Entire home

Steps to Duval-Pool-Hot tub- Sleeps 16- BIG groups

Overlooking a tranquil marina with piers and docks, surrounded by sandy beaches and lush greenery.

Enjoy cooking in this fully equipped kitchen with an oven, microwave, and stainless steel refrigerator.

Relax by the serene pool surrounded by a wooden deck and comfortable lounge chairs.

Relax on the covered porch with comfortable wicker chairs and enjoy the view.

Kitchen equipped with refrigerator, microwave, and oven, featuring a wooden floor and ample countertop space.

Exceptional

Entire home

5 bedrooms4 bathroomsSleeps 162100 sq ft

Popular amenities

Dryer
Washer
Pool
Kitchen
Pet friendly

Add dates for prices

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Steps to Duval-Pool-Hot tub- Sleeps 16- BIG groups

Summary:
Perfect for bachelor and bachelorette parties, these 2 cottages that are quintessential Key West. Some of those most photographed homes, these sleep 16 guests comfortably. Enjoy life just a 30 second walk to Duval street with 2 kitchens, 2 living spaces, 5 bedrooms, 3.5 bathrooms, rooftop sundecks, historic Conch front porches, private laundry, parking, and a large connected back deck with a hot tub and pool.

The Space:
Welcome to the "Almost Southernmost Retreat" in Key West, where the sun is shining, and the fun never stops! This property is the perfect getaway for groups of guys or gals looking for an exciting vacation. With stunning views of Hemingway's house and the lighthouse from your rooftop deck, you'll feel like you're living in paradise.

This place is not only the perfect Key West getaway for groups of friends but is also an ideal spot for unforgettable bachelor and bachelorette parties. Whether you're looking to relax by the pool during the day or hit the town at night, our retreat is the perfect home base for your bachelor or bachelorette party. Don't miss out on the opportunity to create lasting memories with your best friends in one of the most beautiful places in the world.

Located just steps away from Duval street, our retreat is in the heart of Key West's best restaurants, shops, and attractions. Or if you prefer to take it easy, kick back and soak up the island vibes with your private 8-man hot tub, pool, and sunbathing decks.

Our retreat is made up of two cozy cottages connected by a back porch. Let's take a closer look:

House number ONE...
This spacious home boasts three bedrooms, two and a half bathrooms, a pool, a fully equipped kitchen, a cozy outdoor dining area, a living room with plenty of seating, a private sundeck, private laundry, and a front porch perfect for people-watching.

The recently updated kitchen is fully stocked with everything you need to cook up a storm, and the bar that seats eight makes it easy to entertain your crew. An outdoor table is perfect for sharing meals while enjoying the sunshine.

The living room offers ample seating for your entire party, and a queen sleeper sofa is available for extra guests. The downstairs bedroom is complete with a king-size bed and an en-suite bathroom, while the upstairs bedrooms include a queen bed and two queen beds with access to the sundeck.

House number TWO...
This cozy Key West cottage is equipped with two bedrooms, one bathroom, a fully outfitted kitchen, a cozy outdoor dining area, a living room with tons of seating, another private sundeck, a second laundry location, and a front porch perfect for people-watching.

The living room offers plenty of space for your entire group to relax, and a queen sleeper sofa is available for extra guests. The downstairs bedroom has a comfortable queen-size bed and an adjacent bathroom, while the upstairs bedroom features a king-size bed, plenty of storage, and access to the sundeck.

That's two charming Key West cottages with a total of five bedrooms, three and a half baths, private parking, a hot tub, and a pool! Our retreat can comfortably accommodate up to 16 people, making it the perfect choice for your next group getaway.

This place is not only the perfect Key West getaway for groups of friends but is also an ideal spot for unforgettable bachelor and bachelorette parties. Whether you're looking to relax by the pool during the day or hit the town at night, our retreat is the perfect home base for your bachelor or bachelorette party. You will create lasting memories with your best friends in one of the most beautiful places in the world.

Don't wait any longer to book your stay at our "Almost Southernmost Retreat" in Key West. With its unbeatable location and endless amenities, this property is sure to book up fast. We can't wait to welcome you to paradise!

Crawling distance from Duval
300 feet to the Key West Lighthouse
500 feet to Hemingway Home
.4 miles to the Southernmost Point
.4 miles to the Key West Butterfly and Nature Conservation
.7 miles to Sloppy Joe's
.9 miles to Mallory Square
3.7 miles to the airport

Guest Access:
Guests will have access to the entire property.

The Neighborhood:
These quintessential Key West cottages are located in the heart of Old Town just half a block off Duval. You are in walking distance to all of what Key West has to offer...in fact, you are Hemingway's neighbor! Bars, restaurants, shops, and historic sites surround you. You can even peek the lighthouse from your second story sun deck.

Getting Around:
With a central location like this you can walk, bike, scooter, drive, or Uber to all of what Key West has to offer.

Other Things to Note:
Pool can be heated during the winter for $40 per night. Please let us know at least 3 days in advanced.

This unit is pet-friendly. 40lb maximum per pet. $40/night per pet 2 pet max. Please let us know if you plan on bringing your pet. Check the rules for more details.

No smoking inside the home.

Sorry, no early check-in. We need time to make it perfect for your stay!

Property manager

Corey E Breingan

Languages

English

Property amenities

Pool/Spa

Communal pool
Hot tub
Private pool

Internet

Available in the house: WiFi

Parking and transportation

Parking on site

Kitchen

Coffee/tea maker
Cookware, dishware, and utensils
Dishwasher
Microwave
Oven
Refrigerator
Stovetop
Toaster

Bedrooms

5 bedrooms
Bedsheets provided
Sofa bed

Bathroom

3.5 bathrooms
Bathtub
Hair dryer
Shower
Towels provided

Entertainment

Outdoor areas

Balcony
Garden

Laundry

Laundry facilities
Washing machine

Comfort

Air conditioning
Heating

Pets

Pet friendly
Welcoming cats and dogs only
2 pets total (up to 50 lbs per pet)

Suitability/Accessibility

Smoking not allowed

Services and conveniences

Iron/ironing board

Safety features

Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
Smoke detector (host has indicated there is a smoke detector on the property)
First aid kit
Fire extinguisher

General

Garden
Unit size: 2,100 square feet

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Policies

Check-in

Check-in time starts at 4:00 PM

Minimum check-in age: 25

Check-out

Check-out before 11:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Pets

Pets allowed

Service animals are welcome, and are exempt from fees

Welcoming dogs and cats only

2 total (up to 50 lbs per pet)

Note from host: Charge may apply

Children and extra beds

Children are welcome

Important information

You need to know

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

Onsite parties or group events are strictly prohibited

Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip

Host has indicated there is a smoke detector on the property

Safety features at this property include a fire extinguisher and a first aid kit

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

Property is also known as

646ce406ffda59004a524604

About the neighborhood

Key West, FL

What's nearby

Duval Street - 1 min walk - 0.0 miles
Ernest Hemingway Home and Museum - 1 min walk - 0.1 miles
South Beach - 8 min walk - 0.4 miles
Southernmost Point - 9 min walk - 0.5 miles
Mallory Square - 18 min walk - 1.0 mile

Getting around

Key West Intl. Airport (EYW) - 9 min drive

Restaurants

‪Blue Heaven - ‬5 min walk
‪Bourbon Street Pub - ‬5 min walk
‪801 Bourbon Bar - ‬4 min walk
‪Moondog Cafe & Bakery - ‬2 min walk
‪Old Town Tavern Key West - ‬2 min walk

Frequently asked questions

Does Steps to Duval-Pool-Hot tub- Sleeps 16- BIG groups have a pool?

Yes, this property has a pool.

How much does it cost to stay at Steps to Duval-Pool-Hot tub- Sleeps 16- BIG groups?

As of Jul 10, 2025, prices found for a 1-night stay for 2 adults at Steps to Duval-Pool-Hot tub- Sleeps 16- BIG groups on Jul 14, 2025 start from $1,412.0, excluding 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.

Is Steps to Duval-Pool-Hot tub- Sleeps 16- BIG groups pet-friendly?

Yes, this property allows cats and dogs (limit 2 total) with a maximum weight of up to 50 lbs per pet.

What time is check-in at Steps to Duval-Pool-Hot tub- Sleeps 16- BIG groups?

Check-in begins at 4:00 PM.

What time is check-out at Steps to Duval-Pool-Hot tub- Sleeps 16- BIG groups?

Check-out is at 11:00 AM.

Where is Steps to Duval-Pool-Hot tub- Sleeps 16- BIG groups located?

Located in Old Town Key West, this vacation home is steps from Key West Lighthouse and Keeper's Quarters Museum, Duval Street, and Ernest Hemingway Home and Museum. Florida Keys Beaches and Southernmost Point are also within 10 minutes.

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Steps to Duval-Pool-Hot tub- Sleeps 16- BIG groups Reviews

Exceptional

10/10

Cleanliness

10/10 Excellent

Maura R.

Aug 3, 2022

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

A Wonderful Stay

I stayed at the cottages with 10 of my friends for my bachelorette party. We had such a great stay! The location was close to most places we wanted to visit, including the Hemingway House, Historic Lighthouse, Duval Street, and charming restaurants and shops. The cottages themselves were adorable and fit 11 adults comfortably. We really enjoyed the pool and hot tub. As a history lover, I was happy to know the properties are on the National Historic Register. Corey was an amazing hostess. She even left us a charcuterie board and champagne in the fridge, which we enjoyed on our first night. She also was very responsive to messages, including when we needed reassurance that we locked one of the front doors. Definitely a 5 star experience all around!

Stayed 3 nights in Jul 2022