Entire home

Conch style home in Oldtown with private pool AND dock!

Photo gallery for Conch style home in Oldtown with private pool AND dock!

Exterior
Kidnet Shaped Pool - Your kidney shaped, heated pool is surrounded by lush landscaping, several loungers, a grill and outdoor furniture.
Living area
Entry/Foyer
Interior

Reviews

9.8 out of 10
Exceptional
4 bedrooms3+ bathroomsSleeps 10

Popular amenities

  • Private pool
  • Garage parking available
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Barbecue

Explore the area

View map
Key West, FL
  • Place, Key West Naval Station
    ‪1 min walk‬
  • Place, Duval Street
    ‪18 min walk‬
  • Place, Ernest Hemingway Home and Museum
    ‪7 min drive‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪10 min drive‬

Rooms & beds

4 bedrooms (sleeps 10)

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

Bedroom 3

2 Single Beds

Bedroom 4

4 Single Beds

3 bathrooms, 1 half bathroom

Bathroom 1

Toilet

Bathroom 2

+1
Bathtub or shower · Bathtub · Bidet · Toilet · Jetted bathtub

Bathroom 3

Bathtub or shower · Bathtub · Toilet

Bathroom 4

Bathtub or shower · Bathtub · Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony
Dining area

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).

Add dates for prices

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About the area

Key West

Located on the waterfront, this holiday home is in Meadows, a neighbourhood in Key West. Ernest Hemingway Home and Museum and Southernmost Point 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 ecotours and cycling nearby.
Map
Key West, FL

What's nearby

  • Key West Naval Station - 1 min walk - 0.2 km
  • Studios of Key West - 9 min walk - 0.8 km
  • Duval Street - 18 min walk - 1.6 km
  • Ernest Hemingway Home and Museum - 7 min drive - 2.7 km
  • Southernmost Point - 8 min drive - 2.1 km

Getting around

  • Key West, FL (EYW-Key West Intl.) - 9 min drive

Restaurants

  • ‪Dions Truman & White - ‬8 min walk
  • ‪Circle K - ‬9 min walk
  • ‪Sandy's Café - ‬11 min walk
  • ‪Square Grouper Key West - ‬18 min walk
  • ‪Moose Lodge - ‬2 min walk

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 118 out of 132 reviews
Rating 8 - Good. 11 out of 132 reviews
Rating 6 - Okay. 1 out of 132 reviews
Rating 4 - Poor. 2 out of 132 reviews
Rating 2 - Terrible. 0 out of 132 reviews

9.8/10

Cleanliness

10/10

Check-in

9.6/10

Communication

9.4/10

Location

9.6/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Winton J.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a wonderful stay. The house was perfect for large extended family. We can’t wait to come back!
Stayed 7 nights in Apr 2026
Verified

8/10 Good

Beth G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Close enough to walk to Duval yet for enough for privacy
Stayed 7 nights in Mar 2026
Verified

10/10 Excellent

Angela S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 7 nights in Mar 2026
From a partner site

10/10 Excellent

Kyle F.

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.
Verified

10/10 Excellent

Stacy D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 4 nights in Oct 2025
Verified

10/10 Excellent

robyn j.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 3 nights in Aug 2025
Verified

8/10 Good

cissy e.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Stay

Thanks for a great stay! The house was well kept, clean, and beautiful!
Stayed 4 nights in Apr 2025
Verified

10/10 Excellent

JM H.

Liked: Cleanliness, check-in, communication, listing accuracy
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.
Stayed 5 nights in Nov 2025
Verified

10/10 Excellent

Bryan G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Host was great, responsive, and fully accommodating to schedule! Highly recommend.
Stayed 3 nights in Nov 2025
From a partner site

10/10 Excellent

Gina L.

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.
From a partner site

10/10 Excellent

Sara N.

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.
Verified

10/10 Excellent

jeff d.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place!

Our time there was great! The place was clean, had plenty of room, and only a short ride to Duval St.
Stayed 3 nights in May 2023
Verified

10/10 Excellent

Susan D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Eisenhower Retreat

Beautiful spacious home. Would definitely stay there again!
Stayed 4 nights in Jun 2024
From a partner site

10/10 Excellent

Jack S.

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.
Verified

10/10 Excellent

Logan R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Key West girls trip

Beautiful property, great location. Definitely recommend!
Stayed 3 nights in Sep 2022
Response from VrboOwner on 9 August 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

Sandra C.

Great Key West Old Town 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: We celebrated an 80th birthday for my husband with out of town relatives in the Eisenhour Retreat. It was a beautiful place!
Verified

10/10 Excellent

Samantha G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great family stay

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!
Stayed 6 nights in Nov 2024
Verified

10/10 Excellent

Laura Lynne S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fabulous

Lovely property with everything we needed.
Stayed 3 nights in Mar 2025
Verified

10/10 Excellent

Linda R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Three nights close to Duval Street

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.
Stayed 3 nights in Mar 2025
Verified

10/10 Excellent

Caroline D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Holiday respite

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.
Stayed 5 nights in Dec 2023
Verified

10/10 Excellent

Pam F.

Liked: Cleanliness, check-in, communication, listing accuracy

Eisenhower House - Key West

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.
Stayed 4 nights in Apr 2024
Verified

10/10 Excellent

Jennifer B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great spot in Key West!

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!
Stayed 4 nights in Jul 2023
Verified

10/10 Excellent

Samuel W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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
Stayed 3 nights in Jul 2025
Verified

10/10 Excellent

Michelle H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

We loved it!

It was a smooth process with excellent accessibility to property managers!! The house was clean and cozy. Excellent rental for large families.
Stayed 5 nights in Mar 2023
Verified

10/10 Excellent

Kenneth K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Terrific property for large family

Excellent!
Stayed 6 nights in Mar 2024
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