Key West Vacation Rentals: house rentals & more

Discover a selection of 2,000 vacation rentals in Key West 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 swimming pools and private pools. Prices start at $90 per night, and houses and cottages 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 1,904 vacation rentals

Stayed Apr 2021

Wonderful Stay

Very small but nice place with a great location to see Key West. Great small pool on site as well. We really enjoyed the bikes that were available to use at no cost. Not for everyone but if you just need a place to stay so you can explore the island ...

Stayed Apr 2021

Absolute Gem

This property is a must come back to property! I loved everything about it, from being spic and span clean, the pool, the location, the bikes, and even the WiFi was great! I love the decor and how updated this place is. Nothing negative to say and I ...

Stayed Apr 2021

A Little Cottage on a Peaceful Street

A nice little spot to relax in after a day walking in Key West. Quiet street. Neighbors upstairs can be a little noisy at night- mainly walking/knocking around, not partying or loud music. But the AC drowned out most of it. If you're not a really lig...

Stayed Apr 2021

Cute & Quaint

We very much enjoyed our stay here. The facility was very clean. The bed was comfortable. I have to agree with our hers that the seating was not too comfy. We had everything we needed including a cooler, beach towels, and bicycles. There is a nice be...

Stayed Apr 2021

Can’t wait to come back!

We can’t wait to return! The place was clean, great views, and everyone we met on property were very nice and helpful. Tom was great to communicate with. The place had everything we could of needed. We loved being on the outskirts of the island so it...

Stayed Apr 2021

Heaven on The Beach

We cannot say enough about the owner Pam and her stunning beach condo. My husband and I were celebrating our anniversary and couldn’t have imagined a more beautiful, clean place to stay. I am extremely picky when it comes to cleanliness, etc. and was...

Stayed Apr 2021

Awesome Place To Stay

Getting access to the condo was a bit of an inconvenience, but we were eventually able to overcome that. One gentleman (believe a permanent resident) helped us get in direct contact with the maintenance person and we were able to get inside. Once ...

Stayed Apr 2021

Perfectly Key West

Enjoyed the space very much. It is small and intimate, but has everything so cleverly designed into it. The front porch is great for people watching and the neighborhood is very quiet. Close to all the fun things. Mostly used our bicycles which was i...

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Destination guide

Book luxury vacation homes in Key West

Key West is one of the most popular places for luxury rentals in the Florida Keys. One of its highlights is The Ernest Hemingway Home and Museum, which is the former residence of the famous author. You could also visit the landmark for the southernmost point in the continental U.S. or check out Duval Street, a thrilling area filled with unique shops, waterfront dining, and lively bars. For more shopping, Mallory Square is a plaza with boutiques and shops offering a variety of goods and souvenirs. Key West also features an abundance of outdoor activities, such as surfing, diving, snorkeling, hiking, biking, and nature walks to see native wildlife.

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

Activities near Key West vacation homes

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

How to get to and around Key West

Fly into Key West, FL (EYW-Key West Intl.), the closest airport, located 9.1 mi (14.6 km) from the city center.

How many vacation rentals are available around Key West?

Our 2021 property listings offer a large selection of 1,904 vacation rentals around Key West. From 990 house rentals to 114 cottage rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.