Updated on Jul 20, 2026
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Type
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Private vacation home
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Bedrooms
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6
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Bathrooms
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5
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House Rules
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No pets allowed
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Children allowed: ages 0-17
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Smoking is not permitted
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No events allowed
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Max Occupancy
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14
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Host Language
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English
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Property Id
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141726
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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.
Located in Key West, this vacation home is in the city center. Southernmost Point and Ernest Hemingway Home and Museum are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and Fort Zachary Taylor Historic State Park. Ready for a night out? Consider The Key West Theater and Sloppy Joe's Bar. Discover the area's water adventures with motor boating, fishing, and swimming nearby, or enjoy the great outdoors with ecotours.
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