5 STAR HOME 3/2 1/2 + 1/1 cottage, pool, buy 3 weeks get 4th week free.

Key West, Florida
$424 avg/night Minimum Stay 28 Nights
Bed 4

Bed

Home Private Vacation Home

Property Type

Sleep 8

Max Sleeps

Night 28 nights

Min Stay

Our calendar is updated in real time and our rates are accurately displayed. You can book instantly without waiting for owner approval. Flexible cancellation policy. We try to beat rates of all of the other houses in Truman Annex.

Millionaires Row – Welcome to Island Living. Cozy, but upscale.

Truman Annex is the most exclusive private residential community in Old Town Key West, located just off the main drag of Duval Street. Quiet streets lined with palms and beautiful Old Florida Homes. The entrance has a 24 hour staffed guard gate.

Unplug and recharge in wonderful Key West, stop and smell the flowers and the salt air. You will be located only 1 block from mile ZERO.

Truman Annex Waterfront Park is only 2 blocks away and comes complete with a family friendly playground and splash pad, and the Amphitheater where you can enjoy lots of live concerts and events.

If you want sand between your toes instead of the private pool, the beautiful beach at Fort Zachary Taylor Park is just at the end of the street. Enjoy a tour of the fort, snorkeling, fishing, or just sunning and watch the yachts go by.

You will have every luxury and convenience you might want. Large flat screen TV in the living room and flat screens also in other parts of the property. Complimentary, secure Wi-Fi service. Our home is meticulously maintained and immaculate.

First floor is an open floor plan overlooking the private cocktail pool. There is dining space for 10. There is also a first floor bedroom with twin beds and a computer desk.

Upstairs you will find the Owner’s bedroom which is spacious with vaulted ceilings, a king size bed, ample closet and storage area, flat screen TV, and ensuite bath.

There is also a third bedroom upstairs, which is split from the Main bedroom, with a queen bed and flat screen TV. Another bath is adjacent.

The unique guest cottage is complete with vaulted ceilings, queen bed, flat screen TV, full bath, microwave, coffee maker, and refrigerator. It has its own private entrance.

The pool is surrounded by tropical plants and mood lighting.

When you are ready to venture out, walk over to Mallory Square where there is free entertainment every single night before sunset. Great viewing area for Key West’s famous sunsets that set into the ocean. Also within walking distance is The Aquarium, Little White House, The Key West Lighthouse, the Hemingway house, the Audubon House, and Mel Fisher’s Maritime Museum.

You will also be in walking distance to boutique shopping and many art galleries. Be sure to check out the gourmet restaurants and live music venues everywhere.

Nearby there is parasailing, snorkeling trips, fishing charters, and wonderful sunset cruises.

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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    No Pets Allowed
  • BEACH

    Beach Towels
  • DINING

    Dining Table
  • SAFETY

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

    4 Bedrooms Bed Sheets Provided Sofa Bed
  • GENERAL

    Unit Size: 1800 Sq Ft (167 Sq M)
  • KITCHEN

    Coffee/tea Maker Dishwasher Electric Kettle Ice Maker Microwave Oven Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Car Not Required Onsite Parking Onsite Parking Options Include A Garage
  • INTERNET

    Free WiFi
  • OUTDOORS

    Barbecue Grill Fenced Yard Garden Outdoor Furniture Patio
  • POOL/SPA

    Fence Around The Pool Heated Pool Hot Tub Outdoor Pool Private Pool
  • BATHROOMS

    Bathtub Or Shower Hair Dryer Shampoo Soap Toilet Paper Towels Provided
  • WORKSPACES

    Desk Desk Chair
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Fishing Nearby Fitness Facilities Nearby Golf Nearby Golf Privileges Kayaking Nearby Parasailing Nearby Sailing Nearby Scuba Diving Nearby Snorkeling Nearby Water Park Nearby Wildlife And Game Walks Nearby
  • ENTERTAINMENT

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

    Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • LOCATION HIGHLIGHTS

    In The City Center Near A Health Or Beauty Spa Near A Hospital Near The Sea
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Area Rugs In Public Areas Hardwood Flooring In Public Areas If You Have Requests For Specific Accessibility Needs, Please Contact The Property Using The Information On The Reservation Confirmation Received After Booking. No Elevators Smoke-free Property Tile Flooring In Public Areas

CheckIn Check-in : 04:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 8

Map Map

School District Rates & Availability

Review Review

  • Pam

    Submitted Dec 28, 2022

    Stayed Dec 31, 1969

    The property is in a great location with easy walking to tourist attractions, restaurants, and playgrounds. It is a very comfortable home with ample space so that you can enjoy being with your fellow housemates. The pool was enjoyable even though the temperatures in Key West were much cooler than normal. I did have an issue when I first arrived, but the owner answered my text promptly and the issue was resolved. I would highly recommend this property.

  • Stacey V.

    Submitted Jan 5, 2026

    Stayed Dec 27, 2025

    Beautiful home, very comfortable. A great location - you can’t beat it. Host was responsive to questions but honestly we didn’t need anything! Check in was easy, Penny was great. Would love to stay again when in Key West. THANK YOU!

  • John L.

    Submitted Dec 16, 2025

    Stayed Nov 15, 2025

    Great location, very comfortable floor plan – everything about it was perfect!

  • Colin B.

    Submitted Oct 1, 2025

    Stayed Sep 9, 2025

    Nice home. Great location. Would stay again.

  • Megan H.

    Submitted Jul 22, 2025

    Stayed Jul 12, 2025

    We had a wonderful time during our stay in Key West. Penny's home was beautiful and well kept. Great location, close top everything but in a nice quiet neighborhood. The pool was pristine and a lifesaver in the Florida heat. We will definitely be back!

  • Tisha P.

    Submitted Jul 10, 2025

    Stayed Jun 22, 2025

    Our stay was great. Host was very responsive to a couple of unexpected issues that came up. We let our 4 kids (18, 19, 19 and 19) stay in the main house. My husband and I stayed in the guest house in back yard. That was perfect, we had so much privacy, it was like we were on a seperate vacation. The pool was perfect, we relaxed daily in it.

  • Audrey C.

    Submitted Jul 1, 2025

    Stayed Jun 14, 2025

    This was one of the most lovely and accommodating properties we have ever stayed at. The photos didn't do justice to how beautiful and spacious it truly was. Especially the cottage. The house was perfect for our family of 6 to both come together, and spread out. There's even some small details that show how much love has gone into the comfort of this home. Many wonderful memories were made during our stay.

  • Cheryl S.

    Submitted Jun 17, 2025

    Stayed Jun 7, 2025

    Great location. Wonderful house. Loved our daily pool time.

  • Darby S.

    Submitted May 29, 2025

    Stayed May 15, 2025

    We had a fantastic time staying at this home! The location couldn't be better—just a short walk to Duval Street and Fort Zachary Taylor State Park, which made exploring Key West so convenient. The house itself was spotless and nestled in a beautiful, quiet neighborhood that felt both welcoming and private.We were initially concerned that the pool might be too small, but it turned out to be just right. It was perfect for a refreshing midday dip to cool off and relax. Overall, this place exceeded our expectations and was ideal for our trip.

  • Mark L.

    Submitted May 19, 2025

    Stayed Apr 27, 2025

    We had four generations for the week. Accommodations worked out great. Owner responded to all questions and resolved issues quickly. Walked to all restaurants and parks. Great vacation

  • Carole G.

    Submitted Mar 20, 2025

    Stayed Mar 8, 2025

    My family enjoyed the home and cottage. The home was furnished with everything we needed in the kitchen to be able to cook meals. The pool size was disappointing. Also, there was not much sunlight in the pool area. Only had about 3 hours of full sun to be able to sit by pool.My family enjoyed the fact that we could walk to many things in the area.I enjoyed the cottage and being able to have my own private place to relax in. The shower being so small was very challeging, but I made it work.

  • Marge O.

    Submitted Mar 2, 2025

    Stayed Feb 23, 2025

    This property has it all!! First, the location cannot be beat. You will be within walking distance of all the best restaurants, Duval Street shopping, Mallory Square, beaches, and historical sites, parks, and museums. The house is even more beautiful in person too! - the decor and amenities add a personal touch to make you feel instantly welcome and at home. Penny is a great communicator, and accommodating to our needs. The neighborhood is quiet, friendly, and beautifully landscaped. We especially enjoyed a cool dip in the pool and relaxing on the front porch after the day's activities. We've been to Key West many times over the past 10 years, staying in luxury hotels, and this is our favorite rental!

  • Jennifer R.

    Submitted Jan 19, 2025

    Stayed Dec 28, 2024

    We were a family and friends group of 7 with 3 couples and one single. The house was perfect for our group and everyone had enough space while also being able to gather as a group for meals, games, etc. The location was amazing as well. We were close to the action on Duvall street, but you couldn’t hear in the house. It was also central to just about everything, so whether walking, cycling, or scootering, it was perfect! The house was clean and there was plenty of dishware, etc. to cook as needed. Only tiny disappointment was that, even though heated, the dipping pool was never warm enough to use, even with several days in the low 80’s. On the flip side, it encouraged us to go check out various beaches.Also, know that you will need to tell your Uber/Lyft driver to use the Southard entrance which was a little tricky. Overall 9.9 out of 10 experience and I would highly recommend!

  • Trudy S.

    Submitted Jul 21, 2024

    Stayed Jul 12, 2024

    We enjoyed our stay, will be back one day.

  • KATHIE S.

    Submitted Jul 14, 2024

    Stayed Jul 5, 2024

    The property was great. We had a non urgent problem with the pool and the owners had someone to fix the problem within 2 hours. The house is beautiful and highly recommend it

  • Michael J.

    Submitted Jun 29, 2024

    Stayed Jun 22, 2024

    Great setup for us with 3 generations of family all under one roof. Great access to walk to all the hot spots on the island. Great stay and we’d book again in the future.

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Total

Includes taxes and fees
$424+
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