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

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

A white house with a porch, surrounded by lush tropical vegetation.
Pool
A kitchen with a sink, a ceiling fan, and a view of the outside.
A porch with a metal sculpture, bicycles, and a Christmas tree.
A theater with a pink and white facade, a large arched entrance, and a sign that reads "WEST THEATER".

Reviews

9.4 out of 10
Exceptional

Highlights

  • Dive into relaxation
    Unwind in the top-rated pool, your perfect spot for relaxation.
  • Private garden
    A rare find — relax in the peaceful, private garden space.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Close to Duval Street

Popular amenities

  • Patio
  • Private pool
  • Air-conditioning
  • Refrigerator
  • Washing machine
  • Onsite parking available

Explore the area

View in a map
Key West, FL
  • Place, Duval Street
    ‪1 min walk‬
  • Place, Mallory Square
    ‪9 min walk‬
  • Place, Ernest Hemingway Home and Museum
    ‪11 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪11 min drive‬

Rooms & beds

2 bedrooms (sleeps 6)

Bedroom 1

1 King Bed and 1 Double Sofa Bed

Bedroom 2

1 Queen Bed

Common Spaces

1 Double Sofa Bed

2 bathrooms

Bathroom 1

Bathroom 2

Spaces

Deck or patio
Porch or lanai
Kitchen
Garden
Dining area

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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. Discover the area's water adventures with power boating and swimming nearby, or enjoy the great outdoors with ecotours.
View more Holiday homes in Key WestOpens in a new window
Map
Key West, FL

What's nearby

  • Duval Street - 1 min walk - 0.0 km
  • Oldest House Museum and Garden - 3 min walk - 0.3 km
  • Harry S. Truman Little White House - 7 min walk - 0.7 km
  • Mallory Square - 9 min walk - 0.8 km
  • Ernest Hemingway Home and Museum - 11 min walk - 0.9 km

Getting around

  • Key West, FL (EYW-Key West Intl.) - 10 min drive

Restaurants

  • ‪Margaritaville - ‬2 min walk
  • ‪Green Parrot Bar - ‬4 min walk
  • ‪Wendy's - ‬3 min walk
  • ‪Mangoes Restaurant - ‬4 min walk
  • ‪Jack Flats - ‬2 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 27 Oct 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 22 Aug 2027 start from £1,927, 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 The Key West Theater and Duval Street. Mallory Square and Florida Keys Beaches 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.
Learn moreOpens in a new window
Rating 10 - Excellent. 36 out of 45 reviews
Rating 8 - Good. 4 out of 45 reviews
Rating 6 - Okay. 4 out of 45 reviews
Rating 4 - Poor. 0 out of 45 reviews
Rating 2 - Terrible. 1 out of 45 reviews

9.8/10

Cleanliness

10/10

Check-in

9.6/10

Communication

10/10

Location

9.4/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect cottage for girls’ trip. Very convenient within walking distance to many iconic locations. Would book again!
Stayed 5 nights in Sep 2026
Response from VrboOwner on 29 Sept 2026
We appreciate your positive review about your stay at Down Island Digs! So glad this worked for your girls trip and was convenient to many iconic locations. We look forward to welcoming you back!
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
I would rate our stay as Very Good; better than good but not quite excellent. As most reviews state, the location is perfect, so convenient to everything in Old Town. The pool and back yard were so beautiful and relaxing. The AC issues earlier reviews mentioned have been addressed and the bedrooms were comfortable. The living room is very small (not a surprise based on the description and earlier reviews). As long as the weather permitted, this was not an issue as we spent most of our time in the backyard. But, when the rain prevented us from sitting outside, it was very tight for the 3 of us to sit together in the living room.
Stayed 8 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Plant have asked for a better experience!! Leah was AWESOME and lightning fast with communication…can’t wait to come back
Stayed 5 nights in Aug 2026
Response from VrboOwner on 10 Sept 2026
Thank you so much for the fantastic review! We’re thrilled you had such a great experience and truly appreciate your kind words about our team member and her communication. We can’t wait to welcome you back to Key West!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
Great location, clean, zero issues.
Stayed 4 nights in Mar 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 4 nights in Dec 2025
Response from VrboOwner on 22 Jan 2026
Hello Charity,We’re happy you enjoyed the home and its location. Hope to see you back in Key West soon!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Down Island Digs is perfectly situated for anyone looking to enjoy the best of the area. It’s just a block off Duval Street, making it easy to walk to restaurants, bars, shops, and attractions, while still feeling pleasantly tucked away from the busiest crowds. Having Fausto’s Market directly across the street is incredibly convenient for groceries and essentials. The central location makes getting around effortless, whether you’re heading out for sightseeing, dining, or a relaxing day by the pool back at the house. You really couldn’t ask for a better spot.
Stayed 5 nights in Apr 2026
Response from VrboOwner on 19 May 2026
We’re so glad you enjoyed your stay. It was a pleasure hosting you, and we truly hope to welcome you back again soon for another great visit!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Nice area, walking distance to Duval and most restaurants etc. Wonderful backyard. House was equipped.
Stayed 2 nights in Feb 2026
Response from VrboOwner on 24 Feb 2026
Hello Elizabeth,It’s wonderful to hear you enjoyed the convenient location, the backyard space, and the home’s amenities. Providing a comfortable and well-equipped stay is always our goal. Thank you for choosing to stay with us. We hope to welcome you back soon!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Key West trip

This is a great property if you want to be close to all Key West has to offer.
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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location

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.
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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Good Trip

Great location, the property management company was very helpful and would definitely go back again.
Stayed 7 nights in Jan 2021
Response from VrboOwner on 3 Feb 2021
Thank you, Randy! We appreciate your comments! We look forward to hosting you again soon! VHKW Team
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect getaway!

Location was amazing. The space was enough for 4 of us. Great setting.
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 review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect location

Beautiful property! Beautiful backyard/pool! Will definitely stay here again. Everything went so smooth from checking in to checking out! Thank you so much!
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
Verified review

8/10 Good

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.
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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location!

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.
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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great time in key West

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.
Stayed 3 nights in Apr 2025
Response from VrboOwner on 8 Jan 2026
Hello Kimberly,We’re pleased the location was ideal for your stay, and we appreciate your feedback.We look forward to welcoming you back soon.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Key West

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!
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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Key West Getaway

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.
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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Key West treasure!

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.
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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location. Pool a plus!

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.
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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Very old Key West

Exactly as advertised. Rental company was very responsive. Had a problem with pool which was fixed very quickly.
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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Time Was Had

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.
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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Paradise in Key West

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.
Stayed 7 nights in Jun 2020
Response from VrboOwner on 6 Jul 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 review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful Property

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.
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
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
First off, the location was perfect. There is a nice local grocery store directly across the street which was convenient as we did not have a vehicle. You are just far enough away from the popular bars that you do not hear them if you want to go to sleep before they close, but close enough that it was not a long walk to get there. Second the backyard area. It was a perfect private oasis. The pictures online do not do this space justice. It was our favorite spot to spend afternoons sipping on adult beverages and reading a good book. The pool was plenty big enough for a family of four, and the house will really only hold about that many people as well. Lastly, the bad. The air conditioning would only barely keep up with the heat. It was about 85 degrees the entire time we were there, and the A/C in the middle of the day would cool the house down to about 78 degrees. To some people this would be fine, but if I come back, I will make sure to do so in the spring or fall when the heat is not as intense. I think this would be fine if the weather was a bit cooler. The master bedroom area has a dedicated split system and we kept the door closed which helped, but when we go to be we like it very cool and it was not. In the middle of the night it would reach our ideal temp, but it seemed to struggle. Also that super convenient grocery store gets early morning deliveries during the week every day. So don't be surprised to hear loud trucks every morning.
Stayed 7 nights in Jul 2026
Response from VrboOwner on 10 Sept 2026
Thank you for the detailed review. We’re so glad you enjoyed the location, private backyard oasis, and pool. We agree that the outdoor space is a special part of the home, and we’re happy it became your favorite place to relax. We also appreciate your feedback about the A/C. Key West’s intense summer heat can be challenging for any residential cooling system, particularly during the hottest part of the day. We are always looking at ways to maximize comfort during those periods. Thank you again for sharing your experience and for recognizing both what you loved and areas for improvement. We hope to welcome you back during one of Key West’s beautiful cooler seasons!
Verified review

10/10 Excellent

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!
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
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