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Key West Vacation Rentals

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147
The Best of Everything! "Island Days" has it all: Large heated resort style pool with Tiki Hut right outside your French doors. Lush landscaping, off street parking ste...
6
This spacious condo is located at 1800 Atlantic Blvd on the beach, with sunset views right from your own 28-foot balcony. You'll be able to enjoy quiet afternoons with t...
5
If you dream of waking up to expansive water views and island breezes, and walking out your front door right onto the streets of Old Town Key West in the centre of it al...

Rentals

7
Finally, a large vacation home where every member of the family will be happy. From the vaulted living room with three couches and a giant 60-inch TV, to the kitchen lar...
3
This precious 2 bedroom cottage with its coral front door will charm you from the moment you walk in the front gate. The front porch is private, for some quiet time read...
3
This villa 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 means you will b...
Imagine a traditional conch home stunningly restored, then decorated in a post-modern style with vivid colours and sophisticated decor. Every room is adorned with colour...
Imagine a home with floor-to-ceiling panoramic views of the Atlantic Ocean from every room. This freshly renovated condo has been thoughtfully decorated and furnished. T...
Half a block from the Historic Seaport on William Street is a home that has been recognised by the Historic Florida Key Foundation for excellence in preservation: the Ce...
3
If you want to experience Key West at its historic best, this house is the perfect choice for your stay. A wide porch graces the front of the house and the grounds have ...
This villa is an immaculately furnished town home at the Porter Court Complex in Truman Annex, Key West's most desirable gated community, right in the middle of Old Town...
This is a charming turn-of-the-century cigar cottage located in the centre of the historic cigar-making district of old Key West, half a block from Duval Street at 517 L...
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 condo...
This villa is located on 1211 Margaret Street, an area of Old Town that is near the Southernmost Point and the just four blocks from the gallery district of Duval Street...
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) is j...
This home has been whimsically decorated, with furnishings that reflect the laid-back, funky island life style of Key West. Located in the gated community of Coral Hammo...
This unique home has all the charm of a historic Conch home, yet it was built just a few years ago, and with all the modern conveniences you could want. The attention to...
This charming villa is located on the President's Walk in the Truman Annex, Key West's most exclusive gated community, in the heart of Old Town. You'll be just a short w...
For those who realise that a Key West stay is as much about life on the water as it is on land, this villa is the total island accommodation package. An incredibly spaci...
This beautiful vacation villa is to be found in the Truman Annex, Key West's most exclusive gated community. You'll be just around the block from Mallory Square, Duval S...
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Cannot wait to return!
We traveled to Key West and Southard Comfort in January and have booked our return visit for December. Twice in one year is absolutely due to the hospitality of the owners, Nancy and Carl, and their beautiful home. Southard Comfort was our paradis... Read more

We often get questions from college students about minimum age requirements. Although some owners require a parent or guardian to be present, we do offer some Key West vacation rentals for 18 year olds and for 21 year olds. Here are some tips:

  • Shop around. Different owners have different policies, so email several owners before making your choice.
  • Be upfront. Never try to hide your age. Clarify the checkin policies now to avoid surprises.
  • Enlist your parents. Some owners will relax their policies if you have an adult co-sign or vouch for you.
  • Be respectful. You may not agree with everyone's policy, but courtesy and respect are your best tools.

Blog Posts

April 30, 2015
For pleasure or fun, relaxation or rum, there’s one place you must run to enjoy the warm sun,...
December 04, 2014
During my Florida Keys vacation, I ate dinner at the Conch Republic Seafood Company located at 631 Greene Street, Key West, Florida 33040....
September 03, 2014
The Florida Keys offer a constant flow of activities for a great vacation getaway. Whether snorkeling and swimming in the crystal clear gulf waters, boating, or deep-sea fishing, the days’ activities...
November 15, 2013
I was driving into Key West one morning when I saw this vehicle in front of me and it was clear to me that winter is upon us. Seasons are hard to see in Key West when you are used to obvious stuff lik...
November 11, 2013
It was hot and still and summer like. I like this place any time of year but summer in winter is best....
November 06, 2013
Key West needs more restaurants! Not really but eating out is a regional sport around here and entrepreneurs always think their best idea will catch on so let there be no surprise there is a new eater...
November 04, 2013
So now I'm going to do that which I never do which is I am going to try to be a tour guide....
October 28, 2013
These pictures were a lunch break in the early afternoon a week or so ago. There was no great reflection behind them, just that I hadn't been to the beach recently even though this is the route I have...
July 26, 2013
I can see why Ernest Hemingway fell in love with Key West...
July 04, 2013
I’ve lost track of how many times I’ve been to Key West, and every time I go, I discover something new. ...
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