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

Top rated by guests
Private Backyard Oasis with Swimming Pool
kitchen
kitchen
Living Room with Sliding Doors to Pool Deck
Down Island Digs Street View
review stars
9.4Outstanding
(40 Ratings)
Great location, clean cottages, private pool, and responsive maintenance. Would highly recommend!
From real guest reviews summarized by AI
Don't miss out! Price and availability may change
9.4 / 10
Outstanding(40 Ratings)

House in Key West, FL

6 guests · 1 bedroom · 2 baths

Reasons to book

Guests love it hereGuests give this property a top rating
Top-tier experienceA high end property in this area
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About this house rental

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.

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

Non-smoking
No pets allowed
Family friendly

Map of Key West, FL


Ratings and reviews

9.4 / 10
Outstanding(40 Ratings)
review starsSummary of reviews
Great location, clean cottages, private pool, and responsive maintenance. Would highly recommend!
From real guest reviews summarized by AI
10 / 10Outstanding·Feb 2026
Nice area, walking distance to Duval and most restaurants etc. Wonderful backyard. House was equipped.
10 / 10Outstanding·Jan 2026
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.
10 / 10Outstanding·Apr 2025
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.
6 / 10Average·May 2025
I read about the AC issue but booked anyway. No AC in main areas of house or bathrooms. We had to use 6 different fans, which the house provided. It was not good. The house was always hot. Kitchen dishes were sparse. Only one large pot and small pot. One small fry pans and a medium fry pan. No strainer…4 small glass drinking glasses. Don’t plan on cooking any meals because there isn’t enough of anything. The large burner on the stove does not work. Only 2 lounge chairs at pool. Pool deck is caving in and warped in areas! For the money, you seriously can book a much better place to stay. The location was excellent though….

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FAQs

Is parking included with this house?

Parking is not specified as an available amenity at Down Island Digs - 2BR Cottage 1 Block off Duval Street Key West w/Private Pool. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.

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

Unfortunately, this house is not pet-friendly. Try searching again and filter for "Pets Allowed"

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

We found 3 amenities for this rental. This includes non-smoking, no pets allowed, and family friendly.