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...
$189
/nt
1 bed
Key West
This Peaceful and Cozy Efficiency is the Perfect Place to Rest After an Active Day In Key West! Located in vibrant and diverse Bahama Village, the Vangogh Studio for Two...

Listings

$115
/nt
1 bed
Key West
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...
$105
/nt
1 bed
Key West
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...
$370
/nt
2 beds
Key West
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...
$370
/nt
2 beds
Key West
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 ...
$320
/nt
2 beds
Key West
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 ...
$220
/nt
1 bed
Key West
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 ...
$200
/nt
Studio
Key West
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...
$185
/nt
2 beds
Key West
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...
$350
/nt
2 beds
Key West
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 ...
$270
/nt
1 bed
Key West
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...
$200
/nt
2 beds
Key West
"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...
$185
/nt
2 beds
Truman Annex
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...
$130
/nt
2 beds
Truman Annex
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...
$190
/nt
Studio
Key West
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 ...
$265
/nt
2 beds
Key West
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:...
$200
/nt
2 beds
Key West
Comfortable, reasonably priced 2-bedroom condominium in Sunrise Suites Resort. The Resort offers concierge service, heated swimming pool, outdoor spa, gym facilities, te...
$175
/nt
Studio
Galleon
This Vacation Hideaway is located on the 5th floor of the Galleon Resort and Marina. Only one of two efficiencies at this resort with both a king size bed and a balcony ...
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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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