Key West vacation rentals

We found 2,360 vacation rentals — enter your dates for availability

Select from 1362 houses, 269 apartments, and other vacation rentals to find the perfect place for your stay in Key West. Whether you’re staying in a vacation home with family, friends, or just your furry companion, you'll find the best amenities for hanging out with the people that matter most, such as parking and air conditioning. Whatever you're looking for, you'll find a rental for everyone's needs, including accessible or non-smoking choices.

Vacation rentals with weekly discounts - Key West

Showing deals for:Sep 19 - Sep 26

Find out more about Key West

Find out more about Key West

Why visit Key West

  1. Beautiful Beaches: Enjoy the stunning sandy shores and crystal-clear waters perfect for sunbathing and swimming.
  2. Cultural Exploration: Discover the vibrant Old Town filled with historic homes, charming streets, and local art.
  3. Outdoor Adventures: Engage in exciting activities like snorkeling, sailing, and exploring state parks.
  4. Relaxing Atmosphere: Experience the laid-back island vibe ideal for family vacations and romantic getaways.
  5. Diverse Accommodations: Choose from a variety of vacation rentals, including cozy cottages and beachfront condos.

Popular types of accommodation in Key West

If you're planning a getaway to Key West, you'll find a variety of excellent vacation rentals to suit your needs. The most popular options include houses, condos, and charming cottages. Each type of accommodation offers unique features and amenities, ensuring you have the perfect retreat. Explore our selection of Key West rentals and discover the ideal vacation home for your unforgettable trip to this tropical paradise.

  • Houses: The top choice for visitors to Key West, offering spacious accommodations for families or groups seeking comfort and privacy.
  • Condos: A popular option that combines convenience and amenities, perfect for those wanting a modern stay close to attractions.
  • Cottages: Quaint and charming, these rentals provide a cozy atmosphere ideal for couples or solo travelers.
  • Apartments: A versatile choice for vacationers, offering home-like settings for an extended stay.
  • Villas: Luxurious and spacious, these properties are perfect for those seeking a more upscale experience in paradise.**

Top attractions in Key West

Key West is a fantastic destination for families, business travelers, and city explorers alike. Visitors can enjoy stunning beaches, explore national and state parks, and tour historic houses. The area's attractions cater to those seeking cultural experiences, outdoor adventures, and relaxation by the sea. Whether you're looking to soak up the sun or dive into local history, Key West has something for everyone to enjoy.

  1. Duval Street: Experience the vibrant heart of Key West with lively shops, restaurants, and bars. This bustling street is renowned for its nightlife and eclectic atmosphere, perfect for strolling and soaking in the local culture.
  2. Mallory Square: Famous for its stunning sunset celebrations, Mallory Square offers a lively gathering place with street performers, artisan vendors, and breathtaking views of the Gulf. It's an ideal spot to unwind and enjoy the scenic beauty.
  3. Smathers Beach: Relax on this picturesque beach with soft sandy shores and crystal-clear waters. Smathers Beach is perfect for sunbathing, swimming, and water sports, providing a quintessential beach vibe in Key West.

Things to do recommended for families

Families will have a blast at the MLK Community Pool & Community Center in Key West, where they can enjoy swimming and outdoor fun together. The vibrant atmosphere makes it a perfect spot for kids to play while parents relax and soak up the sun.

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

If you're traveling with a group, as a family, bringing along pets, or planning an extended stay, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Key West with a group: Think about how many bedrooms you require, along with features like a full kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for all these options and more on Vrbo.
  • Traveling to Key West with young kids: Traveling with young kids can be a bit tricky. It's important to prioritize their comfort and safety, along with making sure there are suitable amenities, like 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, a family vacation isn't truly fulfilling without their furry companions. If that resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Key West: If you're searching for vacation rentals that offer discounts for extended 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 consider adding features like a parking space, a well-equipped kitchen, or a private pool to enhance your search.

Where to stay in Key West

Key West is a tropical paradise perfect for family vacations and romantic getaways. Explore the vibrant Old Town, where charming streets are filled with history and culture. Enjoy exciting excursions that showcase the island's natural beauty, from snorkeling to sunset sailing. With its relaxed atmosphere and diverse activities, Key West promises an unforgettable experience for every traveler looking to soak up the sun and enjoy island life.

  • Old Town Key West: Old Town Key West is a vibrant neighborhood known for its historic charm and lively atmosphere. Nestled in the heart of Key West, this area offers a unique blend of shopping, dining, and entertainment. Visitors can stroll along charming streets lined with colorful homes and famous landmarks, including the iconic Southernmost Point Buoy. Enjoy the local beaches, perfect for families, or explore boutique shops and galleries that showcase the island's art scene. Old Town is an ideal base for those looking to immerse themselves in the island's rich culture and history while enjoying a laid-back vacation experience.
  • Key West Historic District: The Key West Historic District is a captivating neighborhood that transports visitors back in time with its preserved architecture and rich history. Located close to the waterfront, this district is home to many of Key West's most significant historical sites, including the Ernest Hemingway Home and Museum. As you wander through its picturesque streets, you'll find delightful cafes, shops, and lush gardens. The nearby beaches provide a perfect spot for relaxation, while the area's vibrant nightlife offers plenty of entertainment options. The Historic District is ideal for travelers seeking an authentic taste of Key West's past while enjoying modern comforts.
  • New Town: New Town offers a more contemporary vibe in contrast to the historic charm of Old Town. This neighborhood is perfect for families and business travelers alike, featuring a variety of shopping centers, restaurants, and recreational facilities. New Town is home to spacious parks and beautiful beaches, ideal for sunbathing and water sports. Visitors can easily access local attractions and enjoy a range of activities, from outdoor adventures to dining experiences. With its modern amenities and family-friendly atmosphere, New Town is a great place to unwind while still being close to the action of Key West.

Booking with Vrbo is a breeze

Looking to save money on your next trip? Consider being flexible with your travel dates, as this can lead to significant price differences. Also, extending your stay can often result in even greater savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental.

Unlock savings with One Key

Reserve an eligible Vrbo for your group getaway and earn OneKeyCash™ on your booking. Being the planner definitely has its perks! When you join our travel rewards program, One Key, you'll gain immediate access to member savings and have the opportunity to earn and redeem OneKeyCash™ on qualifying reservations. Sign up today and begin enjoying your savings!

Vrbo Trips: Planning as easy as it gets

Vrbo's cutting-edge Trip Board offers you a convenient way to plan your travels. You can start new trips, pick up right where you left off, or easily view and organize your itineraries. All the properties you've saved or booked are now neatly categorized under Potential, Upcoming, or Current Trips. To explore Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Explore scenic beauty from a Key West villa rental

The unique island city of Key West is one of the best vacation spots for Florida villa rentals. You can experience mile after mile of emerald waters and coral reefs as you drive the Overseas Highway along the Florida Keys archipelago to the farthest southern point that is Key West. You've never had a vacation getaway quite like Key West. This historic former pirate haven is one of the best spots for snorkeling and diving anywhere in Florida. If you love shrimp or crabs, you are in for a delicious treat thanks to the fresh seafood restaurants in Key West.

 

Admire local talent at Studios of Key West

Free-spirited Key West has long been a haven for artists and creatives. There's no better place to discover the scene than The Studios of Key West, a 3-story space showcasing works from local artists. Continue the theme at Hemingway House, a handsome Spanish Colonial estate that was once a sanctuary for the American novelist. If you want to meet one of Key West's most passionate eco-activists, head to Nancy Forrester's Secret Garden. From chirpy parrots to multicolored macaws, this backyard oasis offers a unique opportunity to get up close and personal with exotic Floridian birds.

Splash-happy in Key West

As the sun starts to set, Mallory Square gears up for a night of family-friendly fun. It's essentially one big street party, with fire breathers, tightrope walking dogs, tumbling acrobats and more. You'll also find plenty of action on Duval Street, a lively strip lined with neon-lit bars, theaters, galleries and boutiques. For a quieter scene, why not retreat to the deck of your Key West vacation rental villa for fruity Rum Runner cocktails and Floridian sunsets? For more action, you can snorkel at coral reefs, kayak in crystal-clear water, swim with dolphins, sail on catamarans and more.

Catch Key West's Fantasy Fest celebrations

Craving a dose of winter sunshine? Escape to Key West vacation rentals and you'll find yourself immersed in a tightknit community of locals. Chances are you'll soon be sharing key lime pie with your new neighbors. Locals cite spring as a Key West sweet spot. Crowds taper off and temperatures continue to hover around the 80s. Visit in the last week of October and you'll catch Key West's raucous Fantasy Fest celebrations. The 10-day street party sees the island come alive with pet parades, burlesque shows, costumed events, street food stalls and more.

Pet-friendly vacations in Key West

With a footprint measuring in at just 7 square miles, Key West feels wonderfully intimate. It's part of the Florida Keys archipelago and sits just 90 miles from Cuba. You can find out more about the low-lying archipelago at the Florida Keys Eco-Discovery Center, a family-friendly learning space filled with interactive displays and rainbow-colored sea creatures. traveling with Fido? No problem. Floridians love their furry friends, which means you'll find plenty of pet-friendly Key West vacation rentals.

Transportation to and around Key West

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

Frequently asked questions

What is the best area to stay in Key West when booking a vacation rental?
Make a booking for a vacation property in Old Town Key West and experience one of Key West’s most popular areas. South Beach and Simonton Beach are much-loved attractions here that’ll entertain you during your visit.
What is the most popular type of vacation rental accommodation in Key West?
The most in-demand types of vacation rentals in Key West are condos. Looking for something different? Vrbo has a variety of options to match the needs of our guests, so you’ll see vacation properties in all shapes and sizes. The perfect home away from home is waiting for you — grab yours today.
How much does it cost to rent a vacation rental in Key West?
A range of things can determine how much you pay for a vacation rental in Key West, like the season, length of stay and type of property. But, all of our vacation homes have one thing in common — incredible value. Simply enter your travel dates to find your ideal match.
How much does it cost to rent a beach house in Key West?
Prices for beach houses in Key West vary depending on the style and size of the property and when you’re traveling. Just enter your travel dates into Vrbo and the number of guests to view available options and prices. From there you can use our filters to tailor your search results by ratings, amenities and more.
Are there pet-friendly vacation rentals in Key West?
Pack a squeezy toy and a bone for your beloved pooch because Key West has 1,755 properties that throw out the welcome mat to pets. Let your four-legged pal get in on the family fun at one of our pet-friendly vacation rentals on Vrbo. Simply enter your destination and travel dates, then check the “Pets allowed” filter box.
Can I rent a house with a pool in Key West?
Dig out your swimsuit and inflatable swan, because there are 1,432 houses with a private pool in Key West. Kick back at one of these sought-after vacation homes and you’ll enjoy pool days every day. Simply enter your travel dates into Vrbo, then use the “pool” filter to find the perfect place for a splashing good time!
Are there vacation rentals in Key West that welcome kids?
With 1,733 family-friendly vacation properties to pick from in Key West, now is a superb time to introduce your kids to the pleasures of travel. Click on our “Properties good for families” filter to look for stays that feature conveniences perfect for families on the move, like full kitchens, backyards, hot tubs and bunk beds.
What are the top attractions for families in Key West?
Keeping the kids occupied during your vacation in Key West is simple with these family-friendly attractions:

  • Duval Street
  • Clarence S. Higgs Memorial Beach Park
  • Nancy Forrester’s Secret Garden

Are there vacation rentals with WiFi in Key West?
Key West has 718 vacation rentals with WiFi, so you can stay connected while you’re away. Simply check the “WiFi” box in our handy search filter to find the perfect property. From streaming Hollywood blockbusters to writing and sending emails, these Vrbo homes make it a breeze to get online.
How can I find vacation rentals with air conditioning in Key West?
Pick your dates and then use our filter tool to look for vacation rentals with air conditioning in Key West on Vrbo. With 1,697 air-conditioned properties to choose from here, you can look forward to a cool and comfy stay.
How old do you have to be to rent a vacation rental in Key West?
The minimum required age is usually 16, 18 or 21. It can vary across properties on Vrbo, so check the rules of your chosen Key West vacation rental before booking your stay.
How long can I rent a vacation rental in Key West for?
It’s really down to the Key West property. To see all available options offering extended stays, just enter your travel dates and number of guests into the Vrbo search page. You can enjoy having the entire place to yourself, as well as amenities such as a fully-equipped kitchen, air conditioning and an outdoor space where the kids can run and play. Be on the lookout for long-term stays that offer weekly or monthly discounts.
Does Vrbo offer discounts for vacation homes in Key West?
Whether you’ve got your eye on one of our newly listed homes, or one of our weekly or monthly discounts on vacation rentals, you’re sure to score some incredible deals and discounts on Vrbo. From mini stays to extended vacations, we’ve got the perfect space for your next Key West escape.

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