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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SPECIAL OFFER! Nov. and Dec. special rate $975 per week November 1 - December 18

Secret Garden in Key West – Property 168086

  • Key West rental - condo, 2 bedrooms, sleeps 4, 1 bathroom, downtown, near the ocean, pool
  • $975 - $1,900/week
  • Calendar Last Updated On: Nov 25, 2009
This elegant little hideaway has one foot in Truman Annex and the other in Bahama Village. This great location, together with interiors by one of Key West's favorite...

Tropical Retreat. – Property 207517

  • Key West rental - house, 4 bedrooms, sleeps 7, 3 bathrooms, downtown, pool
  • Calendar Last Updated On: Nov 25, 2009
Came and stay for month or more in our charming hideaway while you experience the magic of Key West. We make your vacation memorable experience.The beautifully...

Top-floor Smathers Beach condo with gorgeous pool, tennis and steps from beach. – Property 254856

  • Key West rental - condo, 2 bedrooms, sleeps 4, 2 bathrooms, beach, pool
  • $1,325 - $2,450/week
  • Calendar Last Updated On: Nov 25, 2009
Beach, Bath & Tennis! La Brisa is a gated oceanfront condo located across the street from Smathers Beach - one of only a few white-sand swimming beaches in Key West.

Duval Sea Turtle – Property 40019

  • Key West rental - house, 2 bedrooms, sleeps 6, 2 bathrooms, 1 half bath, adventure, air-conditioning
  • $500 - $2,610/week
  • Calendar Last Updated On: Nov 25, 2009
` ` ` FABULOUS FALL ESCAPE ` ` ` $995 FOR 7 NIGHTS ` ` ` <br /> <br /> DUVAL SEA TURTLE - The property has two bedrooms and two and one half baths and a balcony off...

Gorgeous Waterfront Condominium With Stunning Views! – Property 163420

  • Key West rental - condo, 2 bedrooms, sleeps 4, 2 bathrooms, beach, waterfront, pool
  • $2,100 - $2,600/week
  • Calendar Last Updated On: Nov 25, 2009
Luxurious! Comfortable! Unforgettable! Located on the Atlantic Ocean with magnificent views, this beautifully decorated tropical island condo offers everything you...

Beach Club #108 – Property 20892

  • Key West rental - condo, 3 bedrooms, sleeps 6, 2 bathrooms, adventure, beach
  • $2,310 - $3,640/week
  • Calendar Last Updated On: Nov 25, 2009
Unique oceanfront living sitting 65 feet from the Atlantic. Listen to the water as ocean breezes cool you. This elegant 3 bedroom/ 2 bath unit features a huge...

Duval Square - The Retreat – Property 76149

  • Key West rental - condo, 2 bedrooms, sleeps 4, 2 bathrooms, beach, clothes dryer
  • $1,330 - $2,870/week
  • Calendar Last Updated On: Nov 25, 2009
In the heart of Old Town, convenient to everything. This nicely decorated townhome/condo feels like a getaway in Duval Square's brick, tree lined courtyard that...

Lighthouse Keep – Property 40029

  • Key West rental - house, 3 bedrooms, sleeps 8, 3 bathrooms, adventure, air-conditioning
  • $500 - $2,250/week
  • Calendar Last Updated On: Nov 25, 2009
Lighthouse Keep is the tropical treat your group has been looking for! Located in Coral Hammock one of the newest gated communities in the Keys and less than a mile...

The Hemingway – Property 40039

  • Key West rental - house, 2 bedrooms, sleeps 6, 2 bathrooms, adventure, air-conditioning
  • $720 - $2,520/week
  • Calendar Last Updated On: Nov 25, 2009
The Hemingway is a beautiful two bedroom two bath townhome located in the Truman Annex which is just 2 blocks from famous Duval Street and the attractions of...

Larkin House – Property 88167

  • Key West rental - house, 2 bedrooms, sleeps 6, 2 bathrooms, 1 half bath, adventure, beach
  • $800 - $3,625/week
  • Calendar Last Updated On: Nov 25, 2009
LARKIN HOUSE is a bright and breezy 2 bedroom 2.5 bath home located in the Admirals Lane neighborhood of the Truman Annex. <br /> <br /> This delightful home has an...

Galleon Resort Efficiency in Old Town – Property 169027

  • Key West rental - studio, sleeps 2, 1 bathroom, resort, waterfront, pool
  • $960 - $1,600/week
  • Calendar Last Updated On: Nov 25, 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).

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 25, 2009
This charming one bedroom cottage is the perfect hideaway. A homey, inviting compound created so owners could enjoy shared tropical outdoor spaces.

Lakeview – Property 88174

  • Key West rental - house, 2 bedrooms, sleeps 5, 1 bathroom, 1 half bath, adventure, beach
  • Calendar Last Updated On: Nov 25, 2009
LAKEVIEW - Come to Key West, where the sun always shines!! Stay in a beautiful two bedroom one and one half bath bungalow in the gated Key West Golf Club Community...

Mar Y Sol – Property 40007

  • Key West rental - condo, 3 bedrooms, sleeps 6, 2 bathrooms, 1 half bath, adventure, air-conditioning
  • $1,000 - $4,188/week
  • Calendar Last Updated On: Nov 25, 2009
MAR Y SOL - Three bedroom two and one half bathroom oceanfront condominium at 1800 Atlantic Condominiums. Only 60 feet from the Atlantic this end property has a...

A Place in Paradise – Property 40067

  • Key West rental - house, 2 bedrooms, sleeps 6, 2 bathrooms, 1 half bath, adventure, air-conditioning
  • $500 - $3,100/week
  • Calendar Last Updated On: Nov 25, 2009
Place in Paradise - Experience the finest in Key West living when you stay in this delightful two bedroom two and one half bath conch-style townhome in beautiful...

Crowner's Jewel – Property 40065

  • Key West rental - house, 2 bedrooms, sleeps 6, 2 bathrooms, 1 half bath, adventure, air-conditioning
  • $500 - $3,100/week
  • Calendar Last Updated On: Nov 25, 2009
Crowner's Jewel at the Truman Annex Experience the finest in Key West living when you stay in this delightful two bedroom two and one half bath conch-style townhome.

Weeks in Truman Annex as low as $800!!!!!!!!! – Property 184913

  • Key West rental - condo, 2 bedrooms, sleeps 6, 1 bathroom, beach, near the ocean, pool
  • $800 - $1,500/week
  • Calendar Last Updated On: Nov 25, 2009
This wonderful 2 bedroom downstairs unit has just been beautifully and professionally redecorated. Fresh paint throughout, all tile flooring, and brand new designer...

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, pool
  • $2,300 - $3,500/week
  • Calendar Last Updated On: Nov 24, 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...

Ocean and Sunset View in Gorgeous Truman Annex – Property 244472

  • Key West rental - condo, 2 bedrooms, sleeps 4, 1 bathroom, near the ocean, town, pool
  • $1,200 - $1,800/week
  • Calendar Last Updated On: Nov 24, 2009
A unique feature of this property is bicycles! Key West is only two miles by four miles, so nothing is very far away. Fly into the Key West airport and take a cab to...

The Victoria House – Property 72851

  • Key West rental - house, 5 bedrooms, sleeps 12, 5 bathrooms, 1 half bath, adventure, air-conditioning
  • $500 - $8,200/week
  • Calendar Last Updated On: Nov 25, 2009
The Victoria House (Formerly Treetop Villa) - This gracious historical property, dating from the early 20th century, was built by prominent cigar manufacturer,...
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