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  • (305) 294-7358
Key West Time
January 26th
6:12am · 75°F

Uptown Island Luxury Villa ~ Weekly Rental

3BR 3.5BA ~ Weekly Rental
Sleeps 6

Island cottage charm meets up with modern elegance to mastermind this remarkable award-winning Key West poolside villa. You’ll only wish you could live right here … ‘happily ever after’ in this 3BR 3.5BA Uptown Island Luxury Villa.

An inspired renovation celebrated all its historic features, while creating a luxurious tropical home. The house is built floor-to-ceiling with ancient longleaf pinewood that is long since extinct. Restored interior walls give a unique warm glow that would be impossible to replicate today. A wide-open great room, finished with a sleek built-in kitchen, is set in perfect harmony with the wooden arts and craft staircase. Ceilings raised to the roofline, give dramatic impact, and spotlight a charming mezzanine at the top of the stairs. Each of the 3 bedrooms provides a private en-suite bathroom. Every space on the property feels immaculate and complete.  

This Uptown Island Luxury Villa is a vintage Key West cottage living up to its full contemporary potential both inside and out. With an eye for luxurious exterior design, the architect added a spacious pool-side lanai on the back of the house. Set as a stylish outdoor living room – even the  poolside restroom is air-conditioned! Yet from all street side appearances, this charming wooden cottage remains historically intact, with a classic front porch, gable roof, and quintessential white picket fence.

A little History about the Neighborhood – Cottages along this narrow block of Catherine Street were built in the early 1900’s as work-force housing for the long gone Gato Cigar Factory. Back then, most of the residents were expatriates from Cuba who were adept at hand-rolling cigars. Now known as the Upper Duval neighborhood, the vicinity between Simonton and Duval streets was aptly known as ‘Gatoville.’ At that time it was one of the most successful industrial communities in the United States!

The first Gato factory burned down in 1915 and was soon rebuilt as a prominent concrete and marble structure that today stands as a local monument. Saved by historic preservation efforts, it was completely rehabilitated and now houses Monroe County offices at 1100 Simonton Street. Today this area is known as the Uptown - Upper Duval neighborhood and is steps away from the more elegant 1100  - 1200 block of Duval Street. Many of the houses, including this one, have been beautifully renovated, according to strict local historic guidelines.

The Uptown Island Luxury Villa is conveniently located close to many sought-after Key West locally owned restaurants and unique destinations. You’ll want to stroll around the corner for a French breakfast at the Banana Café, then head south to the world famous Key West Butterfly Conservancy or for a swim at South Beach. Taste wine in the afternoon from the unparalleled selection at Grand Vin Wine Bar. Dine late at the award-winning restaurant Nine One Five Duval. Don’t miss splurging on a warm waffle cone filled with Flamingo Crossing Ice Cream homemade on the premises. This is just a hint of what’s in the Upper Duval Neighborhood. A quick glance at Google Maps will highlight how easy it is to get to many of Key West’s best restaurants and sought-after destinations in a 5-minute walk.

Interior Design and Layout:

A harmonious blend of coastal and cottage style furnishings placed throughout the home set an upbeat island style. Shades of turquoise, sand, yellow and white look stunning against the bare pinewood walls. From room-to-room to outside spaces, soothing tropical colors, bright pattern fabrics and botanical artwork create a casual theme that sets the tone for relaxation and fun.

Indoor / outdoor living is a one of the most enjoyable features of a Key West tropical home, and the more rooms adjoining an outdoor space the better. By reversing the original downstairs floor plan, Uptown Island Luxury Villa was creatively redesigned so that each downstairs bedroom has private access to the outdoors.

The old downstairs floor plan was completely transposed. The living room was relocated from the front of the house to the back, to become an open concept great room. A master bedroom with en-suite bathroom was also added at the back of the house to create more luxury living space. Single pane sliding glass doors were installed, giving each of the back rooms a view and direct access to the outdoor deck and pool.

With the living room moved to the back of the house, the front room was reconfigured as a front downstairs bedroom with en-suite bathroom. To give exclusive front porch access to the bedroom, the house needed a new main entrance.

The main entrance of Uptown Island Luxury Villa is now located midway at the right side of the house. Cleverly camouflaged by a mature magnolia tree, the entrance is not apparent when you first look at the house. But it is easily accessed through a garden gate at the top of the driveway. Step through the gate and a porch adjoins the main entrance door.

Before entering the house, take note of the ceramic gold star plaque mounted to the left of the door given by the Historic Key West Preservation Board. This prestigious award recognizes superior preservation efforts and outstanding artistic design made in the renovation of this historic structure.


Kitchen / Dining / Living Room:

The main entrance steps directly into the open concept great room on the kitchen side of the house. Step inside and soaring ceilings provide a definite wow factor as you pause to get the layout of the house. Immediately to the right is the craftsman staircase leading to the 2nd floor. To the left a door that connects to the front bedroom. Straight ahead is the kitchen and dining island. To the right, past the staircase, the kitchen flawlessly joins the living room area. The entire space is beautifully lit with recessed ceiling and pendant lighting.

Kitchen / Dining - The L- Shape kitchen and dining area are nicely laid out for cooking and entertaining. Bright white cabinets are a dramatic contrast to the bare long-leaf yellow pine walls. White composite countertops and stainless-steel appliances add a touch of elegance. The fully equipped kitchen provides a French door fridge, electric stovetop with oven below, and a space saver microwave above. A table size dining island, with casual seating for 6, also creates a transition from the kitchen to living room grouping.  

Living Room – The stylish living room grouping is furnished with a full-size sofa, 4 leisure chairs, occasional tables, and lamps. There is plenty of comfortable space for 6 people to relax together. If you want to watch movies or a game, a wall mounted 50 inch flat-screen TV is placed on the wall opposite the sofa. Double sets of sliding glass doors at the back of living room provide an alluring view of the lanai.

Lanai / Back Deck / Pool

When you open the sliding glass doors, the room is set for indoor / outdoor living. The living room flows seamless into the lanai and instantly doubles the size of the great room. Styled with the colors of the Caribbean, comfy wicker furniture is topped with bright blue and green striped cushions. There’s room for 6 to comfortably gather and hang out. A flat screen TV is placed on the credenza across from the sofa. All you need to do is choose your favorite seat and nestle in.

From the lanai you command a full view of the outdoor deck and swimming pool with fountain waterfall. Mature palm trees and tropical landscaping provide added privacy and outdoor beauty. Get laid back and take a dip in the pool or catch some sun on the deck. For outdoor paradise dining, a glass top table, with sun umbrella, is perfectly staged between the lanai and swimming pool.

An air-conditioned half-bath adjoins the lanai, providing convenience and ultimate comfort to the outdoor space. Set with a porcelain free-standing sink, commode, and classy nautical theme mirror, walls are finished with the same authentic pinewood found inside.  


The 1st floor of the Uptown Island Luxury Villa provides two bedrooms, each with a private full en-suite bathroom. The master bedroom suite is at the back of the house, and the second bedroom suite is at the front.

Master Bedroom Suite - The interior door for the master bedroom suite connects with the living room wall beneath the stair landing. Wood walls are painted bright white, and blue-grey coastal style furniture give this bedroom  spa-like feel. Furnishings include a king size bed with matching end tables and lamps. Plus, a bureau and closet provide plenty of room for unpacking.

A flat screen TV is placed on the wall, opposite the bed, for easy viewing. Sliding glass doors provide private access to the deck and pool. The focal point of the master bedroom is the view of swimming pool garden.

The white-on-white en-suite bathroom provides a single vanity sink with long composite countertop. A large square mirror is flanked with two vanity lights. An oversized shower, opposite the vanity, is finished with white subway tiles and frameless glass shower doors.

Front Bedroom Suite - The second downstairs bedroom is at the front of the house. The interior door connects with the kitchen wall, near the main entrance to the house. The front bedroom is furnished coastal style in calming colors of sage green and white. It provides a king size bed with end tables and lamps, and a dresser. Vintage pine walls are left natural, and trim is painted white for contrast.

The en-suite bathroom follows the charm and color theme of the bedroom, featuring both white and bare wood walls. It provides a free-standing sink with large round vanity mirror above. The bright white shower is finished with  subway tiles and a frameless glass door.

A focal point of the second downstairs bedroom is its exclusive access to the front sitting porch. The original front porch was turned into a private outdoor space for this bedroom by closing off the porch railing. The main entrance to the house is now accessed through the side garden.

Laundry Closet - It's amazing how cleverly laundry rooms are added to the renovations of historic Key West cottages. In the redesign of this house, the architect added a laundry closet in the short hallway near the doorway to the master bedroom. 


In the redesign of the Uptown Island Luxury Villa the 2nd floor was reserved exclusively for the upstairs bedroom suite. If you’re looking for story-book island charm and privacy, this bedroom suite is for you. Tucked away upstairs the suite has a feeling of intimacy, romance, and peacefulness. 

Upstairs Bedroom Suite:

Ascend the arts and crafts staircase, to reach the third bedroom suite. But before opening the door, pause at the landing and admire the view of the great room below. By looking down you’ll see how the masterful redesign of this historic house, took it from humble cottage to award-winning Key West luxury villa.

The curvaceous shape of the vintage ceiling adds to the intimate feel and artfulness to the bedroom. Furnishings are cottage style, and include a king size bed, bedside tables and lamps, an easy chair, and a bureau for storing clothes. Two windows bounce the light off the white painted walls and fill the room with natural daylight. A colorful vintage rug and rustic occasional table give an additional touch of classic romantic decor.

When you peek into the en-suite bathroom door, notice how it carries the vintage theme. The free-standing sink, vanity lights, and a round mirror set against warm wood walls create a timeless charming look. But step inside and find the elegant modern over-sized shower. Set with white tile and frameless glass doors, everything is updated and sleek.

Exterior Layout and Grounds: From the curb, everything about this house stays true to its vintage design. The classic front porch, gable roofs, and white picket fence, all reflect its historic origins as a shotgun cottage. While outside in back, the stylishly furnished lanai with soaring ceiling, temperature controlled half-bath, heated swimming pool and sun deck, all meet the luxury standards for a private modern Key West home.

Mature palm trees and tropical landscaping frame the front of the house.

The back yard was redesigned as a private tropical pool garden. The entire backyard is surrounded with a variety of lush tropical foliage that create privacy and sets the tone for relaxation and fun.  

Bedding Summary:

Downstairs -

  • Master bedroom - King size bed
  • Front bedroom – King size bed

Upstairs -

  • King size bed

Amenities: Private pool and sundeck. Tropical gardens. Fully equipped kitchen, central a/c, flat-screen TV’s, washer / dryer, grill. Linens and towels are provided. Catering can be arranged. Maid service can be scheduled.

Parking: Off - Street Parking for one standard or compact size car. "Big Rigs" won't fit.

Activities: Around the corner from the 1100 block of Duval Street where you find excellent restaurants and fun eateries including 915 Duval, Banana Café, Grand Vin wine tasting, and Flamingo Crossing homemade ice cream. Close to the famous Key West Butterfly and Nature Conservatory, Key West South Beach, fine gift and clothing stores, and the Southernmost Point of the United States. Start at the top of Duval St. near the Atlantic Ocean and can take the 20 min stroll to the Gulf of Mexico (remember it takes 3 to 4 Key West streets to equal the distance of a typical city block). Sailing, boating, diving, museums, nightlife.

Area: The Upper Duval Neighborhood Old Town Key West is the more elegant end of Duval Street. Here you find a quieter pace than the bar scene found in the 800 block and 500 block of Duval and below. There are an exceptional variety of outstanding restaurants, wine tasting bar, homemade ice cream, South Beach, boutique shops in the Upper Duval Street Neighborhood. Duval Street is perhaps the ultimate tourist street in Key West and certainly the most famous. Nowhere else in the world can you walk a street that connects point-to-point the Atlantic Ocean to the Gulf of Mexico, with a white sandy beach at the south end and Key West Historic Seaport at the north.

Restrictions: Smoke free house. Smoking permitted outside only. We do not accept guests less than 25 years of age unless accompanied by a family group or guardian.



Book Direct For The Best Price Guaranteed

Dates Weekly Nightly Terms
Jan 22, 2022 - Jan 28, 2022 $5620$1084.005 night minimum - 'within' Sat/Sat Only
Jan 29, 2022 - Feb 18, 2022 $6500$1401.007 night min Sat/Sat Only, but 3-5 nights within 60 days
Feb 19, 2022 - Feb 25, 2022 $7140$1395.507 night min Sat/Sat Only, but 3-5 nights within 60 days
Feb 26, 2022 - Apr 17, 2022 $6500$1401.007 night min Sat/Sat Only, but 3-5 nights within 60 days
Apr 18, 2022 - May 29, 2022 $5525$986.755 night min, but 3-4 nights within 60 days
May 30, 2022 - Jun 10, 2022 $5525$997.255 night min, but 3-4 nights within 60 days
Jun 11, 2022 - Aug 7, 2022 $5600$1045.755 night min, but 3-4 nights within 60 days
Aug 8, 2022 - Sep 30, 2022 $4950$926.754 night min. or 3 night min. 60 days prior to arrival.
Oct 1, 2022 - Oct 20, 2022 $5525$997.254 night min. or 3 night min. 60 days prior to arrival.
Oct 21, 2022 - Oct 30, 2022 $8095$1387.757 night minimum
Oct 31, 2022 - Nov 5, 2022 $5525$997.254 night min. or 3 night min. 60 days prior to arrival.
Nov 6, 2022 - Nov 13, 2022 $5600$1045.757 night minimum
Nov 14, 2022 - Nov 18, 2022 $5525$997.253 night minimum
Nov 19, 2022 - Nov 26, 2022 $6400$1150.007 night minimum
Nov 27, 2022 - Dec 16, 2022 $4950$926.754 night min. or 3 night min. 60 days prior to arrival.
Dec 17, 2022 - Dec 25, 2022 $7325$1308.257 night minimum
Dec 26, 2022 - Jan 2, 2023 $8980$1750.007 night minimum
Jan 3, 2023 - Jan 13, 2023 $6015$1160.254 night min. or 3 night min. 60 days prior to arrival.
Jan 14, 2023 - Jan 22, 2023 $6015$1160.254 night min. or 3 night min. 60 days prior to arrival.
Jan 23, 2023 - Jan 29, 2023 $6580$1288.505 night minimum - 'within' Sat/Sat Only
Jan 30, 2023 - Feb 11, 2023 $7210$1288.507 night min Sat/Sat Only, but 3-5 nights within 60 days
Feb 12, 2023 - Feb 18, 2023 $7740$1327.007 night min Sat/Sat Only, but 3-5 nights within 60 days
Feb 19, 2023 - Apr 8, 2023 $7210$1288.507 night min Sat/Sat Only, but 3-5 nights within 60 days
Apr 9, 2023 - May 29, 2023 $5850$1045.504 night min. or 3 night min. 60 days prior to arrival.
May 30, 2023 - Jun 10, 2023 $5420$1045.504 night min. or 3 night min. 60 days prior to arrival.
Jun 11, 2023 - Aug 7, 2023 $5850$1045.505 night min, but 3-4 nights within 60 days
Aug 8, 2023 - Sep 30, 2023 $5190$1045.504 night min. or 3 night min. 60 days prior to arrival.
Oct 1, 2023 - Oct 20, 2023 $5850$1045.504 night min. or 3 night min. 60 days prior to arrival.
Oct 21, 2023 - Oct 30, 2023 $8640$1481.257 night minimum
Oct 31, 2023 - Nov 5, 2023 $5420$1045.504 night min. or 3 night min. 60 days prior to arrival.
Nov 6, 2023 - Nov 13, 2023 $5850$1045.507 night minimum
Nov 14, 2023 - Nov 18, 2023 $5420$1045.503 night minimum
Nov 19, 2023 - Nov 27, 2023 $6600$1160.007 night min Sat/Sat Only, but 3-5 nights within 60 days
Nov 28, 2023 - Dec 16, 2023 $5055$1045.504 night min. or 3 night min. 60 days prior to arrival.
Dec 17, 2023 - Dec 25, 2023 $7345$1311.757 night minimum
Dec 26, 2023 - Jan 2, 2024 $9205$1578.007 night minimum

Additional Notes:

  • High Season generally requires a 7 night minimum stay. Shorter stays of 3 - 5 nights may be available within 60 days of your arrival date or in special situations. Certain dates may not be available if they minimize optimal booking for the property's reservation calendar. Please contact us to inquire about stays less than 7 nights.
  • Shoulder and Low Season is a 3 - 5 night minimum available on reservations made within 60 days of arrival May through mid-August. From mid-August through mid-December, 3 - 5 night minimum stays are available any time.
  • Short Stays are available if there are open nights that are less than the minimum stay, shorter stays may be possible depending on the property. Please contact us to inquire.
  • Holiday, Festival, and Event Rates are 20% to 25% higher. These include, but are not limited to: Fantasy Fest, Thanksgiving, Christmas, New Years, Power Boat Races, Mini-Lobster Season, Labor Day, Parrot Heads Meeting of the Mind, 4th of July, Easter. A 7 night minimum stay is required for most major holidays, festivals, and events.

Rates and Terms are subject to change without notice. Above rates do not include taxes and fees. Click here for more details on additional fees. Please contact us for specific pricing and to confirm rates. Rates in US Funds. (305) 294-7358 Ext 1 -

Apply here for Travel Guard Trip Cancellation and Interruption Insurance.

VHKW offers promotional specials for purchasing trip insurance for stays between Aug 10 and Oct 20. Please call for more details.

Downstairs -

  • Master bedroom - King size bed
  • Front bedroom – King size bed

Upstairs -

  • King size bed


Nov 09, 2021,
House was beautiful, comfortable, very clean great location pool was a great addition!

Nov 02, 2021,
Beautiful accommodations! Three bedrooms w/their own separate bathrooms, an open living area with lots of seating and then the tropical outdoor area w/seating, TV, bathroom and pool, we couldn’t have asked for anything more! Everything was neat and clean! Would definitely stay here again!

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