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  • (305) 294-7358
Key West Time
September 30th
2:52am · 81°F

Down Island Digs ~ Weekly Rental

2BR 2BA ~ Weekly Rental
Sleeps 2-6

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 renovated U-shaped kitchen is traditional cottage-style with bright white tiles and new 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. Catering can be arranged. Maid service can be scheduled.

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 Fine Foods 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.




Book Direct For The Best Price Guaranteed

special rates available

Sept 28- Nov 19

Weekly $1800
Nightly $400

view all specials

Dates Weekly Nightly Terms
Sep 28, 2020 - Oct 15, 2020 $2485$479.254 night min. or 3 night min. 60 days prior to arrival.
Oct 16, 2020 - Oct 24, 2020 $2485$479.254 night min. or 3 night min. 60 days prior to arrival.
Oct 25, 2020 - Nov 7, 2020 $2485$479.254 night min. or 3 night min. 60 days prior to arrival.
Nov 8, 2020 - Nov 15, 2020 $2485$479.254 night min. or 3 night min. 60 days prior to arrival.
Nov 16, 2020 - Nov 19, 2020 $2485$479.253 night minimum
Nov 20, 2020 - Nov 28, 2020 $3010$537.507 night minimum
Nov 29, 2020 - Dec 18, 2020 $2100$456.004 night min. or 3 night min. 60 days prior to arrival.
Dec 19, 2020 - Dec 25, 2020 $3990$684.007 night minimum
Dec 26, 2020 - Jan 1, 2021 $4690$770.507 night minimum
Jan 2, 2021 - Jan 8, 2021 $2940$588.004 night min. or 3 night min. 60 days prior to arrival.
Jan 9, 2021 - Jan 15, 2021 $3115$623.004 night min. or 3 night min. 60 days prior to arrival.
Jan 16, 2021 - Jan 22, 2021 $3115$600.754 night min. or 3 night min. 60 days prior to arrival.
Jan 23, 2021 - Jan 29, 2021 $3290$634.505 night minimum - 'within' Sat/Sat Only
Jan 30, 2021 - Feb 12, 2021 $3675$656.257 night min Sat/Sat Only, but 3-5 nights within 60 days
Feb 13, 2021 - Feb 19, 2021 $3815$654.007 night min Sat/Sat Only, but 3-5 nights within 60 days
Feb 20, 2021 - Apr 9, 2021 $3675$656.257 night min Sat/Sat Only, but 3-5 nights within 60 days
Apr 10, 2021 - May 30, 2021 $2940$525.005 night min, but 3-4 nights within 60 days
May 31, 2021 - Jun 11, 2021 $2590$499.505 night min, but 3-4 nights within 60 days
Jun 12, 2021 - Aug 8, 2021 $2940$525.005 night min, but 3-4 nights within 60 days
Aug 9, 2021 - Oct 1, 2021 $2100$465.004 night min. or 3 night min. 60 days prior to arrival.
Oct 2, 2021 - Oct 21, 2021 $2590$499.504 night min. or 3 night min. 60 days prior to arrival.
Oct 22, 2021 - Oct 31, 2021 $4060$696.007 night minimum
Nov 1, 2021 - Nov 6, 2021 $2590$499.504 night min. or 3 night min. 60 days prior to arrival.
Nov 7, 2021 - Nov 14, 2021 $2940$525.007 night minimum
Nov 15, 2021 - Nov 19, 2021 $2590$499.503 night minimum
Nov 20, 2021 - Nov 28, 2021 $2940$525.007 night minimum
Nov 29, 2021 - Dec 17, 2021 $2100$465.004 night min. or 3 night min. 60 days prior to arrival.
Dec 18, 2021 - Dec 25, 2021 $3675$656.257 night minimum
Dec 26, 2021 - Jan 2, 2022 $4410$756.007 night minimum

Additional Notes:

  • High Season generally requires a 7 night minimum stay. Shorter stays of 3 - 5 nights may be available within 60 days of your arrival date or in special situations. Certain dates may not be available if they minimize optimal booking for the property's reservation calendar. Please contact us to inquire about stays less than 7 nights.
  • Shoulder and Low Season is a 3 - 5 night minimum available on reservations made within 60 days of arrival May through mid-August. From mid-August through mid-December, 3 - 5 night minimum stays are available any time.
  • Short Stays are available if there are open nights that are less than the minimum stay, shorter stays may be possible depending on the property. Please contact us to inquire.
  • Holiday, Festival, and Event Rates are 20% to 25% higher. These include, but are not limited to: Fantasy Fest, Thanksgiving, Christmas, New Years, Power Boat Races, Mini-Lobster Season, Labor Day, Parrot Heads Meeting of the Mind, 4th of July, Easter. A 7 night minimum stay is required for most major holidays, festivals, and events.

Rates and Terms are subject to change without notice. Above rates do not include taxes and fees. Click here for more details on additional fees. Please contact us for specific pricing and to confirm rates. Rates in US Funds. (305) 294-7358 Ext 1 -

Apply here for Travel Guard Trip Cancellation and Interruption Insurance.

VHKW offers promotional specials for purchasing trip insurance for stays between Aug 10 and Oct 20. Please call for more details.

  • Master bedroom Four Poster king (pillow top mattress) size bed
  • Queen Sleeper sofa
  • Second Bedroom - queen size bed
  • Living room - twin sleeper sofa
Sep 09, 2020,
We visited Down Island Digs the last weekend of August and still thinking about the great time we had. This place was great in every way - layout, pool, location. The staff were great to work with & everything was clear and easy. Thank you so much for all you did to make this stay fun & relaxing! We cannot wait to come back!!

Jul 22, 2020,
Unbelievable customer service. Of note was the service provided by Paige

Jan 18, 2020,
Absolutely enjoyed our location. It was effect. Love the key box so we didn’t have to travel to a main office to check in. The property was just what we needed for outdoor space and location to everything. I will definetly book with you again!

Oct 24, 2019,
Down Island Digs is a wonderful 2/2 cottage with private pool & tropical garden. Great place to relax, but the action is just a half a block away. Loved our visit & VHKW is awesome making it come true now twice. Will use them again for our 3rd. visit to paradise. Hopefully, Down Island Digs will be available after my 5 star review.

Mar 26, 2019,
Great Property!! This was the 2nd time we’ve rented it and will certainly rent it again. Great location in Old Town puts everything within walking distance. That said, it comes with a blessing and a curse? It is located just across the parking lot from Fausto’s Grocery Store which makes buying food and beverages very convenient!!!! However, when do Grocery Stores get their deliveries?? Try about 4 AM, and they are not exactly quiet either!!! And when do they have their dumpster emptied? That would be about 5 AM !!!!! As irritating as this is, I would rent this property again and again, it is still a great rental in a Fabulous location!!

Feb 15, 2019,
VHKW was great to work with. The property was just as described and the check in process was very easy. They were very nice on the phone and answered all questions. Would definitely use them again.

Jan 30, 2019,
We stayed at Down Island Digs and it was great for us!!! I spoke to Paige before arriving and needed to call her before I left - she was extremely helpful and really nice. It was a great time for us and we will definitely use VHKW again...

Jan 23, 2019,
Great fun good location

Jan 09, 2019,
Awesome place and location. We would love to rent again same time this year. It appears to be booked already. If there’s a cancellation, please let me know. Thanks

Aug 09, 2018,
WE were completely satisfied with your company from start to finish. The booking process was easy and we were happy that all of our questions and concerns were answered before we signed our contract. We were extremely happy with our location, the property was perfect, and had everything we needed. Ginette was accommodating during the booking process and addressed all of our questions. Paige was our onsite check in representative and she was wonderful. She gave us info on restaurants too that was helpful. We had some confusion with the lock box and Paige came out personally to assist. We had a small issue with the washer and your maintenance man came immediately. We loved the Down Island Digs and have recommended it to many friends. We have also passed on VHKW to friends thinking about Key West for their next vacation destination. Thanks for making our 2018 vacation awesome!

Jul 03, 2018,
Absolutely wonderful 40th bday girls weekend. The accommodations were exactly as promised. The location was absolutely perfect. Highly recommend this house and this company! We will definitely be staying here again!

Apr 07, 2018,
We stayed an Down Island Diggs and had a GREAT time. Perfect vacation home for our family. Great location too!

Mar 16, 2018,
We have stayed in several homes managed by VHKW over the years. All of the staff is professional, helpful, and responsive. I sell real estate in Michigan, and deal with a lot of property management companies. They are one of the best I've worked with, and we will continue to use them for our annual visits to Key West.

Mar 10, 2018,
Very good Service ! I like the House in 508 Bahama Street!

Feb 19, 2018,
We were four adults and a 22-month old and the space was quite manageable for us. The kitchen is well equipped for a family. The outdoor living is the best feature of the property with a nice pool and new decking. The vegetation appeared to be damaged by Irma but the yard was still very comfortable. Super convenient with Fausto’s across the way and CVS and Walgreen’s a short walk. Terrific for having a little one along.

Feb 04, 2018,
Absolutely superb service from the rental agents. The very few questions we had were answered quickly and precisely. Everything was exactly as described and pictured on the web page, with two exceptions: 1. The beautiful garden was obviously damaged by the hurricane, and many of the trees that had provided complete privacy on the patio were downed, but this was something we expected. 2. The pool was actually MUCH larger than the photographs shown it to be! This was a nice surprise! The rental unit was spotlessly clean upon arrival, as well as the pool and the pool area. We're already planning next year's getaway, and looking forward to again working with VHKW.

Aug 25, 2017,
My wife and I had a wonderful vacation staying in Key West. The home we rented was perfect. The pool and privacy in backyard of home was excellent. It was quite and relaxing. Very close to Duval Street - which we loved. We would rent this property again when visiting Key West. Thank you...

Jul 16, 2017,
The house was perfect - just as described! Just the right amount of room for 2 couples on a kid-free getaway :). The pool and backyard were a wonderful escape and the location of the home was the perfect walking distance to everything!

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