Key West Island Rendezvous - Private Compound Steps Off Duval w/Pool - Sleeps 12

Key West, Florida
$2036 avg/night Minimum Stay 2 Nights
Bed 6

Bed

Bath 5

Bath

Home Private Vacation Home

Property Type

Sleep 14

Max Sleeps

Night 2 nights

Min Stay

Island Rendezvous vacation rental offers the perfect solution for a gathering of family or friends who desire to be in the heart of Old Town Key West. One of the best and most unique Old Town Key West vacatoin rentals, here you will enjoy a completely private retreat with an atmosphere of wonderfully unchanged Caribbean charm. By combining Pavilion Villa and Down Island Digs it won`t take you long to settle into this dreamy stopped-in time island setting where you have two private swimming pools, two sun decks, a roof top deck, two master suites, a balcony, and large mature tropical gardens of orchids, palms, and tropical fruit trees. Pavilion Villa is an award winning newly renovated 2 cottage pavilion style property. Here you find a one story dwelling which houses the living room, kitchen, three bedrooms, laundry room, and full bath with a beautiful indoor/outdoor shower room. The second cottage has 2 full stories with the first floor set up as a sleeping and lounging area. The second floor has a large master bedroom and bathroom. The third bath is a cabana style bath off the pool and deck. The entire pool and deck area are made private with a tall fence.

Right next-door is the Down Island Digs cottage. This is a one-story cottage with a master suite and a poolside bedroom. It has a full kitchen, washer dryer, and two full bathrooms, charming indoor/outdoor living room, and big private back yard.

The focus of this combined property is definitely the Key West quintessential indoor / outdoor living that makes island life so relaxing and wonderful. Here you enjoy the luxury of expansive sun washed decks and a large native tropical shade garden - complete with waterfall for those days you don`t want direct sunlight. Both properties also offer spacious front porches for sitting and watching the island world go by.

A rare and unique feature of this combined Island Rendezvous property is the privacy and spaciousness it offers right in the heart of Old Town. Just a block off lower Duval Street it is just three blocks from Mallory Square, steps from gourmet grocery shopping, excellent restaurants, popular clubs, the Historic Seaport, and tropical shops. The two homes together offer many smaller intimate areas and at the same time plenty of garden and deck space to spread out. It should be considered as an ideal location for a wedding party to reside, but not as a venue to stage the wedding.

Bedding Summary:

Pavilion Villa

Front Cottage (Down stairs) - 1 king size bed, 2 twin beds (can be pushed together to make a king)
Front Cottage (Upstairs) - 1 queen size bed
Back Cottage (Down stairs) - 1 queen sleeper sofa
Back Cottage (Upstairs) - 1 king size bed (master bedroom)
Down Island Digs Cottage

Master bedroom Four Poster king (pillow top mattress) size bed
Queen Sleeper sofa
Second Bedroom - queen size bed
Living room – Twin sleeper sofa
Amenities: Two private swimming pools, two sun decks, roof top deck, balcony, 2 master suites, large lush mature tropical garden, two fenced-in yards. Also, two telephone lines, 3 cable TV`s, a/c, and stereo and 2 washer dryer units. Linens and towels are provided. Off street parking for two cars.

Activities: The most requested location for Old Town Key West vacation rentals, just a half-block off Duval St., three blocks from Mallory Square Sunset Celebration, and a few short streets from the Historic Seaport. Conveniently located across the street from gourmet grocery shopping with excellent wine selection, sushi, deli, and butcher. Close to shopping, art galleries, and a variety of national and international cuisine, coffee shops. Just a short stroll or bike ride to Fort Zachary Taylor Beach.

Area: Downtown Old Town Historic Key West. Just one-half block off Duval Street. Walk to all Old Town Key West features. Great restaurants, shops, galleries, clubs, Hemingway House Museum, Light House Museum, Custom House Museum, Key West Aquarium, Ship Wreck Museum. 10 minute stroll from the famous Sunset Celebration at Mallory Square.

Restrictions: Smoke free house. No pets please. We do not accept guests less than 25 years of age unless accompanied by a family group or guardian.

PAYMENT: Payment for the rental will be processed outside of VRBO according to the terms of your rental agreement (sent for review upon reservation). Payments by credit card are subject to an additional 2.95% merchant processing fee.

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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    No Pets Allowed
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Not Reported (host Has Not Indicated Whether There Is A Carbon Monoxide Detector On The Property; Consider Bringing A Portable Detector) Fire Extinguisher Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    6 Bedrooms Bed Sheets Provided Sofa Bed
  • GENERAL

    Unit Size: 2390 Sq Ft (222 Sq M)
  • KITCHEN

    Coffee/tea Maker Dishwasher Ice Maker Kitchen Island Microwave Oven Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Near Laundromat Washing Machine And Dryer
  • PARKING

    Car Not Required Limited Onsite Parking (max 2 Spaces) Onsite Parking Onsite Parking Includes Off-street Options
  • INTERNET

    Free WiFi
  • OUTDOORS

    Balcony Barbecue Grill Fenced Yard Garden Rooftop Terrace
  • POOL/SPA

    Heated Pool Private Pool
  • BATHROOMS

    5 Bathrooms Bathtub Hair Dryer Towels Provided
  • WORKSPACES

    Desk
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Birdwatching Nearby Ecotours Nearby Fishing Nearby Marina Nearby Power Boating Nearby Swimming Nearby Wildlife And Game Walks Nearby
  • ENTERTAINMENT

    Books TV
  • LIVING SPACES

    Dining Room Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • LOCATION HIGHLIGHTS

    In The City Center Near A Health Or Beauty Spa
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 14

Map Map

School District Rates & Availability

Review Review

  • Nick T.

    Submitted Aug 25, 2025

    Stayed Jul 18, 2025

    Great place for a weekend with friend incredible location and the pool was fantastic. Would recommend for a stay with friends

  • Sandy S.

    Submitted Jan 16, 2025

    Stayed Jan 8, 2025

    Great location and lodging for a family get away. RIght in downtown area - near restaurants, bars, and shops. Perfect lodging for larger family - with separate living areas to spread out a little.

  • Waverly H.

    Submitted Jun 26, 2024

    Stayed Jun 4, 2024

    Island Rendezvous was a great overall stay for us and our group of friends for a wedding in Key West. We were two blocks off of Duval Street and a stones throw from a gourmet grocery store. The two pools and landscaping were well maintained and the grounds were clean and treated before we arrived and during our trip. The key code for the main house worked great. The physical key for the small house was kind of a pain and could be updated for ease. We did have a few things to mention about the property for others that might stay here and for management. The smaller house had A/C units however it was not able to fully cool the house and was quite warm during the day. Also the unit in the smaller room leaked for the entire week we were there. To the point of us leaving a large bucket under the unit and having to empty it almost daily. The sliding glass door in the 'livingroom' also did not fully close which did not help with the problem. The main house did have an awesome ac unit and kept the whole house cold for our entire trip but we just wish that the smaller house could have been remotely cold for the very hot week we were there. The second thing being that there is no connection between the two properties in the back of the houses. Which meant that you were going back and forth between a key locked gate from the small house and the key code door for the large house. A back gate between the two would have made this much better. Overall we would suggest this home to all

  • Andrew M.

    Submitted Dec 29, 2023

    Stayed Dec 9, 2023

    Celebrated the 50th anniversary of my parents, had 3 families there and had the perfect amount of space and comfort. Prime location, walked everywhere. WILL NOT DISAPPOINT!

  • Grace J.

    Submitted Nov 19, 2023

    Stayed Nov 16, 2023

    This property was perfect for a group, with great room variety and pool setup. The kitchen was well equipped and the location could not have been more convenient. Ask for additional information if you are easily confused by lock boxes and/or arriving after sunset. Additionally, the houses are next door but do not adjoin, so be prepared to walk between (~10 feet).

  • Paul B.

    Submitted Jun 24, 2023

    Stayed Jun 18, 2023

    Good place to have at least 3 separate groups of relatives.

  • Joseph W.

    Submitted May 19, 2021

    Stayed May 12, 2021

    The house was perfect for our stay. Clean, roomy, great location for all of the things we wanted to do (walked everywhere). We loved the place and our trip to Key West.

  • Rebecca F.

    Submitted Jul 28, 2020

    Stayed Jul 22, 2020

    The property was great for our big family. We could all have our own space. The amenities were very nice. We had a very memorable trip.

  • Brent C.

    Submitted Jun 24, 2019

    Stayed Jun 16, 2019

    This property is great for a big group. Incredible location. Lots of beds and bathrooms.

  • jana m.

    Submitted Mar 20, 2019

    Stayed Mar 9, 2019

    There are a few minor repairs that are needed but overall everything was very nice. We had a great time.

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Total

Includes taxes and fees
$2,036+
View details