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Key West Caribbean Cottage - On Duval St w Private Pool
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Reviews
9.4 out of 10, Loved by Guests
Top 10% based on
2 bedrooms2 bathroomsSleeps 692 sq m
Popular amenities
Explore the area

Key West, FL
- Place, Duval Street1 min walk
- Place, Ernest Hemingway Home and Museum3 min walk
- Place, Southernmost Point8 min walk
- Airport, Key West, FL (EYW-Key West Intl.)12 min drive
Rooms & beds
2 bedrooms (sleeps 6)
Bedroom 1
1 King Bed
Bedroom 2
1 Queen Bed
2 bathrooms
Bathroom 1
Bathroom 2
Spaces
Kitchen
Garden
Dining area
About this property
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.
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.
Add dates for prices
Amenities
Pool
Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning
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- Pool
- Washing machine
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- Pet-friendly
10.0 out of 10, Exceptional, (5 reviews)
House Rules
Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
No pets 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
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 Southernmost Point are notable landmarks, and the area's natural beauty can be seen at Fort Zachary Taylor Historic State Park and South Beach. Key West Butterfly and Nature Conservatory and MLK Community Pool & Community Center are also worth visiting. Make sure you get close to the area's animals with activities such as game walks and birdwatching.

Key West, FL
What's nearby
- Duval Street - 1 min walk - 0.0 km
- 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
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
Frequently asked questions
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 window9.4/10
Cleanliness
10/10
Check-in
9.8/10
Communication
9.6/10
Location
9.4/10
Listing accuracy
Reviews
Verified
10 March 2026
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 4 nights in Mar 2026
Verified
10/10 Excellent
Nicole L.
1 March 2026
Liked: Cleanliness, check-in, communication, location, listing accuracy
Nicole L.
Stayed 4 nights in Feb 2026
Verified
10/10 Excellent
James H.
26 February 2026
Liked: Cleanliness, check-in, communication, location, listing accuracy
James H.
Stayed 3 nights in Feb 2026
Verified
8/10 Good
Fiona P.
21 January 2026
Liked: Cleanliness, check-in, communication, location, listing accuracy
Fiona P.
Stayed 4 nights in Jan 2026
Verified
10/10 Excellent
Frank P.
22 December 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Frank P.
Stayed 3 nights in Dec 2025
Verified
10/10 Excellent
Kathy Z.
10 December 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Kathy Z.
Stayed 4 nights in Nov 2025
Verified
10/10 Excellent
Tracy D.
6 March 2026
Liked: Cleanliness, check-in, communication, location, listing accuracy
Tracy D.
Stayed 4 nights in Mar 2026
Verified
10/10 Excellent
Mary T.
12 August 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Mary T.
Stayed 4 nights in Aug 2025
Verified
10/10 Excellent
Daniel K.
9 December 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place to stay
Daniel K.
Stayed 7 nights in Nov 2024
Verified
10/10 Excellent
Becky S.
13 January 2026
Liked: Cleanliness, check-in, communication, location, listing accuracy
Becky S.
Stayed 7 nights in Jan 2026
Verified
10/10 Excellent
Ken T.
17 March 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location
Ken T.
Stayed 2 nights in Mar 2025
Verified
10/10 Excellent
Allison L.
3 March 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent location!
Allison L.
Stayed 3 nights in Feb 2025
Verified
10/10 Excellent
Shelley D.
11 April 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Awesome Location
Shelley D.
Stayed 3 nights in Mar 2025
Verified
10/10 Excellent
Sheri V.
6 June 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Better than great!
Sheri V.
Stayed 6 nights in May 2025
Verified
8/10 Good
Ann C.
13 March 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay in Key West
Ann C.
Stayed 4 nights in Mar 2025
Verified
10/10 Excellent
Michelle M.
15 May 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent Location and Stay
Michelle M.
Stayed 7 nights in Apr 2024
Verified
10/10 Excellent
Brent M.
5 October 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Best location
Brent M.
Stayed 6 nights in Sep 2024
Verified
10/10 Excellent
Erin B.
6 April 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location!
Erin B.
Stayed 5 nights in Apr 2025
Verified
10/10 Excellent
Amber H.
3 April 2018
Had a great time in Key West. Location can’t be beat!
Amber H.
Stayed 7 nights in Mar 2018
Verified
10/10 Excellent
JIM W.
2 September 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Yearly trip
JIM W.
Stayed 4 nights in Aug 2024
Verified
10/10 Excellent
Rebecca H.
2 January 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Family Holiday in the Keys
Rebecca H.
Stayed 3 nights in Dec 2023
Verified
10/10 Excellent
Olga M.
23 March 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Lovely cottage
Olga M.
Stayed 2 nights in Mar 2025
Verified
8/10 Good
Diane B.
27 October 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
great location
Diane B.
Stayed 4 nights in Oct 2022
Verified
10/10 Excellent
David F.
8 August 2019
Liked: Cleanliness, check-in, communication, location, listing accuracy
Awesome stay in Key West!
David F.
Stayed 4 nights in Jul 2019
Verified
10/10 Excellent
Ellen R.
1 May 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Key West long weekend
Ellen R.
Stayed 5 nights in Mar 2024
About the host
Hosted by VHKW - Vacation Homes of Key West
Languages:
English
Premier Host
They consistently provide great experiences for their guests
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