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.
Add dates for prices
Have a question?
AI iconBetaBeta
Get instant answers with AI powered search of property information and reviews.
Similar properties
Old Town 2 Bicycles, Grill, WiFi, 1st Floor, Pool! Rent 30 days get 20% discount
Old Town 2 Bicycles, Grill, WiFi, 1st Floor, Pool! Rent 30 days get 20% discount
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.
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
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
We should mention
A car is not required for transport to and from this property
About the area
Key West
Located in Key West, this holiday home is in the city centre. 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. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Harry S. Truman Little White House - 6 min walk - 0.5 km
Ernest Hemingway Home and Museum - 8 min walk - 0.7 km
Mallory Square - 10 min walk - 0.9 km
Florida Keys National Marine Sanctuary - 11 min walk - 1.0 km
Getting around
Key West, FL (EYW-Key West Intl.) - 10 min drive
Restaurants
Margaritaville - 2 min walk
Willie T's - 3 min walk
Jack Flats - 2 min walk
Kermit’s Key West Key Lime Shoppe - 3 min walk
Wendy's - 3 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.
How much does it cost to stay at Down Island Digs - 2BR Cottage 1 Block off Duval Street Key West w/Private Pool?
As of 26 Mar 2026, prices found for a 1-night stay for 2 adults at Down Island Digs - 2BR Cottage 1 Block off Duval Street Key West w/Private Pool on 31 May 2026 start from AU$926, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
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.
How much is parking at Down Island Digs - 2BR Cottage 1 Block off Duval Street Key West w/Private Pool?
On-site parking is available at the 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?
Checkout 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 holiday home is steps away from San Carlos Institute - Casa Cuba and Duval Street. Florida Keys Beaches and Ernest Hemingway Home and Museum are also within 10 minutes.
Reviews
9.4
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Beautiful property! Beautiful backyard/pool! Will definitely stay here again. Everything went so smooth from checking in to checking out! Thank you so much!
Beth P.
Stayed 5 nights in Jan 2025
Response from VrboOwner on 13 Jan 2025
Thank you so much for starting 2025 with us Beth! We are so happy to hear you enjoyed all the home has to offer and that the checkin/out process was a breeze. It was an honor hosting you and we hope to have the chance again the next time you're back in Key West! Best, VHKW
This is a great property if you want to be close to all Key West has to offer.
Leah S.
Stayed 7 nights in Apr 2024
Response from VrboOwner on 2 Dec 2024
Thank you for staying with us at our Down Island Digs and for taking the time to review your experience! We're thrilled you enjoyed the home and its' central location. If you ever find yourself back in Key West, we would be delighted to host you again! Best, VHKW
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.
Heidi A.
Stayed 7 nights in Jan 2024
Response from VrboOwner on 24 Jan 2024
Thanks so much, Heidi for the great review! We're glad you were able to have the relaxing vacation you were hoping for at our property. Hope to see you again!
VHKW
Location was amazing. The space was enough for 4 of us. Great setting.
Regan F.
Stayed 4 nights in Nov 2022
Response from VrboOwner on 16 Dec 2024
Thank you for spending your Key West getaway at our Down Island Digs! We're so happy to hear you enjoyed the home and the location during your stay with us. Best, VHKW
Verified
8/10 Good
cheryl w.
16 Apr 2018
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.
cheryl w.
Stayed 4 nights in Apr 2018
Response from VrboOwner on 13 Jan 2025
Thank you for choosing our Down Island Digs for your Key West getaway Cheryl! We're thrilled to hear you enjoyed your stay and we would be happy to welcome you back anytime you're in town. best, VHKW
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.
Rebecca B.
Stayed 7 nights in Dec 2019
Response from VrboOwner on 30 Dec 2024
Thank you so much for your kind review and for spending your December with us, Rebecca. It was an absolute delight hosting you and your group for your time in town and we hope to have the chance again next holiday season! Best, VHKW
Exactly as advertised. Rental company was very responsive. Had a problem with pool which was fixed very quickly.
Don K.
Stayed 2 nights in Jan 2025
Response from VrboOwner on 20 Mar 2025
Thank you so much for your kind words and your glowing review Don! We're thrilled you had a wonderful time on the island and that we were able to assist with anything that came up during your stay.
Warm Regards,
VHKW
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.
Carol B.
Stayed 4 nights in Apr 2024
Response from VrboOwner on 25 Apr 2024
Carol, thank you so much for the glowing review! We're delighted to hear you had a fantastic stay with us. We hope to welcome you back again soon!
VHKW
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.
Michelle H.
Stayed 5 nights in Apr 2024
Response from VrboOwner on 25 Apr 2024
Thanks, Michelle! It was a pleasure to host you and we're excited to have the opportunity to host you again.
VHKW
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!
Jennifer P.
Stayed 7 nights in Mar 2021
Response from VrboOwner on 2 Apr 2021
Hi Jennifer, thank you for your wonderful comments.
We hope that you and the girls will plan another girls getaway trip to Key West soon and we'd love to host you again! :)
VHKW Team
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.
Courtney T.
Stayed 7 nights in Feb 2021
Response from VrboOwner on 22 Feb 2021
Thank you for staying with us! Wonderful to hear your appreciation for classic Key West homes. We love to share them with guests who are looking for privacy, great location and excellent services! Please do not hesitate to give us a call when you are ready to plan your next Key West vacation.
VHKW Team
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.
Deanne A.
Stayed 5 nights in Jun 2024
Response from VrboOwner on 2 Dec 2024
Thank you for reviewing your stay with us. Deanne! We're happy to hear you enjoyed the home and that we were able to address any notable items immediately. Thank you for choosing our Down Island Digs as your home away from home! Best, VHKW
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.
Verified traveller
Stayed 7 nights in Mar 2023
Response from VrboOwner on 18 Dec 2024
Thank you so much for your kind review, Clint! We're so happy to hear you enjoyed the prime location and privacy our home cottage has to offer. If you ever happen to be back in Key West, we would love the chance to host you again! Best, VHKW
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.
Kathleen P.
Stayed 7 nights in Jun 2020
Response from VrboOwner on 6 July 2020
Thank you for taking the time to share your experience! It's great to hear that you found the property very comfortable for you and your family and that you were able to relax and enjoy the pool and the outdoor space. We hope you will come visit us again soon!
VHKW Team
Verified
10/10 Excellent
Marcie M.
1 Oct 2018
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!
Marcie M.
Stayed 3 nights in Sep 2018
Response from VrboOwner on 13 Jan 2025
Thank you for making our Down Island Digs your home base for your time in Key West! We appreciate your thoughtful review and are so happy to hear you enjoyed your stay with us. Thank you again and we look forward to hosting you the next time you're back in town! Best, VHKW
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!
Kathi L.
Stayed 7 nights in Feb 2021
Response from VrboOwner on 16 Jan 2025
We love to hear that the roosters were a favorite part of your stay as they are an integral part of island life. Thank you for choosing our Down Island Digs and for your glowing review Kathi! We appreciate your kind words and look forward to welcoming you back the next time you're in Key West. Best, VHKW
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!
Amy D.
Stayed 4 nights in Aug 2023
Response from VrboOwner on 14 Aug 2023
Hi Amy, Thank you for the five star review. Sorry to hear about the AC issues. We talked with the owner and they have plans to upgrade the AC unit. I hope your next stay is cooler.
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!!
Carol H.
Stayed 7 nights in Jan 2024
Response from VrboOwner on 29 Jan 2024
Carol, we appreciate you taking the time to leave such a thoughtful review. Thank you for the feedback and we're glad to hear you found that the house and our service exceeded expectations. We look forward to hosting you again in the future.
VHKW
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 ….
Michelle R.
Stayed 3 nights in May 2025
Verified
6/10 Okay
Sam S.
9 Oct 2018
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.
Sam S.
Stayed 3 nights in Oct 2018
Response from VrboOwner on 13 Jan 2025
Thank you for your review and thoughtful feedback, Sam! We appreciate your time and always strive to improve the experience for our future guests. We are happy to hear that you enjoyed our home and it's location, we would be happy to host you again anytime. Best, VHKW
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.
cruisinsherry S.
Stayed 7 nights in Sep 2021
Response from VrboOwner on 26 Nov 2021
Thank you for taking the time to share your experience!
We appreciate your comments very much and will pass on your feedback about the pool, outdoor cushions and chairs to the owner. We are sorry to hear that the grocery store delivery trucks were too noisy, please keep in mind for future stays that we have white noise machines in our office that we can provide to our guests upon request.
We hope that other than these issues you had a wonderful time in Key West and we look forward to your next stay with VHKW.
VHKW Team
Verified
6/10 Okay
Lori A.
13 Apr 2025
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.
Lori A.
Stayed 7 nights in Apr 2025
About the host
Hosted by VHKW - Vacation Homes of Key West
Languages:
English
Premier Host
They consistently provide great experiences for their guests