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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'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: Nov 20, 2009
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: 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...

'OLD TOWN OASIS' @ Truman Annex: Spacious 2 BR Oceanfront Condo – Property 181289

  • Key West rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, downtown, waterfront, balcony
  • $2,400 - $3,950/week
  • Calendar Last Updated On: Nov 20, 2009
What if you could stay right on the dock in Old Town but with the quiet and solitude of an exclusive gated community? The Green Parrot (oldest blues bar in America)...

'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...

'TURTLE CAY SPA' @ the Sanctuary: Walled Yard & 2 Master Suites – Property 226088

  • Key West rental - house, 2 bedrooms, sleeps 6, 2 bathrooms, near the ocean, resort, pool
  • Calendar Last Updated On: Nov 20, 2009
'Turtle Cay Spa' is a bright and airy private home located in The Sanctuary, a quiet gated enclave set within the already gated grounds of the Key West Golf...

“PENNY'S POMPEI” @ Key West Golf Club: Elegant 2BR/1.5BA Townhome – Property 229104

  • Key West rental - house, 2 bedrooms, sleeps 6, 1 bathroom, 1 half bath, near the ocean, resort, pool
  • Calendar Last Updated On: Nov 20, 2009
'Penny's Pompei” is an elegant two-story town home located at the Key West Golf Club, directly across the street from the community's large resort style pool.

'TOP 'O THE COPA' @ Duval: Gorgeous Old Town Penthouse, Available Nightly – Property 229160

  • Key West rental - condo, 1 bedroom, sleeps 4, 1 bathroom, 1 half bath, downtown, village, terrace
  • $1,675 - $2,400/week
  • Calendar Last Updated On: Nov 20, 2009
If you’re going to come to Key West, why not stay right in the middle of it all? “Top o' the Copa” is located on the site of the famous Copa Nightclub, and as soon...

'WATER'S EDGE' @ Gulfview Pointe: Luxurious 4BR Home on Florida Bay – Property 230758

  • Key West rental - house, 4 bedrooms, sleeps 10, 2 bathrooms, 1 half bath, near the ocean, waterfront, pool
  • Calendar Last Updated On: Nov 20, 2009
On the north shore of Key West is an exclusive gated community of 25 homes that sit on the former Monroe County Fairground. Gulfview Pointe has the best of both...

“SOUTHERNMOST ARTS & CRAFTS”, 2BR/2BA Private Home @ South Street – Property 238081

  • Key West rental - house, 2 bedrooms, sleeps 6, 2 bathrooms, downtown, near the ocean, pool
  • Calendar Last Updated On: Nov 20, 2009
On South Street\, there is a home that stands out from its neighbors, with a wide front porch and beautiful Arts & Crafts architectural details.

“CASA BLANCA 1888' @ White Street: Private Home in Old Town, 4BR & Large Pool – Property 238180

  • Key West rental - house, 4 bedrooms, sleeps 10, 3 bathrooms, downtown, resort, pool
  • Calendar Last Updated On: Nov 20, 2009
'Casa Blanca 1888' has everything you would want for your stay in Old Town Key West. Its central location in historic Old Town at White Street and Truman Avenue...

“HEAVENLY ZEN @ GRINNELL”: 4BR Private Home @ The Historic Seaport – Property 238200

  • Key West rental - house, 4 bedrooms, sleeps 8, 3 bathrooms, downtown, resort, pool
  • Calendar Last Updated On: Nov 20, 2009
In the Historic Seaport area of Old Town, there is a house that is very attractive from the street, beautifully maintained with carefully tended landscaping.

New Key West Condo 2/BR - 2.5/BA – Property 246336

  • Key West rental - condo, 2 bedrooms, sleeps 4, 2 bathrooms, 1 half bath, beach, near the ocean, pool
  • $1,500 - $2,000/week
  • Calendar Last Updated On: Nov 20, 2009
Our Beautifully landscaped property and contemporary housing will provide you with a serene tropical setting ideal for a relaxing vacation getaway.

“NOONA'S MANSION-by-the-SEA”: Oceanfront 6BR/5.5BA @ Truman Annex, Private Pool – Property 254512

  • Key West rental - house, 6 bedrooms, sleeps 14, 5 bathrooms, 1 half bath, pool, garden
  • $7,700 - $16,000/week
  • Calendar Last Updated On: Nov 20, 2009
Located in the Truman Annex, a gated community with some of the most impressive homes in Key West, this meticulously furnished estate stands out from all the rest in...

'NATALIE'S BAHAMA CONCH': Lavish 3BR/2.5BA Home w/ Private Pool @ the Sanctuary – Property 254555

  • Key West rental - house, 3 bedrooms, sleeps 7, 2 bathrooms, 1 half bath, near the ocean, resort, pool
  • Calendar Last Updated On: Nov 20, 2009
'Natalie's Bahama Conch' is located in the Sanctuary at the Key West Golf Club. Just about everything in the house has been redone, from top of the line appliances...
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