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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Pita Vacation Home: Just Reduced Pricing! – Property 171742

  • Key West rental - house, 4 bedrooms, sleeps 8, 2 bathrooms, beach, town, pets considered
  • $2,500 - $2,800/week
  • Calendar Last Updated On: Nov 22, 2009
All year round comfort -- just a short walk from the Atlantic Ocean, the beaches at White Street Pier, the dog park, and some of the islands best restaurants.

William Skelton -- Location, Location, Location! in Old Town Key West – Property 172563

  • Key West rental - house, 4 bedrooms, sleeps 8, downtown, near the ocean, garden
  • Calendar Last Updated On: Nov 22, 2009
A hidden gem in Old Town!! This 4 bedroom 3 bath Conch House is so charming with its exposed Dade County Pine walls, private porches, and a widow’s walk on the roof...

Truman Annex - Two-Story Shipyard Cottage – Property 212151

  • Key West rental - condo, 2 bedrooms, sleeps 5, 2 bathrooms, beach, downtown, pool
  • $1,300 - $1,900/week
  • Calendar Last Updated On: Nov 22, 2009
Our recently updated condominium is decorated in a tropical theme with all the amenities of home. The master bedroom has a king-size bed and is located on the second...

Truman Annex 2bed/1bath condo, premier downtown Key West location and amenities – Property 156587

  • Key West rental - condo, 2 bedrooms, sleeps 4, 1 bathroom, downtown, near the ocean, pool
  • $1,050 - $1,800/week
  • Calendar Last Updated On: Nov 22, 2009
Our 2bed/1 bath condo in the lovely gated community of Truman Annex provides the perfect way to experience Key West- like a local.

Beautiful Retreat in Key West Area – Property 188664

  • Key West rental - house, 5 bedrooms, sleeps 12, 3 bathrooms, 1 half bath, beach, waterfront, pool
  • $4,000 - $4,500/week
  • Calendar Last Updated On: Nov 22, 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...

Luxury Waterfront at the Galleon Resort in Old Town – Property 161268

  • Key West rental - condo, 2 bedrooms, sleeps 8, 2 bathrooms, resort, waterfront, balcony
  • $2,400 - $4,150/week
  • Calendar Last Updated On: Nov 22, 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...

Beautiful Waterfront Single Family Home - 5 miles from Key West – Property 322888

  • Key West rental - house, 3 bedrooms, sleeps 6, 3 bathrooms, near the ocean, waterfront, balcony
  • $875 - $1,050/week
  • Calendar Last Updated On: Nov 21, 2009
This is a beautiful Spanish style home on a clean swimming canal 9 miles from Duval Street, Key West. Our home is just 4 houses from the end of the canal and the...

Key West ocean front luxury 3 bedroom vacation condo rental in the Truman Annex – Property 209190

  • Key West rental - condo, 3 bedrooms, sleeps 6, 3 bathrooms, downtown, waterfront, pool
  • $3,000 - $4,500/week
  • Calendar Last Updated On: Nov 21, 2009
Imagine yourself watching the sunset over the ocean from the huge penthouse balcony. This beautiful luxurious Harbor Place ocean front condo is within the...

Luxury Key West Condo -All New Plus So Much More---- 7 Bikes Included Free! – Property 223545

  • Key West rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, 1 half bath, near the ocean, pool
  • $1,100 - $1,400/week
  • Calendar Last Updated On: Nov 21, 2009
Condo located less than 1/2 mile outside of Key West in new gated community in Stock Island. 1100 sq. ft, beautifully decorated in Key West style.

Villa Soleil – Property 72842

  • Key West rental - house, 2 bedrooms, sleeps 6, 2 bathrooms, 1 half bath, adventure, balcony
  • $500 - $3,500/week
  • Calendar Last Updated On: Nov 21, 2009
VILLA SOLEIL is located in the historic Foundry section of Truman Annex, a beautiful gated community in the heart of Old Key West.

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 21, 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...

Casa Atlantica One Bedroom – Property 20895

  • Key West rental - condo, 1 bedroom, sleeps 2, 1 bathroom, adventure, beach
  • $1,120 - $1,820/week
  • Calendar Last Updated On: Nov 21, 2009
Situated on the Atlantic shore of Key West and offering breathtaking panoramas, this outstanding property was featured in Architectural Digest.

'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: Nov 20, 2009
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: Nov 20, 2009
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: Nov 20, 2009
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: Nov 20, 2009
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...

“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: Nov 20, 2009
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...

'SIMPLY IRRESISTIBLE' @ The Pool: 2BR 2.5BA Luxurious Poolside Townhome – Property 206279

  • Key West rental - townhome, 2 bedrooms, sleeps 6, 2 bathrooms, 1 half bath, near the ocean, resort, pool
  • Calendar Last Updated On: Nov 20, 2009
'Simply Irresistible' is a private two-story town home nestled in the lush tropical landscaping that surrounds the gorgeous resort-style private pool in the Key West...

'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
  • $6,500 - $14,000/week
  • Calendar Last Updated On: Nov 20, 2009
'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: Nov 20, 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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