
Key West vacation rentals
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Top-rated vacation rentals in Key West
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Key West house rentals

Cancellation Deal: 07/26 thru 08/09
Eddie’s place was perfect for our family vacation! It was beautifully furnished and decorated. The house was clean and clutter free. There were plenty of linens and towels. The kitchen had everything you need and was well organized. The pool area was so relaxing. The location was incredibly convenient to grocery stores and activities as well as just a short walk to the beach which also had a park and great playground for kids. We hope to come back again soon!

Cudjoe Key Home with a View
Everything was great. We enjoyed the pool, pickleball, and the water. The house was perfect for the area. Definitely recommend!

106 Newly Renovated House with Oceanview and Pool
As always, Michael’s place was spotless, perfectly stocked and just as pictured. We come back here annually to fish at Sugarloaf Marina and are always satisfied. Michaels house is in the perfect location, with the best sunsets, an amazing dock and pool, and the house is always stocked and we're able to relax for another day of tarpon fishing.

Flakey's
Cheryl’s place is in the perfect location in the heart of Islamorada. Listening to the live music on the back deck to wind down every night was an added plus! Cheryl was super accommodating & definitely thinks about bettering her guests’ stay. Couldn’t recommend this place more!

Coral Hammock Poolside Home 3 bdrm 3 bath10 minute
Had a wonderful stay for 3 nights. The house was super clean and was located right behind the pool. The house had everything you could need for a stay in the Keys, including beach towels and chairs. Our only complaint was the upstairs AC struggled to keep up, with a noticeable difference between the upstairs and downstairs. However, there were plenty of fans for us to use making this less of an inconvenience as it would have been. Overall would recommend this property for anyone who wants to stay close to Key West but far enough to have peace and quiet.

Waterfront Home 37.5-ft dock, Cabana Club Included
Yohan and Anna, THANK YOU SO MUCH for hosting us at your home. 💖 We were very comfortable and you were luxury hosts!

Paradise found
The house was clean and a great option for traveling as a large group. It was away from the bustle of Key West, but still easy to get around, and the restaurants nearby are delicious.

OCEAN PARADISE AT VENTURE OUT + 4 BIKES/ 2 KAYAKS!
The house was exactly as pictured and in a very peaceful community. The beds were comfortable, as was the couch (two of our group opted to sleep on the couch itself instead of pulling out the sleeper sofa, and said it was pretty comfy!). Several of our group enjoyed using the bikes at night, and while we didn’t use the kayaks, it’s nice they were available. We didn’t get to do everything we hoped to do on our trip to Keys, but we plan to stay here again someday when we come back!
Key West apartment rentals

Beachside Unit 22 - Private Beach on Atlantic
Very nice condo in key colony beach, affordable, great stay for a family. Clean rooms, nice pool, nice private beach area, will bring family down again.

Newly Renovated 2/2 Bath Condo, with shared pool
We loved our stay with Teri and Scott! Nice location convenient to the airport. Beautifully renovated. Was just what I needed for a group of 4-6. Thanks again yall!

Mango Hideaway @ the Eyebrow House off Duval
Great place with awesome location. Unfortunately I broke my ankle 2 days before our trip so my husband had to carry me on his back up the stairs to get in. I would definitely stay again but without the broken ankle next time!🤣

Key West Condo with Pool & Boat Slip Access
Fantastic waterfront condo! Everything about it was exactly as described on the listing! Very comfortable condo! We will be back!

Studio Near Downtown - The Bartlum
Our first time using Air B&B. My wife loved the experience and location. I liked not having to drive. Parked the car and walked everywhere. Would definitely book again. Thanks for being great hosts!

Key's Cottage Escape
This airbnb was perfectly located and equipped with everything we needed. We loved it and would definitely stay again.

Duval Street Suites full kitchen, free parking, &
We had an outstanding stay at Duval Suites and would definitely look to stay here again. Completely satisfied!! Now we need to come back to do the rest of the things we didn’t have time to squeeze in. Thanks Magen and team, Joe, Terry & Lynn

Beachfront Condo w/ Ocean Views in Marathon
This was our first family trip to the Keys and this location in Marathon was ideal! The condo was welcoming, beautiful and spacious for our family of 3. The balcony was our favorite place, which overlooked the pool and the seashore. The beach was lovely for shorter walks and just "being" with the ocean. Fun seashells & hermit crabs at low tide! Lots to do in the area -- definitely hoping to return next year. Mike was fantastic host & super helpful with questions.
Key West houseboat rentals

Shanty Pineapple Key West
Amazing! Loved this unique experience, you get a chance to disconnect from the outside world and relax with the ocean breeze. 10/10 experience would 100% do again!

A slice of paradise in the Florida Keys
Wonderful night! Only a few bugs around dusk that left by nightfall. Lots of planes took off from 5-7 PM, but again they stopped by nighttime and not sure that it happens every day. The boat itself was perfect, exactly as described!

Houseboat Getaway In Marathon
My husband and I had such a relaxing time staying here! We felt like we were having a mini adventure, but still had all the essentials we needed. We saw manatees, dolphins, and tarpon. And we fished off the back dock at night. It was so beautiful how clear the skies were from the view of this house boat, we saw so many stars. We’ll be back again and I’m already sending the link to friends who were asking about our stay!

Great Ocean Views! No regrets
First time staying on a houseboat and it surely was a great experience! Beautiful views and comfy cozy space! Hosts were very friendly and welcoming and available with any questions we had. Thanks for a lovely experience!

Avoid the traffic, Luxury Houseboat on the water
Great host! Unique air bnb experience. We enjoyed evenings on the upper deck and our boys loved being able to fish!

Key West Outpost: eco-vacation
We wanted to be able to disconnect, enjoy nature and just unwind. This was the perfect place. We kayaked, paddle boarded, floated on a giant raft and just relaxed. The perfect place to rest and recharge. The sunset views are gorgeous. Worth every penny. Rob was super friendly. And had a ton of tips for the rest of our stay in the Key West area. I highly recommend to anyone who wants a marine glamping get away.

Stella on Stock Island
Location is great, as we enjoy the Stock Island marina area. Houseboat is as described and it was nice to have my coffee up top in the mornings. The only thing I would say is to keep in mind that the plumbing is marine/RV style and there’s an odor that comes with that—just bring some air freshener and you’ll forget about it.

Beautiful Houseboat in Key West
This will go down as one of the greatest vacations we’ve ever had—full of unforgettable memories! The houseboat was beautiful, and the location was absolutely incredible. The crystal-clear water was full of life, making it perfect for kayaking, swimming, and fishing. Captain Sergey was amazing—he made us feel more like longtime friends than just guests. He went over every detail about the houseboat and gave us great tips on the best spots for kayaking and fishing in the area. We also took his fishing charter tour, which was fantastic. My son, who loves fishing, had an especially great time. We’ll definitely be coming back in the future. If you’re planning a trip to the Florida Keys, I highly recommend checking out this houseboat experience!
Quick stats about vacation rentals in Key West
Total rentals
2.2K properties
Nightly prices starting at
$10 before taxes and fees
Total number of reviews
65K reviews
Family-friendly rentals
1.4K properties are a good fit for families
Pet-friendly rentals
680 properties allow pets
Rentals with a pool
1.7K properties have a pool
Your guide to Key West
All About Key West
Key West is a town that overflows with zest: turquoise waters and sandy beaches, dive bars that never seem to close, stunning sunsets, pastel-hued homes, great American literary legacies, and a sordid haunted past. Chow down on key lime pie and conch fritters, snap a pic at the southernmost point of the continental United States, and take in as much sea and sun as your eyes can handle.
Key West sits right across the Florida Strait from Cuba, and the influence can be felt in many of the island’s favorite haunts, where you can learn to dance the salsa, sample locally distilled rum, and pile your breakfast plate high with sweet fried plantains and savory beans. However you spend your days, make sure that you’re back in Mallory Square before sunset, when live music from restaurant patios and vendors’ stalls fills the pedestrian-only square and people celebrate the show-stopping sunset with all the fanfare it deserves.
The best time to stay in a vacation rental in Key West
Winter is the most popular season in Key West, as the hot weather draws sun-seekers to the beaches, especially around the December holidays. You can also come in spring for sun and fewer crowds — despite Key West’s bustling nightlife scene, it isn’t typically hit by Spring Break crowds like other places in Florida. It’ll be warm enough to get in the water and enjoy beach time, with fewer people than in winter. Despite a September to November hurricane season, autumn is also a good time to check out Key West’s museums or to revel in the hedonistic Fantasy Fest while enjoying cooler air.
Top things to do in Key West
Snorkeling
Home to the only living Barrier Reef in the continental United States, Key West has some of the most incredible snorkeling in the world. Head out to the cluster of tiny islands known as the Dry Tortugas National Park for the best of the best: this area is home to unspoilt coral reefs, hundreds of species of tropical fish, starfish, and conch.
Ghost tours
Key West is rumored to be one of the most haunted cities in America, in juxtaposition with its sunny, good-time appearance. For fans of classic horror, be sure to ask about a famous local doll and the film franchise he inspired. Listen to ghost stories on board a spooky train tour, go on a guided walk around town, or check out the quirky inscriptions on the local graves at the cemetery.
Key lime pie
Key lime pie can be found on just about any menu here, from dive bars to high-end bistros, and with good reason — the island’s eponymous pie is zesty, creamy, and delicious. Traditionally made from tangy key lime juice and a rich, sweet custard of egg yolk and condensed milk atop a crust, everybody from home cooks to renowned chefs has their own take on how it should be made. Try as many versions as you can while you’re here, and join in on the debate of cooked versus uncooked filling, graham cracker versus pie crust, and whipped cream versus meringue topping.
Frequently Asked Questions
How is the weather in Key West?
Key West has a tropical climate with warm temperatures year-round. Summers, from June to August, can be hot and humid, often reaching 90°F (32°C). Winters, from December to February, are milder, with temperatures typically around 70°F (21°C), and less rainfall.
What are some of the best things to do in Key West?
Popular activities in Key West include exploring the vibrant coral reefs on a snorkeling trip, discovering local marine life at the Key West Aquarium, or visiting the historic Fort Zachary Taylor State Park. A stroll along Duval Street for shopping and local cuisine is also recommended.
What is the best time of year to visit Key West?
Key West is particularly lively between March and May, with milder temperatures and fewer crowds. During these months, you can enjoy events like the Conch Republic Independence Festival and the Key West Songwriters Festival.
What are the best places to stay in Key West?
Some highly-rated areas to stay in Key West include Old Town, a historic district with classic architecture, Truman Annex for its peaceful atmosphere, and New Town for its modern conveniences. Duval Street is also favored for its proximity to dining and shopping options.
What are the best places to visit in Key West?
Key West is known for diverse attractions such as the Ernest Hemingway Home and Museum, where the renowned author once lived, and the Key West Butterfly and Nature Conservatory. Don't miss the stunning sunsets at Mallory Square, and the view from the historic Key West Lighthouse. The Southernmost Point Buoy is also frequently visited.
What are some hiking trails in Key West?
While Key West is not known for its hiking, you can enjoy a leisurely walk at the Key West Tropical Forest and Botanical Garden. The Island City National Historic District also has interesting paths through the town's picturesque streets.
What are some family activities to do in Key West?
Families can enjoy a visit to the Key West Shipwreck Museum, engage with interactive exhibits at the Florida Keys Eco-Discovery Center, or have fun exploring the Key West Aquarium. A ride on the charming Conch Tour Train is also a delightful way to see the city.
What are some of the best day trip ideas in Key West?
For a memorable day trip, explore the natural beauty of Dry Tortugas National Park, which is accessible by ferry or seaplane. Also, consider a wildlife expedition at the Key West Wildlife Center, or learn more about the region's history with a visit to Fort East Martello Museum.
What types of vacation rentals are available in Key West?
Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Key West. From over 20 houseboat rentals, over 430 condo rentals, over 40 cottage rentals, over 330 apartment rentals to over 640 house rentals, we've got you covered. For even more variety, explore our Airbnb Categories to find the ideal space for your getaway.
Are there vacation rentals with a dedicated workspace in Key West?
Yes! Work meets play with ease at over 1,140 vacation rentals in Key West featuring dedicated workspaces. Stay connected and productive in your home away from home.
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