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Key West has the best of both worlds: it’s a colorful outpost where you can get away from it all and it’s a lively center of entertainment, shopping, and restaurants.  Enjoy exciting water sports and relax afterwards by enjyoing the  famous sunsets.  The best part is retreating to a beautiful Key West vacation home at the end of the day.

You can rent Key West vacation homes by the week, 3-day weekend, by the month or longer.  Some are rentable for an entire season, for you snowbirds out there.  One very popular type of Key West vacation home is the condo.  Many of the condos are right on the beach, like 1800 Atlantic.  This resort complex is a mixture of year-round residents plus vacation rentals.  There’s a swimming pool, hot tub, and tennis courts and of course it’s all oceanfront.  Facing south over the Atlantic Ocean, 1800 Atlantic is the best Key West vacation home you can rent if you want no-fuss living that’s close to Old Town. 

Other options include a Key West vacation home from a private owner, in which case you can either go through a realtor that specializes in Key West vacation homes, find one on craigslist, or the local paper.

Key West Cemetery

Sitting 128 miles out to sea between the Gulf of Mexico and the Atlantic Ocean, Key West, FL is a vacationer’s paradise.  While most this tiny tropical city for water sports and Duval Street, it’s worth exploring the lesser-known features that make this sub tropical island special.  For your Key West Florida vacation we recommend all the water sports, plus a day or two for the hidden gems of Key West.

After you’ve experienced world-clas salt water fishing, snorkeling, scuva diving or just lounging on the beach, here are a few ideas for getting to know the rest of Key West.  For starters, try a bicycle tour around the city.  Major points of view include the Key West Cemetery, Truman Annex, and other historical spots in Old Town that are best enjoyed by bicycle rather than tour trolley or car. 

Key West, FL actually has a fascinating history, much of which comes vis the healthy smuggling trade of days past.  Starting with rum in Colonial days, culminati with the  tawdry drug heyday of the 1970s and early 1980s, Key West has a colorful history of smuggling, pirating, and the break-off industry, wrecking.  Learn stories on your bicycle tour, or visit the Key West Shipwreck Historeum for starters.

Kids at Pier House's Private Beach

With history dating back to the 1800s, Key West has its share of historic architecture.  Staying in an historic inn is a great way to round out the complete Key West vacation.   What’s better after a day of water sports or trying the Duval Crawl, then to retreat to a resort that’s steeped in Key West history?  For the ultimate historic inn, try The Weather Station. 

This favorite amongst Key West resorts is located in Truman Annex, which was originally US Navy property.  Now, Truman Annex is a beautiful community of historic homes, white picket fences, and tree-lined streets.  As Key West resorts go, this is very traditional.  Location can’t be beat, but as far as a full service resort, it offers only rooms and concierge.  You won’t find attached services like a restaurant, spa, or other services.  You are steps from everything, though.

For full service Key West resorts, there are several on the waterfront in Old Town Key West.  Pier House is one of the best Key West resorts, with wedding services, spa, and other treats found within its walls.  Nearby and also on Front Street or near Mallory Square are Ocean House, The Westin, and The Hyatt.

One of the nicest Key West resorts is Casa Marina.  It’s located on the other side of the island, on the beach facing south.  Built to be the flagship hotel in Henry Flagler’s group of hotels down the Florida coast, this is the grand jewel in the railroad man’s grand tourism scheme for the Florida Keys.  Now owned by the Waldorf Astoria and fully renovated, it is once again a jewel.

Visitors to Key West will be glad to know that they can also find daily as well as long term Key West vacation rentals. If you’re just visiting the Keys for a short time, you can still enjoy the charm of a unique vacation rental. Usually vacation rentals come with maid service and special attention to your desires, like helping you find restaurants, excursions, shopping or whatever you have in mind for your vacation to Key West.

Book Key West vacation rentals any time of year for whatever duration you desire, but there are times when rates go up or down. The week after Christmas brings a flurry of activity, and rates for Key West vacation rentals go up. Fantasy Fest is another crazily busy time, but mostly in Key West and the lower Keys. Finding a room in Key West during Fantasy Fest requires skill, luck, and months of planning ahead, if not a year or more!

Welcome to Key West, miles and miles of water, sky and sun making the perfect setting for delightful Key West vacation rentals. As you drive down the old Overseas Highway, or US Route 1, you go from Key Largo in the Upper Keys, through Islamorada then Marathon in the Middle Keys, the Big Pine Key and the Lower Keys to the end of the road in Key West. The journey cannot be rushed, since at times there are only two lanes- one coming and one going. Take time to stop and explore, or at least have lunch or a dip in the ocean if you’re pushing all the way through to Key West.

Some of the finest and most deluxe Key West vacation rentals are guest houses and conch cottages, often featured in magazines. There are so many quaint places to stay in this town, you will need a guide to help you find and book the right one. In fact, if you’re staying in the Keys for a longer time, say several weeks or more, do some research online ahead of time and you will find deals and specials, off-season rates or just the right home for your vacation. Furnished houses for rent in Key West are the most common type of Key West vacation rentals here. That’s because Key West has plenty of preserved historical architecture, known as Conch Houses. This town does have its share of chain hotels and motels, but the specialty is charm and preservation of history.