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. 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 always excellent Key West 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. Consider a personal fishing snorkeling and diving trip by Venus Charters. Well known for their women only tours, they also have private charter open to all. Another great excursion idea is a tour by air. Let the “locals” at Key West Sea Planes show you how it’s done.


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. While you are in Key West don’t forget to pick up a slice Key Lime Pie. Heck, try a whole pie! Kermit’s Key West Shoppe is a popular sweet stop for residents and visitors alike.


Key West is different in a good way, and it deserves to be seen with your own eyes. Do yourself a favor and slip into a Key West vacation rentals and start exploring your wild side or consider a Key West vacation condo to excite your senses.

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Vacation Rentals in Key West

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Contemporary Condo at Truman Annex-Walk to Beach/Duval St. – Property 203228

  • Key West rental - condo, 2 bedrooms, sleeps 5, 1 bathroom, accept credit card, beach, downtown
  • $1,300 - $1,925/week
  • Calendar Last Updated On: May 22, 2012
Decorated in casual contemporary style, our second floor condo is newly-renovated, and centrally located in the Truman Annex, within quick walking distance to all...

Key West Boat & Breakfast, Reef Sailing Trips, Island Trips – Property 229193

  • Key West rental - yacht, 2 bedrooms, sleeps 4, 2 bathrooms, accept credit card, downtown, waterfront
  • $1,800 - $2,000/week
  • Calendar Last Updated On: May 22, 2012
Located in Key West's Historic Seaport, choice of 3 sailboats for your dockside lodging. Your stay/sail charter includes 2 hour sunset sail/2 night package or half...

Casa Amor - 3BR Residence 2 Blocks from Duval Street – Property 233509

  • Key West rental - house, 3 bedrooms, sleeps 8, 2 bathrooms, 1 half bath, accept credit card, near the ocean, town
  • Calendar Last Updated On: May 22, 2012
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...

You've Arrived at your Perfect Island Get Away With Private Pool – Property 334157

  • Key West rental - house, 2 bedrooms, sleeps 8, 2 bathrooms, downtown, near the ocean, pool
  • Calendar Last Updated On: May 22, 2012
Enter The Gate To Your Private Pool And Garden. Covered Porch Looks Poolside. Ideal Cottage Setting With Waterfall To Ease Away The Stress Of The Real World.

Oceanfront Bungalow, Dock 80'Heated Pool Deep Channel Tennis 15 min Key West – Property 315267

  • Key West rental - bungalow, 2 bedrooms, sleeps 6, 2 bathrooms, accept credit card, resort, waterfront
  • $950 - $1,550/week
  • Calendar Last Updated On: May 22, 2012
Wonderful, oceanfront, two bedroom, two bath, bungalow home is just ten feet from the open water ...incredible views. Located on the open water, with a 58'...

'Mango Gardens' Charming, Walking Distance to Duval, and Historic Seaport Area – Property 369876

  • Key West rental - house, 4 bedrooms, sleeps 8, accept credit card, downtown, near the ocean
  • Calendar Last Updated On: May 22, 2012
Mango Gardens is a charming historic remodeled home located in Old Town, Key West. Private and spacious home has hardwood floors thru out.

Large private home just 2 blocks to Duval St – Property 272959

  • Key West rental - house, 4 bedrooms, sleeps 8, 4 bathrooms, accept credit card, downtown, town
  • $2,900 - $5,250/week
  • Calendar Last Updated On: May 22, 2012
Step into the luxury Key West lifestyle by staying in this magnificent home. Conch Heaven is conveniently located just 2 blocks from Duval Street, and 4 blocks to...

Paradise Manor with private pool available May and June 2012 – Property 208558

  • Key West rental - house, 4 bedrooms, sleeps 9, 2 bathrooms, accept credit card, beach, near the ocean
  • $1,490 - $2,490/week
  • Calendar Last Updated On: May 22, 2012
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...

Villa Paradiso a Peaceful Private Retreat – Property 489605

  • Key West rental - villa, 3 bedrooms, sleeps 6, 3 bathrooms, accept credit card, beach, near the ocean
  • $2,450 - $5,110/week
  • Calendar Last Updated On: May 22, 2012
Located in a quiet, tranquil and charming residential area, 4 blocks (5-10 min walk) from the beaches on the south of the island, and a 5-minute drive (10 minute...

Townhomes on Windsor #4 – Property 7113903

  • Key West rental - house, 3 bedrooms, sleeps 6, 3 bathrooms, 1 half bath, beach, near the ocean
  • Calendar Last Updated On: May 22, 2012
Elegance and modern sophistication are apparent as you enter any one of these six newly complete townhomes conveniently located in a quiet Old Town neighborhood just...

Coral Suite – Property 7142028

  • Key West rental - condo, 2 bedrooms, sleeps 6, 3 bathrooms,
  • $900 - $1,906/week
  • Calendar Last Updated On: May 22, 2012
CORAL SUITE: If you're looking for a home away from home that will leave you with money in your pocket, Coral Suite is the place for you.

Tropical Serenity – Property 7113892

  • Key West rental - house, 1 bedroom, sleeps 2, 1 bathroom, 1 half bath, beach, near the ocean
  • Calendar Last Updated On: May 22, 2012
30 DAY MINIMUM RENTAL An amazing renovation of mid town historic home with the Washington Street address many desire. This charming one bedroom bungalow has been...

Townhomes on Windsor #3 – Property 7113902

  • Key West rental - house, 3 bedrooms, sleeps 6, 3 bathrooms, 1 half bath, beach, near the ocean
  • Calendar Last Updated On: May 22, 2012
Elegance and modern sophistication are apparent as you enter any one of these six newly complete townhomes conveniently located in a quiet Old Town neighborhood just...

Hemingway Hideaway in the Heart of Key West--Tasteful, Charming – Property 127835

  • Key West rental - house, 3 bedrooms, sleeps 4, 2 bathrooms, beach, downtown, pool
  • Calendar Last Updated On: May 22, 2012
Historic charmer, one block from Ernest Hemingway's home, great location, and off street parking for two cars. There is historic context to Ernest Hemingway with...

Henry's Penthouse on the Ocean in Key West (weekly / nightly rentals) – Property 112032

  • Key West rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, accept credit card, beach, near the ocean, waterfront
  • Calendar Last Updated On: May 22, 2012
Spectacular ocean views from this condo located on the top floor with 1350 sq ft of fabulous living space and a 45 ft private balcony accessible from the living and...

Affordable, Charming, Quiet, Walking Distance to Town, Shopping, Dining, Beach – Property 299544

  • Key West rental - condo, 1 bedroom, sleeps 3, 1 bathroom, beach, downtown, pool
  • Calendar Last Updated On: May 22, 2012
Tree Tops is a stylish and practical one bedroom condo located in the gated community of Truman Annex. Truman Annex is a popular and beautifully landscaped community...

Walking to everything, Close to Beach, Old town – Property 299550

  • Key West rental - house, 3 bedrooms, sleeps 6, 3 bathrooms, 1 half bath, downtown, near the ocean, pool
  • Calendar Last Updated On: May 22, 2012
DUPONT RETREAT is a bright and spacious 3 bedroom, 3 bath home has the best of everything with a private pool surrounded by lush foliage and an extensive deck area...

Truman Annex, Old Town, Key West, Private Setting with Luxury Features – Property 123714

  • Key West rental - house, 2 bedrooms, sleeps 5, 2 bathrooms, 1 half bath, accept credit card, beach, downtown
  • Calendar Last Updated On: May 22, 2012
Fully maintained and cared for, luxury features, just two blocks from Duval and Mallory Square in Old Town Key West, a two story townhome located in the Truman Annex...

***Steps from Duval $79-$129 Night - Free Bikes Included!!!*** – Property 233787

  • Key West rental - studio, sleeps 2, 1 bathroom, downtown, near the ocean, balcony
  • Calendar Last Updated On: May 22, 2012
Looking for the perfect affordable hide-away in Key West? Located in a remodeled Victorian Home - this guest room is just perfect for two!

Stock Island Waterfront Condo with a Boat Slip – Property 352086

  • Key West rental - condo, 3 bedrooms, sleeps 8, 2 bathrooms, accept credit card, waterfront
  • $1,550/week
  • Calendar Last Updated On: May 22, 2012
Like Old Key West Your waterfront vacation place is in the most unique mixed use marina community in the Keys. Watch the fishing boats unload their catch.
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