Entire home

Key West Caribbean Cottage - On Duval St w Private Pool

Vacation home near Duval Street in Key West

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

Outdoor dining
Exterior detail
Exterior
Beach
A heated pool

Reviews

9.2 out of 10
Wonderful

Entire home

2 bedrooms2 bathroomsSleeps 6990 sq ft

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning

Explore the area

View in a map
Key West, FL
  • Place, Duval Street
    ‪1 min walk‬
  • Place, Ernest Hemingway Home and Museum
    ‪3 min walk‬
  • Place, Southernmost Point
    ‪8 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪12 min drive‬

Room options

About the neighborhood

Key West

City center stay.At this Old Town Key West vacation home, you'll be well placed to visit Duval Street and Ernest Hemingway Home and Museum, both within a 5-minute walk. Florida Keys Beaches and Southernmost Point are also within half a mile (1 km).

What's nearby

  • Duval Street - 1 min walk - 0.0 miles
  • Ernest Hemingway Home and Museum - 3 min walk - 0.2 miles
  • South Beach - 6 min walk - 0.4 miles
  • Key West Butterfly and Nature Conservatory - 6 min walk - 0.4 miles
  • Southernmost Point - 8 min walk - 0.4 miles

Getting around

  • Key West Intl. Airport (EYW) - 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.

Similar properties

Property amenities

Pool/Spa

  • Heated pool
  • Private pool

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Car not required
  • Limited onsite parking (max 1 space)

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Microwave
  • Oven
  • Refrigerator
  • Stovetop

Dining

  • Dining table

Bedrooms

  • 2 bedrooms
  • Bedsheets provided
  • Sofa bed

Bathroom

  • 2 bathrooms
  • Hair dryer
  • Towels provided

Living spaces

  • Dining table
  • Living room

Entertainment

  • TV

Outdoor areas

  • Fenced yard
  • Garden

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk

Comfort

  • Air conditioning

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the city center
  • Near a health/beauty spa
  • Near the marina

Things to do

  • Heated pool
  • Birdwatching nearby
  • Ecotours nearby
  • Motor boating nearby
  • Swimming nearby
  • Wildlife walks nearby

Safety features

  • 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 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
Onsite 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 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. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a fire extinguisher and a smoke detector in each 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

How close is Key West Caribbean Cottage - On Duval St w Private Pool to the airport?

This vacation home is 3.5 mi (7-min drive) away from the Key West Intl. Airport (EYW) airport, the closest popular airport to the property.

Does Key West Caribbean Cottage - On Duval St w Private Pool have an airport shuttle?

Airport shuttle services are not available at this vacation home.

How close is Key West Caribbean Cottage - On Duval St w Private Pool to the beach?

This vacation home is a short 5-minute walk from South Beach and 6-minute walk from Florida Keys Beaches. Don't forget your sunscreen!

Does Key West Caribbean Cottage - On Duval St w Private Pool offer free breakfast?

This vacation home does not offer free breakfast.

Is there a casino at Key West Caribbean Cottage - On Duval St w Private Pool?

No, there is no casino at this vacation home.

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

Check-in begins at 4:00 PM.

Is there free parking at Key West Caribbean Cottage - On Duval St w Private Pool?

Free parking is not available at this vacation home.

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

Yes, there's a private pool.

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

There are no spa services available at this vacation home.

How close is Key West Caribbean Cottage - On Duval St w Private Pool to downtown Key West?

This vacation home is 0.4 mi away from Key West.

Key West Caribbean Cottage - On Duval St w Private Pool Reviews

Reviews

9.2

Wonderful

Rating 10 - Excellent. 46 out of 67 reviews
Rating 8 - Good. 16 out of 67 reviews
Rating 6 - Okay. 4 out of 67 reviews
Rating 4 - Poor. 1 out of 67 reviews
Rating 2 - Terrible. 0 out of 67 reviews

9.4/10

Cleanliness

Reviews

8/10 Good

Fiona P.

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
Stayed 4 nights in Jan 2026

10/10 Excellent

Becky S.

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.
Stayed 7 nights in Jan 2026

10/10 Excellent

Frank P.

Liked: Cleanliness
We much enjoyed the house. Its close proximity to Duval Street was a bonus. Will def rent it again in the future.
Stayed 3 nights in Dec 2025

10/10 Excellent

Kathy Z.

Liked: Cleanliness
Great location, private parking, cute house, well-equipped. Host was quick to respond.
Stayed 4 nights in Nov 2025

10/10 Excellent

Mary T.

Liked: Cleanliness
Great location and layout! Everything was as advertised. Bicycle rentals were a short walk away. Thanks for a great vacation!
Stayed 4 nights in Aug 2025

10/10 Excellent

Tiffany H.

Stayed 4 nights in May 2025

10/10 Excellent

Sheri V., Alta Sierra, California

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.
Stayed 6 nights in May 2025

10/10 Excellent

Shelley D.

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!
Stayed 3 nights in Mar 2025

10/10 Excellent

Erin B., Dover

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
Stayed 5 nights in Apr 2025

10/10 Excellent

Olga M.

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.
Stayed 2 nights in Mar 2025

10/10 Excellent

Ken T.

Liked: Cleanliness

Great location

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

8/10 Good

Ann C.

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.
Stayed 4 nights in Mar 2025

6/10 Okay

Greg B.

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.
Stayed 21 nights in Jan 2025

10/10 Excellent

Allison L.

Liked: Cleanliness

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

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

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

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., Papillion, NE

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. ☺️
Stayed 5 nights in Oct 2024

10/10 Excellent

Brent M.

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!
Stayed 6 nights in Sep 2024

10/10 Excellent

JIM W.

Liked: Cleanliness

Yearly trip

Yearly trip
Stayed 4 nights in Aug 2024

10/10 Excellent

Patricia S.

Liked: Cleanliness
Stayed 6 nights in Apr 2024

10/10 Excellent

Tammy K.

Liked: Cleanliness

Absolutely wonderful

Everything was perfect.
Stayed 6 nights in Jul 2024

10/10 Excellent

Christina B.

Liked: Cleanliness

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., Modesto, California

Liked: Cleanliness

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

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