Welcome to Eisenhower's Retreat, a charming old Key West-style home with modern luxury amenities. Enjoy the expansive kitchen, heated pool, and private boat slip. With two master suites and additional sleeping options on the top floor, this retreat is perfect for families or groups of friends.
Reviews
9.89.8 out of 10
Exceptional
Entire home
4 bedrooms4 bathroomsSleeps 102898 sq ft
Popular amenities
Ocean view
Pool
Kitchen
Washing machine
Dryer
Add dates for prices
About this property
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).
Property amenities
Pool/Spa
Heated pool
Massage
Private pool
Internet
Available in the house: Free WiFi
Parking and transport
Onsite parking options include a garage
Kitchen
Coffee/tea maker
Cookware, dishware, and utensils
Dishwasher
Hob
Ice maker
Microwave
Oven
Refrigerator
Toaster
Dining
Chef service
Dining table
Bedrooms
4 bedrooms
Bedsheets provided
Bathroom
3.5 private bathrooms
Bathtub
Bathtub or shower
Bidet
Hair dryer
Towels provided
Living spaces
Dining table
Living room
Entertainment
DVD player
Smart TV with cable/satellite channels
Outdoor areas
Balcony
Barbecue grill
Fenced yard
Laundry
Laundry facilities
Washing machine
Comfort
Air conditioning
Pets
No pets allowed
Suitability/Accessibility
Smoke-free property
Services and conveniences
Concierge services
Housekeeping on request
Iron/ironing board
Meal delivery service
Phone
Location highlights
Near a hospital
Near the bay
Near the marina
Near the ocean
On the waterfront
Things to do
Boat
Heated pool
Tennis
Basketball nearby
Cycling nearby
Ecotours nearby
Fishing nearby
Golfing nearby
Jet skiing nearby
Sailing nearby
Scuba diving nearby
Snorkelling nearby
Swimming nearby
Water skiing nearby
Water tubing nearby
Windsurfing nearby
Safety features
Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
Smoke detector (host has indicated there is a smoke detector on the property)
You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools
Pets
Pets not allowed
Children and extra beds
Children are welcome
Events
No events allowed
Smoking
Smoking is not permitted
Important information
You need to know
This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.
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 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. Southernmost Point is 1.4 mi (2.3 km) away.
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Reviews
Reviews
Exceptional
All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
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!
Overall was wonderful! Check-in was easy and so was check-out. We had plenty of space and loved the house. Which we spent more time in than anticipated due to weather.
Spend the weekend with friends in Key West. The house was clean and well prepped for a group of people to spend the several days there. The check in and out process was quick and easy and everyone had a good time. We didn't end up using the pool but there was plenty to do on the key.
We loved the huge space of the main floor and each bedroom. Well maintained and supplied. Had everything we needed to be comfortable from home. Easy parking and racks for bikes. If you dont have your own transport, about a mile walk to the main attractions, but Uber service is super quick and reliable.
Nancy T.
Stayed 4 nights in Apr 2024
From a partner site
10/10 Excellent
Jack S.
22 Aug 2023
Great Place - Perfect Location - Excellent Experience!
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:
Very nice place. It is well kept, clean, and comfortable. The Mgt did a great job. Overall an excellent experience.
Overall we really enjoyed this home, it was very clean and set up nicely. The pool heater was not working and the decor in the living room was a bit aged. Otherwise everything was great. Be prepared to be woken up by the roosters and the daily musical series at the Naval Base.
My fiance and I love Key West and go every year just us two. This year we invited our friends to come with us! There were 9 of us total and the house was perfect for our group. It was so spacious, and the location was perfect. We even had a situation where we couldn’t get the tub water to stop, and in less than 10 minutes there was someone over and they fixed it right away! We were impressed with how quickly it was resolved. The parking spots were great for our golf cart rentals. It was very clean, nicely stocked and would definitely recommend!
Marissa F.
Stayed 3 nights in Feb 2025
From a partner site
10/10 Excellent
Debra G.
10 Aug 2023
Lots of Room for Family; Mini Lobster week
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:
Kitchen could use some filet knives and cutting boards-I bought a cutting board and left it in home. Beds comfortable, but top floor separate bedroom should be changed to another king-Bed; not much room for adults in small twin beds. Kitchen table perfect for our group & Wi-Fi access easy. Management very good and returns calls quickly. Loved having our boat slip so nice & close.
Debra G.
From a partner site
10/10 Excellent
Laurie B.
25 May 2025
Eisenhower retreat
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 was our third year renting through Key West vacation homes always have a very pleasant experience. The houses are amazing and close to downtown. Couldn’t have a bad time if you wanted to.
Laurie B.
From a partner site
10/10 Excellent
Jack S.
20 Aug 2024
Awesome - Great Location - Beautiful Home
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:
Awesome - Great Location - Beautiful Home. This littel bit of paradise is close to everything, minutes from Duval, Mallory Square, Stock Island, etc. The home is in great shape. - we'll be back!
Jack S.
From a partner site
10/10 Excellent
JITENDER G.
9 Jul 2024
KW 4TH JULY
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:
PERFECT!
JITENDER G.
From a partner site
10/10 Excellent
Michael B.
30 Jun 2024
Key West Birthday Celebration
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
I was more than happy with the location.
I was very satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
The house was perfect, better than we expected. Very clean with plenty of space. The location worked very well with bike rentals and we walked to some restaurants. The pool was used every day. We would rent this house again.
Michael B.
Stayed 4 nights in Jun 2024
From a partner site
10/10 Excellent
Morgan B.
22 May 2024
Great Stay!
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
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:
We had a great experience! The location was perfect, an early/late check in was honored and it was perfect for what our group of gals were looking for. The only downside was the dishwasher was broken and we were unable to use it during our stay. Hoping that the company can give some credit for this! Otherwise, amazing stay and couldn’t have asked for anything better.
Morgan B.
Stayed 4 nights in May 2024
From a partner site
10/10 Excellent
Janell E.
23 Apr 2024
Amazing Vacation Home
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:
The house is absolutely beautiful and in a perfect location! It's within a mile of all of the highlights of Key West. The house is HUGE and gave plenty of room for two families to coexist happily and gave plenty of space for the kids to do their thing while the adults relaxed. We will definitely be staying here again!
Janell E.
Stayed 6 nights in Apr 2024
From a partner site
10/10 Excellent
A guest from East Grand Rapids, MI
3 Feb 2024
Key West done right
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:
Management company was wonderful to work with. They were able to provide several recommendations for a business retreat.
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.
Host was great, responsive, and fully accommodating to schedule! Highly recommend.
Bryan G.
Stayed 3 nights in Nov 2025
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.