Eleanor's Place Key West - Historic Old Town Cottage Dog Friendly

Eleanor's Place is a charming Key West Cottage in the heart of Key West! Featured on HGTV's Island Life, our renovated cottage has all you need for a perfect monthly stay in Key West.

THE PROPERTY: "Eleanor's Place Key West" has everything you might want on your monthly vacation to Key West.

LOCATION: The cottage is in historic Old Town Key West, just steps to Duval, beaches, restaurants, attractions, and an olympic size pool!

VIRTUAL TOURS: Search "Eleanor's Place Key West Cottage Rental" on youtube for virtual tours.

BED CONFIGURATION: Queen Bed on main floor with wall mounted TV - and King Bed in upstairs loft with ensuite bath. (Spare blowup mattress also available.)

LIVING SPACE: The living and dining room are open concept with large windows and ample light. The living room has a new sectional sofa, and the dining room has a table for four. The wall mounted TV can be angled to face either the living room or the dining room.

KITCHEN: The chef’s kitchen is spacious, includes a breakfast bar, stainless steel appliances including a dishwasher and convenient full size laundry machines.

BATHROOMS: There are two full bathrooms. One is located on the main floor and the other is an upstairs ensuite in the King loft bedroom.

OUTDOOR SPACE: The house features a beautifully lush side yard with an inviting patio, made from reclaimed bricks. Enjoy comfortable patio seating, barbecue, and overhead lighting under the stars.

PARKING: Side driveway and street parking.

CLEANING: The cottage is professionally cleaned prior to each check-in. We kindly ask guests to clean their linens prior to checking out. We also have a monthly gardening service.

REVIEWS: Sadly the only review we've received from this platform was our first and only less than 5 star review - the review expressed disappointment in the comfort of the living room furniture, which has since been replaced by a much more comfortable sectional sofa. Many people that stay at our cottage are repeat guests, and as a result there are not many reviews on this site. Below you will find a some reviews from people who've booked privately (they have been cut and pasted from our website and/or from Google reviews and have not been modified):

"We just got home from a one month stay at Eleanor’s Place (June 2025) and I can’t say enough about the cottage or our Host, Lesley. The cottage on Virginia Street is in a quiet friendly neighborhood, and the cottage itself, which is beautifully decorated, provided us with all the comforts of home, including a quaint backyard where we mingled with friends as we grilled on the BBQ. We were close to all the attractions and restaurants as well as the beaches, and Lesley was always quick to respond to any questions we had along with suggestions for our stay. To get around we rented a golf cart from Fun Rentals, which we were able to park in the driveway of the cottage. This was our fourth trip to Key West, and we wanted to live and play like a “local” and Eleanor’s Place helped us do that easily. If you are looking for a comfortable, relaxing, quiet place to stay in Key West…we highly recommend Eleanor’s Place." - Michelle, 2025
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"If I could add more stars I would! I have been going to Key West every year, at least once a year, for close to 15 years. I have stayed in hotels, condos and houses and this is by far the best stay yet! House is spotless, bathrooms are immaculate, fantastic front porch for morning coffee and the patio is an absolute gem. All appliances are clean and work, location couldn’t be better! Walking distance to everything but far enough away from the chaos that your evenings are nice and quiet. Hosts were extremely responsive to any questions. I will say this now…if Eleanor’s Place is available…BOOK IT!" - Paul G., 2025

"Eleanors Place is a thoughtfully renovated shotgun house in the historic Bahama Village section of Key West. Having lived in Key West 22 years, you get the authentic island vibe here. Everything we needed was available and the full size appliances were a big plus. We enjoyed the tropical shaded side yard for dining, reading, and relaxing, and watching our pets play. The off-street parking and friendly neighbors are a bonus. You are only a few blocks to many of the best attractions: Southernmost Point, Hemingway home, lighthouse, Butterfly Conservatory and many good restaurants. We never walked over 1.5 miles to the furthest locations in Old Town, but if we needed transportation it was readily available. The public pool is a block away and they open early in the morning to swim laps. Lesley is a wonderfully responsive host which was much appreciated. Our month stay was delightful." - Delores, 2025

"We stayed at this cottage from mid June through all of July. We absolutely loved it. The booking process was easy and safe. Lesley provided all documentation that I asked for before I sent any money and went out of her way to make sure I was completely comfortable with the process. When we arrived, the cottage was immaculate. The condition of the home was exactly as depicted. The beds were comfortable, the kitchen well stocked and she was available for any questions, concerns and potential problems that could have arisen. I couldn’t have asked for a better experience. We loved the location and the time spent there and will definitely return. Thank you again!" -Denise, 2024


PETS: This home is dog-friendly. Some restrictions apply.

NOTES:
***Due to Key West Bylaws, a minimum stay of 28 nights is required. Guests check in on the 1st of each month. To book more than one month in a row and enjoy discounted pricing, please contact us.***