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!
Add dates for prices
Amenities
Pool
Hot tub
Kitchen
Washing machine
Dryer
Pet-friendly
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Charge may apply
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Smoking
Smoking is not permitted
Guest booking the home must be at least 25 years old.
No parties.
No smoking.
Pool can be heated for $50 per day. Please let us know at least 3...
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
On-site 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 that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
About the area
Key West
Old Town Key West, a neighbourhood in Key West, is home to this holiday home. Ernest Hemingway Home and Museum and Southernmost Point are notable landmarks, and the area's natural beauty can be seen at Fort Zachary Taylor Historic State Park and Florida Keys Beaches. MLK Community Pool & Community Center and Key West Butterfly and Nature Conservatory are also worth visiting.
Ernest Hemingway Home and Museum - 1 min walk - 0.2 km
Key West Lighthouse and Keeper's Quarters Museum - 1 min walk - 0.2 km
South Beach - 8 min walk - 0.7 km
Southernmost Point - 9 min walk - 0.8 km
Getting around
Key West, FL (EYW-Key West Intl.) - 9 min drive
Restaurants
801 Bourbon Bar - 4 min walk
Circle K - 2 min walk
Old Town Tavern - 2 min walk
Rams Head Southernmost - 4 min walk
Moondog Cafe & Bakery - 2 min walk
Frequently asked questions
Does Big Groups Welcome • Pool • Near Duval have a pool?
Yes, this property has a pool.
How much does it cost to stay at Big Groups Welcome • Pool • Near Duval?
As of 10 April 2026, prices found for a 1-night stay for 2 adults at Big Groups Welcome • Pool • Near Duval on 3 August 2026 start from NZ$5,395, 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.
Is Big Groups Welcome • Pool • Near Duval pet-friendly?
Yes, this property allows cats and dogs (limit 2 total) with a maximum weight of up to 23 kg per pet.
How much is parking at Big Groups Welcome • Pool • Near Duval?
On-site parking is available at the property.
What time is check-in at Big Groups Welcome • Pool • Near Duval?
Check-in begins at 4:00 PM.
What time is check-out at Big Groups Welcome • Pool • Near Duval?
Checkout is at 11:00 AM.
Where is Big Groups Welcome • Pool • Near Duval located?
Located in Old Town Key West, this holiday home is steps away 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.
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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!
Maura R.
Stayed 3 nights in Jul 2022
Verified
10/10 Excellent
Paula S.
7 September 2025
Paula S.
Stayed 8 nights in Jul 2025
About the host
Hosted by Corey E Breingan
Hello! I'm Corey. My husband Jon and I love to travel, eat at new places, and spend way to much time at the hardware store. When we aren't traveling or working we enjoy renovating houses and spending time with family. Jon enjoys riding his tractor and hanging out with his super cool wife. Corey could live on salsa and is going to start exercising again next Monday. :)
We are passionate about offering 5 STAR places where friends and families can make memories and have adventures.
Why they chose this property
These homes are located in the HEART of Key West. You can see the lighthouse and Hemingway's house from the sun decks. You can't get any closer to Duval than these places.
What makes this property unique
PARTY headquarters!! If you are planning a bachelor or bachelorette party, you have found the place. These TWO homes can sleep up to 16! Plus, you are a 20 second walk to Duval.
Languages:
English
Premier Host
They consistently provide great experiences for their guests