Entire home

Down Island Digs - 2BR Cottage 1 Block off Duval Street Key West w/Private Pool

Photo gallery for Down Island Digs - 2BR Cottage 1 Block off Duval Street Key West w/Private Pool

A white house with a porch, surrounded by lush tropical vegetation.
Pool
A kitchen with a sink, a ceiling fan, and a view of the outside.
A porch with a metal sculpture, bicycles, and a Christmas tree.
A theater with a pink and white facade, a large arched entrance, and a sign that reads "WEST THEATER".

Reviews

9.4 out of 10
Exceptional

Entire home

2 bedrooms2 bathroomsSleeps 671 sq m

Popular amenities

  • Pool
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning

Explore the area

View map
Key West, FL
  • Place, Duval Street
    ‪1 min walk‬
  • Place, Mallory Square
    ‪9 min walk‬
  • Place, Ernest Hemingway Home and Museum
    ‪11 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪11 min drive‬

Room options

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About the area

Key West

This holiday home puts you in the heart of Key West, steps from Duval Street and within a 10-minute stroll of Mallory Square. Highlights at this holiday home include a kitchen, a private pool and a washing machine. .Home features free WiFi, 2 bathrooms and a patio. In-room dining is easy with a kitchen that comes equipped with a fridge, a microwave and a stovetop. A sofa bed, a living room and a fenced private garden are also available. .Attractions within a 10-minute walk of this Old Town Key West holiday home include Florida Keys Beaches and Ernest Hemingway Home and Museum.

What's nearby

  • Duval Street - 1 min walk - 0.0 km
  • Key West Naval Station - 7 min walk - 0.7 km
  • Harry S. Truman Little White House - 7 min walk - 0.7 km
  • Mallory Square - 9 min walk - 0.8 km
  • Ernest Hemingway Home and Museum - 11 min walk - 0.9 km

Getting around

  • Key West, FL (EYW-Key West Intl.) - 10 min drive

Restaurants

  • ‪Margaritaville - ‬2 min walk
  • ‪Green Parrot Bar - ‬4 min walk
  • ‪Wendy's - ‬3 min walk
  • ‪Mangoes Restaurant - ‬4 min walk
  • ‪Jack Flats - ‬2 min walk

About this property

Entire place

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

Down Island Digs - 2BR Cottage 1 Block off Duval Street Key West w/Private Pool

Everything about this historic Key West tropical gem adds up to make a precious private garden cottage. Sitting in the mature tropical tree garden in the hidden back yard, you would never know you`re just 1/2 block off Duval Street in Old Town Key West. It is indeed rare to find a cottage property in this city centre island location situated on two full private lots with such lush mature tropical landscaping.

A focal point of this unique property is the Key West quintessential indoor / outdoor living that makes island life so wonderful. Even though you are located in the down town Key West area, the entire large back garden is made private with high fences and unless you`ve been back in this yard you would never know this spacious garden is here. A redesign of the garden features an adorable tropical living area complete with lounging hammock stretched between a giant gumbo-limbo and grand palm tree. A round stone garden table set amidst a stage of soft river stones and variety of fanciful foliage, makes a relaxing setting to enjoy a garden lunch that you can buy right across the street at Fausto`s Fine Food Palace. At the front part of the garden, next to the cottage, is a wooden pool deck which is joined by sliding glass doors to the interior living room and pool-side bedroom. The wooden deck surrounds the graceful lounge pool which you enter down a graduated underwater stair case.

In contrast to the expansive back garden, the interior sitting room area of the Down Island Digs holiday cottage is made cosy and charming. Colourful walls of Caribbean blue and sage green create the back drop for whimsically framed mirrors that offset the comfy coral coloured sofette, fan-back `queen chair` and home spun dining table that command the space between the indoors and outdoors. Then over-sized sliding glass doors open up the back of the cottage by connecting the deck on both sides of the living room to draw guests onto the deck to the outdoors. Chocolate coloured wicker outdoor living room furniture provides plenty of pool side seating under a forest green awning to create an irresistible tropical indoor / outdoor living room comfortable for lounging.

The U-shaped kitchen is traditional cottage-style with bright white tiles and light wood cabinets. Adjoining the small dining and living room area, the kitchen is fully equipped, offers a full size electric range, dishwasher, and refrigerator with ice maker and has a nice view of the pool and garden so the cook can be part of the party. The Cottage wooden floors throughout the living room, kitchen, and bedrooms feel nice to bare feet.

The bedrooms have a tropical flare and are comfortable and inviting. The coral coloured spacious master suite is towards the front of the cottage and offers a luxurious king size, cottage-style white 4-poster bed, with pillow top mattress, full size sofa sitting area, and wall mounted flat screen TV. The master suite offers an en-suite bath and has direct outdoor access to the front porch of the cottage for sitting and watching the world go by.

The sage-colored pool side bedroom is towards the back of the cottage and offers a queen size bed and bedside TV and DVD player. This bedroom has a view of the pool and sliding glass doors that open out directly onto the pool deck for that quick dip in the morning.

Interior Layout: The floor plan of this vintage cottage has been re-worked to focus the main living area towards the back of the cottage so that indoor / outdoor pool garden living is maximised. The cottage is not entered through the front door, but instead is accessed through an extra tall locked green garden gate situated immediately to the left of the front of the cottage. Once through the gate a deck leads to the back of the cottage where you enter to the interior. As you enter the cottage you step into the sitting / dining / kitchen area which also has sliding glass doors on the back wall that lead to the pool deck and garden.

Proceeding forward, past the dining area, you find the sage coloured pool-side bedroom which also has a sliding glass doors leading to the pool. Immediately to the right of this bedroom is a full bathroom just off the open hall. At the end of the hall just past the kitchen, is door to the coral coloured master bedroom. Located towards the front of the cottage, the master suite was the original living room space, before the cottage was reconfigured to meet modern requirements of linking the interior to the outdoor pool garden area. An en-suit bathroom joins the master bedroom to the right of the bedroom door.

The front sitting porch, and front door entrance, is visible to the street but has been railed off to block street access and has been re-designed to become a private sitting porch for the master bedroom.

Notes: The layout of this cottage makes it ideal for 2 couples or it is a wonderful space for 1 couple or single who want to spread out. The sleeper sofa in the master suite works great for one couple with a child, or for guests who need extra space and do not mind sharing a bedroom.

If you love this cottage but need to sleep more people, you can rent it with the four bedroom Pavilion Villa. You can combine a rental of both properties and sleep up to 12 by renting the Island Rendezvous holiday compound.

Bedding Summary:

Master bedroom Four Poster king (pillow top mattress) size bed.
Queen Sleeper sofa
Second Bedroom - queen size bed.
Living room - twin sleeper sofa.
Amenities: Swimming pool, pool deck, large tropical gardens. New fully equipped kitchen, a/c, telephone, Internet, cable TV and DVD, stereo, washing machine / dryer. Linens and towels are provided.

Parking: Private off - Street Parking in lot across the street for one car. If you arrive by car plan to park it in your designated private parking space and enjoy walking or biking around the island.

Activities: This property is located right next door to our Pavilion Villa and is just a few blocks from Mallory Square Sunset Celebration, steps from Fausto`s Food Palace for grocery shopping, excellent city centre restaurants, popular clubs, the Historic Seaport, and tropical shops makes this one of the most requested and convenient accommodation in Key West. With the size of the garden in this city centre location we are pleased to offer it as one of our more unique properties available in Old Town.

Area: City centre Old Town Historic Key West. Just one-half block off Duval Street. Walk to all Old Town Key West features. Great restaurants, shops, galleries, clubs, Hemingway House Museum, Light House Museum, Custom House Museum, Key West Aquarium, Ship Wreck Museum. 10 minute stroll from the famous Sunset Celebration at Mallory Square.

Restrictions: Smoke free house. Smoking permitted outside only. Absolutely no pets. (Please don`t ask!) This home is offered as an exclusive holiday rental in the most requested location in Key West. We do not accept guests less than 25 years of age unless accompanied by a family group or guardian.

PAYMENT: Payment for the rental will be processed outside of VRBO according to the terms of your rental agreement (sent for review upon reservation). Payments by credit card are subject to an additional 2.95% merchant processing fee.
PARKING: There is one (1) parking space only for Down Island Digs, but please note it is NOT the driveway to the left of the house. The parking space is kiddy corner, and across the street from the house. With your back to the house, look across the street and to your right, to see the lot.

Park in the space in the lot marked with the parking sign on the fence that reads ‘508 Bahama St.’ DO NOT park in ‘Fausto’s Fine Foods’ car park directly across Bahama St. There is a parking attendant who watches nearly 24 hours a day, and if you park there you will be ticketed or towed.

Short Driveway in front of the House: There is a short driveway in the front to the left side of the cottage, between this property at 508 Bahama St., and the cottage next door at 510 Bahama St. Notice: This space is for loading and unloading only. This space is too short to park a car in, and if your car hangs out even slightly over the pavement, you will most certainly be given a ticket by the diligent parking officers that patrol city centre Old Town Key West. Do not block the gates, or you will be in violation of fire safety regulations.

Similar properties

Property amenities

Pool/Spa

  • Heated pool
  • Private pool

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Car not required
  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Ice maker
  • Microwave
  • Oven
  • Refrigerator
  • Toaster

Dining

  • Dining table

Bedrooms

  • 2 bedrooms
  • Bedsheets provided
  • Sofa bed

Bathroom

  • 2 bathrooms
  • Hair dryer
  • Towels provided

Living spaces

  • Dining table
  • Living room

Entertainment

  • TV

Outdoor areas

  • Fenced yard
  • Garden
  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk

Comfort

  • Air conditioning

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

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

Things to do

  • Heated pool
  • Birdwatching nearby
  • Ecotours nearby
  • Motor boating nearby
  • Swimming nearby
  • Wildlife walks 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)
  • Fire extinguisher

General

  • Garden
  • Unit size: 764 square feet

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in and check-out are 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

PARKING: There is one (1) parking space only for Down Island Digs, but please note it is NOT the driveway to the left of the house.

Pets

  • No pets allowed

Children and extra beds

  • Children are welcome.

Events

No events allowed

Smoking

Smoking is not permitted

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
This property accepts cash
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that 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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business or profession. This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children. If you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room. This property accepts cash. On-site parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher and a smoke detector in all accommodation.

Property is also known as

Down Island Digs Ideal Location Downtown House Key West
Down Island Digs Ideal Location Downtown House
Down Island Digs Ideal Location Downtown Key West
Down Island Digs Ideal Location Downtown
Down Digs With Private Pool
Down Island Digs ~ Downtown With Private Pool Cottage
Down Island Digs ~ Downtown With Private Pool Key West
Down Island Digs ~ Ideal Location Downtown Private Pool
Down Island Digs ~ Ideal Location Downtown Private Pool
Down Digs Ideal Location House
Down Island Digs ~ Downtown With Private Pool Cottage Key West
239270

Frequently asked questions

Are there any beaches close to Down Island Digs - 2BR Cottage 1 Block off Duval Street Key West w/Private Pool?

Yep, Down Island Digs - 2BR Cottage 1 Block off Duval Street Key West w/Private Pool is a short 10-minute walk from Florida Keys Beaches. Fun beach activities include swimming. You can also find motor boats.

Does Down Island Digs - 2BR Cottage 1 Block off Duval Street Key West w/Private Pool have a pool?

Down Island Digs - 2BR Cottage 1 Block off Duval Street Key West w/Private Pool has a heated pool and a pool.

What luxury perks are available at Down Island Digs - 2BR Cottage 1 Block off Duval Street Key West w/Private Pool?

This property features a heated pool, as well as a private pool and a living room.

Is there a private hot tub at Down Island Digs - 2BR Cottage 1 Block off Duval Street Key West w/Private Pool?

No, but there is a private pool.

Is there a free airport shuttle available at Down Island Digs - 2BR Cottage 1 Block off Duval Street Key West w/Private Pool?

No, Down Island Digs - 2BR Cottage 1 Block off Duval Street Key West w/Private Pool does not offer an airport shuttle service.

What time are check-in & check-out at Down Island Digs - 2BR Cottage 1 Block off Duval Street Key West w/Private Pool?

Check-in begins at 4:00 PM. Check-out time is 10:00 AM.

Are pets allowed at Down Island Digs - 2BR Cottage 1 Block off Duval Street Key West w/Private Pool?

No, pets are not allowed.

Down Island Digs - 2BR Cottage 1 Block off Duval Street Key West w/Private Pool Reviews

Reviews

9.4

Exceptional

Rating 10 - Excellent. 36 out of 45 reviews
Rating 8 - Good. 4 out of 45 reviews
Rating 6 - Okay. 4 out of 45 reviews
Rating 4 - Poor. 0 out of 45 reviews
Rating 2 - Terrible. 1 out of 45 reviews

9.8/10

Cleanliness

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Plant have asked for a better experience!! Leah was AWESOME and lightning fast with communication…can’t wait to come back
Stayed 5 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
Great location, clean, zero issues.
Stayed 4 nights in Mar 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Host was excellent to work with and place was nicely appointed. Very easy to get to all the fun and important things Key West has to offer.nloved it.
Stayed 4 nights in Dec 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Down Island Digs is perfectly situated for anyone looking to enjoy the best of the area. It’s just a block off Duval Street, making it easy to walk to restaurants, bars, shops, and attractions, while still feeling pleasantly tucked away from the busiest crowds. Having Fausto’s Market directly across the street is incredibly convenient for groceries and essentials. The central location makes getting around effortless, whether you’re heading out for sightseeing, dining, or a relaxing day by the pool back at the house. You really couldn’t ask for a better spot.
Stayed 5 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Nice area, walking distance to Duval and most restaurants etc. Wonderful backyard. House was equipped.
Stayed 2 nights in Feb 2026
Verified review

10/10 Excellent

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

Key West trip

This is a great property if you want to be close to all Key West has to offer.
Stayed 7 nights in Apr 2024
Verified review

10/10 Excellent

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

Great location

Such a great location to everything. The property was a great break from all of the bustle. I loved the tropical area with the hammock.
Stayed 7 nights in Jan 2024
Verified review

10/10 Excellent

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

Good Trip

Great location, the property management company was very helpful and would definitely go back again.
Stayed 7 nights in Jan 2021
Verified review

10/10 Excellent

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

Perfect getaway!

Location was amazing. The space was enough for 4 of us. Great setting.
Stayed 4 nights in Nov 2022
Verified review

10/10 Excellent

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

Perfect location

Beautiful property! Beautiful backyard/pool! Will definitely stay here again. Everything went so smooth from checking in to checking out! Thank you so much!
Stayed 5 nights in Jan 2025
Verified review

8/10 Good

Great house perfect location

5 sisters on holiday had a great time. The location was perfect and the house was great for us. The living room is super small but the outdoor patio was lovely and that is where we spend our time.
Stayed 4 nights in Apr 2018
Verified review

10/10 Excellent

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

Great location!

We had a great time at this house. The location is perfect and really nice grocery store right across the street. I would definitely recommend it to anyone and definitely stay here again. The AC could be a little stronger, but otherwise it was a beautiful house.
Stayed 7 nights in Dec 2019
Verified review

10/10 Excellent

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

Great time in key West

The location was amazing but the house needs some love. Unfortunately the pool was too cold to enjoy. Would have been much nicer if it was heated.
Stayed 3 nights in Apr 2025
Verified review

10/10 Excellent

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

Key West

Spent a week here for a girls trip and it was perfect! The location is walking distance from so many restaurants. We rented bikes to get to the beach. The backyard is nice we had a few pool days as well. Highly recommend!
Stayed 7 nights in Mar 2021
Verified review

10/10 Excellent

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

Key West Getaway

Cottage was clean, bright and cozy. Pool was private and awesome. Location could not have been better - 1 block to Duval Street, short walk to either end of the island. Grocery store across the street. We thoroughly enjoyed our stay and would definitely come back.
Stayed 4 nights in Apr 2024
Verified review

10/10 Excellent

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

Key West treasure!

A perfect spot to enjoy the entire island. Centrally located, very walkable and plenty of room for 2 couples. Conveniently located across from Fausto’s Grocery plus lots of coffee shops. Check out the Thirsty Mermaid on the corner! Will definitely use VHKW again.
Stayed 5 nights in Apr 2024
Verified review

10/10 Excellent

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

Great location. Pool a plus!

Was right next to all of the fun downtown fun. Wonderful place. House is older like most of key west. But that’s why you are going. To the Keys. If that isn’t your thing get a hotel. Great stay.
Stayed 7 nights in Feb 2021
Verified review

10/10 Excellent

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

Very old Key West

Exactly as advertised. Rental company was very responsive. Had a problem with pool which was fixed very quickly.
Stayed 2 nights in Jan 2025
Verified review

10/10 Excellent

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

Great Time Was Had

This was a great little place to stay! The main bedroom was spacious and cooled off well. The smaller bedroom needs a little work with their AC. The place was clean and comfortable. We had a problem with a locked door and someone was over to help within minutes. You can’t beat the location! Also, having a grocery store right there was a huge bonus. Would definitely stay there again.
Stayed 5 nights in Jun 2024
Verified review

10/10 Excellent

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

Paradise in Key West

This was a perfect house for our family to relax and enjoy Key West. The pool & outdoor space was awesome and the house itself, although small living space, was more than enough space for 5 people. We rented bikes for the week but the property is within walking distance to so much. Fausto’s is Conveniently located across the street but I would go to Publix for a bigger and better selection.
Stayed 7 nights in Jun 2020
Verified review

10/10 Excellent

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

Wonderful Property

This is a great house in Key West. Close to all activities, shops and restaurants…but on a quiet side street. The backyard and pool are your own oasis. Fausto’s market is just across the street for added convenience. Yes the delivery trucks come early, but that’s only a minor issue. I would highly recommend this property.
Stayed 7 nights in Mar 2023
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
First off, the location was perfect. There is a nice local grocery store directly across the street which was convenient as we did not have a vehicle. You are just far enough away from the popular bars that you do not hear them if you want to go to sleep before they close, but close enough that it was not a long walk to get there. Second the backyard area. It was a perfect private oasis. The pictures online do not do this space justice. It was our favorite spot to spend afternoons sipping on adult beverages and reading a good book. The pool was plenty big enough for a family of four, and the house will really only hold about that many people as well. Lastly, the bad. The air conditioning would only barely keep up with the heat. It was about 85 degrees the entire time we were there, and the A/C in the middle of the day would cool the house down to about 78 degrees. To some people this would be fine, but if I come back, I will make sure to do so in the spring or fall when the heat is not as intense. I think this would be fine if the weather was a bit cooler. The master bedroom area has a dedicated split system and we kept the door closed which helped, but when we go to be we like it very cool and it was not. In the middle of the night it would reach our ideal temp, but it seemed to struggle. Also that super convenient grocery store gets early morning deliveries during the week every day. So don't be surprised to hear loud trucks every morning.
Stayed 7 nights in Jul 2026
Verified review

10/10 Excellent

Awesome experience!

Loved the house, pool and location. Very comfortable and close to everything! The only negative I would say and it certainly would not stop us from coming back is that the bedroom and living room do not cool down. The air conditioner is for both rooms and does not meet the need. The master bedroom air works great and was extremely comfortable. We would stay again for sure! The parking spot was a little difficult to find but we figured it out with a little patience. Absolutely a great find and enjoyable stay!
Stayed 3 nights in Sep 2018
Verified review

10/10 Excellent

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

Wonderful week in Key West in the perfect cottage in the perfect location!

Down Island Digs is the perfect location in Key West. My husband, my best friend, and I spent a week in this cute cottage. It is located a block from Duval Street. There are wonderful restaurants, bars & shopping just steps away. We enjoyed the beautiful outdoor area with the pool and garden in the private back yard. While this is an ideal location, it is also directly under the flight path to the Key West airport. Also, Fausto’s Grocery, located across the street from Down Island Digs, receives deliveries from trucks early in the morning. But the famous roosters of Key West begin each morning crowing away and that only reminds you that you are in paradise!
Stayed 7 nights in Feb 2021
Verified review

10/10 Excellent

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

Great vacation location

This was a good sized house for the 5 of us, in a great location. The only thing negative to say it that the air conditioning doesn’t get cold. It was 80 degrees plus in the house with a/c on and fans blowing. The bathroom in the bedroom ‘vents’ to the outside via a window that’s left open, so the bathroom was the same as the outside temperature- 96-98 degrees. It’s August, we knew it would be warm, just not in the house!
Stayed 4 nights in Aug 2023