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29 Reviews
Bedrooms 7
Property type estate
Minimum Stay 4 nights

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Minimum Stay
4 nights


Uptwon/Upper Duval Estate Rental Photos and Description

Lush Duval Street Estate + Private Pool & Grounds, 7 Bedrooms, 7.5 Bathrooms

“Southernmost Hospitality” is a luxurious private estate that occupies an entire corner of Old Town’s famous Duval Street, just a block from the Southernmost Point. Don’t let the address fool you… this upscale home has plenty of privacy in the spacious back yard with a tall fence surrounding the large private pool. Privacy also comes in the form of the all-suites accommodations: each bedroom is complete with an en-suite bathroom and flat screen TV. This fabulous home, combined with Last Key Realty’s Five-Star Guest Services, will make your stay in Key West a memorable one.


If you’ve heard of Key West, you undoubtedly know of the famous “Duval Street” with its selection of fabulous restaurants, shops, galleries, and nightlife. With a prime Duval Street address, “Southernmost Hospitality” is truly the choice location for a group that wants to be in the center of the action of Old Town Key West. Enjoy the views of Duval St passerby from your vast porches both on the first and second floors, or hide behind the tall fence blocking the views of your back yard from the street. Walk down your front steps to any of the handfuls of attractions within walking distance, including the Southernmost Point, Hemingway House, Southernmost Beach, and famous spots like Sloppy Joe’s, The Green Parrot, and any number of delicious restaurants on and off Duval Street. Should you decide to venture off the island, you can park multiple cars in your large off-street private driveway. The driveway also has space for a number of your choice Key West transportation vehicles, be it bicycles, scooters, or electric cars.


A large home deserves a grand living area. The spacious main foyer of this home opens to the spacious living room, with a large comfortable sofa and plenty of seating for a group. The sectional sofa, which also pulls out to a sleeper for extra guests, sits in front of a vast 60-inch flat screen Smart TV with DVD and BluRay player. There is also an iPod/iPhone docking station. Off the living area sits a stately dining area with space for 8 diners, plus additional seating at the kitchen bar. The kitchen is entirely upgraded with state of the art appliances and tools, including a Kuerig coffee maker. Preparing a meal in this home will be a real treat for even a master chef.


It is hard to imagine a Duval Street address having privacy, but “Southernmost Hospitality” was built to provide the optimum group vacation experience and a private pool is a must. The tall privacy fence surrounding the back yard of this property provides the right amount of seclusion from the street and the surroundings. Enjoy a swim, or sit by the heat-optional private pool in any of the number of chaise lounges or plush outdoor furniture and dining sets. A poolside meal is a must at the full outdoor dining set using the deluxe BBQ grill. You’ll have everything you need for a cookout with the whole gang.


“Southernmost Hospitality” was designed to create the ideal amount of space and privacy for a large group. Each room in this upscale home has an en-suite bathroom, a flat screen TV, and big beautiful windows with views of the island. The Master Suite is located on the first floor, with a King sized bed and French doors out to the back patio. Upstairs are four bedrooms: the “Jimmy Buffett Room” has two twin beds that can convert to a King upon request; the “Chicken Coop” also has two twin beds that can convert to a King; the “Robert Doll Room” has a King sized bed; and the “Americana Room” has a Queen sized bed. The remaining two bedrooms are located in the Poolside Guest House, which has two separate bedrooms & bathrooms, each with two Twin sized beds that convert to a King upon request. All of the en-suite bathrooms have showers (or tub/showers with jacuzzi jets) and the flat screen Smart TVs in all rooms are equipped with full cable.


Private Heated Pool, Washer & Dryer, Central Heat and A/C, Ceiling Fans, Off-Street Parking in Private Driveway, Flat Screen State-of-the Art HD TVs in all bedrooms and main living area, DVD & BluRay Player, iPod/iPhone Docking Station, Fully Equipped Chef’s Kitchen with Gourmet Appliances including Keurig coffee maker, Linens and Towels provided. Interim housekeeping provided upon request. Wireless high-speed Internet access and full cable is included. This property will accommodate 14-16 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 job 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 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.


If you decide you want to buy your own piece of paradise, 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 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
  • Minimum Age Limit for Renters
  • children welcome
  • non smoking only
  • pets considered

Property Manager
Last Key Realty
Speaks: english, french, spanish
Manager indicates their response time is:
Within a day
Calendar last updated:
October 22, 2016
Call Manager


based on 29 traveler reviews

average rating of 5.0 based on 29 reviews


  • 5 of 5

We had an amazing month at this beautiful home in Key West. Any and everything you could want this home has it! Lori will help you with your every wish and desire. I only wish I could live here forever!

  • Submitted: Feb 25, 2016
  • Stayed: Jan 2016
  • Source: HomeAway
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1 0

Quite a spectacular Christmas in Key West

  • 5 of 5

We gathered from all over the United States for this Christmas holiday. I was having a difficult time finding a home that could accommodate my large family of children, grand children and great grand children. Lori Bailey was very helpful and found us the perfect place. This home and the adjacent cottage was simply wonderful! We had everything we needed, including Lori geting us the extra tables and chairs I requested and an extra bed for my grandson. She was there to receive the other deliveries we had set up for our stay. When we needed an additional table for puzzles and games, she brought that to us as well. Never have I had such courteous and fast service. As for the home, it was quite the showplace. It was decorated in beautiful red poinsettias for our arrival and it was most clean and well kept. I appreciated the bench for the downstairs walk in shower that was provided for me. My family had the best holiday ever. Giving Lori and this home five stars is not enough for how thankful we all were for the lovely home and for Lori's gracious assistance. We have many photos and fond memories of our holiday in Key West. Thank you again.

  • Submitted: Jan 10, 2016
  • Stayed: Dec 2015
  • Source: HomeAway
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The Perfect Wedding Venue

  • 5 of 5

I can't thank Lori Bailey enough for helping make our week in Key West outstanding. The house we rented through you exceeded our hopes and expectations. The location proved to be ideal as a gathering place for all our guests who attended our son's wedding and our family members who stayed at the house are still commenting on how enjoyable their stay was. Thank you very much for making our transition into and out of the house so easy. Our stay was wonderful, and my wife and I will most certainly enlist your expertise and services

on our next visit to Key West. Lynn and Beth Hawbaker

Bettendorf, Iowa

  • Submitted: Dec 31, 2015
  • Stayed: Nov 2015
  • Source: HomeAway
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Good times in a great house on Duval

  • 5 of 5

We all had a great time staying in this house. Excellent customer service from Lori! Our experience with Last Key Realty and Southernmost Hospitality was definitely worthy of 5 stars.

  • Submitted: Nov 4, 2015
  • Stayed: Oct 2015
  • Source: HomeAway
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Beautiful, spacious property in a perfect location

  • 5 of 5

We had a wonderful time! The house was amazing! It was very spacious and easily accommodated a large group for a girls' getaway. It was so nice that each room had its own bathroom. The entire property was well-maintained and well-stocked with all the essential items. We really enjoyed the outdoor space..the pool area is awesome, as is the front and top decks! The location of the house is perfect! We were able to walk almost everywhere. Lori, the property manager, was very sweet and accommodating. She was always available to help. She made sure everyone was happy. Highly recommend this property! We had so much fun and are already thinking about our next trip back!

  • Submitted: Oct 19, 2015
  • Stayed: Oct 2015
  • Source: HomeAway
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Exceptional home and service

  • 5 of 5

We have a group of college buddies who get together every year to reminisce, play poker and fish. We chose Key West for our destination this year and what a great time we all had. This home was perfectly suited to our needs. Lori's outstanding customer service saved the day. We realized our coffee pot was not working, when we were trying get it ready for the next day. We had an early morning wake up planned for a big fishing trip. She brought us a new coffee pot at midnight. Amazing! Thank you once again and we certainly will recommend your company to all our friends.

  • Submitted: Oct 11, 2015
  • Stayed: Sep 2015
  • Source: HomeAway
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Nearest Airport
2.6 Miles
Key West International Airport
Nearest Barpub
0.01 Miles
La Te Da
Nearest Ferry
0.9 Miles
Key West Bight Ferry Terminal
Nearest Golf
3.9 Miles
Key West Golf Club
Nearest Motorway
0.25 Miles
US 1
Nearest Restaurant
0.01 Miles
Banana Cafe
Nearest Beach
0.2 Miles
Southernmost Beach
Car: not necessary


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Uptwon/Upper Duval Estate Accommodation and Amenities

Property Type:
  • estate
  • Guests provide their own meals
Location Type:
  • Downtown
  • Village
  • Adventure
  • Family
  • Historic
  • Romantic
  • Sports & Activities
  • Tourist Attractions
  • Air Conditioning
  • Clothes Dryer
  • Hair Dryer
  • Heating
  • Internet
  • Iron & Board
  • Linens Provided
  • Living Room
  • Parking
  • Towels Provided
  • Washing Machine
  • Coffee Maker ...
  • Dishes & Utensils
  • Dishwasher
  • Kitchen
  • Microwave
  • Oven
  • Pantry Items
  • Refrigerator
  • Stove
  • Toaster
  • Dining
  • Dining Area
  • seating for 10 people
  • 7 Bathrooms
  • Master Bathroom - toilet , shower
    Chicken Coop Bath - toilet , shower
    Americana Room Bath - toilet , shower
    Robert Doll Room Bath - toilet , shower
    Jimmy Buffett Room Bath - toilet , combination tub/shower , jetted tub
    Guest House Bath 1 - toilet , shower
    Guest House Bath 2 - toilet , shower
  • 7 Bedrooms, Sleeps 16
  • Master Suite - En-Suite Bathroom, Back Patio, Flat Screen TV
    Jimmy Buffett Room - 2 twin/ single , Twins Convert to King Upon Request, En-Suite Bathroom, TV
    Chicken Coop - 2 twin/ single , Twins Convert to a King Upon Request; En-Suite Bathroom; TV
    Americana Room - 1 queen , En-Suite Bathroom; Flat Screen TV
    Robert Doll Room - 1 king , En-Suite Bathroom; Flat Screen TV
    Guest House Room 1 - 2 twin/ single , Twin beds convert to 1 King upon request
    Guest House Room 2 - 2 twin/ single , Twin beds convert to 1 King upon request
  • Books
  • DVD Player
  • Satellite / Cable
  • Stereo ...
  • Television
  • Balcony
  • Deck / Patio
  • Lawn / Garden
  • Outdoor Grill
  • Minimum Age Limit for Renters
  • children welcome
  • non smoking only
  • pets considered
Pool / Spa:
  • Heated Pool
  • 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
  • bird watching
  • eco tourism
  • 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
  • freshwater fishing
  • golf
  • golf privileges optional
  • jet skiing
  • pier fishing
  • roller blading
  • sailing
  • scuba diving or snorkeling
  • snorkeling
  • surf fishing
  • swimming
  • tennis
  • wind-surfing

Learn more about this vacation rental at the manager's website:

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