This holiday home places you in the centre of Key West, steps from Duval Street and within a short 5-minute stroll of Ernest Hemingway Home and Museum. Highlights at this holiday home include a kitchen, a private pool and a washing machine. .Home features free WiFi, 2 bathrooms and a sofa bed. In-room dining is easy with a kitchen that comes equipped with a fridge, a microwave and a stovetop. A living room, a fenced private garden and a TV are also available. .Attractions within a 10-minute walk of this Old Town Key West holiday home include South Beach and Florida Keys Beaches.
Ernest Hemingway Home and Museum - 3 min walk - 0.3 km
South Beach - 6 min walk - 0.6 km
Key West Butterfly and Nature Conservatory - 6 min walk - 0.6 km
Southernmost Point - 8 min walk - 0.7 km
Getting around
Key West, FL (EYW-Key West Intl.) - 7 min drive
Restaurants
Old Town Tavern - 3 min walk
Circle K - 1 min walk
Banana Cafe - 3 min walk
Cuban Coffee Queen (Duval) - 2 min walk
Rum Bar at the Speakeasy Inn - 1 min walk
About this property
Entire place
You'll have the entire home to yourself and will only share it with other guests in your party.
Key West Caribbean Cottage - On Duval St w Private Pool
Overview
Imagine the quintessential Caribbean island village, its cottages nestled hand-in-hand on charming historic pedestrian streets. As people stroll by, sun kissed from an afternoon of beaching and sight seeing, they`ll say hi to one another even if they`ve never met. This is your neighborhood during your stay at the Caribbean Cottage vacation rental. One of the best vacation rental locations on the island - without a doubt. Around the corner `Grand Vin` wine bar stands ready for an evening wine tasting session while `Flamingo Crossing` ice cream parlor offers up a new flavor of home made glace.
Brimming with genuine island charm, our Caribbean Cottage, with private pool, was originally built in the early 1900`s. Artistically renovated to maintain the original wood planked polished floors and vintage hand-hewed beams, the owners added bright blue tile (accented with marble), and Bahama style wooden window shutters tat compliment the historic interior. Original pine walls were painted with elegant historic colors of olive and cream and adorned the sash style windows and French linen curtains. Reserved for owner`s use only for many years, original artwork from their private collection is displayed throughout for you to enjoy.
The living room is a generous cottage size with plenty of room to gather. On the side closest to the kitchen, a dining table is placed to create a roomy eating area. The adjoining `butler-pantry` style kitchen is spacious, has a charming French-Caribbean style ambiance, and is fully equipped and easy to cook in.
The interior lay-out of this cottage maximizes privacy with the bedrooms and bathrooms on one side and common living areas on the other. The cottage has two full bedrooms and two full bathrooms.
Bedding in this vintage cottage includes a king size bed in the master bedroom, and a queen size bed in the other. The master bedroom boasts a beautiful rich wooden armoire, and French doors lead from the bedroom to a pretty outdoor sitting area for reading and lounging. For extra sleeping, the living room has a comfortable queen sleeper sofa.
From the outside front, the cottage has charming curb appeal with a large beautiful Royal Poinciana tree and the Key West quintessential white picket fence, and of course the porch to sit and watch the world go by. The general design and layout of the cottage lends itself perfectly for versatile use. It is ideal for up to four, and can sleep up to five people comfortably.
If you are looking for a truly authentic Key West experience, this cottage could be the perfect one for you. This charming property is located in the Upper-Duval Street historic neighborhood - a special section of Key West offering many up-scale attractions and interesting features including excellent gourmet restaurants, art galleries, boutiques, a high-end wine tasting store, an award winning home made ice cream shop, a coffee and tea house, South Beach around the corner, and .just a short walk to down to Mallory Square.
There is off-street parking for one full size car, but from here you really never need to get in your car. Upper Duval Street is right out your front door, so forget the hassle of parking and enjoy walking or biking everywhere. Enjoy the island to the fullest, and then come home to relax in the pool.
Bedding Summary: - Master bedroom - King size bed - 2nd Bedroom- Queen size bed - Living Room - Queen sleeper sofa
IMPORTANT: How payments work VRBO collects only their service fee. Reservation payments are paid directly to VHKW in two installments in accordance with the terms of your rental agreement (sent for review upon reservation). Payments to VHKW by credit card are subject to an additional 2.95% merchant processing fee.
Amenities: Private pool with bricked courtyard garden, fenced yard, fully equipped kitchen. A/C, washer / dryer, smart TV, wifi. Linens and towels are provided.
Activities: Shopping, restaurants, nightlife, museums, sailing, boating, snorkeling, diving, theatre, night life, family activities. Everything is within walking distance. Cafe neighborhood features art galleries, wonderful eateries and internationally famous fine restaurants, coffee house, fine gift and clothing stores. Right out your gate find Grand Vin Wine Bar, where you`ll enjoy a broad selection of wine by the glass and Flamingo Crossing, the award winning homemade ice cream store with some of the best ice cream you`ll ever eat. Key West South Beach is a 3 minute walk up the street at most Upper end of Duval St.
Area: Upper Duval or `Uptown Key West` has evolved into the `elegant end of Duval` and offers an exceptional variety of restaurants, beautiful boutiques, and art galleries. Walk to South Beach in 3 minutes and the Southernmost Point of the United States is just down the street and around the corner. Walk to the Mallory Square Sunset Celebration in 15 to 20 minutes.
Parking: Off-street parking for one car.
Restrictions: Smoke free house. No Pets. We do not accept guests less than 25 years of age unless accompanied by a family group or guardian.
Note: If you love this cottage but need to sleep more than 4 in beds, you can rent it with the one bedroom Vintage Luxury Cottage. You can combine a rental of both cottages and sleep 8 by renting the Fantasy Resort Villa. When rented together, you have two private swimming pools.
Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
Smoke detector (host has indicated there is a smoke detector on the property)
Fire extinguisher
General
Garden
Unit size: 990 square feet
Policies
Check-in
Check-in time starts at 4:00 PM
Contactless check-in and check-out are available
Minimum check-in age - 25
Check-out
Check-out before 10:00 AM
Special check-in instructions
You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools
Pets
No pets allowed
Children and extra beds
Children are welcome.
Events
No events allowed
Smoking
Smoking is not permitted
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 not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
This property is managed by a professional host. The provision of housing is linked to their trade, business or profession. This property accepts cash. On-site parties or group events are strictly prohibited. For guests' safety, the property includes a fire extinguisher and a smoke detector in all accommodation.
Property is also known as
Caribbean Cottage Duval Street Key West Caribbean Cottage House
Caribbean Cottage Duval Caribbean Cottage House
Caribbean Cottage Duval Street Key West Caribbean Cottage
Caribbean Cottage Duval Caribbean Cottage
Caribbean Cottage Duval Street Key West Caribbean Cottage House
Caribbean Cottage Duval Caribbean Cottage House
Caribbean Cottage Duval Street Key West Caribbean Cottage
Caribbean Cottage Duval Caribbean Cottage
Caribbean Duval St Key West
Caribbean Cottage- Duval St Cottage
Caribbean Cottage- Duval St Key West
Caribbean Cottage- Duval St Cottage Key West
Caribbean Duval Caribbean
239148
Frequently asked questions
Are there any beaches close to Key West Caribbean Cottage - On Duval St w Private Pool?
Yep, Key West Caribbean Cottage - On Duval St w Private Pool is a short 5-minute walk from South Beach.
Fun beach activities include swimming. You can also find motor boats.
Does Key West Caribbean Cottage - On Duval St w Private Pool have a pool?
Key West Caribbean Cottage - On Duval St w Private Pool has a heated pool and a pool.
What luxury perks are available at Key West Caribbean Cottage - On Duval St w Private Pool?
This property features a heated pool, as well as a private pool and a living room.
Is there a private hot tub at Key West Caribbean Cottage - On Duval St w Private Pool?
No, but there is a private pool.
Is there a free airport shuttle available at Key West Caribbean Cottage - On Duval St w Private Pool?
No, Key West Caribbean Cottage - On Duval St w Private Pool does not offer an airport shuttle service.
What time are check-in & check-out at Key West Caribbean Cottage - On Duval St w Private Pool?
Check-in begins at 4:00 PM. Check-out time is 10:00 AM.
Are pets allowed at Key West Caribbean Cottage - On Duval St w Private Pool?
No, pets are not allowed.
Key West Caribbean Cottage - On Duval St w Private Pool Reviews
Reviews
9.4
Exceptional
All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
Rating 10 - Excellent. 50 out of 71 reviews
10 - Excellent
50
Rating 8 - Good. 16 out of 71 reviews
8 - Good
16
Rating 6 - Okay. 4 out of 71 reviews
6 - Okay
4
Rating 4 - Poor. 1 out of 71 reviews
4 - Poor
1
Rating 2 - Terrible. 0 out of 71 reviews
2 - Terrible
0
9.4/10
Cleanliness
Reviews
10/10 Excellent
Donna P.
10 Mar 2026
Liked: Cleanliness
Awesome location, pool was perfect , concierge was extremely helpful - lots of great restaurants, shopping nearby.
Donna P.
Stayed 4 nights in Mar 2026
10/10 Excellent
Tracy D.
6 Mar 2026
Liked: Cleanliness
It was nice to have a private patio and pool.. we really enjoyed that. The house was clean and had all the amenities that we needed. Loved, loved, the concierge service to rent bikes and a golf cart for a day. Both were delivered and picked up, which was great!! We also had our groceries delivered we sent our list to Audrey, and everything was there and put away when we got there. It was perfect. When it was time to come home I contacted the concierge the day before for taxi service to pick us up.. they even offered to have a taxi to pick us up from the airport.Their service is fantastic!! I highly recommend using their services for all your needs. I don’t think they highlight the service enough that’s why I’m going on about it..they made everything we wanted so easy.
Tracy D.
Stayed 4 nights in Mar 2026
10/10 Excellent
Nicole L.
1 Mar 2026
Liked: Cleanliness
Cute cottage, great location, responsive host!
Nicole L.
Stayed 4 nights in Feb 2026
10/10 Excellent
James H., Westport, CT
26 Feb 2026
Liked: Cleanliness
The complimentary coupons for the ice cream shop next door was a very nice touch.
James H.
Stayed 3 nights in Feb 2026
8/10 Good
Fiona P.
21 Jan 2026
Liked: Cleanliness
Property was in an ideal location, just off the southern edge of Duval street, was really well equipped very clean and pretty cute. Beds were comfy and pool was lovely. For four adults you are in quite close proximity to each other in regard to bathroom and bedrooms and the pool was a little noisy through the night but we very much enjoyed our stay here
Fiona P.
Stayed 4 nights in Jan 2026
10/10 Excellent
Becky S.
13 Jan 2026
Liked: Cleanliness
The house was nice. I wish the doors between rooms were not louvered since lights from other rooms illuminate the bedroom. Also, I wish the shower in the smaller bathroom was larger than a telephone booth since it makes it difficult to shave legs. The kitchen was well equipped except we couldn't find a spatula (to flip meat in the pan). We had a great time sunning poolside because we witnessed two iguanas mating three feet away from us! Overall, nice place to stay for the week, super location, lovely back and side deck with pool but the host fee and the service fee is considered ridiculously high. Sorry but keeping it real.
Becky S.
Stayed 7 nights in Jan 2026
10/10 Excellent
Frank P.
22 Dec 2025
Liked: Cleanliness
We much enjoyed the house. Its close proximity to Duval Street was a bonus. Will def rent it again in the future.
Frank P.
Stayed 3 nights in Dec 2025
10/10 Excellent
Kathy Z.
10 Dec 2025
Liked: Cleanliness
Great location, private parking, cute house, well-equipped. Host was quick to respond.
Kathy Z.
Stayed 4 nights in Nov 2025
10/10 Excellent
Mary T.
12 Aug 2025
Liked: Cleanliness
Great location and layout! Everything was as advertised. Bicycle rentals were a short walk away. Thanks for a great vacation!
Mary T.
Stayed 4 nights in Aug 2025
10/10 Excellent
Tiffany H.
23 Jun 2025
Tiffany H.
Stayed 4 nights in May 2025
10/10 Excellent
Sheri V., Alta Sierra, California
6 Jun 2025
Liked: Cleanliness
Better than great!
The home is excellent and the location is perfect. We had a full day of torrential rains and still were able to dodge raindrops and check out sights close enough to visit. The house has a great layout and everything you need. We loved the dip in the pool before the end-of-the-day shower. An excellent Key West adventure.
Sheri V.
Stayed 6 nights in May 2025
10/10 Excellent
Shelley D.
11 Apr 2025
Liked: Cleanliness
Awesome Location
We enjoyed our weekend escape to the Keys and this convenient cottage in the heart of Key West. We walked everywhere and enjoyed all the amazing restaurant options and tourist attractions. Would recommend!
Shelley D.
Stayed 3 nights in Mar 2025
10/10 Excellent
Erin B., Dover
6 Apr 2025
Liked: Cleanliness
Great location!
Perfect location in Key West...near Duval Streeet and all points of interest. Easy to walk or rent scooters/carts. House is very charming, clean and quite pretty. We loved the aesthetic. Back patio, pool is lovely. We appreciated the washer and dryer! Thank you for a lovely place to stay
Erin B.
Stayed 5 nights in Apr 2025
10/10 Excellent
Olga M.
23 Mar 2025
Liked: Cleanliness
Lovely cottage
We had a great stay at Caribbean cottage. Just off Duval street. We really enjoyed that we were so close to all the restaurants and museums and the southmost point. We walked everywhere and didn’t need a car. The cottage was nice full of history, very nice key west vibe. Very lovely.
Olga M.
Stayed 2 nights in Mar 2025
10/10 Excellent
Ken T.
17 Mar 2025
Liked: Cleanliness
Great location
Enjoy our stay and will be back soon
Ken T.
Stayed 2 nights in Mar 2025
8/10 Good
Ann C.
13 Mar 2025
Liked: Cleanliness
Great stay in Key West
The location was perfect. A little noisy in the morning when the ice cream store was receiving their deliveries, but we are early risers so it was not an issue for us. The property had everything we needed and was very comfortable. The pool area was nice as well. Would definitely stay again.
Ann C.
Stayed 4 nights in Mar 2025
6/10 Okay
Greg B.
9 Mar 2025
Disliked: Cleanliness
Fell short
Overall charm was lacking. Basically needs to be updated and get more attention to upkeep. Appliances were great. Pool size was exactly what we like, but area around pool was a disaster with debris and the like not a comfortable pool side area. We noticed in previous reviews 2years ago, that it was commented that the furniture was broken . IT STILL IS! Outdoor furniture was not usable and moldy..if I was the property manager with my name on the listing, I would not continue to list it.
Greg B.
Stayed 21 nights in Jan 2025
10/10 Excellent
Allison L.
3 Mar 2025
Liked: Cleanliness
Excellent location!
Amazing location just steps off Duval. This was exactly what we needed for our trip.
Allison L.
Stayed 3 nights in Feb 2025
10/10 Excellent
Daniel K.
9 Dec 2024
Liked: Cleanliness
Great place to stay
We really enjoyed it great house clean, and close to everything.
Daniel K.
Stayed 7 nights in Nov 2024
8/10 Good
Tania K.
11 Nov 2024
Liked: Cleanliness
Great location and amenities
The location of the home and amenities were spot on. Home was clean but dated. A bit of maintenance needed, that said, the bed was so comfortable and furniture as well. Would’ve liked a keurig over regular coffee maker. Lucky there were coffee shops in both directions on Duval, just steps from the home. Would definitely stay here again!
Tania K.
Stayed 4 nights in Nov 2024
10/10 Excellent
Matthew C.
4 Nov 2024
Liked: Cleanliness
Key West Visit
This property was in perfect proximity to all that was happening in Key West. I would without a doubt rent again. Questions by the proprietors were answered in a timely fashion and completely. Thank you for a great visit
Matthew C.
Stayed 7 nights in Oct 2024
10/10 Excellent
Jennifer C., Papillion, NE
27 Oct 2024
Liked: Cleanliness
Cute Little House in Great Location
We loved the little house. It had everything we needed including the pool in the private backyard. Just steps off Duval it was easy to walk from Southernmost Point to Mallory Square to The Wharf. The beds were comfy and the kitchen had everything we needed. We enjoyed our stay very much. ☺️
Jennifer C.
Stayed 5 nights in Oct 2024
10/10 Excellent
Brent M.
5 Oct 2024
Liked: Cleanliness
Best location
You can’t find a better location to call home for your Key West visit. This was my third visit and by far the best location and home. We highly recommend this rental and hope to return soon!