All properties in Key West, Florida, United States of America

Almost Southernmost Retreat

Vacation home with private pool, near Duval Street

Image gallery

  • Pool
  • Pool
  • Balcony
  • Balcony
  • Pool
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Key West, FL, United States of America
  • 16 guests
  • 5 bedrooms
  • 8 beds
  • 4 bathrooms
  • Parking available
  • Pool
  • Pet-friendly
  • Kitchen
  • Non-smoking
  • Air Conditioning

Property highlights

Main amenities

  • WiFi
  • Onsite parking
  • Non-smoking
  • Air conditioning
  • Hair dryer
  • Towels provided

What’s around

  • In Key West Historic District
  • Duval Street - 1 min walk
  • Ernest Hemingway Home and Museum - 2 min walk
  • Key West Butterfly and Nature Conservatory - 6 min walk
  • Southernmost Point - 7 min walk
  • South Beach - 8 min walk

Sleeping arrangements

Bedroom 1

2 Double Futons

Bedroom 2

1 Queen Bed

Bedroom 3

1 King Bed

Bedroom 4

2 Queen Beds

Bedroom 5

1 King Bed

Bedroom 6

1 Queen Bed

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Enter dates for 2 guests


About this home

"Almost Southernmost Retreat" really is the best way to describe this Truman Avenue deluxe duo. Picture this: two 2-story cottages, with fully stocked modern kitchens, rooftop balcony, front porch swings, and a huge connected back deck. Comfortably sleeping up to 14 guests and equipped with all of your vacation essentials this compound is perfect for your next group getaway.

Just a half a block from Duval street, walk to all of your favorite Key West restaurants, shops, and attractions. Don't feel like leaving the house all day? This property is home to a private 8-man hot tub, pool, and sunbathing decks to keep you entertained all day and night.

The Space:

With 5 bedrooms, 3.5 baths, and private parking, this place has everything!

The first cottage in the compound sleeps up to 8 guests.

Bedroom 1 with an ensuite bath features a king-size bed. Upstairs in the loft is bedroom 2 with a queen-size bed, and bedroom 3 with 2-queen beds, separated by a half bath. While the living room area features a queen-size pullout couch and an additional full bathroom.

The second cottage in the compound sleeps up to 6 guests.

Bedroom 1 just off the kitchen, has a queen-size bed. Upstairs in the loft is king size bed. For extra sleeping, you can find a queen size sleeper sofa in the living room.

Guest Access:

Access code will be provided to the guest prior to check in.

The Neighborhood:

Closer to the southern end of Duval street the Almost Southernmost Retreat is just steps away from the Key West Lighthouse and Hemingway Home and Museum. One block away from locals' favorite boozy brunch spots like Moondog Cafe, Rams Head Southernmost, and Blue Heaven, food is at your fingertips. Or stroll right down the street to Sushi Song for fresh catches or fast-casual burrito bowls from Sinz. Needless to say, this property is in the center of all-thing Key West and more.

Getting Around:

One of the best parts of staying in Key West is how close in proximity you are to everything, this small little 2x4 island offers a variety of ways to get to and from your destination! Don’t feel like walking? Pedal your way to breakfast, or take a bike ride along the water at sunset, by renting from Fury or Island Bicycles who offer both pickup & drop-off of bike services! Feel like you’re on island time when you rent from Minty’s where you can enjoy exploring Key West on a scooter or golf cart! In addition to these non-traditional modes of transportation, you can also Uber, Lyft or Taxi to your next destination. Pink Taxi is an easy, reliable, and affordable way for getting to your rental from the airport.

This unit includes one private parking spot. The designated parking spot is on the left side of the property. There is also paid street parking available on a first-come-first-serve basis.

Other Things to Note:

Private Washer/Dryer.

Private wifi network and cable TV.

It's also possible to rent each cottage separately if you're traveling with a smaller group within 90 days of check-in.

This unit is pet-friendly. Our requirements are as follows:

•40lb maximum per pet

•$15/night per pet

•2 pet maximum

Please let us know if you plan on bringing your pet.

What’s around


  • In Key West Historic District
  • Duval Street - 1 min walk
  • Ernest Hemingway Home and Museum - 2 min walk
  • Key West Butterfly and Nature Conservatory - 6 min walk
  • Southernmost Point - 7 min walk
  • South Beach - 8 min walk
  • Fort Zachary Taylor Historic State Park - 15 min walk
  • Mallory Square - 16 min walk
  • Higgs Beach - 20 min walk
  • Smathers Beach - 41 min walk
  • Key West Lighthouse and Keeper's Quarters Museum - 1 min walk

Getting around

  • Key West Intl. Airport (EYW) - 7 min drive
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Key West, FL, United States of America

The manager

Speaks: Russian, Spanish

The home

Key facts

  • Vacation home (2500 sq ft)
  • Onsite parking
  • WiFi
  • Non-smoking
  • Air conditioning
  • Heating
  • Washer/dryer
  • Pets allowed


  • 5 bedrooms
  • Bedroom one - 1 queen bed
  • Bedroom two - 1 king bed
  • Bedroom three -1 king bed
  • Bedroom four - 1 queen bed
  • Bedroom five - 2 queen beds
  • Other sleeping area one - 2 sleep sofas/futons
  • Bed sheets provided


  • 4 bathrooms
  • Full bathroom one - 1 shower and 1 toilet
  • Full bathroom two - 1 shower and 1 toilet
  • Full bathroom three - 1 shower, 1 bathtub, and 1 toilet
  • Half bathroom - 1 toilet
  • Hair dryer
  • Towels provided


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

Entertainment and recreation

  • Cable/satellite TV


  • Private pool
  • Private spa tub


  • Deck

Other amenities

  • Iron/ironing board

Things to know

House rules

  • Pets allowed
  • Events/parties not allowed
  • No smoking
  • Max. guests: 16
  • Minimum check-in age: 25

Check-in and check-out

  • Check-in after 4:00 PM
  • 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. You will also receive an email from Vrbo with a link to a Vrbo account which will enable you to manage your booking.

Fees & policies

Required at check-in

  • Government-issued photo ID may be required
  • Minimum check-in age is 25

Travelling with others

  • Pets allowed


  • Onsite parties or group events are strictly prohibited.

    Guests can rest easy knowing there's a fire extinguisher and a smoke detector on site.

Also known as

  • 614a1f28619140002c210ce3


  • No, unfortunately, but there's street parking available.
  • Yes, there's a private pool.
  • Yes, pets are welcome.
  • You can check in starting at 4:00 PM. Check-out time is 10:00 AM.
  • Yes. Nearby restaurants include Duffy's Steak & Lobster House (3-min walk), Kermit's Key West Key Lime Shoppe (4-min walk), and La Grignote (5-min walk).
  • Almost Southernmost Retreat has private pools and a spa tub.