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  • (305) 294-7358
Key West Time
October 23rd
11:17am · 81°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.

Recently restored, this historic Caribbean Cottage, with private pool added in September, 2015 in the back yard, has an authentic Caribbean island feel, with original wood planked polished floors, vintage hand-hewed beams, bright blue tile (accented with marble), and Bahama style wooden window shutters. Artist owners painted the original pine walls with elegant historic colors of olive and cream, and adorned the sash style windows with wooden shutters 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 twin daybed.

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 -  Twin daybed

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.

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.

Dates Weekly Nightly Terms
Oct 22, 2017 - Oct 28, 2017 $3700$7007 night minimum
Oct 29, 2017 - Nov 5, 2017 $2250$4253 night minimum
Nov 6, 2017 - Nov 12, 2017 $2600$4257 night minimum
Nov 13, 2017 - Nov 17, 2017 $2250$4253 night minimum
Nov 18, 2017 - Nov 24, 2017 $2600$4257 night minimum
Nov 25, 2017 - Dec 16, 2017 $1900$4253 night minimum
Dec 17, 2017 - Dec 25, 2017 $3100$5007 night minimum
Dec 26, 2017 - Jan 1, 2018 $3700$7007 night minimum
Jan 2, 2018 - Jan 12, 2018 $2800$5007 night minimum
Jan 13, 2018 - Jan 19, 2018 $2875$5007 night minimum
Jan 20, 2018 - Jan 26, 2018 $2875$5007 night minimum - Sat/Sat Only
Jan 27, 2018 - Feb 2, 2018 $3000$5007 night minimum - Sat/Sat Only
Feb 3, 2018 - Feb 16, 2018 $3200$5007 night minimum - Sat/Sat Only
Feb 17, 2018 - Feb 23, 2018 $3450$5007 night minimum - Sat/Sat Only
Feb 24, 2018 - Apr 20, 2018 $3200$5007 night minimum - Sat/Sat Only
Apr 21, 2018 - May 27, 2018 $2675$4504 night min. or 3 night min. 60 days prior to arrival.
May 28, 2018 - Jun 15, 2018 $2300$4254 night min. or 3 night min. 60 days prior to arrival.
Jun 16, 2018 - Aug 9, 2018 $2675$4507 night min. or 3 night min. 60 days prior to arrival.
Aug 10, 2018 - Oct 20, 2018 $2300$4253 night minimum
Oct 21, 2018 - Oct 27, 2018 $3800$7007 night minimum
Oct 28, 2018 - Nov 4, 2018 $2300$4253 night minimum
Nov 5, 2018 - Nov 11, 2018 $2675$4507 night minimum
Nov 12, 2018 - Nov 16, 2018 $2300$4253 night minimum
Nov 17, 2018 - Nov 23, 2018 $2675$4507 night minimum
Nov 24, 2018 - Dec 16, 2018 $1850$4253 night minimum
Dec 17, 2018 - Dec 25, 2018 $3200$5507 night minimum
Dec 26, 2018 - Jan 1, 2019 $3800$7007 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, New Years, Key West Yacht Race Week, Thanksgiving, Power Boat Races, Mini-Lobster Season, Labor Day, Parrot Heads Meeting of the Mind, Biker's Poker Run, 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.

  • Master bedroom - King size bed 
  • 2nd Bedroom-  Queen size bed
  • Living Room -  Twin daybed
Jul 08, 2017,
What a quaint and warm little cottage. We fully enjoyed ourselves. Only issue was the pool is a little small and deck space for sunning was limited. It also could be the time of year, but the sun availability was limited around the pool. But we will visit this cottage again in the future. Well worth the time and money. Much closer to Duvall St activity than website leads you to believe. Fabulous to walk out your front door to get great Ice Cream and staples just at the end of the street (100 feet).

Jun 28, 2017,
We had a great time at the Caribbean Cottage. It was a great location, the home was clean, and the pool was great after a hot walk on duval, we went night swimming ever night. Thanks so much, we had a great vacation.

Jun 19, 2017,
We absolutely loved our accommodations! Great location! Exceeded our expectations!

Jun 09, 2017,
The hardest part of this vacation, was LEAVING!!! Reservations were easy, as was the paperwork and payments. My mom had never taken a vacay like this, but I had, so I knew what to pack, but the house was already prepped with most of the essentials we took! The 506 Virginia was very clean, had a very warm coming home feeling to it, and the private pool was everything! Check in was very easy and I love the fact that VHKW called me prior to arrival to touch base. We will definitely come back to 506 Virginia, and look forward to working with VHKW again! My only suggestion would be to spray the yard, or bring yard guard for the mosquitos! They were really bad early morning and later afternoon...but they didn't keep us from having a blast!

Jun 04, 2017,
Cottage was nice and very easy to access. Our stay was quaint and convenient.

Jun 01, 2017,
Absolutely perfect for two couples to stay at Key West! Homemade ice cream on the corner, 4 short blocks to the beach and southernmost point, and 2 blocks from our favorite restaurant, La Te Da. Accommodations were everything as listed and shown in the pictures. Everything worked and there were no problems at all. Checking in and out was a piece of cake. Pool was private, clean and so refreshing. I would definitely return to this piece of paradise! Vacation Homes of Key West was a pleasure to book with.

May 23, 2017,
This place is near Duval St on the far end from Mallory Square. It was lovely and had the feel of a small cottage with all the amenities of home. It had a parking spot in the driveway for one car and a private pool. Very close the Butterfly and Nature Conservatory which we always visit when in Key West. We highly recommend this place.

Mar 07, 2017,
Great cottage, when we had issues with the pool pump, maintenance came right away. We had an awesome stay. Thanks

Mar 01, 2017,
Wonderful experience. Very quick to reply to any concerns or questions

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