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Key West Vacation Planning
 

Planning your Key West vacation is a breeze.

At Vacation Key West, our relationships with local providers allow us to provide planning services 100% free to you. If you’re looking for a completely customized plan based on your interests, budget, and timeframe, contact our local experts. Take the worrying out of planning, and let us handle it for you – for free.

 
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Welcome to Vacation Key West, where planning your vacation is easy (and free.)

 
 
 

Here at Vacation Key West, all of your planning needs are taken care of in a breeze. Not only is it ridiculously easy to plan your vacation, but it’s also 100% free. Our relationships with local providers allow us to provide planning services at no cost to you. If you’re looking for a completely customized plan based on your interests, budget, and timeframe, contact our local experts. Take the worrying out of planning, and let us handle everything from finding the perfect hotel, planning your day activities, and discovering hidden gems – for free.

 
 

The latest from the Key West blog

Blog
What To Do in Key West for Halloween: All the Haunts and Happenings
What To Do in Key West for Halloween: All the Haunts and Happenings

Discover the best Halloween events in Key West for 2024, from kid-friendly celebrations to spooky ghost tours and haunted pub crawls. Plan your haunted island adventure today!

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Top Things to Do in Key West This Fall: Your 2024 Guide to Island Vibes and Events
Top Things to Do in Key West This Fall: Your 2024 Guide to Island Vibes and Events

Discover the best fall activities in Key West for 2024, including Fantasy Fest, sunset sails, stone crab season, and holiday events like The “Bight” Before Christmas. Plan your unforgettable Key West getaway today!

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Key West Fantasy Fest 2024: Find Your Fanta-Sea
Key West Fantasy Fest 2024: Find Your Fanta-Sea

When October rolls around, most states are ready for cozy sweaters and pumpkin lattes. In Key West, October brings with it a… different type of fun. Check out the top events slotted for Fantasy Fest 2024 here >

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Uncover Unique and Quirky Street Names of Key West
Uncover Unique and Quirky Street Names of Key West

Every July, the sun-soaked streets of Key West come alive with the spirit of Ernest Hemingway. Hemingway Days Festival, held this year from July 17-21, is more than a festival; it’s an homage to one of America’s most revered literary icons.

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Hemingway Days 2024: Key West Comes Alive with the Spirit of Ernest Hemingway
Hemingway Days 2024: Key West Comes Alive with the Spirit of Ernest Hemingway

Every July, the sun-soaked streets of Key West come alive with the spirit of Ernest Hemingway. Hemingway Days Festival, held this year from July 17-21, is more than a festival; it’s an homage to one of America’s most revered literary icons.

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Key West on Two Wheels: Biking Around the Island
Key West on Two Wheels: Biking Around the Island

Key West is a paradise perfect for exploring on two wheels! With its sunny skies, scenic views, and laid-back atmosphere, biking is one of the best ways to experience all that this charming island has to offer. Whether you're a seasoned cyclist or looking for a leisurely ride, Key West has something for everyone.

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Key West, your perfect escape

Who doesn’t like to live every travel experience to the fullest? Take a look at the variety of accommodations, top offbeat attractions & unique things to do in Key West.

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Water experiences

There are so many things to do in Key West. Take a look at the top activities these islands have to offer, discover our beaches, go kayaking or mingle with dolphins.

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Planner’s picks

Take a look at the planner’s faves! These are the spots that we recommend when people ask… “Well, where would you stay?”

 
Blog
The Capitana Key West
The Capitana Key West

Inspired by the famous shipwrecks that dot the shores off the Florida Keys, The Capitana Key West gets its name inspiration from Spain’s 1733 Armada known as “La Capitana” or “Capitana El Rubi Segundo”…

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Sunset Key, Cottages in Key West
Sunset Key, Cottages in Key West

Luxury Oceanfront Cottages located a few minutes by boat from the island of Key West.

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Opal Key Resort & Marina
Opal Key Resort & Marina

With a fabulous location on the Gulf, the Opal Key Resort And Marina has lovely rooms with private balconies, excellent dining & more.

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Beach Time

The number one activity to to here in Key West is simply soak up the sun on one of our warm, white sand beaches.

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Rest & relax

Whether you’re looking for hotels, B&B’s, inns, or timeshares, we have connections at all of the top places to stay in Key West. So, sit back, relax, take a look around, and then contact us so we can help you find exactly what you’re looking for.

 
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The Inn on Fleming

Find The Inn on Fleming nestled on a quiet residential street two blocks from the Historic Seaport. It was transformed from a private home into a beautiful, modern Bed and Breakfast in the 2000s.

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Island City House, Suites & Full Kitchens
Island City House, Suites & Full Kitchens

Located in the heart of Old Town Key West, the Island City House is the oldest operating guesthouse with suites & full kitchens and is rich in Key West history. It is comprised of three unique houses connected by pathways through lush tropical gardens with each house lending it's own unique history and style.

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Westwinds Inn

Secluded in a native tropical setting, hospitality, intimacy and relaxation are the hallmarks of Westwinds Inn. Located in the Historic Seaport District of Old Town, this Inn was built before World War II but has a Victorian compound with the comforts of a modern hotel. Westwinds is a perfect place to relax, unwind and put your worries behind you.

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The Mermaid and The Alligator Bed & Breakfast

When you've seen all you want to, simply "come home" and relax in the beautiful garden setting, in the sun or shade. Enjoy the subtle music and cool off with a dip in our pool.

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Personalize your Key West adventure

Contact one of our local planning experts to help you customize your perfect Key West vacation. We have over 20 years of experience. Plus… we live here! Let us plan your vacation (for free!) to ensure you have an unforgettable stay.

 
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Client’s picks

 

We always want to know what activities our customers enjoyed most. That’s why we’ve highlighted a few of their favorites. Some of these are must-do activities, others are their top-rated places to stay.

 
Blog
7 Incredible Family-Friendly Activities in Key West
7 Incredible Family-Friendly Activities in Key West

Discover the top family-friendly things to do in Key West, from budget-friendly hotels to outdoor adventures and gorgeous beaches.

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A Spring Guide to Key West
A Spring Guide to Key West

Looking to warm up after a long winter? Come join in on all the fun, funky, and fabulous Florida Keys spring activities taking place right here in Key West.

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Miami To Key West: An Epic Road Trip
Miami To Key West: An Epic Road Trip

This is one of the great American road trips with some of the best fishing spots, authentic food experiences, and unique festivals.

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Best Fishing Spots in the Keys: All You Need to Know
Best Fishing Spots in the Keys: All You Need to Know

If you're looking for the perfect fishing vacation spot, you're in the right place. Today we're going out for fishing-related adventures, so get ready to dive into exciting treasure hunts, eco-tours, and explore landmark buildings.

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Unique Key West Festivals You Can't Miss
Unique Key West Festivals You Can't Miss

Key West may be small - but it sure knows how to party. And festivals are some of the best ways to experience Key West’s quirkiness. Whether you'd like to attend one of the naughty events at Fantasy Fest drag-queen-galore, or are looking for a more family-friendly celebration like the "Bight" Before Christmas holiday extravaganza, Key West's festivals won't disappoint.


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