Key West Island Rendezvous - Private Compound Steps Off Duval w/Pool - Sleeps 12
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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Amenities
Pool
Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning
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Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
This property accepts cash
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
About the area
Key West
Located in Key West, this holiday home is in the city centre. Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and South Beach. Mel Fisher Maritime Museum and The Kite House are also worth visiting. Discover the area's water adventures with power boating, fishing and swimming nearby, or enjoy the great outdoors with ecotours.
Harry S. Truman Little White House - 6 min walk - 0.5 km
Ernest Hemingway Home and Museum - 8 min walk - 0.7 km
Mallory Square - 10 min walk - 0.9 km
Fort Zachary Taylor Historic State Park - 14 min walk - 1.2 km
Getting around
Key West, FL (EYW-Key West Intl.) - 14 min drive
Restaurants
Green Parrot Bar - 4 min walk
Margaritaville - 2 min walk
La Concha Bar - 3 min walk
Jack Flats - 2 min walk
Kermit’s Key West Key Lime Shoppe - 4 min walk
Frequently asked questions
Does Key West Island Rendezvous - Private Compound Steps Off Duval w/Pool - Sleeps 12 have a pool?
Yes, this property has a pool. Pool types include heated pools.
How much does it cost to stay at Key West Island Rendezvous - Private Compound Steps Off Duval w/Pool - Sleeps 12?
As of 16 Apr, 2026, prices found for a 1-night stay for 2 adults at Key West Island Rendezvous - Private Compound Steps Off Duval w/Pool - Sleeps 12 on 28 Jun, 2026 start from S$2,319, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
Is Key West Island Rendezvous - Private Compound Steps Off Duval w/Pool - Sleeps 12 pet-friendly?
No, pets are not allowed at this property.
How much is parking at Key West Island Rendezvous - Private Compound Steps Off Duval w/Pool - Sleeps 12?
On-site parking is available at the property.
What time is check-in at Key West Island Rendezvous - Private Compound Steps Off Duval w/Pool - Sleeps 12?
Check-in begins at 4:00 PM.
What time is check-out at Key West Island Rendezvous - Private Compound Steps Off Duval w/Pool - Sleeps 12?
Checkout is at 10:00 AM.
Where is Key West Island Rendezvous - Private Compound Steps Off Duval w/Pool - Sleeps 12 located?
Located in Old Town Key West, this holiday home is steps away from San Carlos Institute - Casa Cuba and Duval Street. Florida Keys Beaches and Ernest Hemingway Home and Museum are also within 10 minutes.
Reviews
9.6
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Great place for a weekend with friend incredible location and the pool was fantastic. Would recommend for a stay with friends
Nick T.
Stayed 2 nights in Jul 2025
Response from VrboOwner on 8 Jan, 2026
Hello Nick,We’re so glad you and your friends had a fantastic weekend! It’s great to hear the pool and location added to your stay. We’d love to host you again.
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.
Sandy S.
Stayed 7 nights in Jan 2025
Response from VrboOwner on 10 Feb, 2025
We're so thrilled to hear you and the family had a memorable stay at our Island Rendezvous! It was a pleasure hosting you all for your time in town and we look forward to the chance to host you again sometime soon.
Warm Regards,
VHKW
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!
Andrew M.
Stayed 5 nights in Dec 2023
Response from VrboOwner on 2 Dec, 2024
Thank you for choosing our Key West Island Rendezvous as your home base for such an exciting anniversary! We're thrilled to have been a part of your trip and that you enjoyed your stay with us. If you're ever back in town, we hope to have the chance to host you again! Best, VHKW
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).
Grace J.
Stayed 3 nights in Nov 2023
Response from VrboOwner on 21 Nov, 2023
Grace,
Thank you so much for taking the time to leave an excellent rating. Great feedback which we will try to improve.
Prime location/great pools but a few short comings
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
Waverly H.
Stayed 5 nights in Jun 2024
Response from VrboOwner on 2 Jul, 2024
Thank you, Waverly, for your feedback on your stay at with us at Island Rendezvous in Key West. We're delighted you enjoyed the convenient location near Duval Street and the well-maintained pools and grounds. We apologize for the challenges with the A/C units and the sliding glass door in the smaller house; we are actively addressing these issues to enhance comfort for future guests. We appreciate your suggestion regarding better connectivity between the two properties and will consider this for improvements. Your recommendation is greatly valued, and we look forward to the opportunity to host you again with an even better experience next time.
VHKW
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.
Joseph W.
Stayed 4 nights in May 2021
Response from VrboOwner on 20 May, 2021
Joseph,
Thank you so much for taking the time to share your experience! You picked the right property for your group - walking distance to all fun activities in town. We'd love to have you back soon!
VHKW Team
This property is great for a big group. Incredible location. Lots of beds and bathrooms.
Brent C.
Stayed 5 nights in Jun 2019
Response from VrboOwner on 22 Mar, 2020
Thank you! Location is indeed amazing!
We hope to have you back in the near future.
VHKW Team
Verified
8/10 Good
jana m.
20 Mar, 2019
The houses are very nice. They are very clean.
There are a few minor repairs that are needed but overall everything was very nice. We had a great time.
jana m.
Stayed 7 nights in Mar 2019
Response from VrboOwner on 22 Mar, 2020
Thank you for your comments. We are glad to hear you had a great time at Island Rendezvous!
We will be in touch to find out about the minor repairs, as we always strive to address any issues as they come up.
Thank you again!
VHKW Team
About the host
Hosted by VHKW - Vacation Homes of Key West
Languages:
English
Premier Host
They consistently provide great experiences for their guests