Entire home

The Hemingway - Beach Houses Key West

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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, coffee table, and ottoman, a kitchen in the background, and a large window providing natural light.
A spacious living room with a large sofa, a coffee table, and a dining area with striped chairs.
A covered outdoor seating area with wooden furniture and a thatched roof.
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
Located at the waterfront, this 3-bedroom vacation home accommodates 6 guests and features 2 bathrooms. Enjoy paddleboarding and beach access while staying in this pet-friendly property. Explore nearby attractions like the Florida Keys Beaches and Sugarloaf Beach for additional outdoor activities.

Highlights

  • 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
3 bedrooms2 bathroomsSleeps 6

Popular amenities

  • Onsite parking available
  • Dog-friendly
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Barbecue grill

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

About this property

The Hemingway - Beach Houses Key West

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. Enjoy you 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.
Our prices include all fees. No hidden fees.

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House Rules

Check in after 4:00 PM
Minimum age to rent: 18
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

Events allowed: family gatherings, birthday parties, weddings
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Pets

Pets allowed: dogs less than 23 kg per pet (limit 2 pets total)
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Smoking

Smoking is not permitted
**MUST BE AT LEAST 30 YEARS OF AGE TO BOOK THIS HOUSE** **No day visitors allowed ** Max 6 guests allowed per booking

Important information

You need to know

Property # 2757806vb
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.
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
Parties and events (including family gatherings, birthday parties and weddings) are allowed on site. Maximum attendees: 29
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
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

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.
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
  • ‪Square Grouper Bar and Grill - ‬19 min drive
  • ‪Geiger Key Marina - ‬22 min drive
  • ‪South Of The Seven - ‬11 min drive
  • ‪My New Joint - ‬19 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 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).

About the host

Hosted by Cadmier Rodriguez

Host profile image
Island Time Vacation Rental is your local vacation rental management company in the Florida Keys. Vacation home owners trust us with their property and trust we deliver world class service throughout your entire vacation. Professional housekeepers clean and stock each home, and our customer service is available around the clock—with a local property manager ready to show up and help out. We offer the best of both worlds: you can enjoy a priceless vacation experience in a unique private property, without compromising on service and convenience. Check out our listings, and get in touch should you have any questions. Your vacation is our priority, and we'd be honored to help you plan your perfect getaway.
Book your Florida Keys vacation today !!!

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English, Spanish

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