Key West Vacation Cottages
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January 15th
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Key West ~ Vacation Cottages

What Are Cottages? Cottages are 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.

View our exclusive Key West vacation rentals. Vacation Homes of Key West can help you find the perfect vacation rental for your next Key West vacation. Don't pay booking fees, save money by booking directly with VHKW today.

* PLEASE NOTE: Some properties displayed may not be available for rent due to other inquiries and pending reservations. Please contact our office to be sure of availability. info@vhkw.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. info@vhkw.com or 305-294-7358 ext. 1


oceana suite oceana courtyard cottage
New
special rates available

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Standard Rates: $1400 - $2885 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

Immaculate cottage in Old Town Key West with a central base to explore. Perfect location for a romantic getaway. So, close your eyes for a few moments, and imagine tropical Key West, and this charming setting waiting for you.


hidden story book cottage
special rates available

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Standard Rates: $3000 - $4850 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.


island cosmopolitan cottage
New

Standard Rates: $5000 - $11350 per month

3 BR 2 BA
Sleeps 4 - 6
Historic Cottage
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. 


key west family cottage villa
New
special rates available

Jan 1 - Jan 31
Monthly $6800

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Standard Rates: $4500 - $8500 per month

4BR 3BA
Fabulous open floor plan
Spacious Custom Kitchen
Quiet residential neighborhood
Large fenced yard
Excellent Value
Pets Allowed

A wonderful home in a quiet neighborhood. Ideal for families and professionals to work remotely more a month or more. Pets are allowed. Walk your dog or bicycle around the wide neiborhood streets and enjoy the convenience of nearby shopping. No place is faraway on the tiny island of Key West so its minutes to get to the beach and downtown Old Town.


key west cottage on the 16th hole
New

Standard Rates: $2850 - $5400 per month

2BR 1.5BA - Sleeps 4
Key West Golf Club Home
Corner Home
Signature View Over looking lake
Covered Wrap-Around Porch
Shared Pools

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." 


cockadoodle cottage on duval
special rates available

Jan 30 - Feb 6
Weekly - $2300

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Standard Rates: $1575 - $3535 per week

2BR 2BA
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.'

 


butterfly garden

Standard Rates: $3000 - $4600 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.


caribbean cottage ~ duval street key west
special rates available

Jan 17 - Jan 22
Nightly $500

Jan 26 - Feb 13
Weekly - $2950

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Standard Rates: $1960 - $4410 per week

2BR 2BA
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. 

 


key west island village cottage
New

Standard Rates: $3800 - $9000 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.


vintage luxury cottage on duval
special rates available

Jan 23 - Jan 30
Weekly $2500

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Standard Rates: $1800 - $4130 per week

1BR 1BA - Sleeps 2-4
Duval Street
Heated pool in garden courtyard.
2 min. walk to South Beach. Perfect couples retreat.

An elegant Cottage with Private Heated Pool in charming hidden courtyard. Situated so it's not visiible from the street. "Best Kept Key West Secret." 


havana moon over duval
special rates available

Jan 11 - Jan 16
Nightly $400

Jan 30 - Feb 6
Weekly $2700

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Standard Rates: $1890 - $4220 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.

 


little red pool garden cottage

Standard Rates: $3600 - $6450 per month

2 BR 1 BA
Sleeps 2 - 4
Private Pool
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.


down island digs
special rates available

Jan 19 - Jan 23
Nightly - $450

Jan 30 - Feb 13
Weekly - $2950

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Standard Rates: $2000 - $4690 per week

2BR 2BA
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.