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  • (305) 294-7358
Key West Time
July 12th
9:30am · 87°F

Caribbean Cottage ~ Duval Street Key West ~ Weekly Rental

2BR 2BA ~ Weekly Rental
Sleeps 2-5

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 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.

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.

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special rates available


July 10 - July 18
July 24 - Aug 9
Nightly $525

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Dates Weekly Nightly Terms
Jun 10, 2024 - Aug 11, 2024 $3620$650.005 night min, but 3-4 nights within 60 days
Aug 12, 2024 - Oct 2, 2024 $2445$550.004 night min. or 3 night min. 60 days prior to arrival.
Oct 3, 2024 - Oct 17, 2024 $2645$550.004 night min. or 3 night min. 60 days prior to arrival.
Oct 18, 2024 - Oct 27, 2024 $5150$885.007 night minimum
Oct 28, 2024 - Nov 3, 2024 $3195$625.004 night min. or 3 night min. 60 days prior to arrival.
Nov 4, 2024 - Nov 11, 2024 $3620$650.007 night minimum
Nov 12, 2024 - Nov 21, 2024 $3195$625.003 night minimum
Nov 22, 2024 - Nov 30, 2024 $3620$650.007 night min. or 3 night min. 60 days prior to arrival.
Dec 1, 2024 - Dec 18, 2024 $2600$575.004 night min. or 3 night min. 60 days prior to arrival.
Dec 19, 2024 - Dec 27, 2024 $4660$900.007 night minimum
Dec 28, 2024 - Jan 3, 2025 $5500$1000.007 night minimum
Jan 4, 2025 - Jan 10, 2025 $4250$820.004 night min. or 3 night min. 60 days prior to arrival.
Jan 11, 2025 - Jan 17, 2025 $4250$820.004 night min. or 3 night min. 60 days prior to arrival.
Jan 18, 2025 - Jan 31, 2025 $4250$820.004 night min. or 3 night min. 60 days prior to arrival.
Feb 1, 2025 - Feb 14, 2025 $4850$855.005 night min, but 3-4 nights within 60 days
Feb 15, 2025 - Feb 21, 2025 $5125$855.005 night min, but 3-4 nights within 60 days
Feb 22, 2025 - Apr 11, 2025 $4850$855.005 night min, but 3-4 nights within 60 days
Apr 12, 2025 - May 28, 2025 $3620$650.004 night min. or 3 night min. 60 days prior to arrival.
May 29, 2025 - Jun 8, 2025 $3195$625.004 night min. or 3 night min. 60 days prior to arrival.
Jun 9, 2025 - Aug 10, 2025 $3295$625.004 night min. or 3 night min. 60 days prior to arrival.
Aug 11, 2025 - Oct 1, 2025 $2445$550.004 night min. or 3 night min. 60 days prior to arrival.
Oct 2, 2025 - Oct 16, 2025 $2645$550.004 night min. or 3 night min. 60 days prior to arrival.
Oct 17, 2025 - Oct 25, 2025 $5150$885.007 night minimum
Oct 26, 2025 - Nov 2, 2025 $3195$625.004 night min. or 3 night min. 60 days prior to arrival.
Nov 3, 2025 - Nov 10, 2025 $3620$650.007 night minimum
Nov 11, 2025 - Nov 20, 2025 $3195$625.004 night min. or 3 night min. 60 days prior to arrival.
Nov 21, 2025 - Nov 29, 2025 $3620$650.007 night min. or 3 night min. 60 days prior to arrival.
Nov 30, 2025 - Dec 19, 2025 $2600$575.004 night min. or 3 night min. 60 days prior to arrival.
Dec 20, 2025 - Dec 27, 2025 $4800$930.007 night minimum
Dec 28, 2025 - Jan 5, 2026 $5650$1030.007 night minimum

Additional Notes:

  • High Season generally requires a 7 night minimum stay. Shorter stays of 3 - 5 nights may be available within 60 days of your arrival date or in special situations. Certain dates may not be available if they minimize optimal booking for the property's reservation calendar. Please contact us to inquire about stays less than 7 nights.
  • Shoulder and Low Season is a 3 - 5 night minimum available on reservations made within 60 days of arrival May through mid-August. From mid-August through mid-December, 3 - 5 night minimum stays are available any time.
  • Short Stays are available if there are open nights that are less than the minimum stay, shorter stays may be possible depending on the property. Please contact us to inquire.
  • Holiday, Festival, and Event Rates are 20% to 25% higher. These include, but are not limited to: Fantasy Fest, Thanksgiving, Christmas, New Years, Power Boat Races, Mini-Lobster Season, Labor Day, Parrot Heads Meeting of the Mind, 4th of July, Easter. A 7 night minimum stay is required for most major holidays, festivals, and events.

Rates and Terms are subject to change without notice. Above rates do not include taxes and fees. Click here for more details on additional fees. Please contact us for specific pricing and to confirm rates. Rates in US Funds. (305) 294-7358 Ext 1 -

Apply here for Travel Guard Trip Cancellation and Interruption Insurance.

VHKW offers promotional specials for purchasing trip insurance for stays between Aug 10 and Oct 20. Please call for more details.

  • Master bedroom - King size bed 
  • 2nd Bedroom-  Queen size bed
  • Living Room -  Queen sleeper sofa
Dec 02, 2023,
Great house! I would just recommend replacing the folding doors in the bathrooms with something a little more private.

Oct 23, 2023,
Easy to make arrangements for the rental. Check in was a breeze. Check out was a bit of a rush with an agency rep standing on the porch, but she was pleasant enough as we rushed to get out.

Aug 31, 2023,
Nice cottage in a perfect location, love the porch and everything you need in the kitchen and otherwise m..

Aug 15, 2023,
Great house and overall trip.

Mar 13, 2023,
We had a lovely stay on a perfect location for seeing Key West on foot. The home was charming and very comfortable. Having the private backyard/patio/pool area was a plus. We had one need to contact VHKW and the issue was resolved very quickly by maintenance. We did hear some road and traffic noise but it was expected (this was not our first trip to Key West). Thank you for the amazing house!

Mar 01, 2023,
This cottage had everything my husband and I needed. The pool was just the right size for cooling off. We liked the location nearer the southern end. The only negative was the size of the shower in the second bathroom. Very tiny, even for a small woman like myself. Loved having the lockbox for the key. Saved us time not having to check in or out of the office. Had enough starter supplies.

Feb 06, 2023,
The property was just as advertised. I would suggest you let renters know that all doors within the house are lovered doors and that includes bedrooms and bathrooms. That was an interesting surprise for us.

Jan 31, 2023,
Excellent location. Perfect cottage. Comfortable, very clean. Had every amenity we needed to cook, grill, swim and relax. This will be our go to rental moving forward. The one car parking driveway was a huge plus. Parking in Key West can be extremely difficult and expensive. Pulled in one time, never moved it again till we left a week later. We rented a golf cart for the week. Next time will bring our bikes or opt for scooter. As you can park them anywhere for free. We loved it

Jan 06, 2023,
Kayla & Kendra were extremely helpful, made our entire stay worry free

Dec 12, 2022,
Great house, good service. I have rented from VHKW many times and will continue to rent from them.

Nov 23, 2022,
Perfect in every way!

Oct 18, 2022,
Wonderful cottage home. Close to everything. Decorated so homey. Very clean & comfortable bedding. Love the private pool & patio. This home had everything you would need. I want to definitely rent again. ?

Oct 04, 2022,
Loved my stay, 8/10 recommended, no stock on toiletries tho

Sep 13, 2022,
Our second stay in the Carribean Cottage. We love the cottage and Vacation Homes of Key West was great to work with. We will definitely stay with them again

Aug 22, 2022,
It was a great place to stay, and loved the pool.

May 09, 2022,
House and pool was great! Convenient location and easy parking with a golf cart. Only comment is need a TV in the master bedroom!

Oct 28, 2021,
Wonderful place to stay in an incredible location! My only silly complaint is that the tv is way too far away from the couch in the living room and the remote didn’t work or the internet. Would definitely stay here again!

Sep 14, 2021,
We had a great vacation. Booking was easy. House was perfect, great location, clean and pool was a great added bonus. Will definitely book through your site again!

Sep 09, 2021,
Everything was great and easy - wish we were still there though.

Aug 23, 2021,
This was such a lovely place to stay. Easy walking distance to everything but on the quiet end of Duval St. The house had everything we needed and the pool made the stay even better. There was a TV with access to the internet so we could stream a movie one night when it was raining, and we were able to watch a preseason football game also. The beds were comfortable and it was very quiet at night. We would definitely stay there again. In fact, I wish we were there right now. VHKW was very easy to work with and we didn’t have any problems with our stay at all.

Jul 14, 2021,
We loved the location of the cottage and the space was perfect. Our favorite amenity was the plunge pool. After a hot day walking around the island it was nice to cool off in the pool!

Jul 07, 2021,
The cottage was ideal for our vacation. Perfectly appointed, very clean and all in very good working order. We will definitely look to rent through you and likely this same accommodation again. Thank you for your easy and great service!

Jun 07, 2021,
The Caribbean cottage was perfect for two couples. Great location! We will be back!!Sent by: Teo ( on 7-Jun-21 5:59 PM Opened Hi Lindsey, It's great to hear that the cottage was perfect for your group of two couples and you enjoyed the location. We'd love to have you back! VHKW TeamFrom: Lindsey Carson on 15-Jun-21 7:20 PM What would I need to do to rent the same cottage next summer?Sent from my iPhone

Feb 23, 2021,
Enjoyed the home ver much. Love the vibe of Caribbean colors and vintage furniture. We had an enjoyable time. Only suggestion would be to chain across the driveway. We found a car parked there and had to call the police. After 30 minutes of frustration, it was determined that the home owner told a friend they could use the parking spot. She didn’t realize the home was rented.

Feb 17, 2021,
We had a fantastic stay!! The house was perfect the process leading up to the vacation was seamless! I would definitely use VHKW again

Jan 08, 2021,
Great experience. So easy and quick.

Jan 02, 2021,
Authentic Key West property! Gorgeous brick paver patio w/pool. Perfect four family of four and beds to spare in living room. Top notch location and proximity to the Rum Bar. Highly recommend.

Dec 08, 2020,
We loved calling the Caribbean Cottage our home-away-from-home for 12 days in November 2020. The house is small but quite comfortable and had everything we needed to make our holiday a good one. We especially liked the outside patio area and the heated pool. The house’s location can’t be beat. We were no more than a 5 to 10 minute cab ride from most of the sights we wanted to see. An extra benefit were the three restaurants - Italian, Japanese and seafood - just across the street from the house.

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