Condo

Waterfront Penthouse sleeps 16 w/Pool & Boat Dock

Waterfront condo with kitchen and balcony

Photo gallery for Waterfront Penthouse sleeps 16 w/Pool & Boat Dock

1st floor common space
View from 1st floor balcony, Polywood Furniture
Dining & Living Room with Balcony
Heated pool & tiki bar
Eating area & Kitchen. Entryway seen to the far right of picture

Reviews

9.6 out of 10
Exceptional
4 bedrooms4 bathroomsSleeps 162400 sq ft

Popular amenities

  • Ocean view
  • Pool
  • Kitchen
  • Washer
  • Dryer
  • Pet friendly

Explore the area

View in a map
Key West, FL
  • Place, Clarence S. Higgs Memorial Beach Park
    ‪17 min walk‬
  • Place, Duval Street
    ‪18 min walk‬
  • Place, Southernmost Point
    ‪4 min drive‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪6 min drive‬

Rooms & beds

4 bedrooms (sleeps 16)

Bedroom 1

1 King Bed

Bedroom 2

2 Queen Beds

Bedroom 3

2 King Beds

Bedroom 4

2 Queen Beds

Living Room 1

2 Twin Beds

4 bathrooms

Bathroom 1

Soap · Towels provided · Toilet · Shower only · Hair dryer

Bathroom 2

Soap · Towels provided · Toilet · Shower only · Hair dryer

Bathroom 3

Soap · Towels provided · Toilet · Shower only · Hair dryer

Bathroom 4

Soap · Towels provided · Toilet · Shower only · Hair dryer

Spaces

Deck or patio
Kitchen
Balcony
Garden
Dining area

About this property

Waterfront Penthouse sleeps 16 w/Pool & Boat Dock

Summary:
Gorgeous completely renovated 2400sqft waterfront Penthouse condo in downtown Key West. Boat slips available on-site with commercial ice machine, fish cleaning station and BBQ. Located in historic downtown Key West. 4B/4B with loft, sleeping 16. Less than 1mi to Duval Street, Historic Seaport, Hemingway House, etc. On-site amenities: heated pool, boat slip, tiki bar & grills, parking, secure keyless entry, & private elevator. Large Park adjacent with tennis courts. 10min from airport (EYW).

The Space:
Welcome to the St. Thomas Penthouse – Two-Story Waterfront Luxury in Key West
Perched atop one of the tallest buildings in Key West, St. Thomas is a stunning 4BR + Loft, 4BA two-story penthouse offering sunrise-to-sunset views, incredible space, and comfort for up to 16 guests — ideal for families, group getaways, or fishing retreats.

🌅 Dual Balconies, Endless Views:
-Oversized rear balcony overlooking the harbor — perfect for morning coffee & boat watching
-Private sunset balcony upstairs with panoramic views over Old Town 🌇

📍 Prime Location:
Less than 1 mile to Duval Street, Historic Seaport, and Hemingway House — walk or bike to the best of downtown Key West 🚶‍♀️🚲

🛋️ Spacious & Stylish Living:
-Living room with floor-to-ceiling glass and water views — ideal for group gatherings
-Fully equipped kitchen with quartz countertops (bring your own spices & oil) 🍳
-Full-size washer & dryer 🧺
-Second living/kids room upstairs in the loft
-High-speed WiFi & flat-screen TVs with cable in every room 📶📺

🛏️ Sleeping Arrangements:
-Downstairs King Master with balcony access & ensuite bath
-Two guest rooms with two Queen beds and ensuite baths
-One guest room with two King beds and ensuite bath
-Loft with bunk beds + two twin beds — perfect for kids or extra guests
✅ Accommodates up to 16 guests comfortably

🚤 Dockage Included!
Bring your boat! Reserved slip with power, fresh water, fish cleaning station, and access to a commercial ice maker — no extra charge.

🏝️ Extras & Amenities:
☀️ Shared Heated pool
🍔 BBQ grills & tiki area
🐾 Pet-friendly
🚗 Free on-site parking
🎾 Adjacent park with tennis courts
🚶‍♀️ Walk or bike to everything — Duval St, Historic Seaport & Hemingway House all <1 mile
🧺 Full-size washer & dryer for added convenience
📶 High-speed WiFi
🔐 Private building elevator
✈️ Just 10 minutes from Key West Airport (EYW)

🎶 Local Tip: Right next door, enjoy a local-favorite restaurant with live music, craft beer, and sunset tiki cruises — a perfect Key West evening!

Guest Access:
Guests will have access to the entire 2400 sq ft penthouse condo, including the oversized balcony with water views, perfect for watching the sunrise and boats. Enjoy the fully equipped kitchen, two living areas, and all four bedrooms, each with an en-suite bathroom. The shared amenities include a heated pool, tiki bar with grills, and a boat slip (available upon request). A private elevator provides secure and convenient access. Boat owners will appreciate the on-site amenities like the commercial ice machine and fish cleaning station. Guests can also enjoy the adjacent park with tennis courts. Parking is available on-site for one vehicle.

The Neighborhood:
Key West is a special place within the U.S. Tropical warm winds year round, thick green foliage, world class fishing and diving, 10+ palm tree species, historic homes, 200+restaurants & bars on this 4mi x 2mi island. The location of this home is perfect for getting anywhere in Key West. Quick access to New Town and grocery stores as well as Duval Street and anywhere else in Downtown Key West. Bayview park is next door with plenty of open spaces, tennis courts, basketball hoops, and festivals on many weekends throughout the year.

Getting Around:
Our location allows you to get around by foot or bicycle. Electric carts are rented frequently on the island - we can accommodate plug in. You won't need a car, unless you're driving down route 1 from mainland FL. Lyft/Uber are plentiful.

Other Things to Note:
Check-in is 4PM and check-out is 10AM. Guests #11+ incur a fee of $100 per person per night, and all guests must be included on the reservation prior to arrival.

We welcome one dog up to 25 lbs with a $200 non-refundable pet fee.

Free parking on-site is guaranteed for two vehicles, which include a golf cart rental.

Dockage details: maximum boat length 40 ft, maximum beam 13 ft, with an 18-ft fixed bridge clearance into the marina. Overnight stays on boats are not permitted. No trailer parking on-site; arrange for off-site storage (City Marina at Garrison Bight or Spencer's Boatyard).

All guests must be at least 25 years of age unless accompanied by a parent.

Tropical Environment Reminder: Our home is treated monthly by professional pest control, but in Key West’s climate, occasional insect sightings are possible. If anything arises during your stay, we will promptly arrange a professional inspection and treatment. Access to the property must be permitted for service.

Interaction with Guests:
I will not be on the premises. Unit are managed by Keys Time Vacation Rentals. No in-person check-in required. Digital access to the property via keyless entry codes to condominium elevator and common spaces. Condo unit code will be provided no less than 24 hours prior to arrival date. Maintenance is accessible during the same.
Our prices include all fees. No hidden fees.

Add dates for prices

Amenities

Pool
Kitchen
Washer
Dryer
Pet friendly
Air conditioning

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
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

Pets allowed: dogs less than 20 lbs per pet (limit one pet total)
Charge may apply
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Smoking

Smoking is not permitted
• PARKING: Free permitted parking is available on-site in the outside parking lot (NOT in the covered garage). o Please place your parking per...

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
This property accepts cash
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 and a first aid kit

About the neighborhood

Key West

Located on the waterfront, this condo is in Meadows, a neighborhood 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. Take an opportunity to explore the area for outdoor excitement like cycling.
Map
Key West, FL

What's nearby

  • Key West Naval Station - 5 min walk - 0.4 km
  • Clarence S. Higgs Memorial Beach Park - 17 min walk - 1.5 km
  • Duval Street - 18 min walk - 1.6 km
  • South Beach - 19 min walk - 1.6 km
  • Southernmost Point - 4 min drive - 1.7 km

Getting around

  • Key West Intl. Airport (EYW) - 7 min drive

Restaurants

  • ‪Circle K - ‬6 min walk
  • ‪Sandy's Café - ‬8 min walk
  • ‪Dions Truman & White - ‬7 min walk
  • ‪El Siboney Restaurant - ‬13 min walk
  • ‪Popeyes Louisiana Kitchen - ‬10 min walk

Frequently asked questions

Does Waterfront Penthouse sleeps 16 w/Pool & Boat Dock have a pool?

Yes, this property has a pool.

Is Waterfront Penthouse sleeps 16 w/Pool & Boat Dock pet-friendly?

Yes, this property allows dogs (limit 1 total) with a maximum weight of up to 20 lbs per pet.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Waterfront Penthouse sleeps 16 w/Pool & Boat Dock?

Check-in begins at 4:00 PM.

What time is check-out at Waterfront Penthouse sleeps 16 w/Pool & Boat Dock?

Check-out is at 10:00 AM.

Where is Waterfront Penthouse sleeps 16 w/Pool & Boat Dock located?

Located in Meadows, this condo building is within 1 mi (2 km) of The Unitarian Universalist Fellowship of Key West, Duval Street, and Florida Keys Beaches. Mallory Square is 1.7 mi (2.8 km) away.

Reviews

9.6

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 22 out of 24 reviews
Rating 8 - Good. 1 out of 24 reviews
Rating 6 - Okay. 0 out of 24 reviews
Rating 4 - Poor. 0 out of 24 reviews
Rating 2 - Terrible. 1 out of 24 reviews

10/10

Cleanliness

10/10

Check-in

9.8/10

Communication

9.6/10

Location

9.8/10

Listing accuracy

Reviews

10/10 Excellent

Lauren W.

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

Perfect for girls trip!

Highly recommend!!!
Stayed 3 nights in Jun 2025

10/10 Excellent

Rocci B.

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

Lovely Home!

Absolutely loved the place!! We would stay here again!! Highly recommend!
Stayed 3 nights in May 2025

10/10 Excellent

Sydney D.

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

Great stay!

Great stay for a wonderful bachelorette weekend! Owners were very helpful, communicative, and resourceful for our group. Would highly recommend this property for anybody traveling to the Key West area.
Stayed 3 nights in Apr 2025

10/10 Excellent

Kyle E.

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

Amazing Penthouse

The location is great with only a short drive to the beach and Duvall St. The room is on the top floor with a balcony over looking the water.Kimberly was very responsive when answering questions and addressing needs
Stayed 3 nights in Jun 2025

10/10 Excellent

Mayur K.

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

Great place to stay with family

Overall very satisfied with the booking. Very close to everything Key West has to offer. Highly recommend it!
Stayed 2 nights in Dec 2024

10/10 Excellent

Diane J.

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

Perfect for a large group

Spacious unit, great bar with music next door, beautiful views
Stayed 4 nights in Nov 2024

10/10 Excellent

Catherine L.

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

Awesome Place

The place was absolutely great! The view was great. The location was great! Everything was great! The only thing not great was that we didn’t get to stay longer! Enjoyed it very much!
Stayed 5 nights in Nov 2024

10/10 Excellent

Amy P.

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

Girls trip

Very friendly and clean. Perfect location
Stayed 4 nights in May 2024

10/10 Excellent

Frank F.

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

Wonderful stay!

This home is absolutely beautiful! We are two couples & single adult; plenty of space to enjoy. The view from the deck was spectacular! The amenities were top notch. We truly enjoyed our stay. Thank you.
Stayed 1 night in Oct 2024

10/10 Excellent

Brendan G.

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

Great property and location

Very clean property and great host! Was very responsive and very accommodating
Stayed 4 nights in Aug 2023

10/10 Excellent

Diane S.

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

Friend Vacation

We loved our stay. The property was perfect for us. Great location with all the amenities. Really fun bar just downstairs. Rosalyn became our new best
Stayed 5 nights in Mar 2024

10/10 Excellent

Tracy C.

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

Great place to stayb

The property was beautiful. We had a few questions after check in and could not reach anyone. Other than initial communication problems everything else was wonderful. Great place to stay and great location.
Stayed 3 nights in Feb 2024

10/10 Excellent

Vaughn K.

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

Great Place / Great Rates

Communication with the owners was great. Condo was spacious, updated, and clean, and the balconies provided for fantastic views. All of this plus the rates made it a welcomed value for our group of nine versus staying in a hotel. Thank you!
Stayed 3 nights in Mar 2024

10/10 Excellent

Robert T.

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

very excellent interior. Exterior and shared area (pool) not great

Pool and outside amenities were weak, and I wish it was a little further off the main road. Lots of traffic noise, but the interior was excellent. Very well kept and clean
Stayed 2 nights in Mar 2023

10/10 Excellent

Abigail H.

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

Girls Trip

We stayed here for a girls trip and it was perfect for a large group. Plenty of beds, bathrooms and a big comfy couch! The porch is amazing and has a great view of the harbor. We used the pool one day and the general area was clean and the water was warm. Pool towels are provided! We took Uber/Lyft to most places we needed to go but everything is so close in Key West. There is a tiki bar adjacent to the property but unfortunately we ran out of time to visit. The kitchen is updated and the washer/dryer option is great. Management was responsive and friendly. Would stay here again!
Stayed 3 nights in Feb 2024

8/10 Good

Craig W.

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

Fishing Trip

Unit was very clean and organized. I am in construction and I was informed of roof work at booking but there was other exterior work on going as well and the elevator was not functioning upon arrival. That was repaired and good from there. Would book again once upgrades are completed.
Stayed 3 nights in Oct 2023

10/10 Excellent

Larry L.

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

Great place

From the communication with the Property Management to check in to our stay and check out. The condo is extremely well maintained, supplied, and clean. We had a wonderful stay. We had a few small requests prior to our visit like an extra coffee maker and some extra dishes and pans. All were supplied and at the house upon our arrival. The only slight inconvenience was that we had a large group and the internet was a little slow. But that could be corrected by installing a better router. And I have a feeling if we had asked, the property manager would have tried to accomplish it before we left. She was so great and if she reads this she will probably have it done before the next guest. Thank you we had a terrific time and loved the condo.
Stayed 5 nights in Jan 2025

10/10 Excellent

Michael D.

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

Awesome place

The place was awesome, very clean and very comfortable. The only thing that was an issue was the water pressure. At some points if more than one person was showing it would almost completely cut off the water. Also the listing says it fits 16 but I really doubt that you could have that many people stay there. Other than those two things which didn’t really bother us that much it was perfect!
Stayed 3 nights in Jun 2023

10/10 Excellent

Terri S.

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

Beautiful and Spacious

I stayed here with 3 other couples, it was so nice that we each got our own private bedroom AND bathroom. The condo was very clean and nicely decorated. We cooked a few meals there and were happy to discover that we had all the pots, pans, dish towels and dishes that we needed. The layout of the condo worked well. You enter through a hallway between the kitchen and one of the bedrooms. The kitchen is on the left and has a half wall with bar stools that is open to the living area. To the right is a bedroom with two queen beds. The bathroom attached to this bedroom has two doors, one that opens to the bedroom and one that opens to the main area. I had this bedroom and locked the main area door at night and in the morning, but left it accessible to the rest of our party during the day. The living area is large with a balcony that stretches across the living room and the second main floor bedroom. This balcony faces East and overlooks the marina. The second lower bedroom has a private bath and one king bed. Upstairs there are two bedrooms that have private bathrooms and a shared balcony facing east. The balcony has a wall at both ends so it is shared with just those two bedrooms. The area above the living room is open to the high ceilings, then above the lower bedroom with the king bed there is a loft with two twin beds and a card table and chairs. There is a short wall in this area that is all windows overlooking the marina.
Stayed 3 nights in Feb 2024

2/10 Terrible

Christina F.

Liked: Cleanliness, check-in, communication, location
Disliked: Listing accuracy

Great location but listing was not accurate

Overall the location was great but the experience was not. The A/C was not working the first night we arrived making it aweful to sleep. The loft and bunkbeds have no central air so you cant even sleep in them. The downstairs Queen bedroom AC is not powerful enough to push any air in the room so it was unbearable to sleep in the entire stay. The pool area was small and outdated and there is no bar by the pool just a shack with no purpose. The toilet in upstairs bedroom was not bolted to floor and the door handle fell off the first night. The kitchen sink sprayer would not stay on unless you held the button. The fridge was not turned on until we arrived so we lost alot of the food we brought with us. This should have been turned on at least 8 hours before we arrived so the fridge would be cold enough to put food into. And the water pressure was aweful. Only one shower downstairs had even water pressure to rinse out your hair. the girls had to share that shower or used the shower outside to rinse the conditioner out of our hair. The elevator was scary and a suffocating hot box. There was no air flow. And the beds were like sleeping on cement. Who puts firm mattress in a vacation rental. They were aweful and nobody got any sleep.
Stayed 5 nights in Jun 2023

10/10 Excellent

Erik G.

Stayed 1 night in Nov 2025

10/10 Excellent

Alexandra F.

Stayed 3 nights in Oct 2025

10/10 Excellent

Kate C.

Stayed 2 nights in Aug 2025

10/10 Excellent

Douglas G C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 3 nights in Apr 2025

About the host

Hosted by Kim Hartselle

Host profile image
I am a native to the Chesapeake Bay area of Virginia and married a Florida native in 2017. Together, we have made both Florida and Virginia our homes, but currently reside in my native area of Virginia since 2020. We have no children but are proud aunts and uncles to our many niblings and have 3 fur babies (cats). We both enjoy being outdoors, spending time with our families, and traveling. Together with my sister, Jennifer, we host visitors of the Florida Keys at our family rental properties in Key West and Marathon. We have hosted over 2,000 nights so far and look forward to hosting many more.

Languages:

English

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