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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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
  • $1,350 - $2,450/week
  • Calendar Last Updated On: Feb 9, 2010
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.

Key West Conch Cottage, 'Casa Louisa'' – Property 135603

  • Key West rental - cottage, 3 bedrooms, sleeps 6, 2 bathrooms, beach, town, pool
  • $2,100 - $3,300/week
  • Calendar Last Updated On: Feb 9, 2010
Just 1/2 block off famous Duval Street. 'Casa Louisa' -- a turn of the century cigar makers cottage - lies in the center of the historic cigar making district of...

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, pool
  • $1,950/week
  • Calendar Last Updated On: Feb 8, 2010
This cute and airy, 2 bedroom bungalow style home, has been tastefully decorated and freshly painted to make your stay comfortable and relaxing.

Ocean Front Condo at 1800 Atlantic - Next to Smathers Beach – Property 174733

  • Key West rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, beach, resort, tennis court
  • $2,450/week, per person
  • Calendar Last Updated On: Feb 8, 2010
Ocean Front Condo at 1800 Atlantic - Next to Smathers Beach 2 bedrooms, 2 full bathrooms, sleeps 6, wireless internet access

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, pool
  • $1,200 - $1,800/week
  • Calendar Last Updated On: Feb 8, 2010
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...

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, pool
  • $1,200 - $1,800/week
  • Calendar Last Updated On: Feb 8, 2010
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...

The Perfect Get-away in Paradise – Property 185263

  • Key West rental - condo, sleeps 4, 1 bathroom, near the ocean, town, balcony
  • Calendar Last Updated On: Feb 8, 2010
The Galleria Condominiums, a wonderful, quiet retreat for a fun-filled and relaxing get-away! Each efficiency condo bears the name of a renowned artist, in salute...

Spacious Ocean Front Resort - 3 Bedroom Condo – Property 232367

  • Key West rental - condo, 3 bedrooms, sleeps 8, 3 bathrooms, beach, sauna
  • $2,500 - $3,150/week
  • Calendar Last Updated On: Feb 8, 2010
This 2,000-square ft-condo is unique in that it has two large master bedroom suites with changing areas and private baths plus a third bedroom w/bath.

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

  • Key West rental - condo, 2 bedrooms, sleeps 4, 1 bathroom, downtown, near the ocean, balcony
  • $800 - $1,400/week
  • Calendar Last Updated On: Feb 8, 2010
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...

Villa Fleur, Elegant Truman Annex condo in the heart of Old Town – Property 207098

  • Key West rental - condo, 2 bedrooms, sleeps 4, 1 bathroom, downtown, near the ocean, pool
  • $1,200 - $1,800/week
  • Calendar Last Updated On: Feb 8, 2010
Villa Fleur 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 U.S.

Private Key West Weekly Vacation rental in the heart of Old Town – Property 187859

  • Key West rental - house, 2 bedrooms, sleeps 4, 2 bathrooms, near the ocean, resort, pool
  • $1,900 - $2,600/week
  • Calendar Last Updated On: Feb 8, 2010
The Pineapple Cottage is a weekly vacation rental that offers what everyone wants: A great location and total privacy! Surrounded by a tropical garden, the Pineapple...

'CONCH CASA GRANDE' @ Truman Annex: 11' Ceilings, Private Pool & 6 Master Suites – Property 177191

  • Key West rental - house, 7 bedrooms, sleeps 12, 7 bathrooms, downtown, near the ocean, balcony
  • $7,000 - $15,000/week
  • Calendar Last Updated On: Feb 7, 2010
Conch Casa Grande might well be the largest home available for vacation rental in the Truman Annex, which is appealing to anyone who wants to have some elbow room...

'HIDDEN TREASURE' @ Casa East: Luxury 3BR's, Baby Grand Piano, Huge Private Pool – Property 177317

  • Key West rental - house, 3 bedrooms, sleeps 6, 3 bathrooms, beach, near the ocean, pool
  • Calendar Last Updated On: Feb 7, 2010
On a quiet lane just 3 blocks from Smathers Beach is a very special home, hidden behind a sheltered front entrance with a five foot high louvered fence.

“FALLING WATER” @ Old Town: Breathtaking 5BR Private Compound with Private Pool – Property 180171

  • Key West rental - house, 5 bedrooms, sleeps 12, 4 bathrooms, 1 half bath, downtown, near the ocean, pool
  • Calendar Last Updated On: Feb 7, 2010
You would never guess what lies beyond the front gate: a dazzling residential compound of 3 custom-designed buildings around a pool with a continuous sheet of...

'COLORFUL CONCH' @ the Sanctuary: Decorator Home with 4BR/3BA & Private Pool – Property 189356

  • Key West rental - house, 4 bedrooms, sleeps 6, 3 bathrooms, beach, resort
  • Calendar Last Updated On: Feb 7, 2010
This beautiful private home has everything you could want in a vacation home. It has been meticulously furnished and maintained inside and out, and is located in...

'SOUTHERN STAR' @ William Street: Luxurious 3BR/3BA Historic Old Town Home – Property 193075

  • Key West rental - house, 3 bedrooms, sleeps 6, 3 bathrooms, village, waterfront, pool
  • Calendar Last Updated On: Feb 7, 2010
Half a block from the Historic Seaport on William Street is a home that was recently recognized by the Historic Florida Key Foundation for excellence in...

'AZURE MORNING' @ Kings Pointe: Luxurious 3 Bedroom Condo on the Atlantic – Property 202314

  • Key West rental - condo, 3 bedrooms, sleeps 8, near the ocean, waterfront, pool
  • $1,600 - $3,000/week
  • Calendar Last Updated On: Feb 7, 2010
Imagine waking up every morning to the sun rising over the azure blue Atlantic Ocean. That's what you will experience with this beautifully furnished three bedroom...

“SOUTHWINDS” @ Key West Beach Club: 2 BR Beachfront Condo, Panoramic Ocean Views – Property 204250

  • Key West rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, beach, waterfront, pool
  • Calendar Last Updated On: Feb 7, 2010
On the south shore of Key West is a home with the best of both worlds: it is less than a mile from Old Town Key West, yet it is right on the beach, with commanding...

'SOUTHERNMOST BELLE' @ The Annex: 7 Bedrooms, Huge Porches & Large Private Pool – Property 225064

  • Key West rental - house, 7 bedrooms, sleeps 14, 5 bathrooms, downtown, resort, pool
  • $6,900 - $15,000/week
  • Calendar Last Updated On: Feb 7, 2010
'Southernmost Belle' is unique among vacation homes in Key West. First of all, is the location: This lavish mansion is located at one of Key West's most exclusive...

'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: Feb 7, 2010
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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