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:: CARIBBEAN FLING @ SOUTHARD :: Delightful Cozy Cottage & Pool / Near Duval...

Bedrooms 2
Half Baths1
Space 600 sq. ft.
Property type house
Minimum Stay 27 nights


About the property

Charming 2BR/1.5BA Conch Cottage On One-Way Street / 29 night minimum stay***

Ever wish you could spend a month or two in one of those perfect little conch houses set along the streets of Old Town, Key West? Take a look inside this classic little conch house with a Caribbean flair, and you’ll find exactly what you’ve been looking for. Set in the ideal Key West location - on Southard Street just two short blocks from Duval Street in one direction and the Historic Seaport in the other – this island jewel is the realization of the Key West dream: sit on the front porch, swim in your private pool, cook and eat outside, and then stroll down to Duval for an evening in the beloved Conch Republic.

***This home is available for lease by the month, in accordance with local ordinances strictly enforced by the City of Key West. The minimum lease is for 27 nights in February and for 29 nights during any other period.


Southard Street is a famous, one-way Old Town street leading directly toward the downtown area of Duval Street. This street is known for its well-used bike path and its quintessential Key West conch houses. “Caribbean Fling” is one of those homes: a little gem perched along the street with a perfect little front porch to sit and watch the passersby and take in the island air. Follow the porch around the backyard to reach your own private oasis – a lagoon-style dipping pool of the perfect size for this lovely little home. Surrounded by outdoor seating and a tropical garden complete with an outdoor shower, you will have to find some very good reasons to leave your little slice of paradise on Southard Street.


Through the lovely blue hurricane shutters and perfect front porch is a gorgeous island cottage, straight out of the pages of coastal living. Luscious island colors and fabrics, seashells and flowers decorate the open living area, complete with a flat screen TV with DVD player and an iPod dock. There is plenty of seating in this living area, including two separate couches and a small dining nook in the corner. One of the couches is a luxurious leather sofa that folds out to a Queen-sized sleeper sofa.


This home has one of the most unique dining areas you will find in Key West: on the walkway between the living and the kitchen is an all open-air dining area with space for 4 under a bamboo-style roof. One wall of the dining area has linen curtains that pull across to provide additional privacy of shelter from an afternoon shower. Follow the dining area to the kitchen, a tiny but very efficient indoor/outdoor space with a fridge, microwave, stove, oven, toaster oven, coffee makers, and all of the utensils and tools you’ll need to whip up a meal. It is island living at its best!


The master bedroom opens up off the living room and has a Queen-sized bed, flat screen TV, large dresser, and ceiling fan. The master bathroom is en-suite with a tile shower. The cozy second bedroom opens up off the outdoor dining area, with twin bunk beds. This cabin-style “bunk room�� has an en-suite half bathroom. Both bedrooms have in-room air conditioning units, so each bedroom can be set at the perfect temperature.


Washer & Dryer, In-Room Programmable LD A/C Units, Ceiling Fans, Gated & Lushly Landscaped Outdoor Area with a Lagoon-Style Private Pool, Charcoal Grill, Flat Screen Cable TVs, Microwave, Toaster Oven, Gourmet Kitchen, Linens and Towels provided. Interim housekeeping provided upon request. Wireless high-speed Internet access is included. This property will accommodate up to 4-6 adults.


As a Vacation Rental broker, we will do everything possible to assure you of a memorable and thoroughly enjoyable stay while you are in one of the homes we manage. Our mission statement is to make sure each home has been maintained to an exceptional standard and has no defects or problems that will spoil your stay. If there is a problem, we pride ourselves in our ability to immediately address and solve that problem before it has intruded on your vacation experience. And in these uncertain times, you'll have added peace of mind knowing that the rental funds you have paid in advance will remain in a secure escrow fund until the day you enter your vacation home.


As your Key West real estate company, we can assist you in making your dream of home ownership in paradise a reality while maintaining the highest level of integrity during the property buying process. As your Exclusive Buyer's Broker we will do our utmost to discover assets and/or defects of a given home or parcel. We will negotiate only on the buyer’s behalf for the best price and term, using every legal and ethical device to obtain the most favorable outcome for the buyer through every step in the property buying process. And that is our commitment, for each and every client we serve, on every transaction we oversee.

More Details

Property Manager
Last Key Realty
Speaks: english, french, spanish
Manager indicates their response time is:
Within a few hours
Calendar last updated:
November 16, 2017


Old Town House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
  • Housekeeper Optional
Floor Area:
  • 600 sq. ft.
House Rules:
  • Check-in: 3:00 PM
  • /
  • Check-out: 11:00 AM
  • Max. occupancy: 6
  • Min. age of primary renter: 25
  • Non smoking only
Location Type:
  • Downtown ...
  • Village ...
  • Adventure
  • Away From It All
  • Family
  • Historic
  • Romantic
  • Air Conditioning
  • Clothes Dryer
  • Hair Dryer
  • Internet
  • Iron & Board
  • Linens Provided
  • Living Room
  • Towels Provided
  • Washing Machine
  • Coffee Maker
  • Dishes & Utensils
  • Kitchen
  • Microwave
  • Oven
  • Pantry Items
  • Refrigerator
  • Stove ...
  • Toaster ...
  • Dining ...
  • Dining Area
  • seating for 4 people
  • 1 Bathroom
  • 1 Half Bath
  • Master Bathroom - toilet , shower
    Bunk Room Bathroom - toilet
    Outdoor Shower - outdoor shower
  • 2 Bedrooms, Sleeps 6
  • Bunk Room - 2 twin/ single , Bunk beds with en-suite half bath, in-room A/C unit
    Master Bedroom - 1 queen , Flat screen TV, en-suite bath, in-room A/C, ceiling fan
    Living Room - 1 sleep sofa /futon , Queen sized sleeper sofa
  • Books
  • DVD Player
  • Satellite / Cable
  • Stereo
  • Television
  • Deck / Patio
  • Outdoor Grill
  • wheelchair inaccessible
Pool / Spa:
  • Private Pool
Onsite Services:
  • Concierge
  • botanical garden
  • churches
  • cinemas
  • coin laundry
  • duty free shops
  • festivals
  • library
  • live theater
  • marina
  • museums
  • playground
  • recreation center
  • reefs
  • restaurants
  • synagogues
Leisure Activities:
  • antiquing
  • beachcombing
  • bird watching
  • eco tourism
  • horseshoes
  • paddle boating
  • photography
  • scenic drives
  • sight seeing
  • walking
Local Services & Businesses:
  • ATM/bank
  • Babysitter
  • fitness center
  • groceries
  • hospital
  • laundromat
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • basketball court
  • cycling
  • deepsea fishing
  • fishing
  • fly fishing
  • freshwater fishing
  • golf
  • golf privileges optional
  • jet skiing
  • pier fishing
  • roller blading
  • sailing
  • scuba diving or snorkeling
  • snorkeling
  • surf fishing
  • swimming
  • tennis
  • water skiing
  • wind-surfing


Exceptional! 5/5 -
(13 traveler reviews)

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:: CARIBBEAN FLING @ SOUTHARD :: Delightful Cozy Cottage & Pool / Near Duval...
average rating of 5.0 based on 13 reviews

The Key West Vacation Home with Everything

  • 5 of 5

We just returned from Key West and a stay at the Caribbean Fling located at 707 Southard. This house had everything we wanted in a vacation home and more. It was located in close proximity to all of the action, but far enough away from the hustle and bustle if you just wanted to chill at the house. We parked the car and walked to the grocery store two blocks away. We were also only two blocks away from Duval Street. We enjoyed sitting on the front porch with our dog (the house is pet friendly) and watching people walk by. Everyone was so friendly. After a long day of relaxing, we slept on the sleeper sofa. It was so comfortable, I am looking for one like it at my home (easy to pull out and put back for daytime use). The house was very clean and well maintained. The kitchen was well equipped and right next to the outdoor dining area. We also used the grill by the pool. The pool was like our private oasis complete with chairs and plants around the deck. My favorite thing about this house was the outdoor shower. My husband and I both thought this was a wonderful feature. (By the way, we are in our sixties.) We would recommend this house to anyone traveling to Key West. We stayed with another couple and there was room for two more. We can't wait to return to Caribbean Fling and experience all that this house has to offer.

  • Submitted: Jan 31, 2017
  • Stayed: November 2016
  • Source: HomeAway
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A Dream Vacation

  • 5 of 5

The arrival to this property was our first visit to Key West. We were thrilled. The house was clean and in good repair. We loved the pool and the privacy of the whole setting. The house was close to dining and the happenings of Duval Street. We were able to rent two bicycles and relive childhood emotions by biking to the ocean/beach and visit all of the area. Our only complaint was that our vacation was too short. There were so many other things to do, restaurants to visit and shops to browse in. I'd be happy to go back and recommend this property to my relatives and friends. Elkins,WV

  • Submitted: Mar 1, 2016
  • Stayed: December 2015
  • Source: HomeAway
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2 0

Great location, close to everything, relaxing

  • 5 of 5

Our typical day was coffee, breakfast and a soak in the pool/warm tub and then on to see the sites for the day, enjoying the warmer, breezy days shopping, seeing the history of Key West. Attended 3 theatre shows while there for the month, one at the Fringe Theatre, Waterfront Theatre and one at the Aqua Lounge. Enjoyed all of them. Another treat was music at most restaurants/bars, not only on Duval St, but in all areas of Key West. Also enjoyed regular movies at the Tropic Theatre and the Regal Cinema. Went on a beautiful sunset cruise, Hemingway House, the Aquarium, Mallory Square, Southernmost Point and all the different memorials. Too many to list, but our favorite restaurants/bars were Chicago on Greene for the jazz and Irish Kevin's for the entertainment. The Carribean Fling rental was very nice to come back to for a break in the afternoon and not have to go out all the time. We walked or biked everywhere. A car definitely would be a nuisance due to parking costs and availability. Will plan a visit back in the future !!

  • Submitted: Feb 11, 2016
  • Stayed: January 2016
  • Source: HomeAway
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4 0

Quaint and Convenient

  • 5 of 5

The property is comfortable and in an excellent location. Dennis Bentley was very helpful and responsive whenever I had questions.

  • Submitted: Nov 20, 2015
  • Stayed: July 2015
  • Source: HomeAway
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1 0

Wonderful vacation at Caribbean Fling @ Southard

  • 5 of 5

My wife and I arrived at the Caribbean Fling on an extremely warm day and were in the pool within minutes, such a great way to cool off. The atmosphere of the cottage was great. We wanted to have a quite vacation and the Fling give us these opportunities.

We were able to enjoy the outdoors, the pool and have a meal in the midst of palm trees and beautiful flowers.

The multitude of options within the Fling, was wonderful TV, music and many books to read. We enjoyed the front porch watching and talking to folks with the many modes of travel.

We were impressed with the tour of Old Town on the train; love the Engineer Tour Guide, and all the History he spoke of. Many shops and restaurants were within walking distance, the walk down Duval Street is a once in a lifetime experience. We decide to try the Jet-Ski for the 27 mile guided tour around the Key West Island, it was beautiful.

What a delightful and comfortable place that we hope to return.

  • Submitted: Jul 26, 2015
  • Stayed: July 2015
  • Source: HomeAway
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4 0
Stillwater, MN

Great property close to all the action

  • 5 of 5

We had a wonderful time in Key West and plan to come again.

Dennis the property manager was very helpful and provided outstanding service.

  • Submitted: Apr 25, 2015
  • Stayed: March 2015
  • Source: HomeAway
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Nearest Airport
2.6 Miles
Key West International Airport
Nearest Barpub
0.2 Miles
Krawl Off Duval
Nearest Ferry
0.3 Miles
Key West Bight Ferry Terminal
Nearest Golf
3.8 Miles
Key West Golf Club
Nearest Motorway
0.2 Miles
US 1
Nearest Restaurant
0.2 Miles
The Cafe
Nearest Beach
1 Miles
Ft. Zachary Taylor State Park Beach
Car: not necessary




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