The Captain's Hideaway: Key West Florida - 3 Bedroom Vacation Rental for Rent

The Captain's Hideaway
The Captain's Hideaway
Fourth Floor Outdoor Entertaining Space
Shared Heated Pool

The Captain's Hideaway: Key West Florida - 3 Bedroom Vacation Rental for Rent

Key West Florida

149 Simonton Street
How Many Bedrooms? 3 Bedrooms • Sleeps 8
How Many Bathrooms? 3 Full, 1 Half Bathrooms
Pool: Pool (Private)
Internet: Internet Access
Television: Television
Washer/Dryer: Yes
Map of Key West

Rates & Availability  
(Displayed in USD)

  • Rates From $397 to $800 per night
  • Rates From $2,779 to $5,600 per week
  • Rates From $11,910 to $23,867 per month
  • Minimum Stay: 30 Days

Season Nightly Weekly Monthly
Jun 01, 2023 - Jun 30, 2023
Minimum Stay: 30 Days
$397 $2,779 $11,910
Jul 01, 2023 - Jul 31, 2023
Minimum Stay: 30 Days
$500 $3,500 $15,000
Aug 01, 2023 - Aug 31, 2023
Minimum Stay: 30 Days
$397 $2,779 $11,910
Sep 01, 2023 - Sep 30, 2023
Minimum Stay: 30 Days
$397 $2,779 $11,910
Oct 01, 2023 - Oct 31, 2023
Minimum Stay: 30 Days
$667 $4,669 $20,010
Nov 01, 2023 - Nov 30, 2023
Minimum Stay: 30 Days
$567 $3,969 $17,010
Dec 01, 2023 - Dec 31, 2023
Minimum Stay: 30 Days
$667 $4,669 $20,010
Jan 01, 2024 - Jan 31, 2024
Minimum Stay: 30 Days
$667 $4,669 $20,010
Feb 01, 2024 - Feb 29, 2024
Minimum Stay: 30 Days
$800 $5,600 $23,867
Mar 01, 2024 - Mar 31, 2024
Minimum Stay: 30 Days
$667 $4,669 $20,010
Apr 01, 2024 - Apr 30, 2024
Minimum Stay: 30 Days
$567 $3,969 $17,010
May 01, 2024 - May 31, 2024
Minimum Stay: 30 Days
$500 $3,500 $15,000

Property Description


Prepare to be utterly delighted with your choice of this luxury 4 story, 3 bedroom - 3.5 bath townhome for your vacation rental. The Captain’s Hideaway is part of a recently constructed 20-villa enclave in the heart of fabulous Key West. The Hideaway features professional landscaping, a private garage, balconies on every floor, a water view, heated pool for the exclusive use of the Old Town Villas gated community, a private elevator from the 1st to the 4th level and that just starts the list. This enclave is a mere block off the infamous Duval Street and steps from the Gulf of Mexico, restaurants, water sports, historic tall ships, and everything else vacationers from around the globe come to Key West to enjoy. Yet at the same time The Captain’s Hideaway is ultra private, ultra quiet, and ultra exclusive.

The first floor foyer sets the tone for ready access with the front door, the garage door, the back door, a short flight of stairs going up, and the elevator bay that takes you from here to the roof top balcony and every stop in between. The residence has a metal roof, impact windows that filter out any outside noises, granite countertops, stainless appliances, two zone AC, and walk-in closets.

The next level (whether you get there by riding or walking up) holds the living, dining, and kitchen areas with a generous pantry. Wireless high-speed internet, full cable, and Sonos sound serve this floor and the others as well. The floor plan is open structure, which avoids superfluous walls, helps spread natural light, and maintains an emphasis on contemporary simplicity of design.

The signature color scheme throughout is in a restful neutral palette, while carefully curated art brings in delightful pops of tropical and marine colors. As you come up onto the second floor, you are looking at cloud white walls and white oak floors. Against one wall is a curved sofa in a complementary cream tone that easily seats four or more. Behind it is a one-of-a-kind branching floor lamp in a brass finish with five light heads. A round, dark wood coffee table and unobtrusive end tables stand ready to hold a beverage or book or the remote for the large flatscreen TV positioned for easy viewing across the room. The end wall is no wall at all. Instead it is French doors opening onto a delightful small balcony for when you want to sit in sunlight. A comfy armchair sits between the glass doors and a low-profile credenza. Its doors hide whatever you want out of sight, and its top is a handy place for keys, cell phones, or whatever.

Next comes a dining table with four chairs. And conveniently next to that is a chef’s kitchen in dark tones with stainless, high-end appliances, including dishwasher. An elevated section of the granite counters forms a sit-at ledge with four stools that is perfect for a quick cup of coffee or leftovers from dinner out the night before. Of course all the food prep and serving amenities are included and ready to be used. Afterwards the dishwasher makes for easy cleanup.

Through the next doorway is a beautifully appointed queen bedroom and full bath. The first thing noticeable about the room is an oversized square window that takes up most of the wall opposite the bed. The window panels open to let in the flow of tropical breezes. Or shut and shade them at night for complete privacy. A closet provides ample room for travel clothing. Overhead a Florida ceiling fan adds ambience and air circulation. A desk and a large-screen TV make the room multi-purpose. And the ensuite full bath is accessible from the hall and of course from the bedroom itself.

The third floor repeats this very livable pattern with two King bedrooms with full ensuite baths each, walk-in closets, ceiling fans, TVs, copious closet space, and other amenities. One bedroom has French doors and the other has a balcony. Conveniently on this floor is also the washer/dryer.

While the fourth floor can function as a fourth bedroom with a queen sleep sofa and half bath, its real purpose is as entertainment central. At one end, a small balcony provides a view of the Historic Seaport where, at the right time of day, you can witness the Jolly Rover and other tall ships heading out for a daytime or sunset sail. At the other end of this level is a large balcony great for entertaining and taking in the spectacular sunset. The chaise loungers and chairs that populate this open-air terrace make for outside Key West style entertaining. Inside between the water view and the entertainment balcony is plenty of seating for conversations, for game night, for watching a movie on the flatscreen. There’s a wet bar for cocktail paraphernalia. And a wine cooler that makes the hardest decision whether to stock bubbly, red, white, or rose.

The residence is a bastion of creature comforts, but one more feature is on offer—the pool oasis. Within the compound is a generous deck, pool, and cabana area. The waters are temperature controlled and for the exclusive use of Old Town Villas guests and owners. Float or swim in the sparkling waters gazing up at the cloudless, endless conch sky. Or stretch out on a chaise lounge to work on a tan, to read, or just relax. Maybe enjoy a late-night dip to polish off an amazing day on an amazing island.

When you’re ready to explore more than your residence, strap on your Fitbit or Apple Watch to enjoy the ever-so-walkable island. Or bike. Or take a pedicab to all that you want to experience. Immediately to the right is the Seaport and Harbor Walk where artists, musicians, writers, locals, and visitors stroll.
Follow the wooden boardwalk along the Gulf of Mexico to find historic tall ships offering cruises. Or take an all-day ferry excursion to the Dry Tortugas. If you’re interested in watersports, you’ll find diving, fishing, parasailing, snorkeling, jet-skiing, and more. If you get hungry, a dozen or so restaurants of varying levels of informality ring the harbor. Don’t miss the Raw Bar, the Boathouse, and Schooner Wharf, where you can eat a fresh Mahi sandwich or Conch Fritters under a banyan tree. Or walk on down to find equally as enticing food spots and watering holes. Be sure to look up to see second-story restaurants like Bel Mar and A&B Lobster. With nearly four hundred eating establishments and forty-three bars on the four-square-mile island, there’s no excuse to go hungry or thirsty. Duval Street is also lined with restaurants and bars, shopping, art galleries, tours, and much more. For even more restaurants, the Atlantic side of the island has Louies Back Yard, Sun-Sun at the Casa Marina, and Salute on the Beach, which is the sister restaurant to the famous Blue Heaven.

For tastes that run toward cultural activities, there’s live music, art exhibitions, and plays. Perhaps catch a movie on one of the screens at the Tropic Cinema. Or stop in at Books & Books to catch a glimpse of the author Judy Blume stocking the shelves. And don’t forget to set your alarm for sunset so you don’t miss the nightly party at Mallory Square, where visitors and locals gather to applaud as the sun slips below the horizon.

**For Pet Friendly (dog) homes there are restrictions that include, but may not be limited to, the following: pet friendly means dogs, no other animal is permitted. Dogs are restricted to one (1) large dog or two (2) small dogs per stay. Due to Homeowner Insurance restrictions we are unable to accommodate the following breeds: Pit Bull Terriers, Staffordshire Terriers, Rottweilers, German Shepherds, Presa Canarios, Chows Chows, Doberman Pinschers, Akitas, Wolf-hybrids, Mastiffs, Cane Corsos, Great Danes, Alaskan Malamutes, Siberian Huskies nor any mixed breed that contain one of the preceding as part of that mix. Guest is responsible for an additional pet fee of $200.

Property Features

» Parking
» Ceiling Fan(s)
» Stereo
» Microwave

Featured Amenities

» Pool (Private)
» Internet Access
» Grill
» Television
» Washer/Dryer
» Dishwasher

Other Property Amenities

    Bed Size 1st/Master: King, Bed Size 2nd Rm: King, Bed Size 3rd Rm: Queen, Beds Pull-out: Queen Sleep Sofa, Number of Baths: 3 Full, 1 Half, Square Footage, Est.: 3,400, Patio: Yes, Air Conditioned: Central, Bldg. Complex Name: Old Town Villas at Key West, Beach Distance: Walking, Dog: w/ Restrictions - See FAQ's.

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