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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...
273
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

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...
54
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 ...
52
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...
75
This 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 Club. The setting is idy...
69
Life in Key West is laid-back, easy-going and a bit quirky. "Muriel's Whimsical Galleria," a two-bedroom penthouse-style apartment perched above Duval Street, was design...
74
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...
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...
35
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...
28
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...
31
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 ...
55
This wonderful little cottage is located in the centre of Old Town, but in its own little tranquil world. With a private front porch, off-street parking, a full back yar...
30
Ever wish you could spend a month or two in one of those perfect little conch houses set along the streets of Old Town, Key West? Take a look inside this classic little ...
25
This meticulously renovated and decorated cottage is so bright and airy it will make you laugh, when the sun is out. There's a large porch where you could spend the whol...
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...
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...
25
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
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...
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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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