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Old Town Key West by Southernmost Beach and Duval Main Street.

21 Reviews
Bedrooms 5
Property type house
Minimum Stay 1 - 7 nights

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Minimum Stay
1 - 7 nights


Uptwon/Upper Duval House Rental Photos and Description

5 Bedroom, 4 Bathrooms, Sleeps up to 12

Prime Old Town Walking Location. Across the Street from Southernmost on the Beach, and down the Street from the Southernmost Point. No need for a car but we do have parking. Large outdoor swimming pool. Balcony seating areas to watch the world go by.

Need a 2 bedroom 2.5 bath home rental Old Town Key West? For rates give me a call 305 393-6900 Currently available January, April, May, and June.

  • Minimum Age Limit for Renters
  • children welcome

Property Manager
Sharon Simpson
Member since: 2009
Speaks: english
Response time:
Within 12 hours
Response rate:
Calendar last updated:
October 24, 2016
Call Manager

About Sharon Simpson

Like the home’s original turn-of-the-century owners, Joyce Moore and her husband, Craig Fazio, landed on Key West from the Caribbean. In 1994, after a period of sailing the turquoise seas in a 33-foot boat Craig built by hand, the pair embarked on a new path of restoring historic properties and innkeeping. While Craig and Joyce focus on the hands-on behind-the-scenes restoration work, their dear friend Sharon Simpson, who they met in Panama in their sailing days. All three are passionate and experienced travelers who know what it takes to create first-class accommodations, so all the little details that make for an easy and memorable vacation are provided at Seaside Place.

Sharon Simpson purchased this house in 1999

Why Sharon Simpson chose Key West

Seaside place is located in a great Old Town neighborhood. Close to the beach and all that Key West has to offer. After hands on renovation and running Casa Key West, a 7 unit Guest House around the corner we decided to downside by selling the Guest House and Opening Seaside Place.


based on 21 traveler reviews

Old Town Key West by Southernmost Beach and Duval Main Street.
average rating of 4.952381 based on 21 reviews

This house and location was amazing!

  • 5 of 5

The house, the pool, and the location was perfect. Could walk everywhere! We really appreciate when the owers care enough to have great bedding -and it was impressive. Nothing is worse than bad mattress and bedding - but not here - very nice!

  • Submitted: Oct 2, 2016
  • Stayed: Sep 2016
  • Source: HomeAway
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  • 5 of 5

We had 5 couples in our party and this house was perfect! The decor immediately puts you in a vacation spirit, it's beautiful and tastefully decorated. The back yard with the outside eating area and the pool....fabulous!! It was so relaxing to hang out at the pool (could have done without the 3 large iguanas that wanted to hang out with us). The house was immaculate and beautiful. The pictures do not do it justice. All in all it is in a perfect location. We were able to walk just about anywhere we needed to go. Sharon, the house concierge, was absolutely AMAZING . She went above and beyond for us and really made the trip that much more enjoyable. Any questions, she has the answers. We will stay here again when we return to Key West. Everyone in our group is ready to go back again! Fantastic vacation!

  • Submitted: Jul 22, 2016
  • Stayed: Mar 2016
  • Source: HomeAway
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Lewes DE

Fun week in paradise

  • 5 of 5

Just finished another week in paradise with family and friends at beautiful Seaside Place! Owners Joyce and Craig and their fantastic property manager Sharon always ensure that all our requests are met and our stay most pleasurable. The outside patio and pool area are outstanding for entertaining. We love Seaside Place!

  • Submitted: May 14, 2016
  • Stayed: Apr 2016
  • Source: HomeAway
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Ruthven, IA

Awesome House!

  • 5 of 5

Family of 6 plus 7 month old baby stayed the last week in January. We used the one bedroom at entry to keep all of the babies things - stroller, car seat, etc. Perfect amount of space for us! It has everything you could ever need. Great location to walk to Duval Street. We rented an 8 passenger golf cart and could park in driveway and plug in with ease every day. The pool was terrific and very clean and with all the towels you could want. Great sitting area to hang out. Felt very safe and street noise was never a problem. Sharon was a text away to help with any questions we had. Would love to go back again and this would be the place we would for sure choose to stay!

  • Submitted: Feb 10, 2016
  • Stayed: Jan 2016
  • Source: VRBO, from HomeAway
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A wonderful place to stay!

  • 5 of 5

This is a most beautiful home! Perfect for our 10 family members. The kitchen is fully equipped for all family needs. Each bedroom is beautifully decorated with its own theme. Several of us took pictures of the decor and wall hangings because of their beauty. The pool is great! The iguanas in the neighboring back yard added flavor to a wonderful family vacation. So many wonderful restaurants and great shopping within easy walking distance. Be sure to get the lobster roll and Florida pink shrimp roll at The Lobster Shack right next door! Other restaurants we loved: Hogfish Bar & Grill, El Ciboney, Bad Boy Burrito, Aboddanza, Southernmost Cafe. The listing description was accurate regarding amenities, etc. This property is very clean and well maintained. The manager, Sharon Simpson, is a wonderful person with whom to work. We would recommend this house to anyone! Get your reservation in early!

  • Submitted: Dec 29, 2015
  • Stayed: Dec 2015
  • Source: HomeAway
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Wedding Party

  • 5 of 5

We thoroughly enjoyed our stay at Seaside Place. The pool is awesome, incredibly good AC system, plenty of bathrooms, fantastic mattresses, 3 extra futons, two washers and dryers, and well stocked. The decor is fun and the location cant be beat. Great parking for cars or scooters. Convenience store and bike/scooter rentals right next door. Would definitely stay again.

  • Submitted: Sep 4, 2015
  • Stayed: Aug 2015
  • Source: HomeAway
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Nearest Airport
5 Miles
EYW Key West (AA, Delta, Continental plus)
Nearest Barpub
0.1 Miles
Across the Street
Nearest Ferry
3 Miles
Key West Express from Ft Meyers Beach
Nearest Golf
5 Miles
Stock Island 1 Island off Main Key.
Nearest Restaurant
0.1 Miles
Across the Street, Next Door
Nearest Beach
0.1 Miles
Southernmost Beach
Car: not necessary

Other Activities: Spa, shopping, kayaking.


Rates & Availability

Uptwon/Upper Duval House Rental Rates

Rental Basis:
per property
Manager accepts payment in:
Convert Currency
Rate Period Nightly Weekend Night Weekly Monthly Event
Fantasy Fest 2016
Oct 22 2016 - Nov 2 2016
7 night minimum stay
Mid Season
Nov 3 2016 - Dec 20 2016
1 night minimum stay
Christmas - New Years
Dec 21 2016 - Jan 4 2017
7 night minimum stay
Jan 5 to April 30, 2017
Jan 5 2017 - Apr 30 2017
1 night minimum stay
May 1 to May 30, 2017
May 1 2017 - May 31 2017
1 night minimum stay
June 10 to June 14, 2017
Jun 10 2017 - Jun 14 2017
4 night minimum stay
Fantasy Fest 2017
Oct 21 2017 - Oct 31 2017
1 night minimum stay
Nov 1 to Dec 15, 2017
Nov 1 2017 - Dec 15 2017
1 night minimum stay
Dec 16 to January 5, 2018
Dec 16 2017 - Jan 5 2018
7 night minimum stay
My Standard Rate
1 night minimum stay

Additional information about rental rates

Refundable damage deposit $500
Cleaning $275
Tax Rate 12.5%

We normally require a 7 night minimum, Many dates we have shorter stays available. Please call me and check to see if a shorter stay is a possibility. Seaside Place requires a deposit of 50% of the rental total in order to hold the reservation, and the remaining balance is due 90 days prior to check in. All of the rates shown are subject to 12.5% tax & end-of-rental cleaning, which are additional. Cancellation subject to rental dates and declared on contract.

Manager's Cancellation Policy

Please ask the manager or check their rental agreement when booking the property.
Enter dates for accurate pricing
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Available arrival
Available stay (no arrival)


Uptwon/Upper Duval House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
  • Housekeeper Optional
Floor Area:
  • 2700 sq. ft.
Location Type:
  • Beach ...
  • Beach View
  • Downtown
  • Historic
  • Tourist Attractions
  • Air Conditioning
  • Alarm Clock
  • Ceiling Fans
  • Clothes Dryer
  • Hair Dryer
  • Heating
  • Internet
  • Iron & Board
  • Linens Provided
  • Living Room
  • Local Activities Guide
  • Local Maps
  • Local Restaurant Guide
  • Paper Towels
  • Parking
  • Sofa Bed
  • Toilet Paper
  • Towels Provided
  • Washing Machine
  • Water Cooler
  • Wireless Internet
  • Blender
  • Coffee Maker
  • Cooking Utensils
  • Dishes & Utensils
  • Dishwasher
  • Freezer
  • Grill
  • Ice Maker
  • Kitchen
  • Kitchenette
  • Microwave
  • Mini Refrigerator
  • Oven
  • Refrigerator
  • Stove
  • Stove
  • Toaster
  • Dining Area
  • seating for 10 people
  • 4 Bathrooms
  • Bathroom 1 - toilet , shower
    Bathroom 2 - toilet , combination tub/shower , Upstairs Hall
    Bathroom 3 - toilet , shower
    Bathroom 4 - toilet , shower
  • 5 Bedrooms, Sleeps 12
  • Bedroom 1 - 1 king , Downstairs
    Bedroom 2 - 1 king , Downstairs
    Bedroom 3 - 1 king , 1 sleep sofa /futon , Upstairs
    Bedroom 4 - 1 queen , Upstairs
    Bedroom 5 - 1 queen , Upstairs
  • We have a Floor Plan of the House on our Web site. Please Call.
  • Books
  • Radio
  • Satellite / Cable
  • Stereo
  • Television
  • Balcony
  • Barbecue
  • Beach Towels
  • Bicycles ...
  • Deck / Patio
  • Lawn / Garden
  • Outdoor Grill
  • Outdoor Grill Gas
  • Porch / Veranda
  • Terrace
  • Unscreened Porch / Veranda
  • Wood Deck
  • 12 garden chairs
  • Minimum Age Limit for Renters
  • children welcome
Pool / Spa:
  • Heated Pool
  • Private Pool ...
Onsite Services:
  • Concierge
  • churches
  • cinemas
  • health/beauty spa
  • library
  • live theater
  • marina
  • museums
  • playground
  • restaurants
  • synagogues
Leisure Activities:
  • antiquing
  • beachcombing
  • bird watching
  • boating
  • eco tourism
  • paddle boating
  • scenic drives
  • shopping
  • sight seeing
  • walking
Local Services & Businesses:
  • ATM/bank
  • fitness center
  • groceries
  • hospital
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • cycling
  • deepsea fishing
  • fishing
  • golf
  • golf privileges optional
  • hiking
  • jet skiing
  • kayaking
  • paragliding
  • parasailing
  • pier fishing
  • sailing
  • scuba diving or snorkeling
  • snorkeling
  • snorkeling/diving
  • swimming
  • tennis
  • water skiing
  • wind-surfing
Large Private Balcony to enjoy smoking a Key West Cigar. Inside smoking not allowed.

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

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