Most Popular

from
$690
/nt
3 beds
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 ...
from
$375
/nt
3 beds
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...
from
$995
/nt
3 beds
The Absolute Best Luxury Private Weekly Vacation Rental Home on Duval Street In Old Town Key West! Just a half block off Duval Street you’ll find your secret paradise a...

Listings

5 beds
An architecturally designed Main House (4 Bedroom 2 bath) and Guest House (2 Bedroom, 2 bath) sleeps up to 16 guests until mid-January 2012. Then the Guest House will ha...
4 beds
from
$185
/nt
4 beds
Why rent one when you can have two great houses? Dos Casas is a unique 4-bedroom property in the heart of the most beautiful part of Old Town. This lovely 2 house compou...
from
$150
/nt
3 beds
1, 2, 3, 4, 5, 6 & 7 BR Luxury Villas in Historic Old Town Key West with Heated Pool, Full Kitchens, Parking and adjacent to the best beach in Key West. Quiet and peacef...
from
$230
/nt
3 beds
These Luxury Oceanfront Villas are among the absolute finest properties available anywhere in the Florida Keys, yet are moderately priced. Convenient location just 5 min...
3 beds
Location! Location! Location! Emma House with Pvt Pool is located in Truman Annex Community which is one of the Best locations in Key West. You can walk to everything! I...
from
$285
/nt
4 beds
4 bedroom, 2 baths ocean front home with a dock and an in-ground heated pool. Central air, all kitchen and bath amenities, to include washer and dryer. Located only 15 m...
from
$890
/nt
3 beds
Private, Gated Three Bedroom, Three Bath Home with Heated Pool and Covered Lanai Location, Location, Location....This amazing property is situated on a quiet and peacef...
from
$2,100
/nt
5 beds
Luxury on Duval Street in historic Key West? Luxury is not what most people visiting Key West associate with Duval Street until you look at Dreaming On Duval! There are ...
from
$630
/nt
4 beds
Welcome to your quiet and relaxing Key West vacation! The Key West Beach Club stretches along the Atlantic Ocean shores. This top floor penthouse has it all: 15 foot va...
from
$1,100
/nt
4 beds
On a lovely tree-lined residential street in the heart of the historic Old Town district, this quiet, historic compound offers three separate vacation suites sharing a l...
from
$800
/nt
3 beds
Location! Style! Elegance! This beautiful home is the fabulous combination of everything a great vacation property should be. One half block to Duval Street in the histo...
from
$720
/nt
4 beds
Beautiful four bedroom penthouse condo steps from the action has been recently upgraded. This four bedroom, 4.5 bath condo is in the heart of the action at Duval Square ...
from
$800
/nt
4 beds
Great location, just half a block off Duval Street, walking distance to restaurants, the Atlantic beaches and the Southernmost Point. Casually decorated in soft pine and...
from
$900
/nt
6 beds
Quiet serenity awaits you at this secluded tropical oasis in the heart of Old Town Key West. Tucked away at the end of one of the most beautiful lanes in Old Town, this ...
from
$745
/nt
3 beds
3 BR, 2 BA Private Home shares the pool with the 2 BR, 2 BA Hangover Cottage (rents separately). Located just 4 blocks off Duval Street and close to Mallory Square and F...
from
$785
/nt
4 beds
Gorgeous 4BR 4BA home with pool - Luxury 4BR home in the heart of Old Towns Truman Annex. Fully appointed with gourmet kitchen and private pool.
Next Page >>
Cannot wait to return!
by Jennie on 10/05/14
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

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. ...
April 16, 2013
For a sweet break, step out of the Florida heat and into the coolness of one of the Blond Giraffe’s pie shops. The first location opened in 1999 and, that same year, won first place in the Key West Ke...
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