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.
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Month of Sept $2700
Month of Oct $3000
Standard Rates: $3000 - $4700 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: $5000 - $11000 per month
3 BR 2 BA
Sleeps 4 - 6
Upscale Renovation and Interior Design
Large Lap-Swimming Pool
Quiet Neighborhood close to White St.
Easy walk to Higgs Beach
An upscale renovation with elegant furnishings, this heritage cottage has all the luxuries you could want and still enjoy the ambiance of staying in an historic Key West property. Mixing a dash of contemporary style with selected cottage pieces, the designer created a unique island style cosmopolitan hide-away in the White Street Gallery district of Old Town Key West.
Sept 18- Sept 25
Oct 2 - Oct 23
Standard Rates: $1400 - $2800 per week
1 BR 1 BA
Sleeps 2 - 4
(maximum of 2 adults and 2 children)
Secluded Free-Standing Cottage
Private Sun / Dining deck
Exclusive gated pool garden w/ 7 other cottages
10 Minute Walk to Duval Street
Whether you are looking for a secluded getaway with a central base to explore, or the perfect location for a romantic get-away, this pool-side cottage will be home away from home. So, close your eyes for a few moments, and imagine tropical Key West, and this charming cottage just waiting for you.
Standard Rates: $2850 - $5200 per month
2BR 1.5BA - Sleeps 4
Key West Golf Club Home
Signature View Over looking lake
Covered Wrap-Around Porch
It's all about the signature view from the living room and spacious wrap-around back porch, that takes this Key West Golf Club cottage-style townhome to a class all on its own. Overlooking the lake at the renowned 16th hole, this property has no neighbors on one side, expanding your view and privacy even more. Now the only question is … "To Tee or Not to Tee."
Standard Rates: $3800 - $8700 per month
2BR 1.5 BA - Sleeps 2-6
Award Winning Historic Cottage
Private Dipping Pool in Tropical Garden
Great For Small Family
Historic Seaport Neighborhood
5 Minute Walk to Seaport Docks
Story-book charm, originally built in 1860, a restoration won it the coveted Star Award by the Historic Florida Keys Foundation, in 1995. Situated on famous Southard St., in the Historic Seaport neighborhood, its unique character has so captured lovers of Key West homes and gardens, that it’s been featured in two books - Mary Emmerling’s American Country Cottages, 1993, and again in Key West Gardens and Their Stories, Frawley-Holler, 2000.
Standard Rates: $3600 - $6230 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.
Sept 20 - Sept 26
Oct 8 - Oct 12
Oct 16- Oct 31
Standard Rates: $1575 - $3500 per week
Sleeps 4 - 6
Great for 2 Couples or Small Family
Jacuzzi Bath Tub
On Charming Upper Duval St.
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.'
Standard Rates: $3000 - $4430 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.
Sept 18 - Oct 3
Oct 10 - Oct 18
Oct 23- Oct 31
Standard Rates: $1900 - $4410 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 ambience plus a private pool with bricked courtyard. Historic construction with original wood planked polished floors, vintage hand-hewn 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.
Sept 26- Oct 10
Oct 24 - Oct 31
Standard Rates: $2000 - $4690 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.
Sept 18 - Sept 25
Standard Rates: $1800 - $4130 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."
Sept 23 - Oct 10
Standard Rates: $1890 - $4200 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.