They Do It Differently in Key West

It’s one of those places that hardly needs an introduction; Key West is the wildest and most rockin’ of all the Florida Keys, themselves known for breaking from tradition and serving as a Caribbean Island experience in our own backyard. It’s a whole different scene for sure, something you should definitely check out if you’re ready for a chance to leave boredom behind.


Warm but never too hot, refreshingly cool water and no record of a single freeze; as far as temperature goes, Key West is A-OK. Pile on a few more primo details, like excellent fishing conditions, a very open-minded and laid-back community, celebrations for everything - including the evening sunset gathering on Mallory Dock - and lots of art, entertainment and every possibility for outdoor adventure.


Shedding your inhibitions and settling into a slower yet quirkier way of life will be pretty darn easy no matter how tightly wound you currently are. The shady streets, the galleries filled with the paintings and sculptures of local artists, Spanish style architecture, coffee shops, dance clubs, Ernest Hemingway’s house…the list is long so be sure to reserve your vacation rental for more than just a couple of days; you’ll want to settle in for a nice long break that will truly acquaint you with this destination that, no offense to Florida’s other fabulous getaway spots, demonstrates a certain sparkle that simply can’t be replicated anywhere else.


Experience Bahama Village, the Historic Seaport District, tropical accents around every corner and the consistent feeling that you’ve just kicked off your shoes and stepped onto a warm sandy beach. Key west is different in a good way, and it deserves to be seen with your own eyes.

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Vacation Rentals in Key West

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A Touch of Bermuda at Truman Annex – Property 102572

  • Key West rental - cottage, 2 bedrooms, sleeps 6, 2 bathrooms, near the ocean, town, accept credit card
  • $2,000 - $2,100/week
  • Calendar Last Updated On: Nov 18, 2008
Envision yourself relaxing in a beautiful wood framed conch cottage with sloping tin roof in the heart of Old Town in Key West.

Tropical Retreat – Property 207517

  • Key West rental - house, 4 bedrooms, sleeps 7, 3 bathrooms, downtown, accept credit card
  • Calendar Last Updated On: Nov 17, 2008
Enjoy the uniqueness of Key West while staying at the gorgeous historic four bedrooms, three-bath home in Old Town. Originally built in 1910’s, this authentic Conch...

Shipyard Treasure -- Luxury Truman Annex Condo in Old Town Key West – Property 203228

  • Key West rental - condo, 2 bedrooms, sleeps 5, 1 bathroom, beach, downtown, swimming pool
  • $1,100 - $1,600/week
  • Calendar Last Updated On: Nov 17, 2008
Decorated in casual contemporary style, this second floor condo is newly-renovated, and centrally located within easy walking distance to all the sites and...

Key West's Sunset Marina Ocean Front Condo – Property 204628

  • Key West rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, waterfront, swimming pool
  • Calendar Last Updated On: Nov 17, 2008
Everything you will need to assure your Key West Vacation is a success is here at my Sunset Marina Ocean Front Condo. The best value-added feature with this...

Key West - Poolside Conch Paradise at Key West Golf Club – Property 164920

  • Key West rental - townhome, 2 bedrooms, sleeps 4, 1 bathroom, 1 half bath, beach, near the ocean, swimming pool
  • $1,250 - $2,450/week
  • Calendar Last Updated On: Nov 18, 2008
This cute and airy, 2 bedroom bungalow style home, has been tastefully decorated and freshly painted to make your stay comfortable and relaxing.

Ocean Front Condo at 1800 Atlantic - Next to Smathers Beach – Property 174733

  • Key West rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, beach, resort, swimming pool
  • $1,750 - $2,750/week, per person
  • Calendar Last Updated On: Nov 18, 2008
Ocean Front Condo at 1800 Atlantic - Next to Smathers Beach 2 bedrooms, 2 full bathrooms, sleeps 6

Truman Annex Shipyard Condo, Old Town Key West – Property 172414

  • Key West rental - condo, 2 bedrooms, sleeps 4, 2 bathrooms, downtown, near the ocean, swimming pool
  • $2,000/week
  • Calendar Last Updated On: Nov 16, 2008
'The Perch' is located within the highly desirable Truman Annex Shipyard Condominium Complex. This second floor unit with, 2 Queen bedrooms, and two full baths is...

GrandReopening OceanView Studio! Beach 30ft Away! Atlantic Ocean see from King – Property 311616

  • Key West rental - studio, sleeps 2, 1 bathroom, beach, downtown, air-conditioning
  • $999 - $2,000/week
  • Calendar Last Updated On: Nov 16, 2008
GOT BEACH? It's Beachy here! OH! So romantic for two in your KING SIZE Bed! Not A - Condo, Timeshare, Hotel or Garden Cottage.... Just the best Key West...

Campbell Courtyard Townhouse 'In the Sky' – Property 167721

  • Key West rental - townhome, 2 bedrooms, sleeps 6, 2 bathrooms, 1 half bath, downtown, accept credit card
  • Calendar Last Updated On: Nov 17, 2008
Few properties in Key West can offer a true combination of quality, location and privacy like this one! Perched above the 600-block of Fleming Street (between...

Sophisticated Elegance on Fleming Street – Property 166595

  • Key West rental - house, 3 bedrooms, sleeps 6, 2 bathrooms, 3 half baths, beach, downtown, accept credit card
  • Calendar Last Updated On: Nov 17, 2008
Constructed in 1859, this prestigious Key West home exemplifies elegant tropical living. Superb renovations in 2006-07 perfect the ideal haven for entertaining with...

Waterfront Luxury in Old Town Key West – Property 166032

  • Key West rental - condo, 1 bedroom, sleeps 5, 1 bathroom, resort, waterfront, accept credit card
  • $1,450 - $2,420/week
  • Calendar Last Updated On: Nov 17, 2008
This is a large (1245 SF) 1BR/1BA condo on the 6th floor of the Galleon Resort & Marina.....and is a one of a kind. It features a fantastic, fully equipped kitchen,...

Hurricane's Rebellion - a Key West Vacation Condo – Property 185408

  • Key West rental - condo, 2 bedrooms, sleeps 6, 1 bathroom, near the ocean, accept credit card
  • $1,200 - $1,800/week
  • Calendar Last Updated On: Nov 14, 2008
We invite you to experience comfortable 'Conch' living at Hurricane's Rebellion. Come to Key West and relax in the privacy and comfort of a home.

Henry's Penthouse on the Ocean in Key West (weekly / nightly rentals) – Property 112032

  • Key West rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, beach, waterfront, accept credit card
  • Calendar Last Updated On: Nov 14, 2008
Spectacular ocean views from this condo located on the top floor with 1350 sq ft of fabulous living space and a 45 ft private balcony accessible from the living and...

Luxury Waterfront at the Galleon Resort in Old Town – Property 161268

  • Key West rental - condo, 2 bedrooms, sleeps 8, 2 bathrooms, resort, waterfront, accept credit card
  • $2,750 - $3,850/week
  • Calendar Last Updated On: Nov 17, 2008
This condo is a 2BR/2BA Penthouse Loft on the 5th floor overlooking the marina. On the first floor is a full sized, fully equipped kitchen, breakfast area, dining...

Galleon Resort Efficiency in Old Town – Property 169027

  • Key West rental - studio, sleeps 2, 1 bathroom, resort, waterfront, accept credit card
  • $1,000 - $1,452/week
  • Calendar Last Updated On: Nov 17, 2008
This efficiency is located on the 5th floor of the Galleon Resort. One of only two efficiencies with both a king size bed and a balcony (resort view).

Royal Street Gardens Tropical Key West Getaway – Property 220727

  • Key West rental - townhome, 1 bedroom, sleeps 2, 1 bathroom, downtown, near the ocean, accept credit card
  • $350 - $500/week
  • Calendar Last Updated On: Nov 13, 2008
Gorgeous Old Town Key West garden getaway. Fully appointed and furnished one bedroom one bath historic Conch House with high ceilings and wooden floors located on...

Available Thanksgiving - Key West Ocean Side Luxury w/ High Speed Internet – Property 174861

  • Key West rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, beach, resort, swimming pool
  • $1,050/week
  • Calendar Last Updated On: Nov 17, 2008
Be our guest at one of the best that 1800 Atlantic Condominiums has to offer. With a wonderful tropical setting on the Atlantic Ocean & Smathers Beach, this...

Fully Equipped Condo in the Heart of Beautiful Key West – Property 162533

  • Key West rental - condo, 2 bedrooms, sleeps 4, 1 bathroom, beach, swimming pool
  • Calendar Last Updated On: Nov 13, 2008
Come and enjoy our newly furnished ground level condo. We are located in historic Truman Annex, centrally located in Old Town Key West.

Key West cottage w. great price has it all,comfort, clean,quiet & great location – Property 184497

  • Key West rental - , 1 bedroom, sleeps 3, 1 bathroom, beach, air-conditioning
  • $645 - $1,150/week
  • Calendar Last Updated On: Nov 16, 2008
You will love staying in this great location where 90% of the residents are local. They each have an interesting Key West tale to tell and are a very warm, friendly...

Gorgeous Waterfront Condominium With Stunning Views! – Property 163420

  • Key West rental - condo, 2 bedrooms, sleeps 4, 2 bathrooms, beach, waterfront, accept credit card
  • $2,100 - $2,800/week
  • Calendar Last Updated On: Nov 12, 2008
Luxurious! Comfortable! Unforgettable! Located on the Atlantic Ocean with magnificent views, this beautifully decorated tropical island condo offers everything you...
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