Most Popular

$690
/nt
3 beds
Key West
Sleeps: 6 Bedrooms: 3 Bathrooms: 2.5 3 Bedrooms, 2.5 Baths - 1 King, 2 Queens “Southard Comfort”, The Ultimate Key West Historic Conch House in Old Town New owners Na...
$375
/nt
3 beds
Key West
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...
$1,500
/nt
5 beds
Key West
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 ...

Listings

5 beds
Key West
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
Key West
3 beds
Key West
Conch Republic Cottage - If you are looking for the spaciousness of a hotel suite, but still want that funky Key West style, the Conch Republic Cottage is just for you. ...
$185
/nt
4 beds
Key West
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...
$150
/nt
3 beds
Key West
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...
$230
/nt
3 beds
Key West
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
Key West
Enjoy a fabulous stay at our beautiful vacation house with your dear ones. This three bedroom retreat is spacious enough to lodge eight guests. The bedrooms include king...
3 beds
Key West
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...
$285
/nt
4 beds
Key West
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...
$995
/nt
3 beds
Key West
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...
$520
/nt
4 beds
Key West
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...
$930
/nt
4 beds
Key West
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...
$890
/nt
3 beds
Key West
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...
$640
/nt
4 beds
Key West
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 ...
$660
/nt
4 beds
Key West
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...
$900
/nt
6 beds
Key West
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 ...
$700
/nt
3 beds
Key West
Deluxe 3 BR, 3 BA Harborfront Penthouse with Beach, Pool, Bar and Marinacan alsobe rented separately as a 2 BR, 2 BA or a 1 BR, 1 BA. The most perfectly located unit in ...
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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.

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...
March 18, 2013
Key West is definitely the party town of the Florida Keys. There is plenty of shopping in the narrow streets that remind you of an old but busy village. Have fun in the ocan with snorkeling, scuba div...
January 30, 2013
There’s one main road between Key Largo and Key West, Overseas Highway, and if you point your car toward west, you’ll run into Betsy the 40-foot-tall, 30-foot-wide lobster sculpture just outside the R...
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