Conch style home in Oldtown with private pool AND dock!
A reflection of old Key West, Eisenhower's Retreat was designed and built with the architectural feel of an old "Conch House", but with all the amenities of a new luxury home. Situated on the edge of Old Town Key West near everything Key West has to offer, your home boasts tall ceilings, large rooms, an expansive and well appointed kitchen with custom cabinets as well as a heated pool and private boat slip. Enjoy the convenience of two off-street parking spaces or simply bike to Duval St. Bayview Park is only a block away and was built on the premise that at one time it overlooked the bay before expanding Key West to include "New Town".
Enter to a "shotgun" view (reference to old Key West homes which would allow, if fired, a shotgun shot to pass from the front door to the back door with out interruption) of the downstairs through which you can view the custom kitchen, dining area, living and lastly, back yard. The kitchen has custom cabinets and stainless steel appliances as well as all teh tools you'll need to prepare the finest of cuisine! Just in front of the kitchen is a large wood dining table seating 6 comfortably. The Living rooms is comfortably situated with a pull out sofa and large HD flat screen with full HD cable.
Wish to enjoy the tropical air? Lounge on your private porch take a dip in your private heated pool.
On the next floor are two master suites with en suite bathrooms in each. Each suite has it's own balcony and walk in closets. All your luxury linens exceed the highest of standards and we aim to provide you with the comfort to make your stay not only memorable, but heavenly as well.
Bring the whole family! The top floor has a loft with 4 twin beds, which can be arranged to make two King beds (with notice) and a central bathroom. The top floor also has a private room with two twin beds as well and can also be joined to make one King bed. Whether its kids or adults, this home provides numerous options to accommodate the widest of sleeping accommodations necessary, not often found in ole Key West. We hope to have you as our guest at Eisenhower's Retreat!
RATES: we have 3 night (not always available) and 4 night rates available. We also have a 7 night and 21+ night discounted rate (automatically provided with dates).
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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
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock
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 on the waterfront, this holiday home is in Meadows, a neighbourhood in Key West. 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. The Kite House and Sails To Rails Museum at Flagler Station are also worth visiting. Jet skiing and scuba diving offer great chances to get out on the surrounding water, or you can seek out an adventure with cycling and ecotours nearby.
Ernest Hemingway Home and Museum - 7 min drive - 2.7 km
Southernmost Point - 8 min drive - 2.1 km
South Beach - 8 min drive - 2.1 km
Getting around
Key West, FL (EYW-Key West Intl.) - 9 min drive
Restaurants
Sandy's Café - 9 min walk
Circle K - 9 min walk
Dions Truman & White - 8 min walk
Square Grouper Key West - 18 min walk
Rainbow Cafe (MARC) - 9 min walk
Frequently asked questions
Is Conch style home in Oldtown with private pool AND dock! pet-friendly?
No, pets are not allowed at this property.
How much does it cost to stay at Conch style home in Oldtown with private pool AND dock!?
As of 8 July 2026, prices found for a 1-night stay for 2 adults at Conch style home in Oldtown with private pool AND dock! on 13 July 2026 start from AU$1,616, 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.
How much is parking at Conch style home in Oldtown with private pool AND dock!?
On-site parking is available at the property.
What time is check-in at Conch style home in Oldtown with private pool AND dock!?
Check-in begins at 4:00 PM.
What time is check-out at Conch style home in Oldtown with private pool AND dock!?
Checkout is at 10:00 AM.
Where is Conch style home in Oldtown with private pool AND dock! located?
Located in Meadows, this holiday home is within 1 mile (2 km) of Bayview Park, Duval Street and Florida Keys Beaches. Ernest Hemingway Home and Museum and Clarence S. Higgs Memorial Beach Park are also within 1 mile (2 km).
Reviews
9.8
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Close enough to walk to Duval yet for enough for privacy
Beth G.
Stayed 7 nights in Mar 2026
From a partner site
10/10 Excellent
Jamie T.
26 May 2026
Home away from home
Rating Details:
The property manager was very helpful.
The vacation rental was very clean.
I was very happy with the location.
I was more than satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
This was a perfect place for our girls trip! It was close to everything and was even perfect for just relaxing at home.
We felt at home! The perfect spot for all of our island adventures and a place to just relax. We had everything we needed. Thank you!
Angela S.
Stayed 7 nights in Mar 2026
From a partner site
10/10 Excellent
Kyle F.
18 May 2026
Fantastic Getaway
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
I was very happy with the location.
I was very satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
Great spot for a group trip. A few minutes outside of downtown which we loved to be a little quieter stay but still close enough for a quick walk, bike ride or uber away. We were a group of 10 (5 couples) and the house was perfect, especially the small pool in the back to cool off after a long hot day outside.
The house was lovely, comfortable and a quick walk to the dock where we saw manatees swimming. It was a little farther from the main areas of town than we had hoped, for walking purposes, but it was quiet at night.
Great house for a family! Lots of space, rooms were large, plenty of beds…the house had everything we needed! Great location too! We loved it!We’ll definitely stay here again!
Great property and host! Host was very responsive with my questions and helpful with everything I asked about. Property was exactly as advertised and better; very clean and felt bigger than the pictures even with 9 people in our party. Back patio and pool deck was a great hangout spot.
Beautiful spacious home. Would definitely stay there again!
Susan D.
Stayed 4 nights in Jun 2024
From a partner site
10/10 Excellent
Sara N.
27 Jan 2026
Perfect weekend
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
I was very happy with the location.
I was very satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
This rental was absolutely beautiful. The host was great and answered promptly, and even let us check-in early. Made my weekend perfect.
Sara N.
From a partner site
10/10 Excellent
Gina L.
25 Feb 2026
FANTASTIC Key West Home
Rating Details:
The property manager was more than helpful.
The vacation rental was spotless.
I was very happy with the location.
I was very satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
The property exceeded our expectations!! We had 8 adults and could have very comfortably fit two more! The home and property are modern, spacious and comfortable. It was an easy bike ride to ALL of our activities.
Beautiful property, great location. Definitely recommend!
Logan R.
Stayed 3 nights in Sep 2022
Response from VrboOwner on 9 Aug 2023
Thank you for the great review! We are glad you enjoyed your stay at Paradise Harbor. Sincerely, Key West Vacation Homes
From a partner site
10/10 Excellent
Jack S.
24 Aug 2025
Love This Place, Beautiful House, Pool, Dock, and Location :)
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
I was very happy with the location.
I was very satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
As described, this place is beautiful and the service is excellent.
We had an amazing time! From the adults to the baby we all enjoyed the house. We had a small issue with a bathtub and a handyman was over in 10 minutes and the rest of our trip was flawless. It was a great stay!
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
I was very happy with the location.
I was very satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
We celebrated an 80th birthday for my husband with out of town relatives in the Eisenhour Retreat. It was a beautiful place!
Eisenhower Retreat is a lovely home to stay in while visiting Key West. It is well appointed, clean and close enough to the historic district to access quickly. At the same time it is far enough away from the bustle to guarantee a quiet night’s rest. Very nice for a short or long vacation.
This house was perfect for a group of friends who appreciated getting away from the heart of Key West but within walking distance of everything. House was well appointed, clean and spacious.
The house was exactly as shown and worked well for our party of 7 girlfriends. It was very clean and check-in directions simple to follow! We enjoyed all the amenities and had such a great time! Would definitely book again for a large group stay.
We really enjoyed the stay in Key West. The home was beautiful with three levels, so plenty of room for friends and family. The kids loved their space upstairs, complete with a Pac-Man machine! Kitchen is well stocked, location was great. Wonderful vacation!