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

pool
Exterior
pool
Pool
living room

Reviews

9.4 out of 10
Exceptional
2 bedrooms2 bathroomsSleeps 6764.2 sq ft

Popular amenities

  • Dryer
  • Washer
  • Parking available
  • Kitchen
  • Pool
  • Outdoor Space

Explore the area

Map
Key West, FL
  • Duval Street
    ‪2 min walk‬
  • Ernest Hemingway Home and Museum
    ‪9 min walk‬
  • Mallory Square
    ‪11 min walk‬
  • Key West, FL (EYW-Key West Intl.)
    ‪10 min drive‬

Rooms & beds

2 bedrooms (sleeps 6)

Bedroom 1

1 Queen Bed

Bedroom 3

1 King Bed

Common spaces

1 Double Sofa Bed

2 bathrooms

Bathroom 1

Bathroom 2

Spaces

Deck or patio
Porch or lanai
Kitchen
Garden
Dining area

About this property

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 downtown 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 vacation cottage is made cozy and charming. Colorful walls of Caribbean blue and sage green create the back drop for whimsically framed mirrors that offset the comfy coral colored 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 colored 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 colored spacious master suite is toward 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 toward 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 toward the back of the cottage so that indoor / outdoor pool garden living is maximized. 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 colored 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 colored 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 vacation 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, washer / 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 downtown restaurants, popular clubs, the Historic Seaport, and tropical shops makes this one of the most requested and convenient accommodations in Key West. With the size of the garden in this downtown location we are pleased to offer it as one of our more unique properties available in Old Town.

Area: Downtown 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 vacation 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’ parking lot 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 sidewalk, you will most certainly be given a ticket by the diligent parking officers that patrol downtown Old Town Key West. Do not block the gates, or you will be in violation of fire safety regulations.

Property manager

VHKW - Vacation Homes of Key West
Premier Host

Languages

English

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Amenities

Pool
Kitchen
Washer
Dryer
Free WiFi
Air conditioning

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0-17
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Events

No events allowed
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Pets

No pets allowed
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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
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 deadbolt lock

We should mention

A car is not required for transportation to and from this property

About the neighborhood

Key West

Located by the sea, this vacation home is in Old Town Key West, a neighborhood in Key West. Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and South Beach. Mel Fisher Maritime Museum and The Kite House are also worth visiting. Be sure to check out the area's animals with activities such as game walks and birdwatching.
Map
Key West, FL

What's nearby

  • Duval Street - 2 min walk - 0.2 km
  • Ernest Hemingway Home and Museum - 9 min walk - 0.8 km
  • Mallory Square - 11 min walk - 1.0 km
  • Fort Zachary Taylor Historic State Park - 16 min walk - 1.4 km
  • Southernmost Point - 16 min walk - 1.4 km

Getting around

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

Restaurants

  • ‪Margaritaville - ‬2 min walk
  • ‪Green Parrot Bar - ‬6 min walk
  • ‪Willie T's - ‬3 min walk
  • ‪Kermit's Key West Key Lime Shoppe - ‬3 min walk
  • ‪Mattheessen's - ‬2 min walk

Frequently asked questions

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

Yes, this property has a pool. Pool types include heated pools.

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

No, pets are not allowed at this property.

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

Check-in begins at 4:00 PM.

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

Check-out is at 10:00 AM.

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

Located in Old Town Key West, this vacation home is steps from San Carlos Institute - Casa Cuba and Duval Street. Ernest Hemingway Home and Museum and Florida Keys Beaches are also within 10 minutes.

Reviews

9.4

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 27 out of 32 reviews
Rating 8 - Good. 1 out of 32 reviews
Rating 6 - Okay. 3 out of 32 reviews
Rating 4 - Poor. 0 out of 32 reviews
Rating 2 - Terrible. 1 out of 32 reviews

9.6/10

Cleanliness

10/10

Check-in

9.4/10

Communication

9.8/10

Location

9.4/10

Listing accuracy

Reviews

10/10 Excellent

KIMBERLY A.

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

10/10 Excellent

Beth P.

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

10/10 Excellent

Don K.

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

10/10 Excellent

Leah S.

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

10/10 Excellent

Heidi A.

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

10/10 Excellent

Carol B.

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

10/10 Excellent

Deanne A.

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

10/10 Excellent

Randy P., Milton De

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

10/10 Excellent

Michelle H.

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

10/10 Excellent

Regan F.

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

6/10 Okay

Lori A.

Liked: Cleanliness, check-in, communication
Disliked: Listing accuracy

Needs TLC but unique

Audrey was awesome! Very friendly and accommodating! The house is small but it was clean. Having a private pool is very nice. The location is good. So many fun things to do within walking distance!An amazing little pizza place right on the corner ! I will say in all honesty the house is cut up inside One bedroom is very large and has a bathroom in it The other bedroom is very small and the bathroom is in the hall. The mini split unit in the spare room wasn’t efficient. We figured it out and could cool the house with the use of numerous fans found in the closet. Lighting could definitely be better, this was challenging. ( no overhead lights or switches)Again it was clean, but the house could use some maintenance. The kitchen is overly large with a bar height counter but no stools. A table was placed in front of it with 3 chairs, one of them, the legs were cut off at a very odd angle. Unusable a lamp on the counter was the only lighting in the kitchen. A house that was to be used for up to 6 people would have no where to sit in any of the rooms or outdoors. The decking around the pool is very warped. I’m sure the Florida sun is to blame. But it is a bit hazardous. It is in a residential neighborhood across the street from a grocery store. Convenient. But They get deliveries very early. No way to sleep through that. All in all we enjoyed the stay. Thanks to Audrey. We didn’t spend much time in the house.
Stayed 7 nights in Apr 2025

8/10 Good

cheryl w.

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

10/10 Excellent

Rebecca B.

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

10/10 Excellent

Jennifer P.

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

10/10 Excellent

Courtney T.

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

10/10 Excellent

Verified traveler

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

10/10 Excellent

Kathleen P.

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

10/10 Excellent

Marcie M.

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

10/10 Excellent

Amy D.

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

10/10 Excellent

Carol H.

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

Convenience!!

The convenience of this cottage is incredible! Other reviews have mentioned the early-morning grocer deliveries, but we were never bothered with noise. Literally 1/2 block off of Duval makes the location top-notch. The pool was the perfect place for afternoons. The cottage is quaint and well appointed. We had trouble with the a/c in guest room. One call to maintenance and it was taken care of immediately. My only "con" was the king bed in the master was VERY firm and not comfortable of me...for others it may be fine. Would we stay there again? Absolutely!!
Stayed 7 nights in Jan 2024

10/10 Excellent

Kathi L.

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

6/10 Okay

Sam S.

Nice property and location. Not worth the price.

Very nice house and pool deck at a great location - close to Duvall and within walking distance of other areas. Very private, relaxing, and comfortable until the grocery store across the street starts their morning loading operations around 4:00 to 6:00 a.m., at which point the sound of idling diesel trucks and banging are constant. The air conditioners in the bedrooms worked well but the living room area could not be cooled to a comfortable level. With all of this being said, the house and the pool/pool deck were all great and well-taken care of. However, it seems overpriced given the small, easy improvements which could be made to enhance guests' comfort and experience.
Stayed 3 nights in Oct 2018

2/10 Terrible

Emma S.

Liked: Check-in, location
Disliked: Cleanliness, communication

Wouldn't Stay Here Again

At first everything was going welll until we moved a piece of furniture in one of the bedrooms. Bugs everywhere that looked like termites. There were hundreds. We found bug spray in the house so we tried spraying them. I reached out to the property manager who me they would get someone out as soon as they could. Never heard back so I reached back out because by this time they were in the bed. They indicated it was swarming season and couldn’t really take care of the issue while we were there but they would work on a solution for us. I don’t know they meant literally. They left a solution of lemon and vinegar at the house for use to spray. We sprayed it and it kept them at bay, however this was short lived and they came back two days later. I reached out to the property manager again to let them know. Luckily that was our last night in the house and these things were everywhere in the bedroom. I’ve never heard another word from the property manager in response to my last email. I even sent them pictures so they would know I was not over exaggerating. I’ve visited Key West in June many times and have never had any issues like this. Disappointed!
Stayed 7 nights in May 2024

6/10 Okay

cruisinsherry S.

Liked: Cleanliness, check-in, communication, location

Home needs updating

we stayed Labor Day week 2021. House is easy to find. Parking is down the street but close. Be aware, the house is next door to Fausto's supermarket-a great store, has everything you need. However, delivery trucks start arriving at 5am. You will not sleep through the noise. Exterior- Pool is clean and private. There are worn cement areas and cement debris gathered on the steps and corners in the pool. There are two lounge chairs and two deck chairs. The patio furniture under the canopy is quite old and the cushions are flat and dirty. The banyon trees around the pool drop alot of leaves and the lizards traveling the fence poop along it and the patio. Easy clean up but would have appreciated a rake and bucket instead of using the household broom and bowls . Interior: very clean, basic neccessities (toilet paper, soap etc.) was available. Towels and linens were available. Beds made and comfortable. All indoor furniture is old and mismatched, worn material, flat cushions. Housewares-bare neccessities, we used paper products.
Stayed 7 nights in Sep 2021

10/10 Excellent

Douglas E.

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

Cute place

Great location
Stayed 7 nights in Jan 2022

About the host

Hosted by VHKW - Vacation Homes of Key West

Host profile image

Languages:

English

Premier Host

They consistently provide great experiences for their guests