HomeAway uses cookies to improve your site experience. Learn more. By continuing, you consent to our use of cookies.
HomeAway uses cookies to improve your site experience. Learn more. By continuing, you consent to our use of cookies.
Verified Review icon check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar svg-report-flag pet-dog svg-multiunit Default Owner Icon heart-filled Family icon
Book Online or call HomeAway Booking Assistance +44 (0) 800 917 5992
Book Online or call HomeAway Booking Assistance +44 (0) 800 917 5992

Down Island Digs ~ Ideal Location Downtown, Private Pool.

Bedrooms 2
Space 770 sq ft
Property type house
Minimum Stay 3 - 7 nights


About the property

House, 2 Bedrooms + Convertible bed(s), 2 Baths, (Sleeps 4-6)

You would never know you're just ½ block off downtown Duval Street in Old Town Key West! Everything about this unique Key West gem adds up to make an ideal precious "down island" hideaway, right in the center of downtown. It is indeed rare to find a cottage property with such a large tropical garden in this location situated on two full private lots with such lush mature tropical landscaping.

This unique vacation garden cottage was refreshed complete with new kitchen and new flooring throughout in 2009. In January 2010 a new landscape design was created for the back garden and the swimming pool was re-stored to brand-new condition. If you have stayed at Down Island Digs before or if you’ve heard about it, you’ll love the upgrades and attention to detail of this authentic vintage circa 1918 historic island cottage. While we have honored its well earned charm, we have added lots of spice and luxurious comfort features.

The focus of this property is definitely the Key West quintessential indoor / outdoor living that makes island life so relaxing and wonderful. The entire large back yard is made very private with high fences and is visually divided into two parts. The front part of the garden is an expansive pool deck which is joined by sliding glass doors to the living room and pool side bedroom. The deck surrounds the graceful lounge pool which you enter down a graduated underwater stair case. Beyond the sun deck walk toward the back and the deck leads you down the middle of the yard into the large native tropical shade garden.

In contrast to the expansive garden, the indoor living room area is made cozy and charming. A whimsically painted sideboard and home spun dining table command the space between the indoors and the outside. Then sliding glass doors open up the space by connecting the decks on all sides of the living room and draw guests onto the deck to the outdoors. Plenty of pool side seating under a pretty awning create an irresistible tropical indoor / outdoor living room comfortable for lounging.

The U-shaped kitchen is open to the living room area. It is updated and easy to cook in. It is fully equipped, offers a full size electric range and dishwasher, and has a nice open view of the pool and garden so the cook can be part of the party.

Throughout the property inside and out are whimsical pieces of island art by local artists. Inside, the cottage has new floors throughout the living room, kitchen, and bedrooms that feel nice to bare feet. The bedrooms have a tropical flare and are comfortable and inviting. The pool side bedroom offers a queen size bed and has sliding glass doors that open out directly onto the pool deck. The master bedroom has a white 4-poster king size bed and is set up as a suite with a queen size sleeper sofa sitting area as well as the bed. The master bedroom has direct outdoor access to a front porch for sitting and watching the world go by. Additional bedding is offered with a twin sleeper sofa in the living room area.

This downtown Key West property is located right next door to our Pavilion Villa. The downtown location is just around the corner from famous Duval Street and steps from grocery shopping, excellent restaurants, popular clubs, the Historic Seaport, and tropical shops makes this one of the most requested and convenient accommodations in Key West. We are so pleased to offer it as one of our more unique properties available in Old Town.

This home is offered as an exclusive vacation rental in the most requested location in Key West. The property will not tolerate smoking inside.

Keywords: House

More Details

Vacation Homes of Key West (VHKW)
Speaks English, Czech, Bulgarian
Response time:
Within a day
Response rate:
Calendar last updated:
19 April, 2018

Why Vacation Homes of Key West (VHKW) chose Old Town

Perfect Key West location just around the corner from Duval Street plus this adorable cottage offers a very large and beautifully landscaped back yard that is hidden from view.

What makes this house unique

While this cottage is in downtown Key West it has a large tropical tree garden in the back yard that is hidden from view.

Guestbook comments from the owner

This is our first time renting from VHKW and they were wonderful to work with! Down Island Digs is a quaint cottage perfect for the two of us. We have always stayed at the Pier House in years prior only for the view, but the backyard in this cottage is wonderful. You can walk anywhere from this home. If your looking for large living area this may not be the home for you. But who stays indoors in Key West?
Feb 2016
  • 1 of 3


Accommodation and facilities for this holiday house in Old Town in Key West

Property Type:
  • house
  • Self-catering
Floor Area:
  • 770 sq ft
House Rules:
  • Check-in: 16:00
  • /
  • Check-out: 10:00
  • Max. occupancy: 6
  • Min. age of primary renter: 25
  • Children welcome
  • Parties/events not allowed
  • Pets not allowed
  • Non smoking only
  • We do not accept guests less than 25 years of age unless accompanied by a family group or guardian.
  • Please refer to your rental agreement for Cancellation Policy for this property
Location Type:
  • city centre
  • near the sea
  • Adventure
  • Family
  • Historic
  • Romantic
  • Tourist Attractions
  • Air Conditioning
  • Broadband Access
  • Clothes Dryer
  • Hair Dryer
  • Internet
  • Iron & Board
  • Linens Provided
  • Living Room
  • Parking
  • Parking Off Street
  • Telephone
  • Towels Provided
  • Washing Machine
  • Catering Available
  • Coffee Maker
  • Cooking Utensils
  • Dishes & Utensils
  • Dishwasher
  • Kitchen ...
  • Microwave
  • Oven
  • Refrigerator
  • Hob
  • Toaster
  • Dining Area
  • 2 Bathrooms
  • Bathroom 1 -
    Bathroom 2 -
  • 2 Bedrooms, Sleeps 6
  • Bedroom 1 - 1 Extra Lg. Double Bed
    Bedroom 2 - 1 Large Double Bed
    Convertible bed(s) - 2 Sofa bed/Futon
  • King size beds (1), Queen size Beds (1), Sleep Sofa or Futons (1)
  • CD Player
  • DVD Player
  • Satellite / Cable
  • Television
  • Terrace ...
  • Lanai / Gazebo
  • Barbecue
Pool / Spa:
  • Private Pool
Onsite Services:
  • Concierge
  • botanical garden
  • churches
  • cinemas
  • festivals
  • Health/Beauty Spa
  • library
  • live theatre
  • marina
  • museums
  • playground
  • restaurants
Leisure Activities:
  • bird watching
  • Boating
  • eco tourism
  • Miniature golf
  • outlet shopping
  • paddle boating
  • photography
  • scenic drives
  • Shelling
  • Shopping
  • sight seeing
  • walking
  • Wildlife Viewing
Local Services & Businesses:
  • ATM/bank
  • Babysitter
  • fitness centre
  • groceries
  • hospital
  • laundrette - serviced
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • Basketball Court
  • cycling
  • deepsea fishing
  • fishing
  • fly fishing
  • golf
  • golf pass optional
  • jet skiing
  • Kayaking
  • Parasailing
  • pier fishing
  • roller blading
  • sailing
  • diving
  • snorkelling
  • Snorkeling/Diving
  • swimming
  • tennis
  • water skiing
  • water tubing
  • wind-surfing
Veranda is roofed with expansive awning


4.7/5 -
(3 traveller reviews)

66% Complete
33% Complete
0% Complete
0% Complete
0% Complete
Down Island Digs ~ Ideal Location Downtown, Private Pool.
average rating of 4.6666665 based on 6 reviews

Great house perfect location

  • 4 of 5

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.

  • Review Submitted: 15-Apr-2018
  • Date of Stay: April 2018
  • Source: VRBO, from HomeAway
Did you find this review helpful?
0 0

Cool Digs

  • 5 of 5

What did you most enjoy about your stay?

Convenience to all Key West has to offer, yet seclusion and privacy, private pool, Barbque, beautiful backyard, fully furnished kitchen, washer and dryer, Pictures acurately depict the property - plenty of space to lounge around

Would you come back again or recommend this home to a friend?

Resounding Yes

Was the property a good fit for the group you were traveling with?

Yes. Husband wife in our late fifties and early sixties and children Young adults 22+

What nearby activities, attractions, or restaurants did you enjoy?

Duval street walk, Hemingway house, Fort Zachary Beach, Fury water adventures -snorkeling, grocery store next door, cuban coffee across the street,speciality pizzas, multiple cigar shops, key lime pies, we had a car so we drove around a bit and went to the beach by the airport and further afield as well - didnt do restaurants as we barbequed every evening - with wine music pool and privacy on vacation couldnt ask for more

What did the owner or property manager do to provide great customer service

didn't have contact - did not need to ....

  • Review Submitted: 21-Jul-2015
  • Date of Stay: July 2015
  • Source: VRBO, from HomeAway
Did you find this review helpful?
2 0
Denver, Colorado

Loved it!!

  • 5 of 5

We stayed at this property recently and was more than pleased! The house could not be in a more perfect location in Key West. Centrally located just off Duval Street, but you would never know it while staying at this house. You can easily get to anywhere in Old Town by walking or quick bike ride. It is beautiful, charming, and quiet. The photos were very accurate to actual appearance. The house and grounds were immaculate. The owners were helpful in answering all of our questions, and the check in process was a breeze. They were also prompt in answering any maintanence phone calls (basically the pool needed to be cleaned after a rain, and they came right over!). The only downfalls to this property were the mattress in the 2nd bedroom was a little too firm for my guest's taste, and the water pressure in the master bedroom was not very good. I would definitely reccomend this property for 2 couples or a family of 4.

  • Review Submitted: 24-Oct-2011
  • Date of Stay: October 2011
  • Source: VRBO, from HomeAway
Did you find this review helpful?
14 1


Nearest Airport
2 Miles
Nearest Barpub
0.1 Miles
sloppy joes
Nearest Golf
3 Miles
key west golf club
Nearest Restaurant
0.1 Miles
Nearest Beach
0.5 Miles
South beach
Car: not necessary

Duval Street is just around the corner. Don't miss the variety of public tropical gardens you can tour. The famous sunset on Mallory Square is a nightly event.


Prices & Availability

Prices for this holiday house in Old Town, Lower Florida Keys

Rental Basis:
per property
Owner accepts payment in:
Convert Currency
Rental Period Minimum Price Additional Nights Weekend Night Weekly Monthly Event Price
24 Feb 2018 - 20 Apr 2018
3 night minimum stay
for 3 nights
21 Apr 2018 - 27 May 2018
4 night minimum stay
for 4 nights
28 May 2018 - 15 Jun 2018
4 night minimum stay
for 4 nights
16 Jun 2018 - 9 Aug 2018
5 night minimum stay
for 5 nights
10 Aug 2018 - 20 Oct 2018
5 night minimum stay
for 5 nights
Fantasy Fest
21 Oct 2018 - 27 Oct 2018
6 night minimum stay
for 6 nights
28 Oct 2018 - 4 Nov 2018
3 night minimum stay
for 3 nights
Boat Races
5 Nov 2018 - 11 Nov 2018
5 night minimum stay
for 5 nights
12 Nov 2018 - 16 Nov 2018
5 night minimum stay
for 5 nights
17 Nov 2018 - 23 Nov 2018
5 night minimum stay
for 5 nights
24 Nov 2018 - 16 Dec 2018
5 night minimum stay
for 5 nights
17 Dec 2018 - 25 Dec 2018
6 night minimum stay
for 6 nights
New Year
26 Dec 2018 - 1 Jan 2019
5 night minimum stay
for 5 nights
My Standard Rate
7 night minimum stay
for 7 nights

Additional pricing information

Cleaning Fee £106.53 + Tax
Processing £53.27 + Tax
Pool Heat £106.53
Tax Rate 12.5%

Owner's Cancellation Policy

  • Cancelled bookings will not receive a refund.
Ask Owner a Question

You might like these similar holiday rentals