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

Bedrooms 5
Space 2,700 sq. ft.
Property type house
Minimum Stay 5 - 7 nights


About the property

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. Seaside place is a five bedroom four bath vacation rental downtown Key West location is 1 1/2 blocks from the southernmost point and 14 blocks away from Malory square.

Property Manager
Sharon Simpson
Member since: 2009
Speaks: english
Response time:
Within a few hours
Response rate:
Calendar last updated:
February 19, 2018

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 Uptown/Upper Duval

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.


Uptown/Upper Duval House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
  • Housekeeper Optional
Floor Area:
  • 2700 sq. ft.
House Rules:
  • Max. occupancy: 12
  • Minimum Age Limit for Renters
  • children welcome
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
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.


Exceptional! 5/5 -
(29 traveler reviews)

96% Complete
3% Complete
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Old Town Key West by Southernmost Beach and Duval Main Street.
average rating of 4.965517 based on 29 reviews
Matfield Green, Kansas

Tropical charm and luxury by the sea

  • 5 of 5

This gorgeous old Key West home was the perfect tropical escape for a couples vacation. Our group of friends enjoyed coffee on the breezy covered porches - the upstairs porch has a partial ocean view, an unexpected surprise! We walked to the beach across the street, which has sunrise and sunset views from the pier in winter, and to nighttime entertainment on Duval Street, just a block and a half away. The huge pool with a waterfall was sparkling clean and surrounded by plenty of lounge chairs. All the beds were super comfortable, and the kitchen is a cook’s dream, fully equipped with modern appliances, cookware and pantry staples. The master bedroom has a new kitchenette/ wet bar with coffeemaker, microwave, sink, fridge and big ice maker - handy for keeping poolside drinks cold. We can’t wait to come back!

  • Submitted: Dec 20, 2017
  • Stayed: December 2017
  • Source: HomeAway
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3 0

Excellent vacation home

  • 5 of 5

Ahhh Seaside Place how I miss it! The perfect vacation spot in Key West, close enough to the action yet far enough when you want to relax. Walking distance to everything, beach, stores, bars, restaurants. Very convenient grocery next door came in handy. The home was clean, neat, quiet and had all the essentials. The backyard pool was beautiful, nice size and serviced twice a week. We had 5 couples in the house and had plenty of room. The front porch is especially nice for people watching. I can't wait to go back.

  • Submitted: Nov 22, 2017
  • Stayed: November 2017
  • Source: HomeAway
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2 0

Excellent time in Key West

  • 5 of 5

Seaside place is awesome, clean spacious and well equipped..each room more unique than the last! Walking distance to everything!!! (Duval street and beyond)Loved having a grocery mart right next door for needed supplies and Cuban coffee & sandwiches❤ backyard pool was A refreshing relief, A stones throw from the beach/cafe/pier with breath taking sunsets and a block to southern most landmark...truly a perfect vacation spot!!❤❤😎😎

  • Submitted: Nov 18, 2017
  • Stayed: November 2017
  • Source: HomeAway
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1 0


  • 5 of 5

What a fantastic house in a a wonderful location. You are steps from a great beach, Duval St and the famous southernmost buoy

Now for the house - clean, big, eclectic, with all the comforts of home. You arrive and the house is equipped with towels for the pool, beach and bathroom. The pool was great, the outdoor furniture was comfortable and we spent every night outside at the table - it was a great house in the perfect location. I'll be back

  • Submitted: Nov 17, 2017
  • Stayed: November 2017
  • Source: HomeAway
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1 0
Hoboken, NJ

Mini Paradise Within Key West

  • 5 of 5

We visit Key West every summer so we have stayed at many different places and this was by far the best we have seen. The backyard and pool area is a perfect place to relax during the day with an extremely large (for Key West rentals) pool and outdoor table ideal for large groups. We had 5 couples staying at the house and no one felt crowded as the rooms are all large enough to fit at least a queen bed and the downstairs/kitchen area is large enough for entertaining. The location is fantastic with Southernmost beach right across the street, bike rentals two doors down, includes parking, and a deli/cafe on the corner. Overall, the house is in impeccable condition and I would absolutely recommend to anyone.

  • Submitted: Jul 25, 2017
  • Stayed: July 2017
  • Source: HomeAway
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3 0
Black Mountain, NC, USA

Seaside Place - Key West

  • 5 of 5

Seaside Place was perfect for our family and friends vacation in Key West! Easily accommodated our 11 adults and one child without feeling crowded. Layout of the house is perfect for a large group and the pool area is just a wonderful extension of the living area. We spent a LOT of time in and around the pool.

Location of the property is perfect! Within easy walking distance of everything 'Key West'.

We so appreciate the wonderful property and the property manager could not have been more helpful or accommodating! Looking forward to our next stay at Seaside Place!

  • Submitted: Jul 20, 2017
  • Stayed: June 2017
  • 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

Taxes and fees are additional

Additional information about rental rates

Cleaning $275
Refundable damage deposit $500
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.

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