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  • (305) 294-7358
Key West Time
December 9th
12:29am · 74°F

The Meeting Point - Key West ~ Weekly Rental

11BR 11BA ~ Weekly Rental
Sleeps 22

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, this is the grandest short-term vacation rental in Key West, both in stature and style. Refashioned in early 2013, by new owners who fell in love with the property, it has been 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 brand 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, sleek granite top pool bar, plus private off-street parking for multiple vehicles.

A creative new 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.

The layout of the interior space offers many different usage options which are described in detail  on the web pages for each property linked above. 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.

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 - 1 king bed, 2 trundle beds (can be made to 4 twin beds or 2 king beds)


  • 2 King size beds, 1 California King bed
  • 1 Full, 1Twin size beds

Amenities: Upscale renovation. 2 swimming pools (1 with Jacuzzi jets), 2 connecting pool decks, 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. Maid service can be scheduled. Long sleek granite pool bar with seating stools at the Villa Nouveau for morning coffee and cocktail hour.  

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. Absolutely no pets please. We do not accept guests less than 25 years of age unless accompanied by a family group or guardian.

Rented as separate units: For Holidays and Festivals this property may only be available as a single estate rental. Depending on availability, it is possible to rent this property as separate suite units listed next. Please inquire about availability to rent separately or together.

Grande Dame Key West – ‘The Watson House - Main 3-Story 1800’s Victorian Home.
Villa Nouveau Key West - New 4 bedroom villa with private swimming pool (with Jacuzzi jets) and private pool deck.


**The graphic shown in our slide show above gives the layout of the property and clarifies the sizes of the beds in each bedroom. 

Book Direct For The Best Price Guaranteed

Dates Weekly Nightly Terms
Nov 30, 2019 - Dec 20, 2019 $10725$25504 night min. or 3 night min. 60 days prior to arrival.
Dec 21, 2019 - Dec 27, 2019 $17375$35005 night minimum
Dec 28, 2019 - Jan 3, 2020 $20520$40005 night minimum
Jan 4, 2020 - Jan 10, 2020 $14725$31504 night min. or 3 night min. 60 days prior to arrival.
Jan 11, 2020 - Jan 17, 2020 $15225$31504 night min. or 3 night min. 60 days prior to arrival.
Jan 18, 2020 - Jan 24, 2020 $15225$31504 night min. or 3 night min. 60 days prior to arrival.
Jan 25, 2020 - Jan 31, 2020 $15775$31505 night minimum - 'within' Sat/Sat Only
Feb 1, 2020 - Feb 14, 2020 $16800$31505 night minimum - 'within' Sat/Sat Only
Feb 15, 2020 - Feb 21, 2020 $17900$31505 night minimum - 'within' Sat/Sat Only
Feb 22, 2020 - Apr 17, 2020 $16800$31505 night minimum - 'within' Sat/Sat Only
Apr 18, 2020 - May 24, 2020 $14775$28004 night min. or 3 night min. 60 days prior to arrival.
May 25, 2020 - Jun 12, 2020 $13075$25504 night min. or 3 night min. 60 days prior to arrival.
Jun 13, 2020 - Aug 7, 2020 $14775$28005 night min, but 3-4 nights within 60 days
Aug 8, 2020 - Oct 15, 2020 $13075$25504 night min. or 3 night min. 60 days prior to arrival.
Oct 16, 2020 - Oct 24, 2020 $20210$40005 night minimum
Oct 25, 2020 - Nov 7, 2020 $13075$25504 night min. or 3 night min. 60 days prior to arrival.
Nov 8, 2020 - Nov 15, 2020 $14775$28005 night minimum
Nov 16, 2020 - Nov 19, 2020 $13075$25504 night min. or 3 night min. 60 days prior to arrival.
Nov 20, 2020 - Nov 28, 2020 $14775$28005 night minimum
Nov 29, 2020 - Dec 18, 2020 $10975$25504 night min. or 3 night min. 60 days prior to arrival.
Dec 19, 2020 - Dec 25, 2020 $17675$35005 night minimum
Dec 26, 2020 - Jan 1, 2021 $20820$40005 night minimum

Additional Notes:

  • High Season generally requires a 7 night minimum stay. Shorter stays of 3 - 5 nights may be available within 60 days of your arrival date or in special situations. Certain dates may not be available if they minimize optimal booking for the property's reservation calendar. Please contact us to inquire about stays less than 7 nights.
  • Shoulder and Low Season is a 3 - 5 night minimum available on reservations made within 60 days of arrival May through mid-August. From mid-August through mid-December, 3 - 5 night minimum stays are available any time.
  • Short Stays are available if there are open nights that are less than the minimum stay, shorter stays may be possible depending on the property. Please contact us to inquire.
  • Holiday, Festival, and Event Rates are 20% to 25% higher. These include, but are not limited to: Fantasy Fest, Thanksgiving, Christmas, New Years, Power Boat Races, Mini-Lobster Season, Labor Day, Parrot Heads Meeting of the Mind, 4th of July, Easter. A 7 night minimum stay is required for most major holidays, festivals, and events.

Rates and Terms are subject to change without notice. Above rates do not include taxes and fees. Click here for more details on additional fees. Please contact us for specific pricing and to confirm rates. Rates in US Funds. (305) 294-7358 Ext 1 -

Apply here for Travel Guard Trip Cancellation and Interruption Insurance.

VHKW offers promotional specials for purchasing trip insurance for stays between Aug 10 and Oct 20. Please call for more details.

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 - 1 king bed, 2 trundle beds (can be made to 4 twin beds or 2 king beds)


  • 2 King size beds, 1 California King bed
  • 1 Full, 1Twin size beds
Jul 09, 2019,
Renting a house from VHKW was the best! They were great to work with throughout the entire process. We loved our time in Key West!!

Jan 21, 2019,
We had a wonderful experience with VHKW. They always responded quickly to any questions or concerns we had. There were 20 of us staying at the meeting place home. We enjoyed every minute. The home was perfect for myself, husband and all our wedding guests. This home will hold special memories for the rest of our lives. VHKW was attentive and they took good care of us. We hope to use their services for all future rentals. Thanks!!

Jul 26, 2018,
Great place to stay! Only a block away from Duval Street and within walking distance to everything. Loved the pool and so much room to relax with family. Both houses were well stocked with just about everything we needed. It truly felt like we were home.

Jun 20, 2018,
The meeting place was perfect for our family vacation. There were 18 of us most days, and 21 of us for a few days. The two homes and pools were exactly what we needed. The bedrooms and baths were all nice places to relax, and to get ready each day! We enjoyed the huge table on the back deck of The Watson House. It was a gathering spot for our family each morning and evening. The living rooms and kitchens in each home were also great places to gather, and were well equipped. We all loved how we were within walking distance of most everything. Everyone in our group...ages 1 to 87, enjoyed our stay at the homes on this property , and many happy memories were made!

Nov 20, 2017,
Great House! Our 4th or 5th time there and always enjoy it.

Jan 09, 2017,
Everyone was responsive and helpful. We had a couple of problems but they were fixed within a short time after we called. Thanks.

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