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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Waterfront Luxury in Old Town Key West – Property 166032

  • Key West rental - condo, 1 bedroom, sleeps 5, 1 bathroom, resort, waterfront, accept credit card
  • $1,700 - $2,420/week
  • Calendar Last Updated On: May 13, 2008
This is a large (1245 SF) 1BR/1BA condo on the 6th floor of the Galleon Resort & Marina.....and is a one of a kind. It features a fantastic, fully equipped kitchen,...

High End Luxury House on Old Town Lane, Pool--Free Wireless Monthly Rentals Only – Property 159918

  • Key West rental - house, 2 bedrooms, sleeps 4, 2 bathrooms, downtown, near the ocean, accept credit card
  • Calendar Last Updated On: May 12, 2008
(Monthly Rentals Only) : 621 Canfield Lane, Key West, Florida Tucked away at the end of a quiet and peaceful Old Town Lane is this luxurious single family home.

Luxury Truman Annex Home - Classic Key West Charm – Property 164696

  • Key West rental - house, 3 bedrooms, sleeps 6, 3 bathrooms, beach, resort, swimming pool
  • Calendar Last Updated On: May 12, 2008
Classic Key West charm and great location within the Truman Annex gated community make this home of distinction an ideal place for that tropical getaway that you...

3 Bed, 3 Bath, Waterfront - 9 Miles from Key West - – Property 322888

  • Key West rental - house, 3 bedrooms, sleeps 6, 3 bathrooms, near the ocean, waterfront, air-conditioning
  • Calendar Last Updated On: May 12, 2008
This is a beautiful Spanish style home on a clean swimming canal 9 miles from Key West. The home is just 4 houses from the end of the canal and the backwaters of the...

A Hop, Skip and Jump to Duval Street (1 1/2 Blocks) – Property 144355

  • Key West rental - townhome, 3 bedrooms, sleeps 8, 2 bathrooms, 1 half bath, downtown, near the ocean, air-conditioning
  • Calendar Last Updated On: May 12, 2008
Perfectly situated Old Town Key West vacation retreatat 624 Fleming Street. Freshly renovated throughout and very clean including granite counters and marble...

New Key West Home – Property 147646

  • Key West rental - , 3 bedrooms, sleeps 6, 3 bathrooms, accept credit card, swimming pool
  • $1,350/week
  • Calendar Last Updated On: May 12, 2008
Newly built Key West single family home situated in a gated community near the airport, golf course and beaches. Surrounded by lush tropical vegetation and situated...

The White House Key West's Finest Monthly Rental/4 BR – Property 187082

  • Key West rental - house, 4 bedrooms, sleeps 8, 3 bathrooms, town, swimming pool
  • Calendar Last Updated On: May 10, 2008
The White House is an address and house of distinction! Finely detailed with unparalleled amenities, this the the perfect vacation home for the discriminating guest...

Direct Oceanfront Free Wireless Internet – Property 149233

  • Key West rental - condo, 3 bedrooms, sleeps 6, 2 bathrooms, 1 half bath, beach, accept credit card
  • $2,350 - $2,450/week
  • Calendar Last Updated On: May 9, 2008
! Nothing between our balcony and the ocean except 20 yards of sand! Free high speed Internet! This very upscale unit is one of the largest in this tropical...

'Colorful Conch' @ the Sanctuary: 3 Bedrooms, 3 Baths & Private Pool – Property 189356

  • Key West rental - house, 3 bedrooms, sleeps 6, 3 bathrooms, beach, resort, tennis
  • Calendar Last Updated On: May 12, 2008
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 a...

Key West private, hideaway cottage for 2, Spring & summer special running now! – Property 184497

  • Key West rental - , 1 bedroom, sleeps 3, 1 bathroom, beach, air-conditioning
  • $745 - $850/week
  • Calendar Last Updated On: May 9, 2008
You will love staying in this great location where 90% of the residents are local. They each have an interesting Key West tale to tell and are a very warm, friendly...

Spring & summer special running now at Private, Key West Hideaway cottage for 2! – Property 158112

  • Key West rental - house, sleeps 3, 1 bathroom, beach, town, air-conditioning
  • $755 - $1,195/week
  • Calendar Last Updated On: May 9, 2008
Please Call Marilyn And Ask About Our Pre-Booking Discounts! You will love staying in this great location where 90% of the residents are local.

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, accept credit card
  • $1,200 - $2,000/week
  • Calendar Last Updated On: May 8, 2008
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...

Henry's Piece Of Paradise On The Ocean In Key West (nightly / weekly) – Property 103905

  • Key West rental - condo, 2 bedrooms, sleeps 5, 2 bathrooms, beach, waterfront, accept credit card
  • Calendar Last Updated On: May 8, 2008
1350 sq ft of fabulous living space located on the 2nd floor, with garden and partial ocean views from a 38 ft private balcony accessible from the living and both...

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

  • Key West rental - house, 2 bedrooms, sleeps 6, 2 bathrooms, 1 half bath, downtown, resort, swimming pool
  • Calendar Last Updated On: May 12, 2008
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...

“Falling Water” @ Old Town: Breathtaking 3-Home Compound with Large Private Pool – Property 180171

  • Key West rental - house, 5 bedrooms, sleeps 12, 4 bathrooms, 1 half bath, downtown, near the ocean, accept credit card
  • Calendar Last Updated On: May 7, 2008
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...

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

  • Key West rental - condo, 2 bedrooms, sleeps 8, 2 bathrooms, resort, waterfront, accept credit card
  • $2,337 - $3,850/week
  • Calendar Last Updated On: May 13, 2008
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...

Galleon Resort Efficiency in Old Town – Property 169027

  • Key West rental - studio, sleeps 2, 1 bathroom, resort, waterfront, accept credit card
  • $1,000 - $1,452/week
  • Calendar Last Updated On: May 13, 2008
This efficiency is located on the 5th floor of the Galleon Resort. One of only two efficiencies with both a king size bed and a balcony (resort view).

Campbell Courtyard Townhouse 'In the Sky' – Property 167721

  • Key West rental - townhome, 2 bedrooms, sleeps 6, 2 bathrooms, 1 half bath, downtown, accept credit card
  • $2,500/week
  • Calendar Last Updated On: May 6, 2008
Few properties in Key West can offer a true combination of quality, location and privacy like this one! Perched above the 600-block of Fleming Street (between...

Beautiful Retreat in Key West Area – Property 188664

  • Key West rental - house, 6 bedrooms, sleeps 10, 3 bathrooms, 1 half bath, beach, waterfront, accept credit card
  • $3,000 - $3,500/week
  • Calendar Last Updated On: May 6, 2008
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...
SPECIAL OFFER! Keys Summer Getaway! May 1 - October 15

Key West Tropical Townhouse – Property 120270

  • Key West rental - townhome, 3 bedrooms, sleeps 8, 1 bathroom, beach, near the ocean, accept credit card
  • Calendar Last Updated On: May 5, 2008
Just minutes away from Old Town Key West is Kelly's Cottage; a beautifully appointed three bedroom and three bath home away from home.
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