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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Casa Amor - 3BR Residence 2 Blocks from Duval Street – Property 233509

  • Key West rental - house, 3 bedrooms, sleeps 6, 2 bathrooms, 1 half bath, near the ocean, town, swimming pool
  • $2,100 - $6,000/week
  • Calendar Last Updated On: Jul 5, 2009
Welcome to Casa Amor, our love nest for ten years has been converted into a vacation rental for you. We are located just two blocks from upper Duval Street…home to a...

Ann Street Studio – Property 20876

  • Key West rental - house, 1 bedroom, sleeps 2, 1 bathroom, pets not allowed, communal pool
  • $1,190 - $1,967/week
  • Calendar Last Updated On: Jul 5, 2009
Perfect for two, this cute studio cottage has it all and is walking distance to everything. Located just one half block off Duval Street and right behind The Curry...

Casa Margarita – Property 56463

  • Key West rental - house, 3 bedrooms, sleeps 6, 3 bathrooms, children welcome, pets not allowed
  • $3,010 - $5,530/week
  • Calendar Last Updated On: Jul 4, 2009
Fantastic location combined with casual elegance makes this Key West cottage a great retreat to experience! And the historic seaport is just steps away with many...

Sunny Days – Property 88164

  • Key West rental - house, 2 bedrooms, sleeps 4, 1 bathroom, children welcome, pets not allowed
  • Calendar Last Updated On: Jul 4, 2009
SUNNY DAYS - This cottage is beautifully maintained while retaining its original style and structure. Dade County pine is throughout the property adding a feel of...

Key West By Beach & Duval Street Old Town – Property 241481

  • Key West rental - house, 5 bedrooms, sleeps 12, 4 bathrooms, downtown, near the ocean, accept credit card
  • $5,700 - $6,700/week
  • Calendar Last Updated On: Jul 3, 2009
Prime Old Town Walking Location. Across the Street from Southernmost on the Beach, and down the Street from the Southernmost Point.

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
  • $1,670 - $2,488/week
  • Calendar Last Updated On: Jul 3, 2009
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...

Key West ocean front luxury 3 bedroom vacation condo rental in the Truman Annex – Property 209190

  • Key West rental - condo, 3 bedrooms, sleeps 6, 3 bathrooms, downtown, waterfront, accept credit card
  • $3,000 - $4,500/week
  • Calendar Last Updated On: Jul 3, 2009
Imagine yourself watching the sunset over the ocean from the huge penthouse balcony. This beautiful luxurious Harbor Place ocean front condo is within the...

Island Spice – Property 7013690

  • Key West rental - house, 2 bedrooms, sleeps 6, 2 bathrooms, 1 half bath, children welcome, pets not allowed
  • $990 - $3,190/week
  • Calendar Last Updated On: Jul 3, 2009
Island Spice is a lovely 2 bed, 2.5 bath townhome, located in the historic Foundry District of the prestigious Truman Annex community.<br /> The brick exterior, 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
  • $2,350 - $3,850/week
  • Calendar Last Updated On: Jul 3, 2009
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...

Duval Roost – Property 20887

  • Key West rental - house, 3 bedrooms, sleeps 6, 3 bathrooms, 1 half bath, pets not allowed, broadband access
  • $2,660 - $4,900/week
  • Calendar Last Updated On: Jul 3, 2009
You would never know that you are one half block from Duval Street in the heart of old town tucked away on a private lane.<br /> <br /> You enter the property down a...

Grinnell Getaway – Property 76143

  • Key West rental - house, 2 bedrooms, sleeps 4, 1 bathroom, 1 half bath, children welcome, pets not allowed
  • $1,820 - $2,940/week
  • Calendar Last Updated On: Jul 3, 2009
Peaceful retreat in the historic district awaits you. This charming Old Town home is located opposite our historic cemetery, just 5 blocks from Duval Street.

Louisa House – Property 20885

  • Key West rental - house, 4 bedrooms, sleeps 8, 4 bathrooms, pets, pets not allowed
  • $3,150 - $5,600/week
  • Calendar Last Updated On: Jul 3, 2009
Great location, just half a block off Duval Street, walking distance to restaurants, the Atlantic beaches and the Southernmost Point.

Whitehead House – Property 20879

  • Key West rental - house, 3 bedrooms, sleeps 6, 2 bathrooms, pets, heated pool
  • $2,240 - $3,990/week
  • Calendar Last Updated On: Jul 3, 2009
Unique two story, three bedroom, two bathroom home nested beside the Audubon House in Old Town Key West. Hidden behind the most photographed "Prohibition fence" in...

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

  • Key West rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, beach, near the ocean, swimming pool
  • Calendar Last Updated On: Jul 2, 2009
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...

Best Deal in Truman Annex - Cead Mile Failte – Property 241645

  • Key West rental - condo, 2 bedrooms, sleeps 4, 1 bathroom, beach, downtown, accept credit card
  • $1,100 - $1,750/week
  • Calendar Last Updated On: Jul 2, 2009
Here's Céad Míle Fáilte to friend and to rover That's a greeting that's Irish as Irish can be It means you are welcome a thousand times over Wherever you come from,...

Contemporary Condo @ Truman Annex-Walk to Beach/Duval St. - $1222/wk total Aug – Property 203228

  • Key West rental - condo, 2 bedrooms, sleeps 5, 1 bathroom, beach, downtown, accept credit card
  • $1,100 - $1,600/week
  • Calendar Last Updated On: Jul 2, 2009
REDUCED RATE AUGUST & SEPTEMBER 2009 -- $900/WEEK RENT. Decorated in casual contemporary style, our second floor condo is newly-renovated, and centrally located in...

Truman Annex 2bed/1bath condo, premier downtown Key West location and amenities – Property 156587

  • Key West rental - condo, 2 bedrooms, sleeps 4, 1 bathroom, downtown, near the ocean, swimming pool
  • $1,200 - $1,800/week
  • Calendar Last Updated On: Jul 2, 2009
Our 2bed/1 bath condo in the lovely gated community of Truman Annex provides the perfect way to experience Key West- like a local.

Key West Boat & Breakfast, Reef Sailing Trips, Island Hopping – Property 229193

  • Key West rental - yacht, 2 bedrooms, sleeps 4, 2 bathrooms, downtown, waterfront, accept credit card
  • Calendar Last Updated On: Jul 2, 2009
Located in Key West's Historic Seaport, choice of two sailboats for your dockside lodging. Your stay/sail charter includes either a 2 hour sunset sail with a 2 night...

Waterfront Luxury in Old Town Key West – Property 166032

  • Key West rental - condo, 1 bedroom, sleeps 5, 1 bathroom, resort, waterfront, accept credit card
  • $1,595 - $2,420/week
  • Calendar Last Updated On: Jul 2, 2009
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,...

Duval Courtyard – Property 40020

  • Key West rental - house, 3 bedrooms, sleeps 6, 2 bathrooms, children welcome, pets not allowed
  • $1,228 - $3,958/week
  • Calendar Last Updated On: Jul 2, 2009
Duval Courtyard Located just steps from famous Duval Street, this two bedroom two bath one-story condo is located on the second floor in Duval Square.
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