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BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL

Holiday home with private pool, near Duval Street

Photo gallery for BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL

Pool
Living area
Private kitchen
Room
Dining

Reviews

10 out of 10
Exceptional
2 bedrooms2 bathroomsSleeps 6113.7 sq m

Popular amenities

  • Hot tub
  • Dryer
  • Parking available
  • Washer
  • Fireplace

Explore the area

View map
Key West, FL
  • Place, Duval Street
    ‪17 min walk‬
  • Place, Southernmost Point
    ‪4 min drive‬
  • Place, Mallory Square
    ‪4 min drive‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪7 min drive‬

Rooms & beds

2 bedrooms (sleeps 6)

Bedroom 2

2 Single Beds

Living Room

1 Double Futon

Master Bedroom

1 King Bed

2 bathrooms

Bathroom 1

Shower only

Bathroom 2

Shower only

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony
Outdoor play area
Garden
Dining area

About this property

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!

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Amenities

Pool
Hot tub
Kitchen
Washing machine
Dryer
Free WiFi

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House Rules

Check in after 4:00 PM
Minimum age to rent: 28
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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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
On-site parties or group events are strictly prohibited
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, a first aid kit and a deadlock

About the area

Key West

Located near the beach, this holiday home is in Key West Historic District, a neighbourhood in Key West. 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. The Kite House and Sails To Rails Museum at Flagler Station are also worth visiting. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Map
Key West, FL

What's nearby

  • Duval Street - 17 min walk - 1.4 km
  • South Beach - 19 min walk - 1.6 km
  • Southernmost Point - 4 min drive - 1.8 km
  • Mallory Square - 4 min drive - 2.0 km
  • Smathers Beach - 4 min drive - 2.4 km

Getting around

  • Key West, FL (EYW-Key West Intl.) - 6 min drive

Restaurants

  • ‪Sandy's Cafe - ‬9 min walk
  • ‪Dairy Queen - ‬10 min walk
  • ‪The Best Coffee In Town - ‬10 min walk
  • ‪Dions Truman & White - ‬6 min walk
  • ‪Mangia Mangia - ‬9 min walk

Frequently asked questions

Does BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL have a pool?

Yes, this property has a pool.

Is BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL pet-friendly?

No, pets are not allowed at this property.

What time is check-in at BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL?

Check-in begins at 4:00 PM.

What time is check-out at BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL?

Checkout is at 10:00 AM.

Where is BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL located?

Located in Key West Historic District, this holiday home is within 1 mile (2 km) of The Unitarian Universalist Fellowship of Key West, Duval Street and Ernest Hemingway Home and Museum. Southernmost Point and Mallory Square are also within 2 miles (3 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 111 out of 114 reviews
Rating 8 - Good. 3 out of 114 reviews
Rating 6 - Okay. 0 out of 114 reviews
Rating 4 - Poor. 0 out of 114 reviews
Rating 2 - Terrible. 0 out of 114 reviews

10/10

Cleanliness

10/10

Check-in

9.8/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

David L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Really great location, friendly accommodating hosts. Just lovely.
Stayed 4 nights in Jun 2025

10/10 Excellent

Brian M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 4 nights in Jul 2025

10/10 Excellent

Ann L.

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

Key West Holiday

Fabulous
Stayed 5 nights in Dec 2024

10/10 Excellent

James D.

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

Key West 23'

Property is very nice. The neighborhood is quiet. We loved our stay. We will definitely be returning in the future.
Stayed 7 nights in Oct 2023

10/10 Excellent

Kevin and Tammie C.

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

Tropical oasis!

My husband and I had an amazing stay in this beautiful home. We spent our entire stay in the beautiful, private, tropical oasis pool and backyard. We had a wonderful relaxing week and will definitely return again in the future! The home was beautiful inside and out! Exactly as described and shown in the photos!
Stayed 7 nights in Aug 2023

10/10 Excellent

Brenda D.

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

Gorgeous Key West experience

We cannot say enough good things about our stay. After our many explorations about the island with sightseeing, water sports, shopping, and dining, each day we returned to the most lovely and relaxing home on the island. Some days we simply didn’t want to leave because the home was so inviting and totally relaxing. We thank the owner sincerely for sharing their home with us. We hope to return one day soon.
Stayed 9 nights in Aug 2023

10/10 Excellent

Paul G.

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

Ahhhh!

A wonderful place to unwind. Great pool, landscaping, and a traditional Key West location. Just a bike ride to anywhere in Old Town or Uber is there in 2-3 minutes
Stayed 17 nights in Oct 2019

10/10 Excellent

Jason C.

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

Amazing home in a perfect spot!

We have been to Key West many many times over the years, but the bottoms up bungalow that we stayed at this past week was perfect! The house was exactly what we wanted and the pictures that depicted the house were spot on. It was a quiet neighborhood and we rented a golf cart and was easy to get around to locations that we wanted to see on the island with family that had never been before. We would highly recommend this location and home again and again to friends and family. Thank you so much for hosting us. We enjoyed it immensely. Five stars!! We will be back!
Stayed 6 nights in Mar 2024

10/10 Excellent

Lindsey W.

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

Best 40th Bday - hands down!

Property was just as described and perfect for our Key West birthdaycation. The house was well equipped and stocked with anything you may need from toiletries to kitchenware. The backyard area was phenomenal in the evenings to come home and cool off in the pool after a hot day of running around and enjoying all the sights of the island. The king bed was so comfortable, I didn't even want for my own bed as I normally would when away from home! The location was perfect and central to just about anything you want to do on the island. There is a little convenience store (sunbeam) just a couple blocks from the house that has anything you might need to grab quickly. The only suggestion would be to bring water shoes when using the hall shower. The pebble floor is neat but a bit hard on the feet. Communication was fantastic and host was very responsive to all inquiries. House was clean and furniture comfortable. Overall this place was just wonderful and we would absolutely return!
Stayed 8 nights in Sep 2024

10/10 Excellent

Joni M.

Liked: Cleanliness, check-in, location
Disliked: Communication, listing accuracy

Wonderful place and location.

Cute bungalow located in the Meadows neighborhood. Pool was wonderful to have in the heat. The Management company was not responsive when inquiring about a listed grill and non-operative Keurig coffee maker. I called in the morning (10 am) regarding these issues. When I had not received a response by 2 PM, the same day, I called and the phone was answered immediately. The woman who answered, said she did not get the previous message and said the grill was not in the listing, which I texted her a photo shot of it. She did not address the Keurig and I did not bring it up because we went back-and-forth on several texts regarding the grill and I was certain she had not listened to the message. I called, around 11 am, two days later regarding renting a golf cart since the number that was listed in the book, went to pressing of numbers and no one answering the phone as well as the coffee maker. After not hearing back, I called back a few hours later. Again the phone was answered , the woman stated there was no message on the machine, she did offer an alternative number for golf carts and had a coffee machine delivered. My complaint is that earlier messages were not returned and she said were not on her machine, yet calling the same number in the mid afternoon we’re answered.
Stayed 7 nights in Jun 2023

8/10 Good

Destiny G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 7 nights in Oct 2025

10/10 Excellent

Jay W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 5 nights in Sep 2025

10/10 Excellent

Fritz R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 4 nights in Jul 2025

10/10 Excellent

Verified traveller

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

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
Stayed 7 nights in Jun 2025

10/10 Excellent

Michelle B.

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

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!
Stayed 7 nights in Apr 2025

10/10 Excellent

Sarah D.

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

Convenient, Relaxing, & Fun

Great place to stay for our spring trip as a family of 3.
Stayed 7 nights in Mar 2025

10/10 Excellent

Jason R.

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

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.
Stayed 7 nights in Mar 2025

10/10 Excellent

Susan S.

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

Great location in Old Town

The house was immaculate, quiet, very comfortable- Highly recommend it
Stayed 4 nights in Feb 2025

10/10 Excellent

Jennifer P.

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

Winter getaway

It was beautifully decorated. Very comfortable and home feel.
Stayed 7 nights in Feb 2025

10/10 Excellent

Theresa D.

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

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.
Stayed 8 nights in Jan 2025

10/10 Excellent

Katherine A.

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

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.
Stayed 11 nights in Dec 2024

10/10 Excellent

Jim B.

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

Great property

Great property Great location. House is very well laid out. Pool area is a tropical oasis. Highly recommend!
Stayed 3 nights in Jan 2025

10/10 Excellent

Kevin and Tammie C.

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

Best little getaway

This was our 2nd stay at Bottoms Up. We absolutely love this home. The pool is private and so relaxing. Love the tiki / lounge area to drink coffee in the mornings and just nap throughout the day. The only time we left the house was to drive around the island in the late evenings. We rarely left the pool. We will be back a 3rd , 4th etc., we just love this place !!! And, it’s quiet.
Stayed 8 nights in Sep 2024

10/10 Excellent

Jennifer R.

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

Beautiful home, great location

We really enjoyed our stay at this home - it was clean and had everything we needed! The pool and outdoor space is wonderful and the location is great. It's about a mile walk to Duval and it's in a great neighborhood. We would stay here again.
Stayed 7 nights in Jul 2024

8/10 Good

Michelle W.

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

Wedding

We had our beach wedding and stayed at this wonderful place. Really enjoyed this stay ;)
Stayed 7 nights in Jul 2024

About the host

Hosted by Conch Collection

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Languages:

English

Premier Host

They consistently provide great experiences for their guests