Entire home·Private host

Hidden Treasure in Old Town: 3BR Home with Pool in Peaceful Gated Enclave

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Photo gallery for Hidden Treasure in Old Town: 3BR Home with Pool in Peaceful Gated Enclave

A spacious living area with a sofa, a wooden coffee table, and a kitchen in the background.
Property video
A white house with a green roof, surrounded by various plants and a red brick pathway.
A covered patio with a wooden ceiling, wicker furniture, and a view of a residential area.
A dining area with a glass table and chairs, a wooden wall with a beach painting, and a door with frosted glass panels.

Reviews

9.6 out of 10
Exceptional

Entire home

3 bedrooms2 bathroomsSleeps 673 sq m

Popular amenities

  • Pool
  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly
  • Free Wi-Fi

Explore the area

View in a map
Key West, FL
  • Place, Key West Naval Station
    ‪2 min walk‬
  • Place, Duval Street
    ‪11 min walk‬
  • Place, Ernest Hemingway Home and Museum
    ‪17 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪9 min drive‬

Room options

Similar properties

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Hidden Treasure in Old Town: 3BR Home with Pool in Peaceful Gated Enclave

Escape to authentic Key West living at Key West Hideaway, a historic 1928 Conch Cottage available exclusively for extended monthly stays. Tucked safely inside a peaceful, gated Old Town enclave on Grinnell Street, this property is designed for travelers seeking the comfort of a true home base.

Whether you're spending the month working remotely, enjoying a winter getaway, or fully immersing yourself in island life, this Cottage gives you the absolute best of both worlds: unbeatable walkability to historic sights and local spots, paired with complete tranquility at the quiet rear of the property.

This Cozy Cottage features two distinct living spaces (the 2-Bedroom Main Home + the Private Studio Suite), offering 2 full bathrooms overall and the ultimate balance of togetherness and privacy.

The Main House (2 Beds / 1 Bath):

-Spacious Living Area: Vaulted ceilings, historic whitewashed Dade County pine walls, custom ambient LED ceiling lighting, and a brand-new sleeper sofa for extra hosting flexibility.
-The Chef's Kitchen (Our Highlight!): Unlike typical vacation rentals, our full-sized kitchen is equipped for real living and daily cooking. Features an induction stove, oven with a built-in air fryer, dishwasher, ample counter space, full cookery, and wine and champagne glasses for special evenings.
-Primary Suite: Features a California King bed, cozy rattan accents, historic solid-oak French doors, and serene coastal decor.
-Second Bedroom/Workspace: Versatile sleeping/working space (daybed opens to a King or two separate twin beds), a dedicated desk area perfect for remote work, and original French doors.
-Full Bathroom: A modern walk-in shower with a wooden vanity, cerulean blue accents, and smart storage options.
-Outdoor Porch: Private screened porch with a swing and bistro seating—ideal for morning coffee or evening breezes.

The Private Studio Suite (1 Bed / 1 Bath):

A Private Retreat: Located on-site with its own entry, high Dade County pine walls, and five oversized windows streaming with natural island light.
Sleeping & Prep Area: Queen-sized bed, high-capacity Cuisinart Digital AirFryer/Toaster Oven, microwave, and mini-prep station.
Luxury Smart Bath: Newly updated bathroom featuring a state-of-the-art smart toilet with bidet, heated seat, auto-open lid, and LED nightlight.


Modern Comforts & Resort Amenities

We've equipped the compound with high-end, brand-new upgrades so your long-term stay feels effortless:
-Brand-New Climate Control: Equipped with state-of-the-art Mitsubishi Split-Unit A/C systems in both the main house and studio for whisper-quiet, custom temperature control.
-Laundry Conveniences: On-site with a brand-new, high-efficiency washer and dryer.
-The Pool: Direct access to a large, sun-drenched pool shared with only six neighboring homes in this quiet gated community. Lounge chairs provided.
-Outdoor Shower & Grill: Rinse off under the open sky after a pool session or beach trip, and enjoy outdoor cookouts on the gas grill.
-Tropical Gardens: Stroll through lush grounds framed by coconut palms, pineapple plants, and an herb garden (Rosemary, Tree Spinach, and Thai Basil).
-Complimentary Bikes: Skip car rentals and parking fees—use our included bikes to cruise the island like a resident.

Unbeatable Old Town Location

Live like a local with incredible neighborhood staples just seconds away:
Across the street (1-Min Walk): Famous Cuban coffee and morning pastries at Five Brothers.
Within 100 Yards: Authentic French-Caribbean dining at Café Solé and fresh homemade pasta at Mangia Mangia.
Duval Street & Historic Seaport: An easy, pleasant 10-minute walk (0.5 miles).
Top Beaches by Bike: Fort Zachary Taylor (8 mins), South Beach (6 mins), Smathers Beach (13 mins).

Experience the real Key West lifestyle for a month or more. Inquire today for monthly availability!
During your stay at this vacation home, you're just a quick walk from Key West Burlesque Theater. Features include an outdoor pool, a gym, and laundry facilities. The vacation home includes amenities such as free WiFi and a kitchen.
  • Air-conditioned home with kitchen, washing machine, and 2 bathrooms
  • Free WiFi (speed: 500+ Mbps (good for 6+ people or 10+ devices))
  • Take a swim in the outdoor pool
  • Amenities include laundry facilities
  • Onsite recreation includes a gym
  • 12 minutes by foot from Duval Street and a 3-minute drive from Ernest Hemingway Home and Museum
This vacation home offers its guests an outdoor pool and a fitness center. This vacation home also features barbecue grills, a garden, and laundry facilities.

Property amenities

Beach

  • Beach nearby
  • Beach towels

Pool/Spa

  • Communal pool
  • Fenced private pool
  • Heated pool
  • Outdoor pool

Internet

  • Available in the house: Free WiFi

Parking and transport

  • No on-site parking available

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Hob
  • Lobster/crab pot
  • Microwave
  • Oven
  • Refrigerator
  • Toaster

Dining

  • Dining table

Bedrooms

  • 3 bedrooms
  • Bedsheets provided
  • Sofa bed

Bathroom

  • 2 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Fireplace

Entertainment

  • Books
  • Smart TV

Outdoor areas

  • Barbecue grill
  • Fenced yard
  • Garden
  • Porch/lanai

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk
  • Desk chair

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming dogs only
  • Up to 453 kg per pet

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • 3 steps to reach entrance
  • Area rugs in public areas
  • Hardwood flooring in public areas
  • No lift
  • Single level property
  • Tile flooring in public areas
  • Well-lit path to entrance
  • Wheelchair-accessible path of travel
  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the city centre
  • Near a health/beauty spa
  • Near a hospital
  • Near a zoo
  • Near the marina
  • Near the sea

Things to do

  • Bicycles
  • Gym
  • Heated pool
  • Birdwatching nearby
  • Cycling nearby
  • Ecotours nearby
  • Fishing nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Parasailing nearby
  • Sailing nearby
  • Scuba diving nearby
  • Snorkelling nearby
  • Surfing/bodyboarding nearby
  • Swimming nearby
  • Water skiing nearby
  • Whale watching nearby
  • Windsurfing nearby

Safety features

  • No carbon monoxide detector or gas appliances (host has indicated there are no carbon monoxide detectors or gas appliances on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher
  • Deadbolt lock

General

  • Bicycles
  • Garden
  • Recycling
  • Unit size: 784 square feet

Policies

Check-in

Check-in time starts at 5:00 PM
Contactless check-in available
Minimum check-in age: 26

Check-out

Check-out before 10:00 AM
Contactless check-out available

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Check-out instructions

The host requires you complete the following before checking out:
Remove personal items, remove leftover food and drinks, and take out the trash
Turn off the lights, lock the doors, and return the keys
Failure to complete these may result in a negative review from the host.

Pets

  • Pets are welcome
  • Only dogs are allowed
  • Maximum 2 (weight limit: 999 lbs per pet)
  • Service animals are exempt from fees

Children and extra beds

  • Children are welcome.

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Long-term renters welcome
Host has indicated there are no carbon monoxide detectors or gas appliances on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadbolt lock
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
You will receive an email from the host with check-in and check-out instructions. You will also receive an email from Vrbo with a link to a Vrbo account which will enable you to manage your booking.

Hidden Treasure in Old Town: 3BR Home with Pool in Peaceful Gated Enclave Reviews

Reviews

9.6

Exceptional

Rating 10 - Excellent. 4 out of 5 reviews
Rating 8 - Good. 1 out of 5 reviews
Rating 6 - Okay. 0 out of 5 reviews
Rating 4 - Poor. 0 out of 5 reviews
Rating 2 - Terrible. 0 out of 5 reviews

9.6/10

Cleanliness

Reviews

Verified review

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great month in KW

We loved our stay here! Quiet cottage in the best location. The pool was lovely and nice to take advantage of during our days. Easy check-in and seamless communication with the owners.
Stayed 27 nights in Feb 2025
Verified review

10/10 Excellent

Jay M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Key West gem.

This little cottage community in Old Town, minutes from Schooner Wharf is the best. Friendly neighbors, great pool, and a wonderful cottage home.
Stayed 28 nights in Dec 2024
Verified review

10/10 Excellent

Carol B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing hosts and place

Location is in a safe and quiet neighborhood. It is also within walking distance or bike ride to places around town…the Basilica, Duval street, Hemingway’s house, local library, etc. The hosts were phenomenal!: quickly responding to inquiries, kind, respectful, and accommodating to our needs. I highly recommend you check it out and choose this place for your stay.
Stayed 152 nights in Apr 2023
Verified review

8/10 Good

lauren g.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great little community

Great location!! Cute little complex of beach shanty homes. Quiet, comfortable This place has lots of potential. It’s a work in or and will only keep getting better and better The owners were amazing! Very pleasant to work with Enjoy this little gem
Stayed 30 nights in Mar 2023
Verified review

10/10 Excellent

Jerry R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Awesome in all the best ways!

The host were amazing from day one! This little place is in a prime location and a short walk or bike ride away from everything! This location also has access to a pool which is awesome to jump in after a nice run or hang out and relax after a long night in the Key West night life! Overall, amazing hosts, prime location, great home and an amazing slice of Key West living!
Stayed 123 nights in Jun 2022