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Key West Caribbean Cottage - On Duval St w Private Pool

Photo gallery for Key West Caribbean Cottage - On Duval St w Private Pool

Private Oasis with Plunge Swimming Pool
Conch Cottage Kitchen with Cooking Utensils
Open Concept Living and Dining Area
Caribbean Cottage Street View
living room

Reviews

9.2 out of 10
Wonderful
2 bedrooms2 bathroomsSleeps 6990.3 sq ft

Popular amenities

  • Dryer
  • Washer
  • Parking available
  • Kitchen
  • Outdoor space

Explore the area

Map
Key West, FL
  • Duval Street
    ‪1 min walk‬
  • Ernest Hemingway Home and Museum
    ‪5 min walk‬
  • Southernmost Point
    ‪7 min walk‬
  • Key West, FL (EYW-Key West Intl.)
    ‪7 min drive‬

Rooms & beds

2 bedrooms (sleeps 6)

Bedroom 1

1 Queen Bed

Bedroom 2

1 King Bed and 1 Double Sofa 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

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


Amenities: Champagne for the newly weds! Private pool with bricked courtyard garden, fenced yard, fully equipped kitchen. A/C, washer / dryer, Flat screen color cable TV, C/D player and stereo, wireless internet. 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.

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.

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.

Property manager

VHKW - Vacation Homes of Key West
Premier Host

Languages

English

Add dates for prices

Amenities

Pool
Kitchen
Washer
Dryer
Free WiFi
Air conditioning

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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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

About the area

Key West

Located by the sea, this holiday home is in Old Town Key West, a neighbourhood in Key West. 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.
Map
Key West, FL

What's nearby

  • Duval Street - 1 min walk - 0.1 km
  • Ernest Hemingway Home and Museum - 5 min walk - 0.5 km
  • South Beach - 5 min walk - 0.5 km
  • Southernmost Point - 7 min walk - 0.6 km
  • Mallory Square - 19 min walk - 1.7 km

Getting around

  • Key West, FL (EYW-Key West Intl.) - 7 min drive

Restaurants

  • ‪Moondog Cafe & Bakery - ‬5 min walk
  • ‪Old Town Tavern Key West - ‬3 min walk
  • ‪Southernmost Point Bar In the USA - ‬5 min walk
  • ‪Rum Bar at the Speakeasy Inn - ‬1 min walk
  • ‪Banana Cafe - ‬3 min walk

Frequently asked questions

Does Key West Caribbean Cottage - On Duval St w Private Pool have a pool?

Yes, this property has a pool. Pool types include heated pools.

Is Key West Caribbean Cottage - On Duval St w Private Pool pet-friendly?

No, pets are not allowed at this property.

What time is check-in at Key West Caribbean Cottage - On Duval St w Private Pool?

Check-in begins at 4:00 PM.

What time is check-out at Key West Caribbean Cottage - On Duval St w Private Pool?

Checkout is at 10:00 AM.

Where is Key West Caribbean Cottage - On Duval St w Private Pool located?

Located in Old Town Key West, this holiday home is steps away from City Zoo Gallery and Duval Street. Ernest Hemingway Home and Museum and South Beach are also within 10 minutes.

Reviews

9.2

Wonderful

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. 40 out of 60 reviews
Rating 8 - Good. 15 out of 60 reviews
Rating 6 - Okay. 4 out of 60 reviews
Rating 4 - Poor. 1 out of 60 reviews
Rating 2 - Terrible. 0 out of 60 reviews

9.4/10

Cleanliness

10/10

Check-in

9.6/10

Communication

9.6/10

Location

9.2/10

Listing accuracy

Reviews

10/10 Excellent

Shelley D.

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

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!
Stayed 3 nights in Mar 2025

10/10 Excellent

Erin B.

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

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
Stayed 5 nights in Apr 2025

10/10 Excellent

Olga M.

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

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.
Stayed 2 nights in Mar 2025

10/10 Excellent

Ken T.

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

Great location

Enjoy our stay and will be back soon
Stayed 2 nights in Mar 2025

8/10 Good

Ann C.

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

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.
Stayed 4 nights in Mar 2025

6/10 Okay

Greg B.

Liked: Check-in, communication, location
Disliked: Cleanliness, listing accuracy

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.
Stayed 21 nights in Jan 2025

10/10 Excellent

Allison L.

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

Excellent location!

Amazing location just steps off Duval. This was exactly what we needed for our trip.
Stayed 3 nights in Feb 2025

10/10 Excellent

Daniel K.

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

Great place to stay

We really enjoyed it great house clean, and close to everything.
Stayed 7 nights in Nov 2024

8/10 Good

Tania K.

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

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!
Stayed 4 nights in Nov 2024

10/10 Excellent

Matthew C.

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

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
Stayed 7 nights in Oct 2024

10/10 Excellent

Jennifer C.

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

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. ☺️
Stayed 5 nights in Oct 2024

10/10 Excellent

Brent M.

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

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!
Stayed 6 nights in Sep 2024

10/10 Excellent

JIM W.

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

Yearly trip

Yearly trip
Stayed 4 nights in Aug 2024

10/10 Excellent

Patricia S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 6 nights in Apr 2024

10/10 Excellent

Tammy K.

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

Absolutely wonderful

Everything was perfect.
Stayed 6 nights in Jul 2024

10/10 Excellent

Christina B.

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

Idyllic Friends Getaway

This little cottage was absolutely perfect for the 4 of us: 2 married couples who love traveling together! This little Shangri-La was so inviting and had all the little pleasantries of an old (1943) Key West home. We were pleased with our bedrooms and bathrooms. We grilled almost every night and enjoyed the amply-stocked kitchen (cooking supplies). The pool afforded us the opportunity to soak after long days roaming the island. We will definitely revisit this little gem.
Stayed 5 nights in Jun 2024

10/10 Excellent

Michelle M.

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

Excellent Location and Stay

The property was just as it was listed and the location is within walking distance to everything. It was the perfect getaway for us!
Stayed 7 nights in Apr 2024

10/10 Excellent

Ellen R.

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

Key West long weekend

We loved this property!! It was so comfortable, great air conditioning, well set up for us. It was really perfect! Would absolutely recommend.
Stayed 5 nights in Mar 2024

8/10 Good

Corinne P.

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

Great spot overall

Convenient place to stay. Didn’t realize all the doors are shutter doors, even the bathrooms, so everything can be heard. You can also hear people right outside behind the ice cream spot and it’s especially loud when they’re throwing out their trash. Some of the towels and bedding that was provided had some staining and hair on them. Trash bin instructions were unclear as to which bins were to be used and where they were located. Had a few problems with the pool the first day after having a good rain, we were able to quickly get ahold of someone and they had someone come out next day and had it fixed. Some of the pool settings/buttons were unclear and we had to search around testing a few switches. Eventually we figured out how to adjust the temperature and turn on the light and waterfall so not a huge deal. Overall it was a pleasant stay, the location and pool alone make it worth. One last thing, the furniture in the living room area could definitely use some updating. Some of the chairs had broken legs and everything felt a bit grungy, very used and uncomfortable.
Stayed 6 nights in Feb 2024

8/10 Good

Beverly D.

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

Key West 2024

Location was very convenient to restaurants, bars and attractions. Some early morning street noise. The pool was a disappointment, we paid $100 to have the pool heated but there was a problem with the pump, A maintenance person came and replaced it on our third day. The pool never came up to temperature. It is shaded all day so the sun did not help. The main bathroom needs an exhaust fan and the fan in the second bathroom does not work and should be replaced. The air conditioner in the second bedroom should be checked, it did not seem to be putting out much cool air
Stayed 6 nights in Feb 2024

8/10 Good

BRANDON W.

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

Key West Brandon

Great location, quirky property, quick response to issue that came up.
Stayed 4 nights in Jan 2024

10/10 Excellent

Rebecca H.

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

Family Holiday in the Keys

Wonderful property and wonderful location. Spacious for Key West and we had everything we might need although we didn’t spend much time inside!
Stayed 3 nights in Dec 2023

10/10 Excellent

Ben B.

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

Gret Stay

Great location. The only issue was that we could not find trash receptacles on the property.
Stayed 7 nights in Sep 2023

10/10 Excellent

Scott R.

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

Fantastic location, but needs some updates.

Great location and cute cottage from afar...up close it needs some improvements. Front door difficult to lock and leave...so we exited out back. Living room ceiling needs patched and painted. Bathroom doors not very private. Living room furniture needs to be replaced as they're extremely outdated and uncomfortable and one of the chairs is broke. But, overall we enjoyed the pool, comfortable beds, and location.
Stayed 5 nights in Aug 2023

10/10 Excellent

Matti M., Stockholm

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

Charming house at a great location

The house is located centrally just off Duval street, near to bars, ice cream and not to far to walk down Duval street to get to other restaurants etc. The pool is small but functional and the kitchen had everything we needed and a nice porch in the the front, to sit on and look at people walking by (mainly on Duval street).
Stayed 6 nights in Aug 2023

About the host

Hosted by VHKW - Vacation Homes of Key West

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Languages:

English

Premier Host

They consistently provide great experiences for their guests