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

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Outdoor dining - Southern snowbird-friendly house with pool, stunning backyard & great location (Key West)
A short walk from Mallory Square and Duval Street, Southern snowbird-friendly house with pool, stunning backyard & great location provides golfing on-site, a garden and more. Stay connected with free in-room WiFi.

Reviews

9.4 out of 10
Exceptional

Entire home

4 bedrooms4 bathrooms256 sq m

Popular amenities

  • Pool
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning

Add dates for prices

About this property

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

  • 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.

Property amenities

Pool/Spa

  • 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
  • Microwave
  • Oven
  • Refrigerator
  • Toaster

Bedrooms

  • 4 bedrooms

Bathroom

  • 3.5 bathrooms
  • Shower
  • Towels provided

Living spaces

  • Living room
  • Separate dining area

Entertainment

  • TV with cable/satellite channels

Outdoor areas

  • Balcony
  • Barbecue grill
  • Fenced yard
  • Garden

Laundry

  • Laundromat nearby
  • Washing machine

Work spaces

  • Desk

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • In a village
  • In the city centre
  • Near a hospital
  • Near the sea

Things to do

  • Golf
  • Birdwatching nearby
  • Cycling nearby
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Parasailing nearby
  • Sailing nearby
  • Scuba diving nearby
  • Snorkelling nearby
  • Swimming nearby
  • Wildlife walks 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

  • Garden
  • Unit size: 2,753 square feet

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  • Kitchen
  • Washing machine
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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 - 25

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.

About the area

Located by the sea, this holiday home is in Old Town Key West, a neighbourhood in Key West. Southernmost Point and Fort Zachary Taylor Historic State Park are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and South Beach. Ready for a night out? Consider Sloppy Joe's Bar and The Key West Theater. Discover the area's water adventures with jet skiing and kayaking nearby, or enjoy the great outdoors with cycling and ecotours. Visit our Key West travel guide
View more Holiday homes in Key West
Map
Key West, FL

What's nearby

  • Harry S. Truman Little White House
    Harry S. Truman Little White House
    1 min walk - 0.2 km
  • Duval Street
    Duval Street
    3 min walk - 0.3 km
  • Mallory Square
    Mallory Square
    6 min walk - 0.6 km
  • Ernest Hemingway Home and Museum
    Ernest Hemingway Home and Museum
    11 min walk - 0.9 km
  • Florida Keys National Marine Sanctuary
    9 min walk - 0.8 km

Getting around

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

Restaurants

  • Key Lime Pie Factory
    5 min walk
  • The Bull & Whistle Bar
    6 min walk
  • Fogarty's and Flying Monkey's
    6 min walk
  • Wendy's
    6 min walk
  • Kermit’s Key West Key Lime Shoppe
    6 min walk

Frequently asked questions

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

No, pets are not allowed at this property.

How much is parking at Southern snowbird-friendly house with pool, stunning backyard & great location?

On-site parking is available at the property.

What time is check-in at Southern snowbird-friendly house with pool, stunning backyard & great location?

Check-in begins at 4:00 PM.

What time is check-out at Southern snowbird-friendly house with pool, stunning backyard & great location?

Checkout is at 10:00 AM.

Where is Southern snowbird-friendly house with pool, stunning backyard & great location located?

Located in Old Town Key West, this holiday home is within a 10-minute walk of Harry S. Truman Little White House, Duval Street and Mallory Square. Florida Keys Beaches and Fort Zachary Taylor Historic State Park are also within 15 minutes.

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Southern snowbird-friendly house with pool, stunning backyard & great location 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. 16 out of 21 reviews
Rating 8 - Good. 3 out of 21 reviews
Rating 6 - Okay. 1 out of 21 reviews
Rating 4 - Poor. 1 out of 21 reviews
Rating 2 - Terrible. 0 out of 21 reviews

8.8

Cleanliness

9.8

Location

Reviews

Verified

8/10 Good

KAREN B.

Liked: Cleanliness, check-in, location, listing accuracy
Disliked: Communication

New Years in Key West

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!
Stayed 7 nights in Dec 2024
Verified

10/10 Excellent

Andrew W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything was terrific. We had a week long sailing race and it was in a great location and a very nice house!!
Stayed 7 nights in Jan 2026
Verified

8/10 Good

louise s.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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
Stayed 7 nights in Nov 2025
Verified

8/10 Good

Nita W.

Liked: Check-in, location, listing accuracy
Disliked: Cleanliness, communication
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.
Stayed 7 nights in Nov 2025
Verified

10/10 Excellent

William B.

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

Big house in a great area

Great place to stay.
Stayed 9 nights in Jan 2022
Verified

10/10 Excellent

Dawson S.

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

Wonderful stay. Absolutely perfect location.

Was a very good stay. We were only a 2 minute walk from Duvall street and could get there by a secure gate from the neighborhood with a key that was provided. Super safe and a beautiful neighborhood.
Stayed 7 nights in May 2022
From a partner site

10/10 Excellent

William B.

Great house

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

10/10 Excellent

Michael B.

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

Great house

Great house with lots of space for entertaining
Stayed 7 nights in Feb 2024
Verified

10/10 Excellent

Tyler M.

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

World Championship Boat Races

House was fantastic!! Close to all the action and very accommodating for a large group!!
Stayed 9 nights in Nov 2023
Verified

4/10 Poor

Karim A.

Liked: Location
Disliked: Check-in, communication, listing accuracy
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.
Stayed 12 nights in Sep 2025
From a partner site

10/10 Excellent

Pamela P.

Truman Annex

Home is beautiful.. Perfect proximity to historical attractions, entertainment venues, restaurants, bars & Mallory Square. Gated community is beautiful..
Verified

10/10 Excellent

kim s.

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

Perfect location beautiful house

All 14 of us had an amazing week! The house is beautiful and in s perfect location. We rented 14 bikes and it was wonderful to store them in the garage. Loved every minute!
Stayed 7 nights in Feb 2021
Verified

10/10 Excellent

Andrea K.

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

Coming back next year

The house was the perfect size for a our family with two babies under two since we could walk everywhere. We are planning to come back again next year. We love the pool and the big open spaces.
Stayed 10 nights in Sep 2022
From a partner site

10/10 Excellent

David P.

Great House!

The house is as good as advertised! It met all of my family needs and then some. If you want to stay at house that can accomodate 7+ people, this is it. Great area and close to all the action. Vacasa was quick to follow-up on minor issues after we arrived for our stay.
Stayed 7 nights in Jul 2021
Verified

10/10 Excellent

Keith D.

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

Great house in an even better location

The house was great for 10 people and had everything we needed. The location was the best surprise. The Truman Annex is an amazing community with gorgeous homes and landscaping. It was an easy walk to Old Town and the waterfront. We rented a car but really didn’t need it. Would definitely rent this home again!
Stayed 8 nights in Dec 2021
From a partner site

10/10 Excellent

Susan M.

Key West Team

The house was beautiful and spacious. We had 9 people and a ton of room to spread out. The pool was awesome and loved that it was deep for adults and shallow area for the kids. The few minor issues we had the management team took care of promptly. Thanks for a great time!
Stayed 7 nights in Jun 2021
From a partner site

10/10 Excellent

Rachel D.

Great Family getaway

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.
Verified

10/10 Excellent

Sam H.

Liked: Cleanliness, check-in, location, listing accuracy
Disliked: Communication

Admirals La

Great location and beautiful property. Renters should be told about no overnight parking and need to obtain a parking pass. Need more information on operation of pool and thermostats. One complaint. One day at 7:30 am a work crew showed up without warning and proceeded to install new gutters, which involved loud banging and ladders outside the rooms. Should have been done when no renters on property
Stayed 7 nights in Dec 2021
Verified

6/10 Okay

Joe R.

Liked: Check-in, location
Disliked: Cleanliness, communication, listing accuracy

Underwhelming, Oversold, Overpriced

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.
Stayed 7 nights in Dec 2022
Verified

10/10 Excellent

Sherri A.

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

Exceeded expectations!

Our first trip to Key West did not disappoint. This house was nestled in the most beautiful historic neighborhood that we saw on the island. It was very well maintained and close to all the action. Tons of shopping and restaurants within a short walk or bike ride. The home was perfect for our group of ten. There are 5 bedrooms and 3 separate living/seating areas. The main floor has a full bath (but no bedrooms). Second floor has 4 bedrooms and 2 bathrooms. Loft area has 2 twin beds and a full bathroom. All closets had plenty of hangers. We had plenty of hot water - I don’t think anyone had to take a cold shower or wait for the heater to recover. The kitchen was amply supplied with dishes, utensils, serving bowls, pots/pans, toaster, blender, etc., and it has both a Keurig and a drip coffee maker. There are a few books and games in the main TV cabinet, not many. There are 7 TVs throughout with good cable (one in each bedroom plus a huge one in the main living area and another in the smaller living area). A little sunroom off the kitchen and living room has accordion glass walls that open to the pool and a small patio with a really nice gas grill. The pool is absolutely beautiful, with a soothing fountain, plenty of clean chairs, and lots of beautiful trees (with a few resident iguanas). 😊 Perfect balance of sun and shade. It was very refreshing after a hot day at the beach and bike riding to take a dip in the cool, clean water. We rented bikes from Island Safari Rentals, and they were delivered and waiting for us when we arrived. They were in pristine condition and we rode all over the island every day - easy, flat rides. Plenty (like lots!) of towels (bath and beach) were provided, as well as blankets and extra sheets for sofas. The washer and dryer are extra large and new. The 2-car garage was very tight for our two large vehicles (a minivan and a Yukon) but with skilled drivers and mirrors folded in, they fit. 😂 A third vehicle had to be parked in a lot nearby for a daily fee. There’s no driveway and no street parking allowed. A couple of minor irritations were addressed fairly quickly by the property managers, but nothing worth noting. The only thing that we noticed was lacking throughout the house was towel racks/hooks. There were not enough places to hang damp towels and bathing suits. With so many people, hanging them over shower doors was not ideal. But that’s a small complaint for an overall great place.
Stayed 7 nights in Jun 2022
Verified

10/10 Excellent

Frank N.

Stayed 7 nights in Mar 2025