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Key West Vacation Rentals

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1 review
“Southard Comfort”, True Island Living in Downtown Historic Old Town Key West Two story, 3 bedroom, 2.5 bath plus outdoor shower. Nancy & Carl welcome you to their Key ...
182
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...
36
Hidden behind an unassuming wall on a residential street in the Casa Marina East neighbourhood is a very special estate, designed to be your own private oasis in Key Wes...

Rentals

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 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 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...
23
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...
53
Upscale island living is re-defined with the brand new home. This newly built home is tall, spacious, and modern with a tropical theme and in a prime location for walkin...
32
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 ...
29
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...
17
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...
17
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...
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This villa is a classic conch home located right across the street from Bay view Park, with its tennis courts and community activities. This stately home has many of the...
15
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...
21
In the heart of Old Town is a classic Conch House that has been completely renovated and updated while retaining all of its historic charm. Surrounded by lush tropical f...
13
For those who desire the upscale coastal life in Key West complete with serene water views and spacious island-inspired accommodations, this villa is your match. Fully e...
The Meadows is one of the nicest neighbourhoods in the Old Town area, but this exquisitely detailed home on 1510 Petronia Street truly stands out. As you turn onto this ...
Imagine your whole group staying in one home, with each couple in their own private bedroom suite. At this villa all four bedrooms are laid out as suites: each with a pr...
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...
The Living Area This home has a unique setting, with a wide canal out back, and a panorama of Florida Bay in front, offering stunning sunset views from the front porch ...
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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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