Most Popular

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
$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
$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 ...

Listings

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
$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
$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:...
from
$485
/nt
2 beds
Deluxe 2 BR, 2 BA Home with Shared Pool and Jacuzzi. Located just 1/2 block off Duval street yet Quiet as there are no bars or restaurants next door. Located 1 block fro...
from
$430
/nt
2 beds
This 2 bedroom, 2 bath Penthouse Loft is located on the 5th floor overlooking the marina & harbor. On the first floor is a full size, fully equipped kitchen, breakfast n...
from
$375
/nt
2 beds
Beachfront Key West Condo - The Best of Key West gets even better! Beachside Resort & Conference Center is a seven acre luxury waterfront resort condominium with lush tr...
from
$300
/nt
2 beds
Island Wind welcomes you to a tropical sun drenched oasis in the heart of Old Town. This charming Bahamian style townhome with tin roof and white spindled decks reminisc...
from
$260
/nt
2 beds
2 BR, 1 BA Poolside Cottage at Fort Zachary Taylor State Park & Beach in Old Town Key West.
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...
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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