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

Island Rendezvous - Like Having Your Own Little Private Resort

Bedrooms 6
Property type house
Minimum Stay 4 - 7 nights


About the property

House, 6 Bedrooms + Convertible bed(s), 5 Baths, (Sleeps 12-16)

An Award Winning Villa and Caribbean Style Cottage side-by-side just 3.5 short blocks from Mallory Square

Island Rendezvous offers the perfect solution for a gathering of family or friends who desire to be in the heart of Old Town Key West. 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 rooftop 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, two bedrooms, a third sleeping area, 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 one block off lower Duval Street, it is just 3 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.

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-color cable TVS, a/c, stereo, and 2 washer dryer units. Linens and towels are provided. Catering can be arranged. Off street parking for two cars.

Activities: The most requested location in Key West just 1 block off Duval St., 3 blocks from Mallory Square, 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, a variety of national and international cuisine, coffee shops. Close to the beach.

Smoking permitted only outside please.

Keywords: Resort Compound

More Details

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

Guestbook comments from the manager

My fiancee (now wife) and I rented this compound for our guests when we got married in Key West and everyone couldn't have been happier! Each property of the compound has a distinctive vibe with plenty of room for everyone to spread out and find their own perfect little spot to relax. The two large pools were also great and offered everyone plenty of options. We'd recommend these properties to anyone looking for a great location in Key West. We'll definitely be back in a few years!
Aug 2016
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Old Town House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
House Rules:
  • Check-in: 4:00 PM
  • /
  • Check-out: 10:00 AM
  • Max. occupancy: 16
  • 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.
Location Type:
  • Downtown
  • Near The Ocean
  • Away From It All
  • Family
  • Historic
  • Romantic
  • Air Conditioning
  • Clothes Dryer
  • Hair Dryer
  • Internet
  • Iron & Board
  • Linens Provided
  • Parking Off Street ...
  • Telephone
  • Towels Provided
  • Washing Machine
  • Catering Available
  • Cooking Utensils
  • Dishwasher
  • Ice Maker
  • Kitchen ...
  • Microwave
  • Refrigerator
  • Dining Area
  • 5 Bathrooms
  • Bathroom 1 -
    Bathroom 2 -
    Bathroom 4 -
    Bathroom 5 -
    Bathroom 3 -
  • 6 Bedrooms, Sleeps 16
  • Bedroom 1 - 1 king , 2 twin beds (can be pushed together to make a king)
    Bedroom 2 - 1 queen
    Bedroom 5 - 1 king , Four Poster king (pillow top mattress) size bed
    Bedroom 3 - 1 king
    Bedroom 4 - 1 king , Four Poster king (pillow top mattress) size bed
    Bedroom 6 - 1 queen
    Convertible bed(s) - 3 sleep sofa /futon
  • King size beds (1), Queen size Beds (1), Twin or Single Beds (1), Sleep Sofa or Futons (1)
  • CD Player
  • DVD Player
  • Satellite / Cable
  • Television
  • Balcony
  • Deck / Patio
  • Lanai / Gazebo
  • Outdoor Grill
Pool / Spa:
  • Private Pool
Onsite Services:
  • Concierge
  • botanical garden
  • churches
  • cinemas
  • festivals
  • health/beauty spa
  • live theater
  • museums
  • playground
  • restaurants
Leisure Activities:
  • antiquing
  • bird watching
  • boating
  • eco tourism
  • outlet shopping
  • paddle boating
  • photography
  • shopping
  • shuffleboard
  • sight seeing
  • walking
  • wildlife viewing
Local Services & Businesses:
  • ATM/bank
  • Babysitter
  • fitness center
  • groceries
  • hospital
  • laundromat
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • basketball court
  • cycling
  • deepsea fishing
  • fishing
  • golf
  • jet skiing
  • kayaking
  • parasailing
  • roller blading
  • sailing
  • scuba diving or snorkeling
  • snorkeling
  • snorkeling/diving
  • swimming
  • tennis
  • wind-surfing
Combination of "Pavilion Villa" and "Down Island Digs," Comprises two properties with three cottages. Offers 2 full kitchens, 1 kitchenette, 2 private swimming pools, cabana bath, multiple level decks, large private tree garden.


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Car: not necessary

Located Down Town Old Town Key West. Few minute walk to Mallory Square Sunset Celebration. Walk to all Old Town Key West features.


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Cleaning Fee $440 + Tax
Pool Heat $300
Processing $75 + Tax
Tax Rate 12.5%

Manager's Cancellation Policy

  • Canceled bookings will not receive a refund

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