City center stay.Your stay at this Key West Historic District vacation home places you within 2 miles (3 km) of Duval Street and Florida Keys Beaches. Southernmost Point and Mallory Square are also within 2 miles (3 km).
Ernest Hemingway Home and Museum - 20 min walk - 1.1 miles
Southernmost Point - 7 min drive - 2.5 miles
Getting around
Key West Intl. Airport (EYW) - 6 min drive
Restaurants
Dions Truman & White - 6 min walk
Circle K - 12 min walk
Sandy's Café - 9 min walk
Square Grouper Key West - 14 min walk
Moose Lodge - 3 min walk
About this property
Entire place
You'll have the entire home to yourself and will only share it with other guests in your party.
BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL
Welcome to Bottom’s Up Bungalow — Your Private Tropical Escape in Old Town Key West
Step into a world of comfort and island charm at Bottom’s Up Bungalow, perfectly situated in the serene Meadows subdivision, just minutes from the vibrant heart of Key West. This immaculate 2-bedroom, 2-bathroom single-family home combines classic Florida bungalow appeal with modern amenities to create an inviting retreat that has earned over 100 glowing five-star reviews from delighted guests.
Home Highlights & Features
Spacious & Inviting Living Room Bright and airy, the living room is designed for relaxation and socializing. Sink into the plush sectional sofa that easily converts into a sleeper for additional guests, or unwind in the comfortable sitting chair while enjoying your favorite shows on the large flatscreen TV. Natural light floods the room through large windows, creating a warm and welcoming atmosphere.
Elegant Formal Dining Just off the living room, the formal dining area comfortably seats four — perfect for intimate dinners or leisurely breakfasts. The classic design complements the polished hardwood floors that flow throughout the home.
Chef’s Dream Kitchen The heart of the home is a spacious, open-concept kitchen featuring generous counter space, high-quality appliances, and all the essential cookware and utensils to prepare anything from casual snacks to gourmet meals. A breakfast bar with stools offers a casual dining option, while the adjacent informal dining nook provides a cozy spot for family meals. Double French doors open onto the poolside patio, inviting fresh air and natural beauty inside.
Tranquil Primary Suite The primary bedroom is a serene sanctuary, outfitted with a luxurious king-size bed, a sturdy chest of drawers, and a large closet with a full-size washer and dryer tucked inside for your convenience. Step through elegant French doors to the pool and garden, perfect for early morning coffee or evening relaxation under the stars.
Spa-Like Primary Bathroom Located just outside the primary suite, the hallway bathroom boasts a spacious custom shower with sleek tilework, a large vanity with ample storage, and a linen closet to keep all your essentials neatly organized.
Flexible Guest Bedroom The second bedroom features two twin beds that can easily be converted into a king bed upon request, ideal for couples or friends traveling together. This room also includes a chest of drawers, a roomy closet, and a private en-suite bathroom complete with a shower, vanity, and toilet — providing comfort and privacy for your guests.
Resort-Style Pool & Outdoor Living Step outside to your private tropical paradise. The oversized pool, heated from December through May, is perfect for a refreshing swim any time of year. The attached whirlpool spa (note: not a hot tub) offers soothing bubbles to relax tired muscles. Surrounding the pool is an elevated deck with two sun loungers — ideal for soaking up the Florida sun. Enjoy meals or drinks at the outdoor dining table shaded by an umbrella, or retreat to the custom-built gazebo featuring a wet bar and bespoke seating, making it the ultimate space for entertaining or unwinding.
Lush Tropical Gardens & Privacy The beautifully landscaped gardens are enhanced by tasteful lighting and privacy fencing, creating a secluded oasis that feels worlds away from the bustle of downtown Key West. The tranquil greenery invites you to savor quiet moments with family and friends in any season.
Parking & Convenience One assigned parking space is available in the driveway for your ease and security. Additional vehicles can be parked roadside, subject to availability, allowing you to bring along extra guests or rental cars with peace of mind.
Prime Location Near the Best of Key West Tucked away on a quiet one-way street within a peaceful community, Bottom’s Up Bungalow offers the perfect balance of tranquility and accessibility. You’re less than one mile from the excitement of Duval Street, famous beaches, and the marina. Enjoy the vibrant nightlife, eclectic dining, and unique shops of Old Town, then retreat to your calm, private sanctuary at day’s end.
Why Choose Bottom’s Up Bungalow?
Whether you’re here for a romantic getaway, a family vacation, or a fun trip with friends, Bottom’s Up Bungalow provides the perfect home base. With its spacious layout, thoughtful amenities, lush outdoor spaces, and unbeatable location, this bungalow promises a memorable Key West experience filled with relaxation, adventure, and island charm.
We invite you to be our guest and experience the magic of Bottom’s Up Bungalow on your next trip to Key West!
Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
Smoke detector (host has indicated there is a smoke detector on the property)
First aid kit
Fire extinguisher
Deadbolt lock
General
At least 80% lighting from LEDs
Bicycle parking
Bicycle storage
Garden
Local artist showcase
Locally-owned and organized tours and activities
Recycling
Unit size: 1,224 square feet
Water-efficient toilets
Policies
Check-in
Check-in time starts at 4:00 PM
Minimum check-in age: 28
Check-out
Check-out before 10:00 AM
Special check-in instructions
You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools
Pets
No pets allowed
Children and extra beds
Children are welcome.
Events
No events allowed
Smoking
Smoking is not permitted
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 indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock
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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector, a first aid kit, and a deadbolt lock in each accommodation.
Property is also known as
Bottom's Up Bungalow House Key West
Bottom's Up Bungalow Key West
Bottom's Up Bungalow Key West
Bottom's Up Bungalow Private vacation home
Bottom's Up Bungalow Private vacation home Key West
Frequently asked questions
How close is BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL to the airport?
This vacation home is 3.1 mi (6-min drive) away from the Key West Intl. Airport (EYW) airport, the closest popular airport to the property.
How much does it cost to stay at BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL?
As of May 14, 2026, prices found for a 1-night stay for 2 adults at BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL on Jun 3, 2026 start from $1,437, 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.
Does BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL have an airport shuttle?
Airport shuttle services are not available at this vacation home.
How close is BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL to the beach?
This vacation home is 1.1 mi (3-min drive) from Florida Keys Beaches and 1.3 mi (9-min drive) from South Beach. Don't forget your sunscreen!
Does BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL offer free breakfast?
This vacation home does not offer free breakfast.
Is there a casino at BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL?
No, there is no casino at this vacation home.
What time is check-in at BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL?
Check-in begins at 4:00 PM.
Is there free parking at BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL?
Free parking is not available at this vacation home.
Does BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL have a pool?
This vacation home features an outdoor pool.
Does BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL have a spa?
There are no spa services available at this vacation home.
How close is BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL to downtown Key West?
This vacation home is 0.7 mi away from Key West.
BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL Reviews
Reviews
10
Exceptional
All reviews shown are from real guest experiences. Only travelers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
Rating 10 - Excellent. 118 out of 123 reviews
10 - Excellent
118
Rating 8 - Good. 4 out of 123 reviews
8 - Good
4
Rating 6 - Okay. 1 out of 123 reviews
6 - Okay
1
Rating 4 - Poor. 0 out of 123 reviews
4 - Poor
0
Rating 2 - Terrible. 0 out of 123 reviews
2 - Terrible
0
10/10
Cleanliness
Reviews
10/10 Excellent
Samuel S.
Apr 25, 2026
Samuel S.
Stayed 3 nights in Apr 2026
10/10 Excellent
Anna M.
Apr 12, 2026
Liked: Cleanliness
My family and I had a wonderful time at the cottage. Beautifully decorated, extremely clean, fully stocked kitchen with everything you need for cooking meals. The beds were all so comfortable. With one exception, we felt a little warm at night in the master bedroom. We noticed the thermostat was set at a certain temperature and were not able to adjust it to a temperature that was more comfortable for us. The cottage itself was in a prime location. Walkable around town. We did UBER when we went to the beach and to farther locations.The main draw was the pool at the cottage. The pool was clean, comfortable temperature and size for our family. We enjoyed having our cups of coffee in the mornings, afternoon and evening cocktails poolside. Beautiful, quiet and relaxing atmosphere. We highly recommend staying at Bottoms Up! We hope to be back again soon!
Anna M.
Stayed 5 nights in Apr 2026
6/10 Okay
Emily Ann J.
Mar 13, 2026
Liked: Cleanliness
Rented this house very specifically for the pool and “hot tub”… Hot tub being key and found out only after check in that the pool and hot tub are same temp so if pool isn’t heated you not only have no hot tub but it’s truly not a hot tub at all.
Emily Ann J.
Stayed 5 nights in Jan 2026
10/10 Excellent
Terra M., Lithia, FL
Mar 2, 2026
Liked: Cleanliness
Home was clean and exactly as described.
Terra M.
Stayed 2 nights in Jan 2026
10/10 Excellent
Edward M.
Mar 1, 2026
Liked: Cleanliness
Great little house for a family
Edward M.
Stayed 3 nights in Feb 2026
10/10 Excellent
Amy D.
Feb 28, 2026
Liked: Cleanliness
Truly EXCELLENT property! Exactly as pictured in the photos and as described by other reviews. Beautiful pool and patio area…perfect for morning coffee and relaxing evenings.VERY clean, and great amenities. The owners thought of everything, and provided plenty of “starter” items for our use.A 5-7 minute bike ride to everything on Key West, and in a very quiet, safe neighborhood.Temps were down into the 40s for two days during our stay….and plenty of extra blankets in the home, and the furnace worked like a charm! It made for a cozy couple of island days for some Midwesterners…we felt right at home!This is a place I would definitely return to stay at, and would highly recommend to family and friends. 10 out of 10!
Amy D.
Stayed 7 nights in Feb 2026
8/10 Good
Brooke B.
Feb 17, 2026
Liked: Cleanliness
Perfect location. Nice house. Pool heater broke, but they did their best to make it right and fixed it, but then it broke again. If it were hot out, it wouldn’t have mattered.
Brooke B.
Stayed 13 nights in Feb 2026
10/10 Excellent
Lauren B., Gainesville, FL
Jan 19, 2026
Liked: Cleanliness
The house is the perfect size for a small party of people or family, its wonderfully set up, and the location is ideal - very walkable to old town and duval, but far enough to be quiet. Would highly recommend.
Lauren B.
Stayed 5 nights in Jan 2026
10/10 Excellent
Marc E.
Jan 8, 2026
Liked: Cleanliness
Good location, very clean and comfortable stay in Key West. We enjoyed the heated pool and the parking spot! Key west was very busy this week but we enjoyed being able to relax here.
Marc E.
Stayed 5 nights in Dec 2025
10/10 Excellent
David L.
Oct 16, 2025
Liked: Cleanliness
Really great location, friendly accommodating hosts. Just lovely.
David L.
Stayed 4 nights in Jun 2025
8/10 Good
Destiny G.
Oct 11, 2025
Liked: Cleanliness
We had a great time at this house. We do wish that the pool had more sunlight, there were over grown trees that needed to be cut. All other aspect of the house fit our needs. I would recommend this house to others.
Destiny G.
Stayed 7 nights in Oct 2025
10/10 Excellent
Jill B.
Sep 22, 2025
Liked: Cleanliness
Jill B.
Stayed 3 nights in Aug 2025
10/10 Excellent
Jay W.
Sep 17, 2025
Liked: Cleanliness
We had a great experience and thought the pictures did not do this home justice. It truly is this nicest place we have stayed in, great feel and very well decorated.
Jay W.
Stayed 5 nights in Sep 2025
10/10 Excellent
Brian M.
Aug 13, 2025
Liked: Cleanliness
Everything was as advertised! Pool was great to come back to after spending days roaming the streets of Key West. Facilities (kitchen, bathrooms, bedrooms) were all clean and comfortable. Would 100% recommend to anyone wishing to stay.
Brian M.
Stayed 4 nights in Jul 2025
10/10 Excellent
Fritz R.
Jul 21, 2025
Liked: Cleanliness
Bottoms Up is a great place to stay. It has everything that a person could need on a vacation. A great location (and a driveway parking spot), fully equipped kitchen, very efficient A/C, TV in every room, ceiling fans in every room (thank you), and a fabulous pool and deck where we relaxed at the end of each day. I've stayed at numerous rental homes and this one ranks on top of all of them. Great place - highly recommend.
Fritz R.
Stayed 4 nights in Jul 2025
10/10 Excellent
Verified traveler
Jul 16, 2025
Liked: Cleanliness
Absolutely Perfect!
We had a mother/ daughter/ Grandmother week together in Key West, and we picked the most perfect house to stay in! Every single thing about the house, location, and the host was perfect! Thank you
Verified traveler
Stayed 7 nights in Jun 2025
10/10 Excellent
Michelle B.
Apr 21, 2025
Liked: Cleanliness
Fantastic!
Sometimes the ad and the pictures are just a bit of a stretch, but not this place! It’s perfect. The location is awesome, the neighborhood is great, the house is super. We had the best stay!
Michelle B.
Stayed 7 nights in Apr 2025
10/10 Excellent
Sarah D., Richmond
Apr 15, 2025
Liked: Cleanliness
Convenient, Relaxing, & Fun
Great place to stay for our spring trip as a family of 3.
Sarah D.
Stayed 7 nights in Mar 2025
10/10 Excellent
Jason R.
Mar 17, 2025
Liked: Cleanliness
Quiet spot with easy access to the action
My wife, adult daughter and I recently stayed here for a week. Communication before arrive was good and check in easy. It’s a lovely 2 bedroom home with great outdoor space. The beds and furniture were comfortable and the place was clean. The kitchen is well stocked with cooking equipment. There is a smart TV in the living room to stream shows if you need some late night relaxation. There is a nice sitting area and table outside. We are breakfast there every morning. The pool temperature was good. There is a “spa tub” but note that it isn’t a “hot tub”. The temperature is the same as the pool. The neighborhood is quiet. We rented bikes for the week and it was very easy to get all around the island that way. Duvall Street is only about a 7 minute bike ride from the house. I would highly recommend getting bikes. Eaton Bikes is only a 15 minute walk from the house. They will pick up the bikes at the house at the end of the week. In summary we had a great week and would absolutely recommend this house.
Jason R.
Stayed 7 nights in Mar 2025
10/10 Excellent
Susan S.
Mar 3, 2025
Liked: Cleanliness
Great location in Old Town
The house was immaculate, quiet, very comfortable- Highly recommend it
Susan S.
Stayed 4 nights in Feb 2025
10/10 Excellent
Jennifer P.
Feb 16, 2025
Liked: Cleanliness
Winter getaway
It was beautifully decorated. Very comfortable and home feel.
Jennifer P.
Stayed 7 nights in Feb 2025
10/10 Excellent
Theresa D.
Feb 2, 2025
Liked: Cleanliness
Bottoms Up in January
Very nice house in a quiet neighborhood. Private driveway was perfect since we rented a golf cart while in Key West. Pool is heated so we could use it even during cool days. A railing on the pool stairs would be nice.
Theresa D.
Stayed 8 nights in Jan 2025
10/10 Excellent
Katherine A., Massachusetts
Jan 20, 2025
Liked: Cleanliness
Nice private oasis
We had a great stay at this very nice comfortable home. The pool area is very relaxing and private. The heated pool was a definite plus. The beds and the linens were all very comfortable especially the master bedroom. Would definitely rent this property again. ( just wish that the weather was warmer)May start renting in March instead of January.The location of this home is perfect. Close to Old Town, and good restaurants.
Katherine A.
Stayed 11 nights in Dec 2024
10/10 Excellent
Ann L.
Jan 20, 2025
Liked: Cleanliness
Key West Holiday
Fabulous
Ann L.
Stayed 5 nights in Dec 2024
10/10 Excellent
Jim B.
Jan 19, 2025
Liked: Cleanliness
Great property
Great property Great location. House is very well laid out. Pool area is a tropical oasis. Highly recommend!