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

Top rated by guests
Pool
bathroom 4
bedroom 5
Bathroom
Bathroom
review stars
9.6Outstanding
(12 Ratings)
"Great place for a weekend with friend incredible location and the pool was fantastic. Would recommend for a stay with friends"
Nick T.
Don't miss out! Price and availability may change
9.6 / 10
Outstanding(12 Ratings)

House in Key West, FL

14 guests · 6 bedrooms · 5 baths

Reasons to book

Guests love it hereGuests give this property a top rating
Top-tier experienceA high end property in this area
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About this house rental

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.

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

Non-smoking
No pets allowed
Family friendly

Map of Key West, FL

city location on map

Ratings and reviews

9.6 / 10
Outstanding(12 Ratings)
8 / 10Excellent·Jul 2026
Property in great location. Grocery store across the street. Wonderful bakery Sunny Eggs for breakfast, coffee goodies. Appliances not in great working order. Lamp and some shades broken or damaged. Houses need a bit of TLC.Owner very responsive. Could let people know that toiletries such as shampoo , conditioner body wash is not provided. Great trip and overall experience.
8 / 10Excellent·May 2026
Location was incredible. So close to downtown and accessible to so much. Only bad thing is it’s across the street from Fausto’s grocery store so delivery trucks extremely noisy in early morning hours making sleep a bit of a challenge. Especially at the 510 address. Pools were a lot of fun. Great way for family to really enjoy the place and have a great time. The last night we were there we fired up the grill and had a huge cook out and partied. All 3 cottages were clean and comfortable. Plumbing was ok, lots of hot water, but a couple of drains were slow and one of the sink faucets missing an aerator. Host was very responsive and professional. Overall I’d give the place a Very Good rating but that was not an option.
10 / 10Outstanding·Aug 2025
Great place for a weekend with friend incredible location and the pool was fantastic. Would recommend for a stay with friends
10 / 10Outstanding·Jan 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.

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FAQs

Is parking included with this house?

Parking is not specified as an available amenity at Key West Island Rendezvous - Private Compound Steps Off Duval w/Pool - Sleeps 12. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.

Is Key West Island Rendezvous - Private Compound Steps Off Duval w/Pool - Sleeps 12 pet friendly?

Unfortunately, this house is not pet-friendly. Try searching again and filter for "Pets Allowed"

What amenities are available at Key West Island Rendezvous - Private Compound Steps Off Duval w/Pool - Sleeps 12?

We found 3 amenities for this rental. This includes non-smoking, no pets allowed, and family friendly.