The Hemingway - Beach Houses Key West

Photo gallery for The Hemingway - Beach Houses Key West

A covered outdoor seating area with wooden furniture and a thatched roof.
A tropical resort with a clear blue pool surrounded by lush palm trees and a thatched-roof hut.
A spacious living area with a sofa set, a coffee table, and a dining table.
A spacious living room with a large sofa, a dining table, and a view of the ocean through large windows.
A resort with a thatched-roof hut and a white building with a sloped roof, surrounded by palm trees and a clear sky.

Reviews

9.6 out of 10
Exceptional

Highlights

  • Made for relaxation
    Top-rated for comfort — guests feel right at home here.
  • Paddleboard available
    A rare find — hit the water on a paddleboard right here.
  • Your private hideaway
    Guests love the secluded location for peace and quiet.
  • Discover nearby landmarks
    Close to Florida Keys Beaches

Popular amenities

  • Balcony
  • Dog-friendly
  • On-site fitness centre
  • Barbecue grill
  • Air-conditioning
  • Refrigerator

Explore the area

View in a map
Upper Sugarloaf Key, FL
  • Place, Florida Keys Beaches
    ‪1 min walk‬
  • Place, Sugarloaf Beach
    ‪8 min walk‬
  • Place, Duval Street
    ‪41 min drive‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪35 min drive‬

Rooms & beds

3 bedrooms (sleeps 6)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Bedroom 3

1 Queen Bed

2 bathrooms

Bathroom 1

Bathroom 2

Spaces

Kitchen
Balcony
Garden

Add dates for prices

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  • Dryer
  • Pet-friendly
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About the area

Summerland Key

Located in Summerland Key, this holiday home is on the waterfront. Florida Keys Beaches and Great White Heron National Wildlife Refuge reflect the area's natural beauty and area attractions include Wilhelmina Harvey Park and Key West Tropical Forest and Botanical Garden. Looe Key National Marine Sanctuary and Big Munson Island are also worth visiting.
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Map
Upper Sugarloaf Key, FL

What's nearby

  • Florida Keys Beaches - 1 min walk - 0.0 km
  • Sugarloaf Beach - 8 min walk - 0.7 km
  • Duval Street - 41 min drive - 40.1 km
  • Southernmost Point - 42 min drive - 40.5 km
  • Mallory Square - 42 min drive - 40.7 km

Getting around

  • Key West, FL (EYW-Key West Intl.) - 31 min drive

Restaurants

  • ‪Circle K - ‬18 min drive
  • ‪Baby's Coffee - ‬13 min drive
  • ‪Square Grouper Bar and Grill - ‬19 min drive
  • ‪Geiger Key Marina - ‬22 min drive
  • ‪Mangrove Mama's - ‬15 min drive

Frequently asked questions

Is The Hemingway - Beach Houses Key West pet-friendly?

Yes, this property allows dogs (limit 2 total) with a maximum weight of up to 23 kg per pet.

How much does it cost to stay at The Hemingway - Beach Houses Key West?

As of 6 Nov 2026, prices found for a 1-night stay for 2 adults at The Hemingway - Beach Houses Key West on 3 Apr 2027 start from £5,152, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at The Hemingway - Beach Houses Key West?

On-site parking is available at the property.

What time is check-in at The Hemingway - Beach Houses Key West?

Check-in begins at 4:00 PM.

What time is check-out at The Hemingway - Beach Houses Key West?

Checkout is at 10:00 AM.

Where is The Hemingway - Beach Houses Key West located?

Situated on the waterfront, this holiday home is steps away from Lower Sugarloaf Sound and Florida Keys Beaches. Sugarloaf Beach and Upper Sugarloaf Sound are also within 3 miles (5 km).

Reviews

9.6

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 6 out of 8 reviews
Rating 8 - Good. 2 out of 8 reviews
Rating 6 - Okay. 0 out of 8 reviews
Rating 4 - Poor. 0 out of 8 reviews
Rating 2 - Terrible. 0 out of 8 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

9.6/10

Location

9.8/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

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

Wonderful spot Great Host

Great place for our family of 5 A little off the beaten path which is exactly what we wanted Great host who answered all our questions promptly Sunrise and sunsets here were magnificent Great fishing off the dock as well
Stayed 4 nights in Nov 2024
Verified review

10/10 Excellent

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

Great getaway

Perfect location way off the path if you like seclusion.
Stayed 3 nights in Apr 2025
Verified review

8/10 Good

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

Great place

We love this secluded hideaway. Ask about the potential sea grass washed up on the shores creating a very big stink but otherwise a wonderful place
Stayed 4 nights in Sep 2024
Verified review

10/10 Excellent

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

The perfect getaway spot

Secluded, quiet, beautiful property!! Has everything you'd need, from an amazing pool to private dock, bar by the pool, kayaks, hammock, bikes, laundry, gym... we had a blast and we are hoping to be back again!!
Stayed 4 nights in Sep 2024
Response from VrboOwner on 2 Oct 2024
Excellent guests !!!
Verified review

10/10 Excellent

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

Perfect Sugarloaf Rental

We had a fantastic stay at this property. The house was in a perfectly quiet location, was clean and had every amenity that we needed. We loved the pools and hottub area! The staff was very friendly and attentive. We could not have asked for more.
Stayed 4 nights in Mar 2023
Response from VrboOwner on 10 Mar 2023
Thank you for staying with us.
Verified review

10/10 Excellent

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

Beautiful views, responsive host, clean place

Interior dated but clean and comfortably accommodated our large group of 8. Views were incredible and we thoroughly enjoyed grotto. For our particular unit the sweeping views were a bit shrouded by a fogged window in a couple places which was a bummer, but otherwise no complaints.
Stayed 3 nights in Feb 2023
Verified review

10/10 Excellent

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

Sugarloaf Spring Retreat

Great place to sit back and relax! Lots of peaceful places to hangout with the family. Awesome to walk out right onto the beach (aside from all the seaweed that floated in). Loved the clear kayak and paddle board! So much sea life. Lagoon pool was the best! Wish we had more days.
Stayed 3 nights in Mar 2023
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a fantastic stay in August! The location was perfect—right on the water, with kayaks available. The bedrooms were comfortable and all had great views. Our favorite place was the tiki for morning coffee and afternoon cocktails. It was the first vacation we had in a few years, and relaxation was fulfilled by the Hemingway House and Key West!We did spend some time figuring out the HVAC system. One thermostat seemed to be the main one while the second acted as a satellite.
Stayed 4 nights in Aug 2025
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