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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Paradise manor with private pool and patio – Property 208558

  • Key West rental - house, 4 bedrooms, sleeps 9, 2 bathrooms, near the ocean, garden
  • Calendar Last Updated On: Nov 8, 2009
Beautiful and spacious house with private pool in quiet neighborhood. The house has a living room with TV, DVD, VCR, CD/radio, dinning room, fully equipped kitchen...

Size Does Matter! Biggest Luxury Vacation Home on the Island – Property 265312

  • Key West rental - house, 5 bedrooms, sleeps 10, 4 bathrooms, near the ocean, pool
  • Calendar Last Updated On: Nov 8, 2009
This is a brand new build, that has never been lived in. Built by a British designer with no attention to detail left out. European style molding's throughout the...

(Quiet) House with Guest Cottage – Property 232130

  • Key West rental - house, 3 bedrooms, sleeps 8, 3 bathrooms, 1 half bath, beach, near the ocean, pool
  • Calendar Last Updated On: Nov 7, 2009
This is a newly renovated and furnished property. Let the outdoors in and the indoors out at Casa Louisa. Four sets of French doors open up off the tastefully...

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

  • Key West rental - condo, 2 bedrooms, sleeps 4, 1 bathroom, downtown, near the ocean, balcony
  • $1,000 - $1,400/week
  • Calendar Last Updated On: Nov 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...

Verandah – Property 7013694

  • Key West rental - house, 2 bedrooms, sleeps 4, 2 bathrooms, beach, DVD
  • Calendar Last Updated On: Nov 7, 2009
VERANDAH - Tucked away on Historic Frances Street lies your island escape… Verandah is a stunning two bedroom two bath home with a private pool and plenty of space...

Ann Street Cottage – Property 20878

  • Key West rental - condo, 1 bedroom, sleeps 2, 1 bathroom, non smoking only, outlet shopping
  • $1,050 - $1,960/week
  • Calendar Last Updated On: Nov 7, 2009
This charming one bedroom cottage is the perfect hideaway. A homey, inviting compound created so owners could enjoy shared tropical outdoor spaces.

Egret – Property 40076

  • Key West rental - house, 1 bedroom, sleeps 4, 1 bathroom, adventure, air-conditioning
  • $500 - $2,370/week
  • Calendar Last Updated On: Nov 7, 2009
Egret. The Colony Suites is a charming Historic Key West Style Conch Cottages nestled in the heart of Historic Old Town Key West, just three blocks from famous...

Casa Louisa – Property 72847

  • Key West rental - house, 3 bedrooms, sleeps 6, 2 bathrooms, adventure, beach
  • $1,200 - $4,625/week
  • Calendar Last Updated On: Nov 7, 2009
CASA LOUISA – Is an authentic cigar makers cottage and located a hop, skip and a jump (just 1/2 block) from famous Duval Street.

Linger Longer – Property 82030

  • Key West rental - house, 2 bedrooms, sleeps 5, 1 bathroom, 1 half bath, adventure, beach
  • $720 - $2,520/week
  • Calendar Last Updated On: Nov 7, 2009
Linger Longer Enjoy an easy vacation in this beautifully decorated, 2 bedroom 1.5 bath townhome located in the President's Walk of the Truman Annex.

Sunny Days – Property 88164

  • Key West rental - house, 2 bedrooms, sleeps 4, 1 bathroom, adventure, air-conditioning
  • Calendar Last Updated On: Nov 7, 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...

Casa Atlantica One Bedroom – Property 20895

  • Key West rental - condo, 1 bedroom, sleeps 2, 1 bathroom, adventure, beach
  • $1,120 - $1,960/week
  • Calendar Last Updated On: Nov 7, 2009
Situated on the Atlantic shore of Key West and offering breathtaking panoramas, this outstanding property was featured in Architectural Digest.

Bamboo Key – Property 40025

  • Key West rental - condo, 2 bedrooms, sleeps 4, 2 bathrooms, adventure, air-conditioning
  • $1,100 - $5,220/week
  • Calendar Last Updated On: Nov 7, 2009
Bamboo Key - Style is supreme in this two bedroom two bath condo in the Harbor Place neighborhood of the Truman Annex. This property has a beautiful view of both...

Heron – Property 40078

  • Key West rental - house, 1 bedroom, sleeps 4, 1 bathroom, adventure, air-conditioning
  • $500 - $2,370/week
  • Calendar Last Updated On: Nov 7, 2009
Heron. These cottages are some of several cottages located at the Colony cottages, formerly the Colony Guest House. These one bedroom one bath accommodations have a...

Banana Key – Property 40031

  • Key West rental - condo, 2 bedrooms, sleeps 4, 2 bathrooms, adventure, air-conditioning
  • $800 - $3,850/week
  • Calendar Last Updated On: Nov 7, 2009
Banana Key Style is supreme in this two bedroom two bath condo in the Truman Annex with a beautiful view of the gulf. Bedding: K/2T<br /> <br /> $2600 per week...

Tropical Vineyard – Property 40036

  • Key West rental - condo, 1 bedroom, sleeps 2, 1 bathroom, adventure, air-conditioning
  • $500 - $2,030/week
  • Calendar Last Updated On: Nov 7, 2009
Tropical Vineyard - Is an upstairs one bedroom one bath Shipyard condominium located in the Truman Annex. Living area extends out, through French doors, to a very...

Nantucket South – Property 40023

  • Key West rental - condo, 2 bedrooms, sleeps 4, 2 bathrooms, adventure, air-conditioning
  • $600 - $3,080/week
  • Calendar Last Updated On: Nov 7, 2009
Nantucket South - Beautiful and spacious 2 bedroom 2 bath single family home. Nantucket South is the only stand alone home in the Shipyard complex.

Island Time – Property 7028685

  • Key West rental - house, 3 bedrooms, sleeps 8, 3 bathrooms, 1 half bath, adventure, beach
  • Calendar Last Updated On: Nov 7, 2009
ISLAND TIME - Located in Old Town Key West near the famous Casa Marina, You are welcome home even before you walk in the door.

Luxurious Ocean Front Oasis in Key West – Property 257495

  • Key West rental - condo, 3 bedrooms, sleeps 6, 2 bathrooms, beach, waterfront, tennis court
  • $2,500 - $3,500/week
  • Calendar Last Updated On: Nov 6, 2009
No attention detail spared in this fabulous oasis. Perfect for a get-away with friends or family. A touch of Vegas in Key West, black marble floors, cedar lined...

“MANATEE MANOR” @ Geiger Key: 3BR 2BA Luxurious Canalside Private Home, 60’ Dock – Property 195245

  • Key West rental - house, 3 bedrooms, sleeps 8, 2 bathrooms, near the ocean, waterfront, jacuzzi
  • Calendar Last Updated On: Nov 6, 2009
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...

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

  • Key West rental - house, 4 bedrooms, sleeps 10, 4 bathrooms, 1 half bath, downtown, resort, pool
  • Calendar Last Updated On: Nov 6, 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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