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Penthouse Two Master Waterfront Suite with Rooftop

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Interior
Fridge, microwave, oven, stovetop
Smart TV, stereo
Interior
Exterior detail

Reviews

10 out of 10
Exceptional

Entire condo

2 bedrooms3 bathroomsSleeps 41600 sq ft

Popular amenities

  • Dryer
  • Washer
  • Kitchen
  • Outdoor Space

Explore the area

Map
Portland, ME
  • Casco Bay Lines Ferry Terminal
    ‪3 min walk‬
  • Cross Insurance Arena
    ‪8 min walk‬
  • State Theatre
    ‪15 min walk‬
  • Portland, ME (PWM-Portland Intl. Jetport)
    ‪8 min drive‬

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About the neighborhood

Portland

Seaside stay .A stay at this Downtown Portland condo places you steps from Fore Street Gallery and within a 5-minute walk of Casco Bay. Casco Bay Lines Ferry Terminal and Merrill Auditorium are also within half a mile (1 km).
View more Condo Rentals in PortlandOpens in a new window

What's nearby

  • Casco Bay Lines Ferry Terminal - 3 min walk - 0.2 miles
  • Cross Insurance Arena - 8 min walk - 0.5 miles
  • Portland Museum of Art - 13 min walk - 0.7 miles
  • State Theatre - 15 min walk - 0.8 miles
  • Maine Medical Center - 2 min drive - 1.2 miles

Getting around

  • Portland Transportation Center - 9 min drive
  • Portland Intl. Jetport Airport (PWM) - 18 min drive

Restaurants

  • ‪Luke's Lobster Portland Pier - ‬3 min walk
  • ‪DiMillo's On the Water - ‬3 min walk
  • ‪The Porthole - ‬2 min walk
  • ‪Gritty McDuff's - ‬2 min walk
  • ‪Standard Baking Co. - ‬3 min walk

About this property

Entire place

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

Penthouse Two Master Waterfront Suite with Rooftop

2023 City of Portland Registration #20185280-ST
Back-to-front top-floor penthouse suite with modern amenities, exposed beams and brick, whitewashed poplar walls. Rooftop deck with 360 degree views of harbor and city. A monthly parking for one car is provided for the lot next door.

Separate master suites, each with custom shower, hand wand, and one with soaking tub. Very desirable exposed brick and vaulted ceilings with skylights in each suite. Black out curtains and skylight shades in bedrooms.

Spacious, modern kitchen with white shaker cabinets, wine cooler, stainless appliances including gas cooktop, pots and pans, bowls, wine glasses, cutting board, dishware, 12-cup auto drip coffee maker. granite-top island and bar stools. Dining table next to kitchen and living area in open concept space.

Gas-fired Jotul stove and floor-to-ceiling windows in living room.

Washer/dryer in unit. Individual heating and air conditioning. Easy elevator access.

Wi-Fi, satellite TV, built-in speakers with stereo system, closet and pantry space, linens, bedding, pillows, paper products, hair dryer, shower essentials, iron and board.

Very safe and secure. Two security cameras in common hallway by elevator and one security camera at back common exit stairwell.

On Portland's working waterfront, overlooking the very popular Dimillo's Marina. Watch the yachts come and go and stop at the famous Dimillo's floating restaurant for dinner or a drink. Located in the heart of the Old Port on the working waterfront, this is Portland, Maine at its core. See a mix of lobster boats and fisherman as well as busy professionals.


Must see spots nearby:
*Harbor Fish: the go-to spot for just-caught fish
*Casco Bay Ferry: visit the islands
*J's Oyster: classic cocktails, seafood, and an unbeatable mix of locals and tourists alike
*The Holy Donut: Maine potato donuts
*Exchange Street: shopping
*Novare Res Bier Bar: large selection of craft brews

Whole Foods, Trader Joe's, and Hannaford within a 1 mile drive.

Property manager

Scott Lindsay

Languages

English

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Property amenities

Internet

  • Available in the condo: WiFi

Parking and transportation

  • Car not required
  • Parking on site

Kitchen

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

Dining

  • Dining table

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

  • 2.5 bathrooms
  • Bathtub
  • Hair dryer
  • Heated bathroom floor
  • Shower
  • Towels provided

Living spaces

  • Dining table
  • Living room
  • Wood stove

Entertainment

  • Smart TV with cable/satellite channels
  • Stereo

Outdoor areas

  • Balcony
  • Rooftop terrace

Laundry

  • Laundry facilities
  • Washer/dryer

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Elevator
  • Smoke-free property
  • Note from host: Strict.

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the city center
  • Near a hospital
  • Near the bay
  • Near the marina
  • Near the ocean
  • On the waterfront

Things to do

  • Optional golf privileges
  • Basketball nearby
  • Birdwatching nearby
  • Fishing nearby
  • Golfing nearby
  • Hiking/biking trails nearby
  • Ice skating nearby
  • Mountain biking nearby
  • Sailing nearby
  • Surfing/bodyboarding nearby
  • Swimming nearby
  • Water tubing nearby
  • Whale watching nearby
  • Windsurfing nearby
  • Winery tours nearby

Safety features

  • 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

General

  • Unit size: 1,600 square feet

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in available
Minimum check-in age: 30

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

  • No pets allowed
  • Note from host: Strict.

Children and extra beds

  • Children are welcome.
  • Note from host: Children must be supervised. See House Rules.

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 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
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 private host, not a professional engaged in trade or business. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector, and a first aid kit in each accommodation.

Property is also known as

Henry Penthouse Suite Amazing Views Waterfront Heart Condo
Henry Penthouse Suite Amazing Views Waterfront Heart Old Port
Henry Penthouse Suite Amazing Views Waterfront Heart
Henry Penthouse Suite Amazing Views Waterfront Heart Condo
Henry Penthouse Suite Amazing Views Waterfront Heart Old Port
Henry Penthouse Suite Amazing Views Waterfront Heart Condo
Henry Penthouse Suite Amazing Views Waterfront Heart Old Port
Henry Penthouse Suite Amazing Views Waterfront Heart

Frequently asked questions

How close is Penthouse Two Master Waterfront Suite with Rooftop to the airport?

This condo is 5.1 mi (18-min drive) away from the Portland Intl. Jetport Airport (PWM) airport, the closest popular airport to the property.

How much does it cost to stay at Penthouse Two Master Waterfront Suite with Rooftop?

As of Jun 18, 2025, prices found for a 1-night stay for 2 adults at Penthouse Two Master Waterfront Suite with Rooftop on Jun 24, 2025 start from $709.0, 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.

Does Penthouse Two Master Waterfront Suite with Rooftop have an airport shuttle?

Airport shuttle services are not available at this condo.

How close is Penthouse Two Master Waterfront Suite with Rooftop to the beach?

This condo is 15.3 mi (31-min drive) from Old Orchard Beach and 1.1 mi (2-min drive) from East End Beach. Don't forget your sunscreen!

Does Penthouse Two Master Waterfront Suite with Rooftop offer free breakfast?

This condo does not offer free breakfast.

Is there a casino at Penthouse Two Master Waterfront Suite with Rooftop?

No, there is no casino at this condo.

What time is check-in at Penthouse Two Master Waterfront Suite with Rooftop?

Check-in begins at 4:00 PM.

Is there free parking at Penthouse Two Master Waterfront Suite with Rooftop?

Free parking is not available at this condo.

Does Penthouse Two Master Waterfront Suite with Rooftop have a pool?

This condo does not have a pool.

Does Penthouse Two Master Waterfront Suite with Rooftop have a spa?

There are no spa services available at this condo.

How close is Penthouse Two Master Waterfront Suite with Rooftop to downtown Portland?

This condo is 0.4 mi away from Portland.

Penthouse Two Master Waterfront Suite with Rooftop Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 239 out of 245 reviews
Rating 8 - Good. 6 out of 245 reviews
Rating 6 - Okay. 0 out of 245 reviews
Rating 4 - Poor. 0 out of 245 reviews
Rating 2 - Terrible. 0 out of 245 reviews

10/10

Cleanliness

Reviews

10/10 Excellent

Frank F., Norfolk

Liked: Cleanliness

Maritime

We stay here twice a year, in the spring and fall. Highlights are the farmers market, fish market, restaurants and hiking. We also love to just sit in the living room and watch the boats.
Stayed 3 nights in May 2025

10/10 Excellent

david l.

Liked: Cleanliness

Wedding weekend in Portland

We were in town for a wedding weekend (2 couples). The Henry suite was outstanding. Great lication and accommodations. Easy access to all points of interest and the hosts were great! I would recommend this to all my friends and relatives!
Stayed 3 nights in May 2025

10/10 Excellent

jeanette b., Dallas

Liked: Cleanliness

Would Stay Again

Excellent lodging and location, Would absolutely stay again.
Stayed 3 nights in May 2025

8/10 Good

Leon J.

Liked: Cleanliness

Keep Coming Back

Have stayed at this location at least 6 times. Feel very comfortable here. View of the harbor is wonderful. Availability for parking is essential. Great kitchen and appliances. Washer/dryer is great. Response from owner is immediate. The problems we had this time have happened every time we have stayed. The tv connection is impossible to correct. Even when assistance was provided by the wonderful technician working for the owner, the tv's still are inconsistent from day to day, losing signals, and can't find major tv networks. Also, this time I couldn't use my laptop as them internet connection could not be made. Gave up trying. When I went to other outside locations in Portland, my laptop worked fine. These two issues, while possibly related, need looking into. We keep coming back for all the good things about it, but the items I have mentioned make our stay incomplete.
Stayed 4 nights in Apr 2025

10/10 Excellent

Jack L.

Liked: Cleanliness

Perfect Location!

We absolutely loved staying here. It is a modern, beautiful, centrally located place. The windows are fantastic-the showers were amazing. Walking to and from shops and local eateries was easy. The parking was beyond easy! We highly suggest this location!
Stayed 2 nights in Mar 2025

10/10 Excellent

Catherine P.

Liked: Cleanliness

Family and friends fun

Enjoyed our 2nd stay..great location
Stayed 3 nights in Mar 2025

10/10 Excellent

Susan S.

Liked: Cleanliness

Portland waterfront

We can’t say enough how pleased we were with this location, perfect for walking to the restaurants and the Eastern Promenade trails. We enjoyed the evening sounds of boats and gulls. Check in was very easy and well written instructions for departure.
Stayed 4 nights in Mar 2025

10/10 Excellent

Jarrett W.

Liked: Cleanliness

Beautiful Condo Amazing Location

This property was wonderful and met all of our needs. The home is very clean and had everything needed for our stay. The location and views were amazing!!! Highly recommended and we'll definitely be staying here again. Thank you!!
Stayed 3 nights in Feb 2025

10/10 Excellent

Cheryl F.

Liked: Cleanliness

Friends winter vacation!

The Henry penthouse was such a great place. Location and views were amazing! From the minute we arrived everything was smooth and described perfectly. Wish we would have booked more nights, we will definitely be back! Thank you Scott & Liz
Stayed 3 nights in Feb 2025

10/10 Excellent

Mallory S.

Liked: Cleanliness

Worth every penny!

Booked this for a winter getaway and my husband and I were impressed from the start. Not only was the communication crystal clear with the hosts, the property was immaculate. The apartment itself was well furnished, and the view is stellar. We took full advantage of the kitchen, and didn’t lack for a thing— including an oyster shucker. The cherry on top was the parking, which was such a great amenity and convenience.
Stayed 4 nights in Feb 2025

10/10 Excellent

Kathleen G., Asheville

Liked: Cleanliness

A Memorable Stay at Henry's Penthouse in Portland

We had a fantastic stay, and it was a great pleasure to make this charming place our home while visiting our newborn granddaughter, daughter-in-law, and son. The penthouse apartment is beautiful and has everything you could wish for. The bathroom and bedroom were terrific, and the cooking appliances and equipment made settling in a breeze.Moreover, the apartment's location is a traveler's dream, allowing for convenient foot exploration of downtown Portland. The neighborhood is safe, the view is breathtaking, and the parking is designed for easy access to the unit.The check-in process was a breeze, with easy access points from the back and front doors. The apartment is surrounded by various amenities, including shopping outlets, bars, and restaurants, all within a short walk. Our personal favorites, Harbor Fish and Jay's Oysters were just a few steps away.We are immensely grateful to the owners for their warm hospitality and for making our stay memorable. We wholeheartedly recommend Henry's Penthouse to anyone looking for a comfortable and enjoyable stay in Portland.
Stayed 5 nights in Jan 2025

10/10 Excellent

Megan R.

Liked: Cleanliness

Gorgeous view, cosy comfort

We loved our stay. The apt is equipped with everything you need and so cozy with the fireplace and sun streaming in the windows.
Stayed 3 nights in Jan 2025

10/10 Excellent

Ryan M.

Liked: Cleanliness

Everything you need & more - plus the VIEW !

Location is first and foremost the best part, close to everything in the heart of Old Port. Views are incredible and has every amenity you could ask for. Property managers communication was a amazing and the building is super secure with multiple coded entries. Will stay again for our next trip back!
Stayed 3 nights in Jan 2025

10/10 Excellent

Nick

Liked: Cleanliness

Old Port

Great property in the heart of the Old Port.
Stayed 3 nights in Dec 2024

10/10 Excellent

Michaela S., Cambridge, MA

Liked: Cleanliness

Henry Penthouse

Great location and wonderful harbor views! Walkable to restaurants, shops, and nearby Harbor Fish Market. Kitchen was well equipped. Communication with host was easy.
Stayed 2 nights in Dec 2024

10/10 Excellent

Verified traveler

Liked: Cleanliness

This is the 1

If you’re debating where to stay in the Old Port, this is the place. Lovely unit with an amazing view and excellent location. It is even better than in the photos.
Stayed 4 nights in Dec 2024

8/10 Good

Rebeccah S.

Liked: Cleanliness

Another Gorgeous Portland Weekend

This is our fourth visit to one of Scott & Karen’s Portland penthouse properties—and as always, it was excellent. The apartment is in a fantastic area to explore everything Portland has to offer, and offers a lovely respite to return to after a busy day. This was the first year we had a little hiccup—the internet wasn’t working properly our first night, and required several calls to Scott’s property manager, as well as the cable company to get things sorted out. I was able to connect with Scott after the trip and give my feedback about the cable issues and slow communication from property management.
Stayed 2 nights in Dec 2024

10/10 Excellent

Mindy B.

Liked: Cleanliness

Great stay

Great property with an amazing view and location.
Stayed 7 nights in Nov 2024

10/10 Excellent

Carolyn S.

Liked: Cleanliness

Perfect

Excellent location, amenities, views... no detail was overlooked by the hosts. We had a lovely time.
Stayed 3 nights in Nov 2024

10/10 Excellent

Cindy H.

Liked: Cleanliness

Spectacular Penthouse in Portland!

What a beautiful property that has everything needed for a great stay in Portland. We were celebrating with our daughter and husband and this was just perfect. We walked to all types of amazing restaurants and took day trips out of town for additional activities. The small deck and rooftop patio are easy to access and a great place to sit and enjoy the day. We’re coming back as quickly as we can!
Stayed 5 nights in Nov 2024

10/10 Excellent

Marcy F.

Liked: Cleanliness

Just like the pictures

Beautiful, comfortable, centrally located!
Stayed 2 nights in Nov 2024

10/10 Excellent

Klose F.

Liked: Cleanliness

A+ View and Location

This modern apartment has stunning almost 180 degree views of the harbor. It is in an ideal location to walk to many highly rated restaurants and to take advantage of tourist activities. The beds were very comfortable and the showers and tub were luxurious. The unit lacks a few minor amenities like tissues but that certainly didn't affect our five star rating.
Stayed 4 nights in Oct 2024

10/10 Excellent

Doug E.

Liked: Cleanliness

Portland condo

Best of the best. Beautuful views
Stayed 2 nights in Oct 2024

10/10 Excellent

SR 7/28-8/1Barney N., Portland, OR

Liked: Cleanliness

New England tour

Super clean and in great location. Would have loved to use rooftop deck but weather didn’t cooperate. Modern design and well outfitted.
Stayed 2 nights in Oct 2024

10/10 Excellent

Emily M.

Liked: Cleanliness

Perfection

We absolutely loved staying here! The property was beautiful and spacious, views were stunning, and location was perfect! We hope to stay here again!
Stayed 2 nights in Oct 2024