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Conch style home in Oldtown with private pool AND dock!

Waterfront holiday home with private pool and kitchen

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Exterior - Conch style home in Oldtown with private pool AND dock! (Key West)
A heated pool - Conch style home in Oldtown with private pool AND dock! (Key West)
Exterior - Conch style home in Oldtown with private pool AND dock! (Key West)
4 bedrooms, iron/ironing board, free WiFi, bed sheets - Conch style home in Oldtown with private pool AND dock! (Key West)
Outdoor dining - Conch style home in Oldtown with private pool AND dock! (Key West)
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

9.8 out of 10
Exceptional

Entire home

4 bedrooms4 bathroomsSleeps 10269 sq m

Popular amenities

  • Ocean view
  • Pool
  • Kitchen
  • Washing machine
  • Dryer

Add dates for prices

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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

Beach

  • Beach nearby

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
  • Shower
  • 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
  • Golf
  • 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)
  • First aid kit
  • Fire extinguisher
  • Deadbolt lock

General

  • Housekeeping (on request)
  • Unit size: 2,898 square feet

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Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in and check-out are available
Minimum check-in age - 31

Check-out

Check-out before 10:00 AM

Special check-in instructions

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 EU regulations about consumer rights, property booking services are not subject to the right of withdrawal.

Property is also known as

Extra Large Conch Style Home Oldtown Privavte Pool Dock House
Extra Large Conch Style Home Oldtown Privavte Pool Dock Key West
Extra Large Conch Style Home Oldtown Privavte Pool Dock
Extra Large Conch Style Home in Oldtown With Privavte Pool Dock!
Extra Large Conch Style Home Oldtown Privavte Pool Dock House
Extra Large Conch Style Home Oldtown Privavte Pool Dock Key West
Extra Large Conch Style Home Oldtown Privavte Pool Dock House
Extra Large Conch Style Home Oldtown Privavte Pool Dock Key West
Extra Large Conch Style Home Oldtown Privavte Pool Dock
Extra Large Conch Style Home in Oldtown With Privavte Pool Dock!
Extra Large Conch Style Home in Oldtown With Privavte Pool Dock!
2328-138985

About the area

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 Fort Zachary Taylor Historic State Park and Florida Keys Beaches. 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. Visit our Key West travel guide
View more Holiday homes in Key West
Map
Key West, FL

Getting around

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

Restaurants

  • Circle K
    9 min walk
  • Dions Truman & White
    8 min walk
  • Square Grouper Key West
    18 min walk
  • Sandy's Café
    11 min walk
  • The Dive Bar Shirt Club - Grub House

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 The Unitarian Universalist Fellowship of Key West, Duval Street and Florida Keys Beaches. Mallory Square is 1.6 mi (2.6 km) away.

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Conch style home in Oldtown with private pool AND dock! 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.
More informationOpens in a new window
Rating 10 - Excellent. 113 out of 126 reviews
Rating 8 - Good. 10 out of 126 reviews
Rating 6 - Okay. 1 out of 126 reviews
Rating 4 - Poor. 2 out of 126 reviews
Rating 2 - Terrible. 0 out of 126 reviews

9.8

Cleanliness

9.4

Location

Reviews

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

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

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

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

10/10 Excellent

Emily M.

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

Christmas in Key West

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.
Stayed 5 nights in Dec 2024

10/10 Excellent

Robyn L.

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

Fun days

We enjoyed the home that we shared with our friends. It was nice to be able to come back to a quiet and peaceful home at the end of a fun day.
Stayed 4 nights in Oct 2023

10/10 Excellent

Verified traveller

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

Nice location and vibe

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.
Stayed 3 nights in Sep 2023

10/10 Excellent

Nancy T.

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

Fantastic space for family

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.
Stayed 4 nights in Apr 2024
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Jack S.

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.
Stayed 7 nights in Aug 2023

10/10 Excellent

Julie A.

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

Key West Girls Weekend

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.
Stayed 3 nights in Jan 2025

10/10 Excellent

Marissa F.

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

Amazing property!

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!
Stayed 3 nights in Feb 2025
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Debra G., Brooksville, Fl

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.
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Laurie B.

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.
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Jack S.

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!
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

JITENDER G.

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!
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Michael B.

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.
Stayed 4 nights in Jun 2024
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Morgan B.

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.
Stayed 4 nights in May 2024
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Janell E.

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!
Stayed 6 nights in Apr 2024
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

A guest from East Grand Rapids, MI

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.
Stayed 3 nights in Jan 2024

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

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

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
This review comes from a trusted partner site and has not been verified.

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.
This review comes from a trusted partner site and has not been verified.

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!

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