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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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
  • $2,750/week, per person
  • Calendar Last Updated On: Dec 1, 2008
Ocean Front Condo at 1800 Atlantic - Next to Smathers Beach 2 bedrooms, 2 full bathrooms, sleeps 6

The Perfect Get-away in Paradise – Property 185263

  • Key West rental - condo, sleeps 4, 1 bathroom, near the ocean, town, accept credit card
  • Calendar Last Updated On: Dec 1, 2008
The Galleria Condominiums, a wonderful retreat for a fun-filled or relaxing get-away! Each unit bears the name of a renowned artist, in salute to the artistic...

Classy, Comfortable Waterfront Single Family Home - 9 Miles from Key West - – Property 322888

  • Key West rental - house, 3 bedrooms, sleeps 6, 3 bathrooms, near the ocean, waterfront, air-conditioning
  • Calendar Last Updated On: Dec 1, 2008
This is a beautiful Spanish style home on a clean swimming canal 9 miles from Key West. The home is just 4 houses from the end of the canal and the backwaters of the...

Truman Annex Shipyard with Tropical Garden – Property 102625

  • Key West rental - condo, 2 bedrooms, sleeps 4, 1 bathroom, beach, downtown, accept credit card
  • Calendar Last Updated On: Dec 1, 2008
Decorated in shades of sea foam and coral, this sparkling yet affordable two bedroom condominium is within easy walking distance of all of Key West's best...

“Manatee Manor” at Geiger Key: 3BR 2BA Private Home, 60’ Dock – Property 195245

  • Key West rental - house, 3 bedrooms, sleeps 8, 2 bathrooms, near the ocean, waterfront, accept credit card
  • $1,800 - $3,300/week
  • Calendar Last Updated On: Nov 30, 2008
Just 10 miles from Old Town you’ll find a seaside neighborhood that recalls Lower Keys life in the good old days, when you would go fishing in the morning, have...

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
  • $1,250/week
  • Calendar Last Updated On: Nov 28, 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...

Key West ocean front luxury vacation condo rental – Property 209190

  • Key West rental - condo, 3 bedrooms, sleeps 6, 3 bathrooms, downtown, waterfront, accept credit card
  • $2,700 - $4,500/week
  • Calendar Last Updated On: Nov 28, 2008
Imagine yourself watching the sunset over the ocean from the huge penthouse balcony. This beautiful luxurious Harbor Place ocean front condo is within the...

Key West Vacation Townhouse in the Truman Annex – Property 209088

  • Key West rental - townhome, 2 bedrooms, sleeps 6, 2 bathrooms, 1 half bath, downtown, near the ocean, accept credit card
  • $1,450 - $2,500/week
  • Calendar Last Updated On: Nov 28, 2008
Attractive tropical conch style 2 story Presidents Walk townhouse on Southard St within the prestigious Truman Annex in Old Town.

Luxury Condo-Walk to Beach/Duval St. $1450/wk total till 12/26 – 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 28, 2008
Decorated in casual contemporary style, our second floor condo is newly-renovated, and centrally located in the Truman Annex, within quick walking distance to all...

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: Dec 1, 2008
This cute and airy, 2 bedroom bungalow style home, has been tastefully decorated and freshly painted to make your stay comfortable and relaxing.

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: Dec 1, 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,...

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: Dec 1, 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: Dec 1, 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).

Truman Annex - Just Renovated with Private Garden Area – Property 151840

  • Key West rental - condo, 1 bedroom, sleeps 4, 1 bathroom, beach, downtown, swimming pool
  • Calendar Last Updated On: Nov 26, 2008
This one bedroom, fully furnished condo is located in the Truman Annex, a gated community of private homes and condos within two blocks of Duval Street and Ft.

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 26, 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...

Live Like a 'Resident Conch' at the Key West Golf Club – Property 314751

  • Key West rental - townhome, 2 bedrooms, sleeps 6, 2 bathrooms, 1 half bath, near the ocean, swimming pool
  • Calendar Last Updated On: Nov 25, 2008
Visit Key West and stay in the gracious, comfortable style as a 'Resident Conch' not as a tourist in an impersonal hotel. This is a gated community with 24 hr...

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 25, 2008
Envision yourself relaxing in a beautiful wood framed conch cottage with sloping tin roof in the heart of Old Town in Key West.

Hemingway's Hideaway Truman Annex Key West – Property 195479

  • Key West rental - townhome, 2 bedrooms, sleeps 6, 2 bathrooms, 1 half bath, beach, downtown, swimming pool
  • $1,700 - $2,800/week
  • Calendar Last Updated On: Nov 24, 2008
Location, Location, Location, Best in Truman Annex, private yet has front deck plus deck off main bedroom. Near all major attractions, 200ft.

Secret Garden in Key West – Property 168086

  • Key West rental - condo, 2 bedrooms, sleeps 4, 1 bathroom, downtown, near the ocean, accept credit card
  • $1,100 - $2,100/week
  • Calendar Last Updated On: Nov 29, 2008
This elegant little hideaway has one foot in Truman Annex and the other in Bahama Village. This great location, together with an interior by one of Key West's...

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 23, 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...
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