The Hemingway - Beach Houses Key West

Upper Sugarloaf Key, Florida
$1133 avg/night Minimum Stay 1 Nights
Bed 3

Bed

Bath 2

Bath

Home Private Vacation Home

Property Type

Sleep 6

Max Sleeps

Night 1 nights

Min Stay

If you’re reading this, you’re already on the path to paradise! Thank you for considering us for your dream vacation—we can’t wait to host you.

We are pet friendly !!!

Off the beaten path you will find a unique location and a beach front bungalow with endless unobstructed views of the ocean from every bedroom. Featuring an open family area, full kitchen, deck and its own tiki, excellent for grilling, having a cold drink or just gazing at the ocean. Enjoyyou day on the beach, dock or our coral inspired pool, with swim up tiki bar, waterslide and grotto.

The Hemingway is 1 of 5 secluded bungalows nestled in a 10 acre ocean / beach front paradise. This unique property has close to 1000’ of private sandy beach, 2 docks extending out 450’ from the shore, great for docking your boat, jet ski or enjoying the great fishing action right off our pier. At the heart of our resort is our featured amenity, our newly remodeled grotto style pool inspired by natural Coral coast such as you would find in South Florida. The pool area features 2 pools; a smaller chill pool with a cascading waterfall bench. Our larger pool has a water slide, a waterfall hidden grotto, a swim up bar and a hot tub for those days you need to relax after a great day out fishing. Amenity’s also include complimentary paddle boards, our fitness center, 8 bikes to cruise the island, 2 tiki huts on the beach great for grilling as you feel the ocean breeze, or just soaking it all in on a hammock.

Also a Great place for weddings, corporate retreats and family reunions (fees apply)

Other Amenities include :
Jet ski rental
Golf cart rental
In suite massage
Fishing charter tours
*fees apply

Our guests are our top priority, and we are dedicated to exceeding their expectations. Your host is available 24/7, 365 days a year, ready to assist with anything you need—from providing extra towels to recommending the perfect restaurant.

*The Florida Keys even though surrounded by water is not known for its beaches. Our unique property does have a natural setting beach, meaning that seaweed and debris from the ocean does make its way to our shoreline. Specifically in the hotter months, extreme amounts of seaweed will accumulate on our shoreline and beyond.

A vehicle is required to get around

***Self check in

*Upon check in, a refundable damage deposit will be collected*

****During Hotter Months, extreme amounts of seaweed mixed with debris from the ocean will accumulate on our beach and beyond (Please contact us if needed to get up the moment seaweed condition)

****Our property is located on what is considered to be a turtle nesting beach. We must follow environmental guidelines when trying to remove any type of seaweed that washes ashore.

****Its is strongly recommended to bring mosquito and no see um repellent (No-see-ums are tiny flying insects that are incredibly difficult to spot. Also known as biting midges, punkies, sand flies or biting gnats, these flying insects are small enough to fit through the mesh screens of windows and doors. They are also easy to overlook when they swarm around you or land on your skin.
No-see-um bites are painful and itchy.

**** Must be at least 30 years old to book.

**** We are committed to the conservation and protection of all our resources. We are constantly looking for ways to improve our efforts. Water is one of our most important life resources. You can protect and conserve this vital source by turning the faucet off while brushing your teeth or shaving, not using the toilet as a trash receptacle, being sure faucets are turned completely off, report leaky faucets and re using towels.

*In the event of a cancellation, guest will be refunded what is applicable per the cancellation guidelines minus the credit card transaction fee
**MUST BE AT LEAST 30 YEARS OF AGE TO BOOK THIS HOUSE**

**No day visitors allowed

** Max 6 guests allowed per booking

**Pets must be on a leash when outside. Pets are not allowed in the pool area.

** NO SMOKING

**NO FRYING FISH, TURKEYS OR ANYTHING ON THE DECK

**Quiet time 10:00PM - 7:00AM

**Protective footwear suggested while in the water

**Check out 10:00AM (Check out strictly enforced additional $50.00 will be charged for every hour up to four hours, after four hours a full day charge will be accessed)

**$250.00 fee per dog per stay, smaller non aggressive breeds only ( Failure to advice on pet in the house will cause an additional cleaning fee)

**All dirty dishes, pots, pans, cups, glasses, silverware must be left in the dishwasher

**All dirty towels to be left in a in a corner of the bathroom floor

**We ask all guest to please wipe their feet prior to entering the house in order to keep the sand to a minimum inside the house

**Leaving the house with excess trash and in a unsanitary condition would be subject to an additional cleaning fee of up to $300.00

We love our guests to enjoy our beach house. Please bear in mind that our property is situated on the Ocean and from time to time we get items and seaweed that wash a shore.

**Depending on the season and weather, seaweed could accumulate in our beach.

We are committed to the conservation and protection of all our resources. We are constantly looking for ways to improve our efforts. Water is one of our most important life resources. You can protect and conserve this vital source by turning the faucet off while brushing your teeth or shaving, not using the toilet as a trash receptacle, being sure faucets are turned completely off, report leaky faucets and re using towels.

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

Feature Features

  • PETS

    2 Total (up To 50 Lbs Per Pet) Pet Friendly Welcoming Dogs Only
  • BEACH

    Near The Beach
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Fire Extinguisher Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    3 Bedrooms Bed Sheets Provided
  • GENERAL

    Unit Size: 1765 Sq Ft (164 Sq M)
  • KITCHEN

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

    Laundry Facilities Near Laundromat Washing Machine And Dryer
  • PARKING

    Car Not Required Onsite Parking
  • INTERNET

    WiFi Available
  • OUTDOORS

    Balcony Barbecue Grill Garden
  • BATHROOMS

    2 Bathrooms Bathtub Hair Dryer
  • LANGS SPOKEN

    English Spanish
  • THINGS TO DO

    Boat On Site Fitness Center Kayak On Site Paddleboard On Site
  • ENTERTAINMENT

    TV
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Travel Crib
  • LOCATION HIGHLIGHTS

    On The Waterfront
  • 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 : 6

Map Map

School District Rates & Availability

Review Review

  • David J.

    Submitted Sep 6, 2025

    Stayed Aug 22, 2025

    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.

  • Jonathan L.

    Submitted Apr 29, 2025

    Stayed Apr 18, 2025

    Perfect location way off the path if you like seclusion.

  • Brian K.

    Submitted Dec 8, 2024

    Stayed Nov 23, 2024

    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

  • Zita D.

    Submitted Oct 1, 2024

    Stayed Sep 11, 2024

    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!!

  • William O.

    Submitted Sep 26, 2024

    Stayed Sep 19, 2024

    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

  • Brenda S.

    Submitted Mar 30, 2023

    Stayed Mar 27, 2023

    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.

  • Kim R.

    Submitted Mar 10, 2023

    Stayed Mar 5, 2023

    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.

  • Thomas G.

    Submitted Feb 12, 2023

    Stayed Feb 9, 2023

    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.

Your dates are Available!

Total

Includes taxes and fees
$1,133+
View details