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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 ...
144
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...
225
Newly renovated first floor corner condo perfect for 2 plus space for visiting friends and family! Monthly Rental A surprise awaits you inside the gates of the Southard...

Rentals

5
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...
6
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 ...
5
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...
6
If ever a home was a precious jewel, it is this immaculate restoration located on 320 Elizabeth Street just two blocks from the Historic Seaport. When you enter through ...
6
This villa 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 in the kitchen to t...
2
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...
5
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...
5
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...
2
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...
1
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...
5
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...
5
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...
13
If your idea of a perfect Key West stay is a spacious upscale home centered around a breathtaking water view, this apartment is everything you are looking for. Located i...
2
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
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 ...
3
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 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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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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