Entire home

Pool, Pet-friendly, Bicycles and 5 min walk to Beach

Vacation home with kitchen, 9-minute walk to Duval Street

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In Key West's charming Old Town, The Headquarters offers a relaxing retreat for small families and close friends. Enjoy the shared swimming pool, nearby beach access, and explore shops and restaurants within walking distance. Unwind on the couch with free WiFi or whip up a meal in the kitchen.

Reviews

10 out of 10
Exceptional

Entire home

2 bedrooms1 bathroomSleeps 464 sq m

Popular amenities

  • Pool
  • Kitchen
  • Washer
  • Dryer
  • Pet friendly
  • Air conditioning

Add dates for prices

About this property

Entire place

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

Pool, Pet-friendly, Bicycles and 5 min walk to Beach

Conched Out Cottage

Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'

Please note: This home requires a minimum stay of 28 nights or longer, as enforced by the HOA. No exceptions can be made.

Welcome to Conched Out Cottage, your ideal long-term island escape in the heart of Old Town Key West. This charming, dog-friendly monthly rental is perfect for small families, couples, or close friends looking to settle into the relaxed rhythm of island life—just minutes from the beach and the best of Key West.

Set in a quiet residential neighborhood just down the street from Higgs Beach, this inviting retreat offers the perfect balance of tranquility and convenience. You’re close to Duval Street’s lively restaurants, bars, and boutiques, as well as endless opportunities for outdoor island adventures. Spend sunny afternoons lounging by the heated shared pool (shared with only three other units), or explore the historic streets on the provided adult bikes.

Inside, you’ll find a bright, welcoming living space with comfortable seating, a flat-screen TV with cable, and free high-speed WiFi—ideal for both relaxing evenings and remote work. The fully equipped kitchen makes it easy to prepare home-cooked meals, while the private backyard patio with outdoor seating is the perfect spot for morning coffee, afternoon reading, or sunset cocktails.

Thoughtful conveniences include a private washer and dryer, central air conditioning, and off-street private parking. Up to two well-behaved dogs are welcome with a small nightly fee, so your furry companions can enjoy island living too.

Whether you’re planning a snowbird stay, a remote-work-friendly getaway, or simply a relaxing monthly rental in paradise, Conched Out Cottage offers a comfortable, charming home base to truly experience the Key West lifestyle.

Book your extended tropical stay today!

Please note: last-minute bookings cannot be made online. Please call us for additional details.

This property is managed by Vacasa Florida LLC.

If you are bringing a dog on your trip, the pet fee is already included in your quote when selecting ‘Yes’ to pets. If you would like to add more dogs, please contact us.

Parking notes: There is free parking available for 1 vehicle.

Please note: this home resides in a noise-sensitive area and the owners participate in our Good Neighbor protection program. Our smart home technology will alert our team if excessive decibel or occupancy levels are detected, allowing us to reach out directly with a reminder of maximum occupancy and quiet hours. This technology is privacy compliant, and only monitors the presence of decibels and devices-not any personal conversation or information. Thank you for supporting our efforts to be good neighbors!

Damage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.
More information can be downloaded from the "Rental Agreement" on the checkout page.

Due to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

Property amenities

Pool/Spa

  • Communal pool

Internet

  • Available in the house: WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Microwave
  • Oven
  • Refrigerator
  • Stovetop

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

  • 1 bathroom
  • Free toiletries
  • Hair dryer
  • Towels provided

Living spaces

  • Living room

Entertainment

  • TV with cable/satellite channels

Outdoor areas

  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning

Pets

  • Pet friendly

Suitability/Accessibility

  • Smoking not allowed
  • Note from host: Smoking is not permitted anywhere on the premises.

Services and conveniences

  • Iron/ironing board

Location highlights

  • Near the sea

Things to do

  • Bicycles
  • Fishing nearby
  • Swimming nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • First aid kit
  • Fire extinguisher

General

  • Bicycles
  • Unit size: 694 square feet

Similar properties

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in available
Minimum check-in age: 25

Check-out

Check-out before 10:00 AM

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

Rules

For information about quiet hours, please refer to the listing description.

Pets

Pets allowed
Service animals are welcome, and are exempt from fees
Note from host: Dogs only. Max of 2.

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted
Smoking is not permitted anywhere on the premises.

Important information

You need to know

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
Host has indicated there is a carbon monoxide detector 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 first aid kit
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
Property Registration Number 32512

Property is also known as

10845

About the neighborhood

Located by the sea, this vacation home is in Old Town Key West, a neighborhood in Key West. Southernmost Point and Ernest Hemingway Home and Museum are notable landmarks, and the area's natural beauty can be seen at Fort Zachary Taylor Historic State Park and Florida Keys Beaches. Key West Butterfly and Nature Conservatory and MLK Community Pool & Community Center are also worth visiting. With fishing and swimming nearby, you'll find plenty of adventures in the water. Visit our Key West travel guide
View more Vacation Homes in Key West
Map
Key West, FL

What's nearby

  • Duval Street featuring signage
    Duval Street
    9 min walk - 0.8 km
  • South Beach featuring a sandy beach and general coastal views as well as a small group of people
    South Beach
    9 min walk - 0.8 km
  • Key West Butterfly and Nature Conservatory featuring zoo animals, animals and flowers
    Key West Butterfly and Nature Conservatory
    9 min walk - 0.8 km
  • Southernmost Point showing signage
    Southernmost Point
    11 min walk - 1.0 km
  • Ernest Hemingway Home and Museum featuring heritage elements and a house
    Ernest Hemingway Home and Museum
    12 min walk - 1.0 km

Getting around

  • Key West Intl. Airport (EYW)
    8 min drive

Restaurants

  • Dions Truman & White
    5 min walk
  • Sandy's Café
    4 min walk
  • Morrison's Market
    9 min walk
  • El Siboney Restaurant
    2 min walk
  • Tipsy Rooster
    10 min walk

Frequently asked questions

Does Pool, Pet-friendly, Bicycles and 5 min walk to Beach have a pool?

Yes, this property has a pool.

Is Pool, Pet-friendly, Bicycles and 5 min walk to Beach pet-friendly?

Yes, pets are allowed at this property.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Pool, Pet-friendly, Bicycles and 5 min walk to Beach?

Check-in begins at 4:00 PM.

What time is check-out at Pool, Pet-friendly, Bicycles and 5 min walk to Beach?

Check-out is at 10:00 AM.

Where is Pool, Pet-friendly, Bicycles and 5 min walk to Beach located?

Located in Old Town Key West, this vacation home is within a 10-minute walk of Key West Firehouse Museum, Duval Street, and Florida Keys Beaches. South Beach and Southernmost Point are also within 15 minutes.

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Pool, Pet-friendly, Bicycles and 5 min walk to Beach Reviews

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travelers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
Rating 10 - Excellent. 6 out of 6 reviews
Rating 8 - Good. 0 out of 6 reviews
Rating 6 - Okay. 0 out of 6 reviews
Rating 4 - Poor. 0 out of 6 reviews
Rating 2 - Terrible. 0 out of 6 reviews

10

Cleanliness

10

Location

Reviews

This review comes from a trusted partner site and has not been verified.

10/10 Excellent

William N.

Experience Key West

Great home, centrally located, great neighborhood and close to everything!

10/10 Excellent

Suzanna G.

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

Book it!

Great stay!
Stayed 28 nights in Feb 2025
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Martha C.

June 2025

Such an adorable little cottage. Perfect quiet location close to everything. Great friendly neighbors. The pool was perfect and just steps out the back door. Ceiling fans in every room were crucial to keeping the place cool. Comfy beds. Great appliances. Can’t wait to book again next year.
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Kevin P.

Kperry

Location Location Location close to Higgs beach close to Duval street both walking distance gym also walking distance tons of places to eat great neighbors all good.
Stayed 31 nights in Dec 2019

10/10 Excellent

William W.

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

Awesome location and comfortable stay

The house was perfect for the two of us. Bedding was comfortable. My only con is the temperature of the pool stayed in the 90’s. In the pic, it showed a tarp partially covering the pool. There was no tarp.
Stayed 28 nights in Jun 2022
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Laura C.

Bungalow in Paradise

This was the best vacation I have ever gone on in my entire life. Experienced many new and exciting things and the home could not of been in a better location. Would recommend this wonderful getaway to anyone wanting to live the Key West dream!