popular, with about 608 options that typically include communal amenities like swimming pools and fitness centres. These rooms often come with modern furnishings and conveniences such as laundry facilities.

Apartments, numbering around 237, offer a more compact yet comfortable alternative for couples or solo travellers, usually featuring essential amenities like kitchenettes and living areas. Cottages and even a few unique houseboats, with 125 and 53 listings respectively, provide a quaint, distinctive experience, often located near the beach or scenic spots.
Are there any family house rentals in Key West?
In Key West, there are numerous family-friendly house rentals available, with around 1,350 options spread throughout the island. Neighbourhoods like Old Town and New Town offer a variety of spacious rooms great for families. Properties in Old Town often feature inviting living areas, full kitchens for preparing family meals, and private pools, all within walking distance to local attractions such as the lively Duval Street and the historic Ernest Hemingway Home and Museum.

Meanwhile, New Town is known for its larger homes that come with multiple bedrooms, expansive gardens, and entertainment spaces, including game rooms. This area also provides easy access to Bayview Park, where families can enjoy playgrounds, sports courts, and picnic areas, ensuring plenty of outdoor fun. See all family-friendly rentals in Key West.
Can I rent a holiday home with a pool or hot tub in Key West?
In Key West, there are many holiday homes available for rent that come with pools or hot tubs, with approximately 1,765 options to choose from. The island offers a variety of neighbourhoods where these properties are situated, including the vibrant Old Town, known for its historic charm and close proximity to famous attractions, as well as the more tranquil areas like New Town, which provide a peaceful retreat. Find your rental in Key West with a pool or a hot tub.
Can I find long-stay holiday rentals in Key West?
A long-stay holiday rental 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Key West?
In Key West, there is a wide selection of pet-friendly house rentals available, with around 864 options to choose from. Many of these holiday homes come equipped with amenities such as private pools, spacious outdoor areas, and fully equipped kitchens, making them suitable for families or groups travelling with pets.

The historic Old Town area is particularly popular, offering charming houses that often feature wraparound porches and gardens, allowing pets to enjoy the Florida sunshine. Proximity to local attractions such as the Ernest Hemingway Home and Museum and the vibrant Duval Street adds to the appeal, as many nearby cafes and shops are also pet-friendly. See all pet-friendly rentals in Key West.
Are there any remote work holiday rentals in Key West?
In Key West, there is an abundance of remote work-friendly holiday rentals, with around 2,184 options available for travellers. This vibrant island offers a unique blend of relaxation and productivity, making it an ideal destination for those looking to work remotely. Many properties come equipped with essential amenities such as high-speed Wi-Fi, dedicated office spaces, desks, and comfortable chairs, ensuring a conducive work environment. Some rentals even feature additional tech setups, including computer monitors and laptop workspaces, great for professionals needing to stay connected. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Key West holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals 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 on Vrbo 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.
What are popular rental amenities in Key West?
In Key West, popular rental amenities include kitchens, allowing guests to prepare their own meals, and complimentary Wi-Fi, which is essential for staying connected. Many holiday rentals also feature shared pools, with some offering heated options for a more comfortable swim experience.
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 January to March, with March being particularly popular. This vibrant period attracts a diverse crowd of travellers who revel in the island's stunning weather and lively atmosphere. Expect warm temperatures averaging around 24-26 degrees Celsius, making it great for outdoor activities such as exploring the beautiful beaches, snorkelling in crystal-clear waters, and enjoying the famous sunset celebrations at Mallory Square.

In March, you'll find a bustling yet enjoyable environment, with plenty of opportunities to indulge in water sports, experience local festivals, or simply unwind at a beachside café. The pleasant climate invites you to take leisurely strolls through the historic streets, soaking up the unique architecture and vibrant culture of Key West.

For those seeking a more budget-friendly experience, October is an excellent month to consider. While this is the low season, it offers a quieter atmosphere with fewer tourists, allowing you to enjoy the local charm without the crowds. The weather remains warm, typically around 29 degrees Celsius, making it ideal for leisurely outdoor activities such as biking or visiting the Dry Tortugas National Park.
How early should I book a Key West holiday rental?
Book your Key West holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Key West?
In Key West, visitors can experience firsthand a range of attractions that highlight the island's unique charm. The historic Old Town is a focal point, where the famous Duval Street buzzes with nightlife, restaurants, and shops, as well as landmarks like the Ernest Hemingway Home and Museum. Nearby, the Southernmost Point Buoy offers a picturesque photo opportunity, marking the southernmost tip of the continental United States.

The scenic waterfront area is great for leisurely strolls and watching the sunset, especially at Mallory Square, which hosts a lively sunset celebration each evening. For those interested in marine activities, the nearby Dry Tortugas National Park is accessible by boat or seaplane and boasts stunning natural beauty and historical significance.
Can I change or cancel my Key West home rental booking on Vrbo?
To find Key West holiday rentals with free cancellation, just use Vrbo'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". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo 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, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Key West holiday rental prices shown on Vrbo?
Vrbo 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.

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