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
$195
/nt
1 bed
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...
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...

Listings

from
$155
/nt
1 bed
Beautifully Renovated Second Floor Studio for Two - Incredible Location in the Historic Seaport section of Historic Old Town Key West Gorgeous studio apartment on the s...
from
$400
/nt
2 beds
Enjoy the resort-style amenities of 1800 Atlantic Condominiums while relaxing in a residential setting amongst neighbors. 1800 Atlantic sits on 400 feet of oceanfront pr...
from
$340
/nt
1 bed
Tucked away in an inviting compound you'll find the perfect hideaway called Ann Street Cottage; a charming one bedroom cottage. The quiet compound is located just one b...
from
$460
/nt
2 beds
This charming Key West style cottage is just a short walk to a selection of great restaurants, art galleries, and shopping. Catherine House is located only ½ block from ...
from
$350
/nt
2 beds
In the heart of Old Town, with the beautiful community of private homes and condominium of Truman Annex, this Shipyard Condominium is great access to Zachary State Park ...
from
$340
/nt
1 bed
This charming one bedroom cottage is the perfect hideaway.The home is part of an inviting compound created so owners could enjoy shared tropical outdoor spaces. Across f...
from
$260
/nt
1 bed
Situated on the Atlantic shore of Key West and offering breathtaking panoramas, this outstanding property was featured in Architectural Digest. Filled with a mixture of ...
from
$250
/nt
Studio
A spacious studio apartment and large deck make this the perfect romantic getaway; feast your eyes on the breathtaking views of the Atlantic Ocean. Enjoy complete privac...
from
$99
/nt
2 beds
***Due to licensing restrictions, this Key West Condo rental requires minimum stay of 30 nights*** Seaside Breeze is a true Key West island paradise. It is a wonderful ...
from
$185
/nt
2 beds
This original Conch house located 5 blocks from Duval Street was completely restored in October 2009 with attention to detail in mind. Furnished with high quality furnit...
from
$350
/nt
2 beds
Lovely, private, conch home in a lush, tropical garden setting located less than 10 min. walk to Smathers ocean beach. Here you can kayak, volleyball, para-sail, jog or ...
from
$270
/nt
1 bed
The Heron is one of several of the Colony Suites in historic Key West, Florida. A conch style cottage nestled in the heart of Historic Old Town Key West, just two blocks...
from
$200
/nt
2 beds
"Tee By The Sea" vacation rental (we include 6 bikes free for our guests!) If you love. Golf, Sport Fishing/Boating, ART/Theater And Fantastic Live Entertainment.than yo...
from
$185
/nt
2 beds
Available for weekly, or longer, rentals this three-story townhouse is located on a picturesque street in the beautiful gated Truman Annex community. It's close to all t...
from
$130
/nt
2 beds
Truman Annex is located in the heart of Key West's Old Town. Walking or biking distance from all the shops, restaurants, bars & attractions, you don't even need a car. F...
from
$190
/nt
Studio
Enjoy a Unique Vacation Experience in Nancy's Forrester's Guest Cottage. Nancy is an enviromental activist and artist tht lives on this amazing one-acre property in the ...
from
$265
/nt
2 beds
Beautifully remodeled, 1374 sq. ft,2 bedroom (King Beds) 2 Bathroom condo- Beautifully landscaped & Located On The Ocean-Sleeps 6. (Right Next To Smathers Beach!) Visit:...
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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