Conch style home in Oldtown with private pool AND dock!

Key West, Florida
$1113 avg/night
Bed 4

Bed

Bath 3

Bath

Home Private Vacation Home

Property Type

Sleep 10

Max Sleeps

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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Total

Includes taxes and fees
$903+
View details
  • Feature Features
  • Map Map
  • School District Availability
  • Review Review

Feature Features

  • PETS

    No Pets Allowed
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Deadbolt Lock Fire Extinguisher First Aid Kit Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    4 Bedrooms Bed Sheets Provided
  • GENERAL

    Unit Size: 2898 Sq Ft (269 Sq M)
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Dishwasher Ice Maker Microwave Oven Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Onsite Parking Onsite Parking Options Include A Garage
  • INTERNET

    Free WiFi, With Speed Of 250+ Mbps (good For 3–5 People Or Up To 10 Devices)
  • OUTDOORS

    Balcony Barbecue Grill Fenced Yard
  • POOL/SPA

    Heated Pool Massages Private Pool
  • BATHROOMS

    3.5 Bathrooms Bathtub Or Shower Bidet Hair Dryer Jetted Bathtub Towels Provided
  • LANGS SPOKEN

    English Spanish
  • THINGS TO DO

    Basketball Nearby Boat On Site Cycling Nearby Ecotours Nearby Fishing Nearby Fitness Facilities Nearby Marina Nearby Sailing Nearby Scuba Diving Nearby Tennis On Site Water Skiing Nearby Windsurfing Nearby
  • ENTERTAINMENT

    DVD Player Smart TV With Cable/satellite Service
  • LIVING SPACES

    Living Room
  • CLIMATE CONTROL

    Air Conditioning
  • FAMILY FRIENDLY

    Babysitting Service Available
  • LOCATION HIGHLIGHTS

    Near A Hospital Near The Bay Near The Ocean Near The Sea On The Waterfront
  • SERVICES AND CONVENIENCES

    Chef Concierge Services Housekeeping (on Request) Iron/ironing Board Local Meal Delivery Service Phone
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 10

Map Map

School District Availability

Review Review

  • Beth G.

    Submitted Mar 29, 2026

    Stayed Mar 21, 2026

    Close enough to walk to Duval yet for enough for privacy

  • Angela S.

    Submitted Mar 25, 2026

    Stayed Mar 11, 2026

    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!

  • Gina L.

    Submitted Feb 25, 2026

    Stayed Feb 19, 2026

    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.

  • Sara N.

    Submitted Jan 27, 2026

    Stayed Jan 23, 2026

    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.

  • Stacy D.

    Submitted Jan 7, 2026

    Stayed Oct 8, 2025

    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.

  • evan c.

    Submitted Jan 5, 2026

    Stayed Dec 19, 2025

    Plenty of room for at least 10 people, unfortunately, some of our guests failed to show up. Comfortable for the most part.We had 3 cooler days and wished the house had heat. The pantry could use some new pots and pans, along with flatware/dinner wear for 12. (There were 11 large plates, but only 4 bowls, and not enough coffee mugs). The pool was too small for 3 people, and barely got sun, except early in the morning.

  • JM H.

    Submitted Dec 10, 2025

    Stayed Nov 24, 2025

    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.

  • J H.

    Submitted Nov 16, 2025

    Stayed Nov 6, 2025

    House had a mold smell which was picked up on all our clothes. Pool heater didn’t work so pool was unusable

  • Bryan G.

    Submitted Nov 15, 2025

    Stayed Nov 12, 2025

    Host was great, responsive, and fully accommodating to schedule! Highly recommend.

  • Sandra C.

    Submitted Sep 24, 2025

    Stayed Sep 19, 2025

    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!

  • robyn j.

    Submitted Sep 5, 2025

    Stayed Aug 29, 2025

    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!

  • Jack S.

    Submitted Aug 24, 2025

    Stayed Aug 16, 2025

    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.

  • Samuel W.

    Submitted Jul 16, 2025

    Stayed Jul 10, 2025

    Wonderful experience with a group of adult friends. Enough beds to cover everyone and the pool at the end of the night was perfect. Great host communication. 10/10

  • Michael B.

    Submitted Jul 1, 2025

    Stayed Jun 26, 2025

    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 the second year we rented this house for a family vacation. The house is excellent; good location, very clean and large rooms. We highly recommend this house and Key West Vacation Homes customer service. We will rent this house again.

  • Virgil T.

    Submitted May 26, 2025

    Stayed Apr 28, 2025

    We loved this house, everything about it! It was beautiful. This was the best vacation I ever had, the house was just the icing on the cake. I remember cringing at the price point when we booked it because the photos make it look so narrow. But as soon as we stepped in we immediately knew this house was something special. The owners should just let us come stay a few weeks every year to make sure everything is still in order. What a delightful stay. Oh, and the neighbor lady is lovely, we had a few nice chats. I wish we stayed longer. Thank you for everything that this vacation was. (Now there were a couple of small hiccups, but no biggie. Everything was worked out) This place is highly recommended.

  • Laurie B.

    Submitted May 25, 2025

    Stayed May 17, 2025

    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.

  • cissy e.

    Submitted Apr 15, 2025

    Stayed Apr 11, 2025

    Thanks for a great stay! The house was well kept, clean, and beautiful!

  • Laura Lynne S.

    Submitted Mar 16, 2025

    Stayed Mar 13, 2025

    Lovely property with everything we needed.

  • Linda R.

    Submitted Mar 8, 2025

    Stayed Mar 4, 2025

    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.

  • Marissa F.

    Submitted Mar 3, 2025

    Stayed Feb 13, 2025

    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!

  • Julie A.

    Submitted Jan 28, 2025

    Stayed Jan 24, 2025

    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.

  • Emily M.

    Submitted Jan 3, 2025

    Stayed Dec 26, 2024

    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.

  • Samantha G.

    Submitted Dec 8, 2024

    Stayed Nov 21, 2024

    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!

  • Jack S.

    Submitted Aug 20, 2024

    Stayed Dec 31, 1969

    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!