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Book Online or call HomeAway Booking Assistance 888-640-7927
Book Online or call HomeAway Booking Assistance 888-640-7927

The Meeting Point ~ Key West - Elegant and Grand

Bedrooms 12
Space 6,500 sq. ft.
Property type house
Minimum Stay 4 - 7 nights


About the property

11 Bedroom 11 Bathroom - Historic Victorian Home Plus New Villa

The Meeting Point – Key West is by-far the most spacious and classically elegant vacation rental property on the island. Situated in the heart of Old Town, there is nothing else like it. If you’re looking for luxury and plenty of room, The Meeting Point is the grandest vacation rental in Key West, both in stature and style. Refashioned in early 2013, by owners who love the property, it was thoughtfully re-designed to create an exclusive vacation rental compound to meet the specific needs of larger groups with discerning tastes.

A combination of the renovated stately centurion 7 bedroom 7 bathroom 3-story Victorian mansion, Grande Dame Key West – ‘The Watson House’ and the new ‘L-Shape’ 4 bedroom 4 bathroom courtyard villa, Villa Nouveau Key West, this vacation property compound is ideal to stage a reunion of family and friends or corporate gathering. In concert, the grounds provide 2 private swimming pools with lounge decks (one pool has Jacuzzi jets), 2 classic Victorian front porches overlooking a beautiful historic street, 2 covered terraces with look-down views of the back pool garden, long sleek granite pool bar, plus private off-street parking for multiple vehicles.

The Main Victorian Home: The interior of this wooden 1800’s Victorian home provides 3 stories of living space with 7 bedrooms and 7 bathrooms. The first floor is comprised of a traditional Victorian parlor style living room, 'game-room' style family room, full dining room, and a fully renovated chef’s kitchen styled with granite counter tops, tile floors, and stainless steel appliances.

Ceilings throughout the 1st floor are an impressive 12+ feet height and the original ceiling architectural detail still exists. There are two bedrooms and two full bathrooms on the 1st floor. One bedroom has a queen size bed provides an en-suite bathroom. The 2nd bedroom, with a king size bed, is set in the original mansion ‘sun room. The bathroom for the 2nd bedroom is located just steps from the bedroom.

The graceful banister staircase topped with elegant chandelier, leads to the 2nd floor to 4 more bedrooms and 4 bathrooms. All bedrooms on the 3rd floor are styled differently. The spacious front bedroom has a queen size bed and French doors that open to a porch that spans the entire width of the home overlooking historic Simonton Street. The west side bedroom features a queen size pencil-style four poster bed off-set with knotty pine wainscoting, original Dade pine planked wood floors, and large sash windows to let in plenty of sun light.

The east side bedroom features vintage wallpaper with wicker furnishings and a queen size bed. The back bedroom is more contemporary, offering a king size bed and double sets of French doors leading to a large covered terrace with a dramatic down-look view of the courtyard garden, and swimming pool below.

Moving up to the 3rd floor, we find a beautiful private split-level ‘pent-house style’ suite with lounging sofa, large screen TV, small kitchen, bedroom, an additional sleeping space, and a full bathroom with tub. Since the upper level of the 3rd floor also provides all these amenities on a private floor, it is an ideal place for a couple who are traveling with a group to find a private “love nest.”

The focus of the space is the media area with lounging sofa and large screen TV on the first level. The scene is set with beautiful hardwood floors. It is built-out to feel spacious with soaring ceilings that are set right up next to the roof line. Double sets of French doors lead to a private verandah and the additional height from the 3rd floor captures even a more dramatic view from the terrace outside that overlooks the courtyard garden swimming pool below.

The 3rd floor bedroom is neatly tucked into an alcove. It’s cozy, but becomes an adorable little intimate hideaway space when the double set of doors is closed. It offers a trundle bed that can be made as a king size bed or 2 twin beds. Outside the door, on the opposite side of the room, a 2nd trundle bed, that can also be made up as 2 twins or a king size bed, offers a 2nd sleeping space.

The 4-Bedroom Villa: Nearly everything about this 4 bedroom 4 bathroom vacation villa was built new from the ground up in February 2013. Only the original roof line and front entrance walls were kept to protect the historic exterior. The interior décor has a color palate of soft tropical blue and sand tones with elegant wood and leather modern furnishings. Floors throughout are tiled with earth tone travertine marble. Interesting architectural angles and detail make the spaces fresh and interesting. An open concept kitchen-dining room-living room that is just large enough is finished with granite counter tops, upscale stainless steel appliances and fixtures, an entertainment center with a flat-screen TV and wet-bar.

For sleeping, the bedrooms shown on the graphic as number 1 - provides California king size bed, 2 and 3 - king size beds, while bedroom number 4 provides 2 twin beds. Each of the 4 bedrooms provides a private en-suite bathroom. Bedrooms with king size beds provide spacious walk-in showers, while the bedroom with the twin beds offers a bath tub with in-tub shower.

The layout of the interior space in each dwelling offers many different usage options. But we would like to point out excellent options that meet private housing needs for special gatherings, such as a bride and groom or even grandparents who need some solitude from a larger family group. The flexible design concept imagined options that include the possibility of reserving the 3rd floor penthouse suite of the Victorian home, or parlaying the open-concept living room/kitchen plus back bedroom/en-suite bathroom of the villa, which has a privacy lock-out door in the hall. Both spaces offer private entrances and doors that can be locked off to make a private accommodation.

Grounds: A creative layout of the back grounds of the property set a tall plank-board wall between the l800’s Victorian home and the new villa allowing for privacy between the two buildings. But when rented together, a French door style gate is set at the far left corner of the wall to connect the 2 pool decks. Depending on the needs of your group, this gate can be opened or kept closed.

Location: As for location, you can’t get more central or convenient. Prominently set on Simonton Street, in the 500 block, just a 2 minute walk to Duval Street, The Meeting Point property is set back off the street just enough, and bounded by a fence it offers an ideal balance of privacy, luxury, and location. In Old Town Key West, where many of the larger historic Victorian homes have been transformed into guest houses or businesses, this private vacation rental is in a class all of its own.

Bedding Summary:

Main House:

• First Floor - 1 Queen size bed, 1 King size bed

• Second Floor- 2 Queen size beds, and 2 King size beds

• Third Floor - 2 trundle beds (can be made to 4 twin beds or 2 king beds)


• 3 King size beds

• 2 (double) full size beds

Amenities: Upscale renovation. 2 swimming pools (1 with Jacuzzi jets), 2 connecting pool decks, long sleek granite top pool bar with stools, courtyard, gardens, covered terraces, expansive porches, and privacy fences. 2 fully equipped kitchens, central a/c, cable TV’s, stereos, 2 washer / dryers. Linens and towels are provided. Private off- street parking for 3 to 4 cars. Catering can be arranged. Maid service can be scheduled.

Activities: Ideal place to relax with family and friends, but if you’re looking for more active fun, you’re never more than a short stroll to international restaurants, shopping, spas, museums, famous bars, art galleries, night life, Key West Historic Seaport, boating, diving, family activities, and the beach. Heart of Key West's designated historic district. Walk to all Old Town features, no need for a car. Just one short street from Duval St. Conveniently located to Fausto’s Fine Food Palace local gourmet grocery store with excellent wine selection, sushi deli, and butcher.

Area: An historic tree-line residential - commercial street in the tiny section of Key West is in the “island urban” area. When you stay in this tiny district it’s amazing how much there is to see on each street. The mid-section of famous Duval Street in Old Town Key West grew up as the central downtown area. The original city infrastructure was built here in the 1800’s to create a diverse array of shopping, offices, entertainment, restaurants, bars, hotels, and churches, and these features are still offered in a modernized mode. From this area you can walk to the Mallory Square Sunset Celebration in 10 to 15 minutes.

Restrictions: Smoke free property. While this property is ideal for families and groups to unite, it is not suitable for staging loud parties

More Details

Property Manager
Vacation Homes of Key West (VHKW)
Speaks: english, czech, Bulgarian
Response time:
Within a few days
Response rate:
Calendar last updated:
January 9, 2018


Old Town House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
  • Housekeeper Optional
Floor Area:
  • 6500 sq. ft.
House Rules:
  • Check-in: 4:00 PM
  • /
  • Check-out: 10:00 AM
  • Max. occupancy: 24
  • Min. age of primary renter: 25
  • Children welcome
  • Parties/events not allowed
  • Pets not allowed
  • Non smoking only
  • We do not accept guests less than 25 years of age unless accompanied by a family group or guardian.
  • Please refer to your rental agreement for Cancellation Policy for this property
  • Adventure
  • Family
  • Historic
  • Romantic
  • Tourist Attractions
  • Air Conditioning ...
  • Clothes Dryer ...
  • Hair Dryer
  • Internet
  • Iron & Board
  • Linens Provided
  • Living Room
  • Parking ...
  • Towels Provided
  • Washing Machine ...
  • Coffee Maker ...
  • Dishes & Utensils ...
  • Dishwasher ...
  • Ice Maker
  • Kitchen ...
  • Microwave ...
  • Refrigerator ...
  • Stove ...
  • Toaster
  • Dining ...
  • Dining Area
  • 11 Bathrooms
  • Bathroom 1 -
    Bathroom 2 -
    Bathroom 3 -
    Bathroom 4 -
    Bathroom 5 -
    Bathroom 6 -
    Bathroom 7 -
    Bathroom 8 -
    Bathroom 9 -
    Bathroom 10 -
    Bathroom 11 -
  • There are 11 bathrooms total, with 7 bathrooms in the 7 bedroom Victorian house and 4 bathrooms in the 4 bedroom villa. 3-Story Victorian House: 1st floor - 2 bathrooms; 2nd floor - 4 bathrooms, 3rd floor - 1 bathroom. 1 - Story Villa: 4 bathrooms. All En-Suite. A door from the living room joins one of the bathrooms.
  • 12 Bedrooms, Sleeps 24
  • Bedroom 1 - 1 queen
    Bedroom 2 - 1 king
    Bedroom 3 - 1 queen
    Bedroom 4 - 1 queen
    Bedroom 5 - 1 king
    Bedroom 6 - 1 king
    Bedroom 7 - 4 twin/ single , can be made to 4 twin beds or 2 king beds
    Bedroom 8 - 1 king
    Bedroom 9 - 1 king
    Bedroom 10 - 1 king
    Bedroom 11 - 1 double
    Bedroom 12 - 1 double
  • Trundle bed on 3rd floor in penthouse suite of main house can be made as 2 twin beds or as a King size bed.
  • Books
  • DVD Player ...
  • Satellite / Cable ...
  • Stereo ...
  • Television ...
  • Balcony ...
  • Boat ...
  • Deck / Patio ...
  • Golf ...
  • Kayak / Canoe ...
  • Outdoor Grill
  • Tennis ...
  • Water Sports Gear ...
  • limited accessibility
Pool / Spa:
  • Heated Pool
  • Private Pool ...
  • botanical garden
  • churches
  • cinemas
  • festivals
  • health/beauty spa
  • library
  • live theater
  • marina
  • museums
  • playground
  • recreation center
  • restaurants
  • synagogues
Leisure Activities:
  • antiquing
  • beachcombing
  • bird watching
  • boating
  • eco tourism
  • miniature golf
  • outlet shopping
  • paddle boating
  • photography
  • scenic drives
  • shopping
  • sight seeing
  • walking
  • wildlife viewing
Local Services & Businesses:
  • ATM/bank
  • Babysitter
  • fitness center
  • groceries
  • hospital
  • laundromat
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • cycling
  • deepsea fishing
  • fishing
  • fly fishing
  • golf
  • hiking
  • jet skiing
  • kayaking
  • mountain climbing
  • parasailing
  • pier fishing
  • roller blading
  • sailing
  • scuba diving or snorkeling
  • snorkeling
  • snorkeling/diving
  • swimming
  • tennis
  • water skiing
  • water tubing
  • wind-surfing
There is nothing else like The Meeting Point - Key West on the island available to rent as a private vacation rental. Situated in the heart of Old Town, just a a minutes walk from the 500 block of Duval St., there is nothing else like it. If you’re looking for luxury and plenty of room, The Meeting Point is the grandest vacation rental in Key West, both in stature and style.


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Nearest Airport
1 Miles
Key West
Nearest Barpub
Jimmy Buffet's Margaritaville - 1 block away
Nearest Ferry
0.5 Miles
Historic Seaport
Nearest Golf
4 Miles
Key West Golf Club
Nearest Motorway
3 Miles
U.S. Highway 1
Nearest Restaurant
Sara Beths - Across the street
Nearest Beach
0.5 Miles
Fort Zachary Taylor State Park Beach
Car: not necessary

Heart of Old Town Key West. Prime Downtown location close to all Old Town Key West attractions. This tiny section of Key West is the 'island urban' area. When you stay in this tiny district it's amazing how much there is to see on each street. The mid-section of famous Duval Street in Old Town Key West grew up as the central downtown area. The original city infrastructure was built here to create a diverse array of shopping, offices, entertainment, restaurants, bars, hotels, and churches, and these features are still offered in a modernized mode. Just around the corners off either side of Duval Street an impressive array of historic Victorian and cottage style residences stand, and some are available to rent.


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Pool Heat $300
Cleaning Fee $765 + Tax
Processing $75 + Tax
Tax Rate 12.5%

Rates and Terms are subject to change without notice. Please contact us to confirm rates and terms. Guests are advised to purchase Travel Insurance to protect their vacation rental investment.

Manager's Cancellation Policy

  • Canceled bookings will not receive a refund

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