Southern snowbird-friendly house with pool, stunning backyard & great location

Key West, Florida
$1726 avg/night
Minimum Stay 1 Nights
Bed 4

Bed

Bath 3

Bath

Home Private Vacation Home

Property Type

Sleep 10

Max Sleeps

Night 1 nights

Min Stay

Situated in the heart of Key West, this unbelievable retreat will be the perfect place for entertaining the whole family! With three stories, high-end furnishings, and ample areas to spread out, there will ample room for everyone to indulge in their own kind of vacation. As if that isn't enough, recent renovations to enhance your stay include new carpet, updates to the upstairs bathrooms, and adding a waterfall to the pool. The interior is absolutely stunning with a gourmet kitchen, French doors throughout, and sunrooms to dive into your favorite book, yet stepping outside to the lush backyard will also be a treat. When days heat up, everyone can take a dip in the sparkling pool or simply lounge under the shade of the palms and banana trees as the chef of the group cooks up some burgers on the gas grill. Dine al fresco or gather with the whole family in the formal dining room to reminisce about the day's adventures. When the sun dips below the horizon, cozy up on the sectional sofa and play a movie on the TV with a bowl of popcorn. With so much fun to be had right at your fingertips, no one will want to leave this southern oasis!

Located in Truman Annex, an exclusive private residential community in Old Town Key West, this home is situated on a small cul-de-sac just off Duval Street and close to great entertainment, dining, shopping, and attractions. When you want to venture out a bit, head over to the Key West Aquarium or Mallory Square, both sitting within walking distance of your front door. Little White House, the Key West Lighthouse, the Hemingway House, and Mel Fisher Maritime Museum are all great options as well within a few miles of home base. Don't forget to pop into some of the local restaurants and grab some seafood!

Things to Know
Check-in time: 4:00 p.m.
Check-out time: 10:00 a.m.
All guests shall abide by the good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 p.m. to 8:00 a.m.
No smoking is permitted anywhere on the premises.
This property is managed by Seven Keys Vacations by Casago.

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

Feature Features

  • PETS

    No Pets Allowed
  • 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
  • GENERAL

    Unit Size: 2753 Sq Ft (256 Sq M)
  • KITCHEN

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

    Near Laundromat Washing Machine And Dryer
  • PARKING

    Onsite Parking Onsite Parking Options Include A Garage
  • INTERNET

    Free WiFi
  • OUTDOORS

    Balcony Barbecue Grill Fenced Yard Garden
  • POOL/SPA

    Private Pool
  • BATHROOMS

    3.5 Bathrooms Shower Towels Provided
  • WORKSPACES

    Desk
  • THINGS TO DO

    Birdwatching Nearby Ecotours Nearby Golf Nearby Golfing On Site Kayaking Nearby Parasailing Nearby Power Boating Nearby Scuba Diving Nearby Swimming Nearby Windsurfing Nearby
  • ENTERTAINMENT

    TV With Cable/satellite Service
  • LIVING SPACES

    Dining Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Children's Dinnerware
  • LOCATION HIGHLIGHTS

    In A Village In The City Center Near A Hospital Near The Sea
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • 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

  • Andrew W.

    Submitted Jan 24, 2026

    Stayed Jan 17, 2026

    Everything was terrific. We had a week long sailing race and it was in a great location and a very nice house!!

  • Nita W.

    Submitted Dec 11, 2025

    Stayed Nov 22, 2025

    This is a stunning house in a great location. The appliances were top of the line as was the furniture. On arrival were surprised by the level of cleanliness We arrived to find beer bottles under the bed, insects upstairs, and debris in the pool. The garage door was not operational during our stay. The tires on the bikes were flat. Without any house specific information we were challenged to figure out the air conditioning system and how to access the neighborhood at night. We spent a great deal of time chatting with the management company.

  • louise s.

    Submitted Nov 11, 2025

    Stayed Nov 3, 2025

    Great location, very spacious and perfect for large groups.House is a bit dated and had some issues that property manager tried to resolve in timely manner.Would consider staying here again

  • Karim A.

    Submitted Oct 5, 2025

    Stayed Sep 23, 2025

    We have been coming regularly for years to KW and it is the first experience that did not go well for us.1.checking was difficult even though the property was empty we could not checking earlier.2. Mattresses in the bedrooms were poor quality resulting in poor sleep.3. None of the TVs worked. We reported few times about the issue.5. Pool dirty. It was quickly cleaned 1 time.6. Gaz tank of BBQ was empty.

  • KAREN B.

    Submitted Jan 4, 2025

    Stayed Dec 28, 2024

    We had a wonderful stay at Southernmost Comfort House! The property was perfect for our group, and the communication with the host was great up to check in. The house was appointed well and had most everything we needed for a lovely vacation.That said, there were a few minor issues that could be addressed to improve the experience. Some lights were burnt out, and the TV remotes were not working properly. A few wear-and-tear items could use attention as well such as loose towel bars in the bathrooms. Additionally, we noticed there weren’t enough extra blankets or glassware for things like juice and cocktails, which would have been a nice touch. These items were communicated with Vacasa without response. One helpful suggestion for future renters would be to list the height of the garage in the property description. Our golf cart didn’t fit in the garage, so knowing this in advance would have been helpful.Overall, we enjoyed our stay and think this property has a lot to offer with just a few tweaks. Future renters might want to double-check specific needs (like extra blankets or glassware) before arriving. We’d definitely recommend Southernmost Comfort House for a relaxing getaway! The proximity to Duval as well as great shopping and restaurants is unbeatable!

  • Michael B.

    Submitted Mar 6, 2024

    Stayed Feb 12, 2024

    Great house with lots of space for entertaining

  • Tyler M.

    Submitted Dec 7, 2023

    Stayed Nov 4, 2023

    House was fantastic!! Close to all the action and very accommodating for a large group!!

  • William B.

    Submitted Jan 24, 2023

    Stayed Dec 31, 1969

    The location is excellent and the large house can accommodate a big family.

  • Rachel D.

    Submitted Dec 25, 2022

    Stayed Dec 31, 1969

    This home had plenty of space for 5 adults and 2 kids with room for more. It was nice having separate living areas for kids and adults to play! We enjoyed the heated pool. The location was perfect for us as it was close to pretty much everything. Make sure you have the key to the gates which lock at 6pm. We didn’t have a key the first night and got locked out which was a bit frustrating with two tired kids but we eventually made it back and got a key the next morning. Make sure to stop by Hank’s for the best live music and casual food.

  • Joe R.

    Submitted Dec 18, 2022

    Stayed Dec 3, 2022

    The house is 'generally' as advertised, but was missing many things, including outside dining furniture, a working pool, kitchen basics to name a few. Everything was filthy - particularly the floors, upstairs carpets (stained and tired) and the BBQ was disgusting - full of garden trash. We had to clean everything ourselves. It took Vacasa 3 days to even respond to our multiple calls - and only after we marched to their office in the town - before we started getting any action. We spent the entire vacation dealing with getting things resolved and never reached the state where the property matched the listing. NOT what you want on a very expensive family vacation. The listing does not mention that all gates/roads bar one to the community are locked at 6pm, which can mean a very long walk to return to the house, depending on where you are. Was a problem as we had someone with mobility challenges in our party. A key was finally provided after 5 days, but most surprisingly, Vacasa didn't even know about it. This is without doubt the worst vacation rental experience we have ever had, as well as being the most expensive. The house (when fixed) gets 4 stars, Vacasa get 1.

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Total

Includes taxes and fees
$1,600+
View details