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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Luxury Condo-Walk to Beach/Duval St.-$1799/wk total in Feb – 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: Jan 8, 2009
Take advantage of our unbooked week in February -- $1799 total cost for a week. Decorated in casual contemporary style, our second floor condo is newly-renovated,...

Key West Tropical Townhouse – Property 120270

  • Key West rental - townhome, 3 bedrooms, sleeps 8, 3 bathrooms, beach, near the ocean, accept credit card
  • Calendar Last Updated On: Jan 8, 2009
Just minutes away from Old Town Key West is Kelly's Cottage; a beautifully appointed three bedroom and three bath home away from home.

Beautiful Duval St. Condo, Location, Location!!!! – Property 156723

  • Key West rental - condo, 2 bedrooms, sleeps 4, 1 bathroom, downtown, near the ocean, accept credit card
  • $1,000 - $1,500/week
  • Calendar Last Updated On: Jan 7, 2009
Location, Location, Location!!! You can't find a better location than Duval St. One of only three unique units. This Condo is above and behind Antonia's...

Hemingway Hideaway in the Heart of Key West--Tasteful, Charming – Property 127835

  • Key West rental - house, 3 bedrooms, sleeps 8, 2 bathrooms, beach, downtown, swimming pool
  • Calendar Last Updated On: Jan 7, 2009
Historic charmer, one block from Ernest Hemingway's home, great location, and off street parking for two cars. There is historic context to Ernest Hemingway with...

Luxurious 4 bedroom/3 full bath home with private pool in Old Town Truman Annex – Property 220630

  • Key West rental - townhome, 4 bedrooms, sleeps 8, 3 bathrooms, downtown, near the ocean, accept credit card
  • $2,700 - $4,500/week
  • Calendar Last Updated On: Jan 7, 2009
Enjoy all the charm Key West has to offer in this beautiful, newly renovated 4 bedroom/3 full bath house with private heated pool in the heart of Old Town.

Grand Reopening Ocean View Studio! Beach 30ft Away! See Atlantic Ocean from King – Property 311616

  • Key West rental - studio, sleeps 2, 1 bathroom, beach, downtown, air-conditioning
  • $900 - $1,800/week
  • Calendar Last Updated On: Jan 7, 2009
GOT BEACH? Reply to this listing WITH PROMO CODE 1YESFUN55 w/your phone number THE BEST stay in key west that has an oceanview..

Villa Soleil, Elegant Truman Annex condo in Old Town Key West – Property 188516

  • Key West rental - condo, 2 bedrooms, sleeps 4, 1 bathroom, downtown, near the ocean, accept credit card
  • $1,200 - $2,000/week
  • Calendar Last Updated On: Jan 6, 2009
Villa Soleil is a newly redecorated condominium in the Shipyard Condominiums at the Truman Annex. The Shipyard is in the heart of Old Town Key West on the former...

Luxury Waterfront & Beachfront Condo at Marriott Key West Beachside Resort – Property 225611

  • Key West rental - condo, 2 bedrooms, sleeps 4, 2 bathrooms, 1 half bath, resort, waterfront, accept credit card
  • $1,499 - $2,995/week
  • Calendar Last Updated On: Jan 6, 2009
The Best of Key West gets even better! Beachside Marriott Key West Resort & Conference Center is a seven acre luxury waterfront resort condominium with lush tropical...

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: Jan 5, 2009
This cute and airy, 2 bedroom bungalow style home, has been tastefully decorated and freshly painted to make your stay comfortable and relaxing.

Beautiful Retreat in Key West Area – Property 188664

  • Key West rental - house, 6 bedrooms, sleeps 10, 3 bathrooms, 1 half bath, beach, waterfront, accept credit card
  • $3,500/week
  • Calendar Last Updated On: Jan 5, 2009
Our beautiful home is located on the bayside in Big Coppitt Key. Wake up in the morning to stunning views of the bay. The house is located in over 2 1/2 acre lot...

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
  • $1,650/week
  • Calendar Last Updated On: Jan 7, 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...

Waterfront Luxury in Old Town Key West – Property 166032

  • Key West rental - condo, 1 bedroom, sleeps 5, 1 bathroom, resort, waterfront, accept credit card
  • $1,875 - $2,420/week
  • Calendar Last Updated On: Jan 7, 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,...

Truman Annex - Foundry Townhouse - One of a Kind! – Property 200634

  • Key West rental - townhome, 2 bedrooms, sleeps 4, 2 bathrooms, 1 half bath, beach, near the ocean, swimming pool
  • $1,800 - $2,250/week
  • Calendar Last Updated On: Jan 4, 2009
Once you see this roomy two storey townhouse, you won’t want to stay anywhere else! Filled with natural light, this end unit is ‘tucked away’ in an exclusive 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: Jan 7, 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...

Galleon Resort Efficiency in Old Town – Property 169027

  • Key West rental - studio, sleeps 2, 1 bathroom, resort, waterfront, accept credit card
  • $1,100 - $1,450/week
  • Calendar Last Updated On: Jan 7, 2009
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 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: Jan 4, 2009
'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...

Villa Nomade, Elegant Truman Annex condo in the heart of Old Town – Property 158403

  • Key West rental - condo, 2 bedrooms, sleeps 4, 1 bathroom, downtown, near the ocean, accept credit card
  • $1,200 - $2,000/week
  • Calendar Last Updated On: Jan 2, 2009
Villa Nomade is a newly redecorated condominium in the Shipyard Condominiums at the Truman Annex. The Shipyard is in the heart of Old Town Key West on the former...

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: Jan 2, 2009
Location, Location, Location, Best in Truman Annex, private yet has front deck plus deck off main bedroom. Near all major attractions, 200ft.

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: Jan 5, 2009
Ocean Front Condo at 1800 Atlantic - Next to Smathers Beach 2 bedrooms, 2 full bathrooms, sleeps 6, wireless internet access

'GEORGIA PEACH' 4BR Luxury Home in the Meadows @ Old Town – Property 225229

  • Key West rental - house, 4 bedrooms, sleeps 10, 4 bathrooms, 1 half bath, downtown, resort, accept credit card
  • Calendar Last Updated On: Jan 2, 2009
On Georgia Street in 'the Meadows' of Key West is a house that is truly a peach among vacation homes. As soon as you walk onto the deep front porch and see the...
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