pinterest facebook instagram twitter youtube google my business
  • (305) 294-7358
info@vhkw.com
Key West Time
July 12th
11:01am · 88°F

Sort Properties


Rental Period


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


ultimate sunset guest house
New

Standard Rates: $19,140 - $25,000 per month

2BR 2BA - Sleeps 2-4
Private Tropical Resort Island
Front Line Ocean Views
White Sandy Beaches
Custom Fantasy Swimming Pool w/ Waterfalls

Sit back, relax, and choose your favorite mesmerizing view from one of the magnificent private decks on this private island property, 500 yards from the ''main island' of Key West.  Unhurried sunrise, serene sunset, warm turquoise waters, and white sandy beaches – from any direction, it’s divine.

locate on map pin


little digs key west
special rates available

1BR 1BA

July 14 - Aug 31

Monthly $3700

view all specials


Standard Rates: $3,600 - $6,000 per month

1 BR 1 BA
Sleeps 2 - 3
Luxury Interior Upgrades
Solares Hill Neighborhood
Center of Old Town
5 Minute Walk to Duval Street

Diminutive in size but huge in style, Little Digs Key West, authenticates how ‘big things’ really do happen in small spaces. Spacious design. A complete luxury makeover of this 1933 historic cottage. It sits in proud harmony with other historic residential cottages, on a narrow one-way lane in the middle of Old Town Key West. 

locate on map pin


casa bella petite le bleu
New
special rates available

2BR 2 Bath

view all specials


Standard Rates: $6,000 - $18,000 per month

2BR 2BA - Sleeps 4
Award Winning Historic Cottage
Gorgeous Interior Re-design
Swimming Pool

First impressions are everything. And its love at first glance with this Old Town Key West cottage. The 2BR 2BA Casa Bella Petite le Bleu is a luxurious charming pool-garden home. Situated on the quiet upper end of famous Elizabeth Street, this stylish house is filled with authentic charm. 

The impressive renovation of this 18th Century wooden cottage earned it the coveted Historic Florida Keys Foundation Preservation Award. It provides off-street bricked parking with a Tesla charging station.

An ideal cottage for 2 to 4 people, if more people decide to join you in Key West - No Problem! Right across the street is the extraordinary 5BR 5.5 BA  Bella Grand Premier Estate.

 

locate on map pin


hidden story book cottage
special rates available

1BR 1BA

July 14 - Aug 31
Monthly $3,800

view all specials


Standard Rates: $3,700 - $6,175 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

Tucked away down a short walking path in the Center of Old Town Key West, this precious 1BR 1BA Hidden Story-Book Cottage is completely hidden from the street. Comfortable as it is adorable, it even offers a fenced in yard. Perfect for one or two people, here you can set up home and live as a local for a month or more - or settle in to work remotely.

 

locate on map pin


villa corazon
New
special rates available

3BR 3.5BA

July 14 - Aug 31

Monthly $ 6850

view all specials


Standard Rates: $7,900 - $17,500 per month

3BR 3BA
Private garden with heart-shaped pool
Luxury renovation with upscale furnishings
Private Guest Cottage in Garden
Casa Marina Neighborhood
Close to Higgs Beach

There’s lots to love about the luxurious 3BR 4BA Villa Corazonit even has a heart shaped pool. Experience ultimate resort style living in this private home retreat. A perfect pairing of a renovated Key West gingerbread cottage with an elegant free-standing cottage that are seamlessly joined with a tropical pool-garden.The interior is a harmonious sweet spot between modern aesthetics and laid-back Caribbean. 

locate on map pin


cockadoodle cottage on duval
special rates available

2BR 2BA

July 15 - Aug 12


Nightly $450
Weekly $1900




view all specials


Standard Rates: $2,095 - $4,760 per week

2BR 2BA
Sleeps 4
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.'

 

locate on map pin


butterfly garden
special rates available

1BR !BA

July 14 - Aug 31
Monthly $3800

Dec 1 - Jan 15
Rental $7500

view all specials


Standard Rates: $3,975 - $6,300 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.

locate on map pin


on hemingways rounds
New
special rates available

2 BR 2 BA

Sept 1 - Sept 30

Monthly $5900

view all specials


Standard Rates: $6,500 - $14,650 per month

2BR 2BA - Sleeps 4
Beautifully Renovated 1920 Bungalow
Private Swimming Pool & Sun Deck
Upscale Amenities
On Famous Whitehead St.
1 Block off Duval Street

On Hemingway's Rounds, is an inspired renovation of a classic circa 1920 American Bungalow redone Key West style. Private swimming pool garden and deck in the fenced back yard. Historic front porch with comfy chairs to relax and watch Key west go by. Interior design is imaginative and elegant. Less than one block from the Hemingway Home and Museum. 

 

locate on map pin


havana moon over duval
special rates available

2BR 2BA

July 19 - July 22
Aug 2- Aug 7
Nightly $550
Weekly $2600

view all specials


Standard Rates: $2,475 - $5,820 per week

2BR 2BA - Sleeps 4
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.

 

locate on map pin


island cosmopolitan cottage
special rates available

3 BR 2 BA

July 14- Aug 31

Monthly $6500

view all specials


Standard Rates: $6,900 - $15,200 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. 

locate on map pin


caribbean cottage ~ duval street key west
special rates available

2BR 2BA

July 10 - July 18
July 24 - Aug 9
Nightly $525

view all specials


Standard Rates: $2,445 - $5,650 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. 

 

locate on map pin


key west island village cottage
special rates available

1 1/2 BR 1BA

Monthly

July 14 - Aug 31
Monthly $4975

view all specials


Standard Rates: $4,750 - $11,300 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.

locate on map pin


vintage luxury cottage on duval
special rates available

1BR 1BA

July 11 - July 14
July 19 - July 25
Aug 5 - Aug 17
Nightly $475
Weekly $2250

view all specials


Standard Rates: $2,390 - $5,550 per week

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

Vintage Luxury Cottage on DuvalRomantic hideaway. Completely hidden from the street! Private Heated Pool in charming bricked courtyard garden. Expansive covered porches. Nothing else like this extraordinary cottage in Key West.  

locate on map pin


down island digs
special rates available

2BR 2BA

July 10- July 18
July 23 - Aug 1
Aug 24 - Aug 31
Nightly $550
Weekly $2500

view all specials


Standard Rates: $2,580 - $6,250 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.

 

locate on map pin