Cottages - Smaller than a Villa with 'cottage style' architectural details such as planked floors, open beam ceilings, dormered windows, and romantic or antique style decor. Most cottage properties are one or two bedroom abodes and may be 'free standing' or a flat.
Choose from our inventory of Key West vacation rentals. We offer something for everyone; from charming cottages, to beachfront condos, to luxury estates, to tropical pool-garden homes.
* PLEASE NOTE: Some properties displayed may not be available for rent due to other inquires and pending reservation. Please contact our office to be sure of availability. email@example.com or 305-294-7358 ext. 1
There are no properties available that fit all of your search options. Please contact our office if you would like assistance. firstname.lastname@example.org or 305-294-7358 ext. 1
Jan 21- Jan 24
Mar 19- Mar 23
Standard Rates: $2400 - $4250 per week
2BR 2BA - Sleeps 4
Private Heated Pool
Private Sun Deck
Less than 1 Block from Duval St.
An artistic fusion of past meets present provides a decidedly refreshing and modern interpretation of a classic Key West style. On Simonton St., only one short street from the 500 block of Duval Street, on historic Simonton Street, this could be your perfect spot. Rent separate or with Villa Nouveau Key West or Grande Dame Key West - The Watson House estate.
Standard Rates: $4000 - $6050 per month
2 BR 1 BA
Sleeps 2 - 4
Idyllic Pool-Garden Island Cottage
Close to the Beach
Quiet Neighborhood on lane less traveled
‘Heads Up’ to all of you incurable romantics who are looking for the perfect Old Town Key West garden cottage retreat close to the beach. Dream worthy and authentic, it’s a little bit like ‘Little Red Riding Hood’s cottage merges with a ‘Fantasy Island’s’ private pool garden,’ and the two are seamlessly blended.
Standard Rates: $1700 - $3325 per week
Sleeps 4 - 6
Great for 2 Couples or Small Family
Jacuzzi Bath Tub
Charming Upper Duval St. Neighborhood
1 minute walk to South Beach.
Key West cottage architecture has been time-tested in island life and culture in this infamous little wooden 'cigar maker's' cottage located on famous Duval Street, at the 'classier upper-end.'
Mar 9- Mar 16
Standard Rates: $1850 - $3625 per week
2BR 2BA - Sleeps 4
Manicured Tropical Swimming Pool Garden
Shared Heated Pool
Walk to Duval St. in 3 minutes
I must confess, there’s something about walking along an exotic tropical pool-garden path that sends me to an instant state of calm. Palm fronds gently dancing in the breeze, orchids hanging in the trees, manicured gardens, a pristine swimming pool set with comfortable lounge chairs. This is what you’ll experience as you make your entrance to this beautiful Bahamian ‘eyebrow’ style home, nestled away in private back corner of the small Old Town Key West gated community of Windward Park.
Standard Rates: $3200 - $4550 per month
1 BR 1 BA
Sleeps 2 - 3
Free-Standing Story-Book Cottage
Gorgeous Interior Upgrades
On a Hidden Walking Path
5 Minute Walk to Duval Street
As I stand on the front porch of this little Hidden Story-Book Cottage in the Old Town Key West, I could swear I’m in a neighborhood in the Bahamas on Green Turtle Cay. But as diminutive as it is, impressive interior upgrades that give it a proportionately larger and luxurious feel.
Standard Rates: $3200 - $4300 per month
1BR 1BA - Sleeps 1-2
Historic meditation garden.
Quiet Living Exclusive Casa Marina neighborhood.
Close to Higgs Beach
Completely hidden from the street, this historic Butterfly Garden flat provides you with two private entrances off the large gated meditation garden. A private covered sitting porch outside your front door beckons you to sit in the freshness of the garden and watch for the butterflies.
Mar 2- Mar 9
Standard Rates: $1850 - $3925 per week
Sleeps 2 - 5
Charming Upper Duval Street
Private Heated Pool and Bricked Courtyard
2 min. walk to South Beach.
Great for 2 Couples or Small Family
Just steps from Duval Street, this unique Key West cottage has an authentic Caribbean feel plus a private pool with bricked courtyard, with original wood planked polished floors, vintage hand-hewned beams, bright blue tile kitchen and Bahama style wooden window shutters. One of the oldest houses in Key West, exudes authentic charm with all the comforts of home.
Standard Rates: $1950 - $4300 per week
Sleeps 2 - 6
1/2 block off Duval Street
Traditional Key West Cottage-Style Charm
Hidden Large Back Yard Rare for Downtown Location
Private Manicured Pool-Side Garden.
Everything about "Down Island Digs" adds up to make a private precious pool- garden cottage. Sitting in the large hidden back-yard garden, you would never know you're just 1/2 block off Duval Street.
Standard Rates: $1800 - $3850 per week
1BR 1BA - Sleeps 2-4
Hidden pool and courtyard.
2 min. walk to South Beach. Perfect couples retreat.
Vintage Luxury Cottage - An elegant Cottage with Private Heated Pool in hidden courtyard. "Best Kept Key West Secret."
Standard Rates: $1475 - $2900 per week
2BR 1BA - Sleeps 2-5
Private Renovated Cottage
Private Jacuzzi Tub
Steps from Duval St.
Welcome to a little piece of hidden paradise you never knew existed. Once you're nestled into this hideaway, you'll never know you're right in the center of Old Town Key West.
Jan 12- Jan 17
Jan 25-Jan 27 - 2 nights
Standard Rates: $1900 - $4075 per week
2BR 2BA - Sleeps 4-6
Private Swimming Pool
On Upper Duval St. - 1 min. walk to South Beach.
Great for 2 couples or small family
Originally built in the late 1800’s as a 'cigar makers’ cottage, the authentic exterior of this turn-of-the-century cottage is protected by historic preservation rules and today stands renovated to form, to be proud and handsome. But the interior of Havana Moon, is an entirely different story. Inside the owners had creative license to redesign in order to bring the cottage upscale modern vacation standards, with all the luxurious accoutrements. The cottage also has a swimming pool and large deck for lounging and sunning. Open the front door of this hand crafted Key West cottage and look south toward Havana Cuba and you'll catch a view of the ocean where the full moon rises with a soft salt southern breeze.