Key West, FL Vacation Rentals: boat rentals & more

Discover a selection of 2,500 vacation rentals in Key West, FL that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including high chairs for kids and kitchens. Prices start at $221 per night, and boats and hotels are popular options for a stay in Key West. Either way, you'll find a rental for everyone's needs.

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Find the best place to stay — Key West

Search 2,396 vacation rentals

Stayed Sep 2023

Awesome overall

The place was cute, clean, accommodating and the local was perfect to walk. Our only complaint was the bed every time one of us moved the darn thing made noise and woke the other up. If they changed the bed this place is a perfect and affordable plac...

Stayed Aug 2023

Unbelievable Views and spacious property

Late night arrival and property management had sent email information a week prior to arrival with all pertinent information provided. A little confusion about the proper door to get into the mailbox but once we obtained the key paperwork we were goo...

Stayed Aug 2023

Short Time in Paradise

The condo exceeded all our expectations. You're close enough for all the fun activities but far enough for peace and relaxation. The views from the condo made everything so peaceful. Virtually everything you're gonna need is in the condo, it's very c...

Stayed Jul 2023

Great Stay!

We had a wonderful experience here! This was our first trip to Key West and we hope to come back. When we do, we will reach out to Bill to see if we can stay at his condo. Everything was perfect...the property was described accurately, was very clean...

Stayed Jul 2023

Perfect weekend!

This place was perfect for a long weekend in beautiful key west! The studio was exactly as described. It was cute, clean, and had everything we needed! The bikes were an added bonus! Perfect for exploring the island! Ken was an amazing host and gave ...

Stayed Jul 2023

Hemingway Days Hub

Perfect location: right on Duval Street, but more Old Town chill than pub-crawl insanity. Highlight is clearly the front second-floor balcony offering fresh air relaxation overlooking Duval St action without over-the-top drunken noise. Dual, front & ...

Stayed Jun 2023

Location

The location was perfect! The pool was nice and the view of the sunset was gorgeous! The room was smaller than the pictures show and was outdated but clean. The balcony is too small to use and the view from the room is the parking lot. We were not ...

Stayed Jun 2023

Excellent

Thank you Angela for making my stay amazing. The apartment is so clean and has everything you need. The bed is comfortable and there are plenty of spare sheets to change. I changed the bed every week and washed due to it being so hot. I stayed 4 week...

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Destination guide

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.

Things to do

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.

Activities

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.

Weather

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.

Natural features

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.

How to get there

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.

What is the best area to stay in Key West when booking a vacation rental?

Among the most popular locations to enjoy a vacation home in Key West is Key West Historic District. Base yourself here and you won't be far from some leading visitor attractions like Ernest Hemingway Home and Museum and Audubon House and Tropical Gardens.

How many vacation rentals are in Key West?

Whether you want a city apartment, lakeside lodge or something else, choosing a Vrbo vacation rental means you'll always have the entire property to yourself — no sharing with strangers. Our current selection of vacation rentals in Key West is ${propertiesCount}.

What is the most popular type of vacation rental accommodation in Key West?

Based on our data, houses are the most popular type of vacation property in Key West. But that goes without saying, everyone's idea of the perfect stay isn't the same. Vrbo has vacation homes in a variety of shapes and sizes, and we'll help you locate the perfect match.

How much does it cost to rent a vacation rental in Key West?

Different factors can influence what you'll pay for your vacation rental in Key West, like the length of stay, season and type of property. However, all our vacation homes have one thing in common — unbeatable value. Simply enter your travel dates to find your perfect fit.

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 determine the cost of your beachside vacation rental. Type in your Key West travel dates to view your available options on Vrbo. Can't live without a private pool? Use the filters to choose the features and amenities you want in your rental.

Are there pet-friendly vacation rentals in Key West?

Yes, there are. You can choose from 1,825 vacation rentals that cater to pets in Key West. Some of our pet-friendly vacation rentals even have a backyard for your fur child to have fun in, complimentary treats, special dog beds and proximity to parks. Apply the 'Pets allowed' filter to find your pawfect vacation home on Vrbo.

Can I rent a house with a pool in Key West?

Tick the 'pool' box in our handy filter tool and pick from 1,496 houses with private pools in Key West on Vrbo. Morning soak, afternoon splash or midnight swim? How you spend your leisure time is up to you when your Vrbo vacation home has a swimming pool.

What are popular rental amenities in Key West?

When it comes to rental amenities that guests are on the lookout for in Key West, a chef, a water view and tennis rank the highest. With Vrbo vacation homes, you'll enjoy options to suit your style and taste, whether you're going on a trip with family members, friends or even pets.

Are there large group vacation rentals in Key West?

Key West has 191 vacation homes that can host 10 or more guests. These stays come with enough space to share good times with your favorite people.

Are there vacation rentals in Key West that welcome kids?

With 1,818 family-friendly vacation rentals to choose from in Key West, now is a fantastic time to introduce the kids to the thrills of travel. Just click on our "Properties good for families" filter box to look for stays that feature conveniences perfect for traveling families, like kitchens, patios, hot tubs and bunk beds.