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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Key Lime Calypso – Property 20880

  • Key West rental - house, 2 bedrooms, sleeps 4, 1 bathroom, pets, heated pool
  • $1,820 - $2,800/week
  • Calendar Last Updated On: Mar 22, 2010
The best of Key West, in the middle of Historic Old Town and a half block from Duval Street and the gates to Bahama Village, a perfect location for visitors to our...

Casa de Cuba – Property 20884

  • Key West rental - house, 3 bedrooms, sleeps 6, 2 bathrooms, pets not allowed, wireless broadband
  • $3,010 - $5,530/week
  • Calendar Last Updated On: Mar 22, 2010
Location! Style! Elegance! This beautiful home is the fabulous combination of everything a great vacation property should be.

Havana Lane – Property 20875

  • Key West rental - house, 2 bedrooms, sleeps 4, 2 bathrooms, pets, broadband access
  • $2,100 - $3,710/week
  • Calendar Last Updated On: Mar 22, 2010
Thoughtfully restored, Havana Lane, hearkens back to a time when cigar makers lived in the neighborhood, gathering on porch stoops to pass on the latest news.

Villa Paradiso – Property 20874

  • Key West rental - house, 3 bedrooms, sleeps 6, 3 bathrooms, pets, broadband access
  • $2,380 - $5,110/week
  • Calendar Last Updated On: Mar 22, 2010
This mid-town Key West home is newly renovated and beautifully decorated in jewel tones of the Mediterranean. It features three bedrooms and three baths.

Beach Club #303 – Property 20894

  • Key West rental - condo, 2 bedrooms, sleeps 4, 2 bathrooms, pets not allowed, communal pool
  • $1,750 - $3,430/week
  • Calendar Last Updated On: Mar 22, 2010
Unique oceanfront living sitting 65 feet from the Atlantic. Listen to the water as ocean breezes cool you. This 2 bedroom 2 bath unit has a wonderful tropical flare.

Vista Verde – Property 20889

  • Key West rental - condo, 2 bedrooms, sleeps 4, 2 bathrooms, pets not allowed, communal pool
  • $1,540 - $2,660/week
  • Calendar Last Updated On: Mar 22, 2010
Enjoy the resort-style amenities of 1800 Atlantic Condominiums while relaxing in a residential setting amongst neighbors. 1800 Atlantic sits on 400 feet of...

Beach Club #103 – Property 20891

  • Key West rental - condo, 2 bedrooms, sleeps 4, 2 bathrooms, pets not allowed, broadband access
  • $1,750 - $3,290/week
  • Calendar Last Updated On: Mar 22, 2010
Unique oceanfront living sitting 65 feet from the Atlantic. Enjoy an ocean view as ocean breezes cool you. This spacious 2 bedroom unit features a largee...

Beach Club #108 – Property 20892

  • Key West rental - condo, 3 bedrooms, sleeps 6, 2 bathrooms, pets not allowed, communal pool
  • $2,310 - $3,640/week
  • Calendar Last Updated On: Mar 22, 2010
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 Roost – Property 20887

  • Key West rental - house, 3 bedrooms, sleeps 6, 3 bathrooms, 1 half bath, pets not allowed, broadband access
  • $2,660 - $4,613/week
  • Calendar Last Updated On: Mar 22, 2010
This sanctuary is located one half block from Duval Street in the heart of Old Town tucked away on a private lane. Enter the property through a secure privacy fence...

Duval Square #31 – Property 20899

  • Key West rental - condo, 3 bedrooms, sleeps 4, 2 bathrooms,
  • $2,030 - $3,430/week
  • Calendar Last Updated On: Mar 22, 2010
In the heart of Old Town, convenient to everything. These newer townhomes are in Duval Square's brick, tree lined courtyard that includes shops and restaurants.

La Brisa #405E Sea Orchid – Property 20903

  • Key West rental - condo, 2 bedrooms, sleeps 4, 2 bathrooms, broadband access, communal pool
  • $1,330 - $2,590/week
  • Calendar Last Updated On: Mar 22, 2010
La Brisa beach condominiums offer a Florida charm that is relaxing, easy and captivating. Named for the ocean breezes that flow around the pretty blue and white...

La Brisa #403E Ocean Vista – Property 20902

  • Key West rental - condo, 2 bedrooms, sleeps 4, 2 bathrooms,
  • $1,330 - $2,590/week
  • Calendar Last Updated On: Mar 22, 2010
La Brisa beach condominiums offer a Florida charm that is relaxing, easy and captivating. Named for the ocean breezes that flow around the pretty blue and white...

Catherine House – Property 89119

  • Key West rental - house, 2 bedrooms, sleeps 4, 2 bathrooms, pets, wireless broadband
  • $1,820 - $2,800/week
  • Calendar Last Updated On: Mar 22, 2010
This charming Key West style cottage is just a short walk to a selection of great restaurants, art galleries, or shopping on Duval Street.

Colony Poolside – Property 76142

  • Key West rental - bungalow, 1 bedroom, sleeps 2, 1 bathroom, coffee maker, toaster
  • $1,050 - $2,240/week
  • Calendar Last Updated On: Mar 22, 2010
Located just a step away from Old Town area surrounded by coconut palms and blooming bougainvilleas this charming one bedroom bungalow is a true island hideaway .The...

Grinnell Getaway – Property 76143

  • Key West rental - house, 2 bedrooms, sleeps 4, 1 bathroom, 1 half bath, children welcome, pets not allowed
  • $1,820 - $2,800/week
  • Calendar Last Updated On: Mar 22, 2010
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.

Pete's East Cottage – Property 20883

  • Key West rental - house, 2 bedrooms, sleeps 4, 1 bathroom, pets not allowed, heated pool
  • $1,680 - $2,800/week
  • Calendar Last Updated On: Mar 22, 2010
This brand new property has it all! This award winning renovation has been completed recently and offers the styling of the original shot gun homes of Key West...

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: Mar 22, 2010
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...

Duval Square Penthouse – Property 20897

  • Key West rental - house, 4 bedrooms, sleeps 8, 4 bathrooms, 1 half bath, children welcome, pets not allowed
  • $2,730 - $5,040/week
  • Calendar Last Updated On: Mar 22, 2010
Perfect Island retreat located on famous Duval Street. Easy walking distance to shopping, restaurants, art galleries, museums, groceries, entertainment, and the...

Villa Tropicale – Property 56462

  • Key West rental - house, 4 bedrooms, sleeps 8, 4 bathrooms, children welcome, pets not allowed
  • $4,830 - $8,540/week
  • Calendar Last Updated On: Mar 22, 2010
Tropical seclusion best describes this oasis in the Casa Marina District. Enter the splendor of this large estate through a private gate; stroll down brick pathways,...

Southard Street - Queen Conch – Property 20888

  • Key West rental - house, 4 bedrooms, sleeps 8, 4 bathrooms, pets not allowed, private pool
  • $4,760 - $7,350/week
  • Calendar Last Updated On: Mar 22, 2010
On a lovely tree-lined residential street in the heart of the historic Old Town district, this quiet, historic compound offers three separate vacation suites sharing...
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