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

Top rated by guests
Pool
Living area
Interior
Private kitchen
Private kitchen
review stars
9.4Outstanding
(21 Ratings)
"Great house with lots of space for entertaining"
Michael B.
Don't miss out! Price and availability may change
9.4 / 10.0
Outstanding(21 Ratings)

House in Key West, FL

10 guests · 4 bedrooms · 3 baths

Reasons to book

Guests love it hereGuests give this property a top rating
Top-tier experienceA high end property in this area
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental

About this house rental

The Southernmost Comfort House

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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 neighborpolicy 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.

Parking notes: There is free parking available for 2 vehicles.



Damage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.
More information can be downloaded from the "Rental Agreement" on the checkout page.

Due to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.

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

Free WiFi/internet
Air conditioning
Pool
Non-smoking
TV
Coffee/tea maker
Refridgerator
Kitchen
Balcony/Terrace
WiFi/Internet
Private pool access
Microwave
Dishwasher
Washing machine
Dryer
Patio
Kitchenware
No pets allowed
Garden
Oven
Stove
Laundry services
Sofa bed
Ironing facilities
Towels

Map of Key West, FL


Ratings and reviews

9.4 / 10.0
Outstanding(21 Ratings)
8.0 / 10.0Excellent·Dec 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.
8.0 / 10.0Excellent·Nov 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
8.0 / 10.0Excellent·Jan 2025
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!
6.0 / 10.0Average·Dec 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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FAQs

Is parking included with this house?

Parking is not specified as an available amenity at Southern snowbird-friendly house with pool, stunning backyard & great location. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

Yes, a swimming pool is available for use at Southern snowbird-friendly house with pool, stunning backyard & great location. Enjoy the water!

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

Unfortunately, this house is not pet-friendly. Try searching again and filter for "Pets Allowed"

What amenities are available at Southern snowbird-friendly house with pool, stunning backyard & great location?

We found 25 amenities for this rental. This includes free wifi/internet, air conditioning, pool, non-smoking, and tv.


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