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  • (305) 294-7358
Key West Time
June 16th
5:51am · 85°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 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, smart TVs, 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.




Book Direct For The Best Price Guaranteed

special rates available


June 21 - June 29
July 6- July 18
Nightly $625
Weekly $3325

view all specials

Dates Weekly Nightly Terms
Jun 10, 2024 - Aug 11, 2024 $3790$680.005 night min, but 3-4 nights within 60 days
Aug 12, 2024 - Oct 2, 2024 $2580$600.004 night min. or 3 night min. 60 days prior to arrival.
Oct 3, 2024 - Oct 17, 2024 $2710$600.004 night min. or 3 night min. 60 days prior to arrival.
Oct 18, 2024 - Oct 27, 2024 $5255$900.007 night minimum
Oct 28, 2024 - Nov 3, 2024 $3325$640.004 night min. or 3 night min. 60 days prior to arrival.
Nov 4, 2024 - Nov 11, 2024 $3790$680.007 night minimum
Nov 12, 2024 - Nov 21, 2024 $3325$640.003 night minimum
Nov 22, 2024 - Nov 30, 2024 $3790$680.007 night minimum
Dec 1, 2024 - Dec 18, 2024 $2660$600.004 night min. or 3 night min. 60 days prior to arrival.
Dec 19, 2024 - Dec 27, 2024 $5015$950.007 night minimum
Dec 28, 2024 - Jan 3, 2025 $6030$1050.007 night minimum
Jan 4, 2025 - Jan 10, 2025 $4360$840.004 night min. or 3 night min. 60 days prior to arrival.
Jan 11, 2025 - Jan 17, 2025 $4360$840.004 night min. or 3 night min. 60 days prior to arrival.
Jan 18, 2025 - Jan 31, 2025 $4600$880.004 night min. or 3 night min. 60 days prior to arrival.
Feb 1, 2025 - Feb 14, 2025 $5215$955.005 night min, but 3-4 nights within 60 days
Feb 15, 2025 - Feb 21, 2025 $5450$955.005 night min, but 3-4 nights within 60 days
Feb 22, 2025 - Apr 11, 2025 $5215$955.005 night min, but 3-4 nights within 60 days
Apr 12, 2025 - May 28, 2025 $3790$680.004 night min. or 3 night min. 60 days prior to arrival.
May 29, 2025 - Jun 8, 2025 $3325$640.004 night min. or 3 night min. 60 days prior to arrival.
Jun 9, 2025 - Aug 10, 2025 $3790$680.004 night min. or 3 night min. 60 days prior to arrival.
Aug 11, 2025 - Oct 1, 2025 $2580$600.004 night min. or 3 night min. 60 days prior to arrival.
Oct 2, 2025 - Oct 16, 2025 $2710$600.004 night min. or 3 night min. 60 days prior to arrival.
Oct 17, 2025 - Oct 25, 2025 $5255$900.007 night minimum
Oct 26, 2025 - Nov 2, 2025 $3325$640.004 night min. or 3 night min. 60 days prior to arrival.
Nov 3, 2025 - Nov 10, 2025 $3790$680.007 night minimum
Nov 11, 2025 - Nov 20, 2025 $3325$640.004 night min. or 3 night min. 60 days prior to arrival.
Nov 21, 2025 - Nov 29, 2025 $3790$680.007 night min. or 3 night min. 60 days prior to arrival.
Nov 30, 2025 - Dec 19, 2025 $2660$600.004 night min. or 3 night min. 60 days prior to arrival.
Dec 20, 2025 - Dec 27, 2025 $5215$990.007 night minimum
Dec 28, 2025 - Jan 5, 2026 $6250$1090.007 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
Oct 23, 2023,
We always choose to rent through VHKW! Each rental has been clean and just as described. Communication is easy! As always we had the best vacation in Key West!

Aug 09, 2023,
House was great and the location perfect for our vacation.

Jun 29, 2023,
A good week was had by our three families

Apr 10, 2023,
Very nice house. Perfect location. Unfortunately some roosters nearby.

Apr 03, 2023,
Excellent location! We were able to walk everywhere we wanted to go. The multiple living areas worked out great for my group. I would suggest a few maintenance fixes such as the outdoor toilet needs to be re-seated and the deck has some serious issues and unstable. Other than that everything was wonderful. The refrigerators were cold, the air worked great, and we encountered no plumbing issues and the beds were very comfortable. Very enjoyable stay.

Mar 27, 2023,
We had a great time, experiencing no problems. The houses were perfect for our purposes and very clean and well maintained.

Feb 14, 2023,
We loved the house and it’s location.

Jan 17, 2023,
Always a great place to stay

Oct 18, 2022,
Only feedback is that we thought the two houses would be connected. Also if there was a code system to the door instead of key! Other than that, very clean, plenty of dishes and amenities. Clean pool. Good amount of towels for pool and showers

Sep 07, 2022,
We had a great experience with VHKW and would definitely book with them again! Loved the easy check in & the key waiting for us in the lockbox at our rental made our arrival stress free. Thank you!

Jul 25, 2022,
Great home to stay in! Very clean and close to Duval!

May 10, 2022,
I hate to recommend Down Island Digs because it only makes it harder to book, but folks.....location, location. The house itself is a bit quirky basically being a 2 bedroom, 2 bath, no living room set up, but that backyard and pool are worthy of not expanding the footprint of the home. VHKW was super easy to work with. We didn’t see them, they didn’t hear from us. Thank you so much. This the third time we have rented this property. Will not be the last.

May 09, 2022,
Really enjoyed our stay at Down Island Digs, place was clean and well kept. The pool and location were awesome! I will definitely use VHKW for future visits to Key West!

Mar 08, 2022,
The place was really nice and clean. It was perfect size for 2 couples. The pool area was the best.

Feb 02, 2022,
Cute place, clean, nicely decorated Easy walk to Duval Street and beaches

Dec 09, 2021,
We had a fantastic stay! A very cozy house and the backyard and pool were awesome.

Nov 23, 2021,
Down Island Digs was a great place for two couples to stay comfortably. The unit was extremely clean. We loved the location. It was really central to everything you want to do and places were very walkable although we did have a golf cart too. Would stay here again. KWVH’s processes for check-in and check-out were very easy.

Nov 04, 2021,
This is the second time we’ve rented the home. We have been happy with the VHKW contacts. Please fix the water damage that is evident in the kitchen, master, and master bath floors. It would be considerate to provide toilet paper and paper towels for an 8 night stay.

Oct 28, 2021,
Thank you VHKW, and a special thank you to Anastasia who was so helpful. We enjoyed our stay at Down Island Digs. There was five of us and we felt very comfortable there and the location was perfect . Would definitely stay there again.

Jun 30, 2021,
VHKW went above and beyond to help and support us.

Jun 16, 2021,
Another great stay at Down Island Digs. Everything was perfect and the staff was very accommodating. My only suggestion would be to replace the entry door.

May 09, 2021,
We loved the very artistically decorated private pool garden villa! The pool was awesome and where we spent most of our time. Our curly tail lizard friends and iguanas fulfilled our wishes for a tropical vacation. We took morning walks to get delicious Cuban coffee and sandwiches at local stores. The grocery store Fausto’s was also very convenient. Higg’s Beach was a 5 minute walk away where we enjoyed several meals at Salute’s. We will definitely return to this lovely property on Laird Street!

Feb 26, 2021,
Perfect house for one couple! Pool and back garden were great!

Jan 15, 2021,
Perfect. We will rent again in aprilb

Jan 13, 2021,
We had a great experience with VHKW. They answered my questions and were very clear in their instructions. The house was perfect. Cozy inside but deceptively spacious outside. The pool was awesome. Hammock was amazing. The location could not be beat.

Dec 31, 2020,
Very clean, cute home in a great location. Manager was very responsive to any help needed. Only suggestion would be maybe a TV in the living/kitchen area, but overall great spot!

Oct 26, 2020,
The house was as described and was very clean. My only suggestion would be to put a larger TV in the master bedroom as we had a day that was a rainout and we stayed in and watched TV and it would have been nice to have a larger TV.

Sep 30, 2020,
Great trip. My family and I have rented in many places over the years in Key West and you cannot beat this location. Faustos grocery store is across the street and Duval St is one block away around the corner. House was perfect for our group of 4 adults and 1 toddler. Rental office and maintenance were also a pleasure to deal with. We will definitely be renting with them again in the future.

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

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