Key West holiday rentals

We found 2,304 holiday rentals — enter your dates for availability
Select from 1008 houses, 295 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:9 Oct - 16 Oct

Image gallery for Living the Dream Key West Style

Marina
10 out of 10, Exceptional, (61 reviews)
Exceptional
(61 reviews)

Living the Dream Key West Style

Key West

8% off
Price is AU$4,620
for 7 nights, 1 houseboat
AU$660 per night
includes taxes & fees
Living the Dream Key West Style

Find spaces that suit your style

  • 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

Why visit Key West

  • Rich cultural heritage: Explore historic houses and charming streets that capture the island’s vibrant local culture.
  • Pristine beaches: Enjoy scenic, near-beach experiences on sunlit shores ideal for relaxation.
  • Outdoor adventures: Indulge in picturesque excursions and diverse outdoor activities amidst tropical surroundings.
  • Lively waterfront: Experience the dynamic waterfront lounges and vibrant nightlife that add to Key West’s unique appeal.
  • Iconic island living: Revel in the blend of history and laid-back island charm that makes Key West unforgettable.

Popular types of accommodation in Key West

Discover the charm of Key West, Florida, where history meets laid-back island living. Whether you’re seeking a private holiday home, cosy cottage or a chic condo, you’ll find a perfect spot to relax near iconic beaches. Explore hotels, house rentals with pools and even unique kite houses, all while enjoying the local attractions and experiences that make Key West a truly unforgettable destination.

  • Private Holiday Homes: Enjoy the freedom and privacy of a standalone house, ideal for families and groups seeking a bespoke holiday experience in Key West.
  • Condos: Relish the convenience of a modern apartment-style dwelling, perfect for couples or small groups with a penchant for comfort and style.
  • Cottages: Experience a quaint and charming retreat in a cosy cottage, offering a homely feel amid tranquil surroundings.
  • Apartments: Choose a compact apartment, blending practicality with a central location for a hassle-free stay.
  • Villas: Indulge in a luxurious villa, providing an opulent escape with spacious living areas and elegant design.**

Top attractions in Key West

Key West, Florida, United States of America offers a blend of culture, beachside relaxation and outdoor adventures. The city is renowned for its pristine beaches, historic houses and vibrant local heritage. With attractions that cater for family, city-themed and business holidays, visitors can immerse themselves in the local culture and enjoy scenic outdoor experiences. Key West is a must-visit destination that promises memorable and diverse experiences.

  • Duval Street: This vibrant street is the heart of Key West, lined with eclectic shops, lively bars, and restaurants. Experience the lively atmosphere filled with street performers and art galleries, making it a perfect spot for people-watching.
  • Mallory Square: Known for its stunning sunsets, Mallory Square hosts a daily sunset celebration with local artists, musicians, and food vendors. The bustling square offers picturesque views of the harbour and a vibrant social scene.
  • Smathers Beach: This beautiful sandy beach is ideal for sunbathing, swimming, and water sports. Enjoy the laid-back beach vibes, with palm trees swaying in the breeze and plenty of space to relax by the ocean.

Things to do recommended for couples

Key West offers a charming escape for couples. Enjoy a sunset sail on the turquoise waters or explore the picturesque streets lined with vibrant bougainvillea. Don't miss a romantic dinner at a seaside restaurant, where you can savour fresh seafood while watching the sun dip below the horizon.

Things to do recommended for families

Families will love exploring the vibrant sea life at the Key West Aquarium, taking a scenic bike ride along the charming streets, or enjoying a sunset at Mallory Square, where street performers entertain visitors as the sun dips below the horizon.

Things to do recommended for groups

Explore the vibrant atmosphere of Mallory Square for sunset celebrations, or embark on a thrilling group snorkelling adventure at the stunning Dry Tortugas National Park. Don’t miss the chance to indulge in fresh seafood at local eateries, celebrating the unique flavours of Key West.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

Whether you're travelling with a group, as a family, with your pets, or seeking extended stays, ensure you apply the appropriate filters based on your priorities. Here are some Stayz booking tips for you.

  • Traveling to Key West with a group: Think about how many bedrooms you require, along with amenities like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and much more on Stayz.
  • Traveling to Key West with young kids: Travelling with young children can be quite demanding. It’s important to prioritise their comfort and safety, alongside ensuring access to suitable amenities, like a private swimming pool. Additionally, it would be wise to think about your closeness to family-friendly attractions.
  • Taking your pets with you to Key West: For many, a family holiday is not complete without the presence of their four-legged companion. If this resonates with you, consider exploring Stayz properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring everyone feels at home.
  • Planning for a long term stay visiting Key West: If you're seeking holiday rentals with special offers for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include additional features in your search, such as a parking space, a well-equipped kitchen, or a private pool.

Where to stay in Key West

Key West offers an enticing blend of family-friendly and romantic attractions. Visitors can enjoy the vibrant waterfront lounges and lively nightlife, alongside charming streets perfect for sightseeing. The island’s tropical ambience is complemented by scenic excursions and picturesque near-beach experiences, ensuring a memorable visit to this iconic Floridian destination.

  • Old Town Key West: Nestled in the heart of Key West, Old Town Key West offers a blend of urban sophistication and a relaxed island vibe. Its central location makes it an ideal starting point for exploring the city’s bustling shopping areas, expansive shopping mall centre, and a variety of resorts. The neighbourhood is renowned for its family-friendly attractions and vibrant streets that meander close to beautiful beaches and family-friendly seaside spots. The mix of city-themed and business-themed experiences provides travellers with a dynamic blend of cultural exploration and leisure.
  • Stock Island: Positioned as a naturally featured island near Key West, Stock Island delivers a unique travel experience that combines a family-oriented atmosphere with city-themed and business-oriented attractions. Visitors can enjoy the local shopping areas, modern shopping mall centre, and a well-kept golf course. The island’s scenic streets lead to expansive beaches and family-friendly coastal areas, providing an excellent backdrop for both relaxation and vibrant urban exploration.
  • Key West Historic District: Steeped in rich history and cultural heritage, the Key West Historic District is a charming neighbourhood that captivates visitors with its blend of family-focused, city-themed and business-themed experiences. Amidst its bustling shopping areas and large shopping mall centre, travellers can immerse themselves in the timeless streets and picturesque beach scenes. The district’s proximity to family-friendly coastal attractions makes it a compelling destination for those seeking a mix of historical allure and modern amenities.

Booking with Stayz is simple

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, booking for an extended period can often result in significant savings. To discover the ideal Stayz property that suits your budget, utilise our filters to search by price, location, and type of holiday rental.

Stayz Trips: Planning made easy

Stayz’s innovative Trip Board offers a dedicated space where you can begin planning new journeys, pick up where you left off, or review and organise your travel plans. Properties you have previously saved or booked are now conveniently organised under Potential, Upcoming, or Current Trips. To access your Trip Boards, simply visit: https://www.stayz.com.au/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. Take in top local attractions such as Duval Street and Mallory Square. 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:

  • Southernmost Point (0.6 mi / 1 km)
  • Florida Keys Beaches (16 mi / 25.8 km)
  • Audubon House and Tropical Gardens (0.3 mi / 0.6 km)
  • Key West Butterfly and Nature Conservatory (0.6 mi / 1 km)
  • South Beach (0.7 mi / 1.1 km)
  • Simonton Beach (0.8 mi / 1.2 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 home?
Snap up your holiday property in Key West Historic District and you'll be in the heart of one of Key West's leading neighbourhoods. Ernest Hemingway Home and Museum and Audubon House and Tropical Gardens are two major attractions here that'll entertain you during your visit.
What is the most popular type of holiday home accommodation in Key West?
Based on our research, houses are the most desirable property type in Key West. But naturally, everyone's idea of the perfect stay differs. Stayz has holiday homes of all shapes and sizes, and we'll help you to find your perfect match.
How much does it cost to rent a holiday home in Key West?
Length of stay, property type and season are some of the things that can influence the price of a holiday home. Simply enter your dates of travel to find your perfect fit. From cosy chalets to expansive villas, all Stayz holiday homes offer incredible value.
How much does it cost to rent a beach house in Key West?
When you travel and the style and size of the property will influence the cost of your beachside stay. Put in your Key West travel dates to see all your options on Stayz. Looking for a backyard so the kids can run around, or a pool to keep them busy? Use our filters to choose the amenities and features you want in your beach house.
Are there pet-friendly holiday homes in Key West?
Yes. You can pick from 1 ,825 holiday homes that cater to pets in Key West. Lots of our pet-friendly holiday homes even come with an outdoor area for your four-legged friend to play around in, doggie beds, complimentary treats and proximity to parks or green space. Apply the "Pets allowed" filter to find your pawfect place on Stayz.
Can I rent a house with a pool in Key West?
Mark the "pool" box in our filter tool and take your pick of 1 ,496 houses with private pools in Key West on Stayz. Morning swim, sunset soak or midnight dip? How you spend your free time is up to you when your Stayz holiday property boasts a swimming pool.
What are popular home amenities in Key West?
Some of the most popular home amenities people are searching for in Key West include mountain views, a lake view and a barbecue grill. Whether you're on the road with buddies, family or even pets, Stayz holiday properties have the best amenities for chilling out with your loved ones.
Are there large group holiday homes in Key West?
You can pick from 191 holiday properties in Key West that can host a group of 10 or more guests. Whether you're organising time away with the family or an event like an anniversary, there's enough room to get your loved ones together under the same roof.
Are there holiday homes in Key West that welcome kids?
Bring the entire group together for a fun-filled adventure in Key West at one of our 1 ,818 family-friendly holiday properties. Many of these stays offer amenities that are suitable for getaways with the kids, such as full kitchens, extra bedrooms and pools. Just check the "Properties good for families" filter box and choose your favourite.
What are the top attractions for families in Key West?
There are loads of amazing things to see and do with the family in Key West, including:

  • Smathers Beach
  • South Beach
  • Higgs Beach

Are there one-bedroom holiday homes in Key West?
You can choose from 451 one-bedroom homes in Key West. Whether you're searching for a townhouse or a cabin, our one-bedroom properties are just right if you don't require loads of space. One of the perks of having your own digs? You'll never need to share your holiday with strangers.
Can I find two-bedroom holiday homes in Key West?
Take your pick of 670 two-bedroom holiday homes in Key West. Settle the kids into the second room or fill it with a couple of your besties. There's a spot for whoever's fortunate enough to be coming along.
Are there holiday homes with WiFi in Key West?
You can choose from 568 holiday homes with WiFi in Key West. If you'd like to disconnect from the world while on holiday, but still need to be connected to the web, these properties are for you. Narrow your search by applying the WiFi filter on Stayz.
How can I find holiday homes with air conditioning in Key West?
Key West has 1 ,762 holiday homes where you can unwind in air-conditioned comfort. To book a stay on Stayz offering this perk, enter your travel dates and use the handy filters to select the "air conditioning" box.
How old do you have to be to rent a holiday home in Key West?
The minimum age is usually 16, 18 or 21. It can change between properties on Stayz, so check the rules of your chosen Key West holiday home before you book.
How long can I rent a holiday home in Key West for?
How long you can book a holiday home in Key West is down to the property. Just enter your preferred dates to display a list of options offering extended stays. With a range of creature comforts like kitchens and air conditioning, as well as some offering weekly or monthly discounts, you're sure to get somewhere just right to call your home away from home in Key West.