Holiday rentals in Old Port, Portland

4.78 out of 5 average rating, 733 reviews

Flat in West End

BEST location! HUGE 1 bedroom downtown Portland

License#STHR0011152019 Spacious 1 bedroom w/living room, eat-in kitchen and bath in ideal Portland peninsula location, walk to all. situated on the edge of the west end and downtown. 2 blocks from the ocean. Walk everywhere in this central, historic, perfect location. Easy street parking. Simple furnishings, older retro flair. 2nd floor of 3 unit Victorian on dead end, quiet street. Queen bed. There is no parking but often spaces are available on this dead end street. Note steep steps going up

4.98 out of 5 average rating, 149 reviews

Modern Luxury with Bay Views * 5 Star Location!

Well-appointed, high-end private apartment with wide plank pine floors sourced from Western Maine, luxury bathroom and bedroom. Shared patio with grill and fire pit. A short walk to the Eastern Prom or restaurants of the Old Port and Washington Street. I pay attention to details such as cleanliness, local coffee, quality linens, furniture and furnishings. Queen bed with a view of the harbor. This is a non-smoking, non-cooking space. Not suitable for infants children. Hi speed internet.

4.98 out of 5 average rating, 313 reviews

Light-Filled Getaway with Private Porch

Spacious (1100 sqft), updated early Victorian (1838) apartment bordering the Arts District in Portland's historic and beautiful downtown West End. The apt. has great natural light, ample workspace, free on-street parking, a private garden entrance, and a sheltered, leafy screened porch. With a Walk Score of "95-A Walkers Paradise", you'll be able to stroll to nearby restaurants, cafes, museums, parks and Old Port. Then, return to a relaxing space that you'll be very happy to call 'home'!

4.97 out of 5 average rating, 270 reviews

Old Port Penthouse Suite - Amazing Harbor Views

2023 City of Portland Registration #20182242-ST Private Old Port Penthouse w/Breathtaking Views + Your Own Cupola. Quiet + Secure. Gorgeous contemporary suite full of light located right across from the working waterfront. Lobster and seafood off the boat is 100 meters from your front door. Watch the ferries to the islands from the cupola. Smell the salt air from your private deck. Welcome to Portland! Please note: animals (including assistance animals) not allowed due to owner's health.

Guest suite in Downtown Portland

4.96 out of 5 average rating, 687 reviews

Studio, Walk to everything, Parking

5 to10 minute walk to all Portland has to offer; restaurants, breweries, galleries, shops, and famers markets. Located in a vibrant, safe, and transitional neighborhood. Steps from Portland's Arts district + Congress Street, (Portland Public Market, Broken Arrow, Regards, Portland School of Art). Home to Batson River Brewing & Distilling, ISA, Wilson BBQ. Short walk to downtown and the Old Port. Park your car and leave it for the duration of your stay. License # 20180110-ST

4.82 out of 5 average rating, 484 reviews

Walk-able Portland Studio

NEWLY RENOVATED! Cozy studio apartment in a historic building, located in Portland's East End Neighborhood. This location can't be beat! The Space features original hardwood floors, and large windows, subway tiled shower and thoughtful decor. Portland Food Co-Op is directly next door, as is the Walgreen's. Walking distance to Eventide, Honey Paw, Duck Fat, Hugos, Little Woodfords, LB Kitchen, Washington Ave Breweries and Distilleries and Old Port shopping district.

4.93 out of 5 average rating, 629 reviews

Adorable getaway on the Eastern Promenade

Lovely third-floor apartment on the East End just steps from the glorious Eastern Promenade. Cozy and cute, this adorable spot resides in the neighborhood which boasts the best restaurants, breweries, and coffee shops in the city all within walking distance. On a quiet residential street, there is plenty of on-street parking. This apartment is on the 3rd floor of the house . **Please note that the last 9 steps leading up to the apartment are quite steep.

4.92 out of 5 average rating, 282 reviews

Guest suite in East End

Gorgeous Studio 2 Blocks from Eastern Prom!

Located in Portland's trendy East End and within walking distance to the Old Port and Downtown, this beautiful studio is only 2 blocks from the Eastern Promenade and Casco Bay! You will have the Unit entirely to yourself with its own entrance, air conditioning, kitchenette, queen sized bed and an additional pull out single. Easily walk to all of the cool breweries, great restaurants, coffee shops, and night life! Welcome to Portland!

4.97 out of 5 average rating, 574 reviews

Cozy & Comfortable apartment in a perfect location

Bright sunny 1 bedroom private apartment in a quiet, Owner Occupied building. Perfect location. A short walk to Duckfat, Eventide and the rest of Portland. Top floor with full kitchen, work/desk area, comfortable living room, full bath with tub and shower, bedroom with a comfortable Queen bed. If you're a book lover, you'll enjoy it even more! Includes Reserved off street parking. Portland City License #STHR-000980

Apartment in Downtown Portland

4.92 out of 5 average rating, 167 reviews

Coastal Penthouse - Center of Downtown Portland!

Overlooking Portland’s historic downtown rests this coastal penthouse located on the most vibrant street in the city! This one-bedroom apartment is fitted out with all of the amenities needed for a Maine vacation! Enjoy relaxing in luxury while only feet away from Portland’s most popular destinations. This penthouse is perfect for those here for business or a Maine getaway!

4.89 out of 5 average rating, 345 reviews

Flat in West End

Airy+Modern Studio + Portland's Historic West End!

Small studio with kitchen, breakfast bar, full bathroom. We look forward to hosting you in the beautiful West End. This early 1900's building has all the comforts of a modern apartment with the charm of historic Portland architecture! Walk to restaurants and bars, markets, State Theater, downtown arts district and the Old Port. We offer free parking and easy self check in.

Apartment in Downtown Portland

5 out of 5 average rating, 142 reviews

Stylish Downtown Loft – Prime Location | A/C

This stylish 1-bedroom condo is perfectly situated in the heart of Portland's vibrant Old Port, right on iconic Exchange Street. Step outside and explore award-winning restaurants, breweries, gourmet coffee shops, and unique boutiques – everything Portland has to offer is right at your doorstep! License number: STHR-006583-2024 Check-in: 3PM, Check-out: 10AM

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Other great holiday rentals in Old Port, Portland

4.99 out of 5 average rating, 96 reviews

Chic Portland Penthouse, 2BR

JoeRating, 5 stars1 week ago

Amazing place in a fantastic walkable part of town. The host was super communicative and responsive, and the apartment was beautiful, clean, and had great amenities. We were in town with another couple and had an amazing time eating around town (highlights include Central Provisions and Duck Fat), went bowling at Bayside Bowl, went on a Narrow Gauge train tour, and caught a concert in Thompson’s Point. With the exception of the concert, everything was walking distance and frankly I don’t think the apartment could be in a better location.

5 out of 5 average rating, 51 reviews

Private Rooftop Deck/Artsy Apt/Old Port Arts Dist

ChalidaRating, 5 stars1 week ago

Dena was such a great host! The place was beautiful and in the perfect location. Just a short walk to so many awesome restaurants. The bed was really comfy, and the place actually looked even nicer in person than in the photos. We had a great stay and would definitely come back!

4.95 out of 5 average rating, 61 reviews

Charming Apartment- Munjoy Hill

RebeccaRating, 5 stars1 week ago

My partner and I loved this Airbnb! Inside was great and it was in a quiet and safe, but still walkable area. We appreciated the local recommendations - the hosts were very helpful!

4.96 out of 5 average rating, 227 reviews

Guest suite in West End

West End Artist's Getaway

LiamRating, 5 stars3 weeks ago

Erin’s place was great for my wife and I to celebrate our anniversary and baby moon. Centrally located and easily walkable made experiencing all that Portland has to offer a breeze. The parking lot is convenient and offered safe storage of my truck and the ability to explore outside the city limits as well. She was super responsive when we asked her for recommendation but otherwise let us do our own thing. The apartment had everything we needed and nothing that we didn’t. I would describe the space as a peaceful and quaint ‘hotel room’ with full kitchen at a good value. If we come back to Portland we will definitely stay with Erin again!

Guest suite in Downtown Portland

4.97 out of 5 average rating, 76 reviews

Spacious light filled retreat in the Arts District

LindseyRating, 5 stars8 months ago

A wonderful stay in the apartment at Andrea’s home! The description matched the apartment, it was clean, organized and larger than I expected. The location was fantastic and we were able to walk down to the Old Port to have some delicious food and a great time. We really appreciated the recommendations for restaurants provided in the book, we were NOT let down. Andrea was very accommodating and let us know we were the last guests of the season so were able to check out later and leave our car in the designated spot. The weekend for my wife’s birthday was truly special and we can’t wait to come back!

5 out of 5 average rating, 4 reviews

Old Port Loft - 302

MarieRating, 5 stars3 days ago

Great location, close to so much to do! Loved the bed - super comfy! It is in the heart of a lot- so at night it is bright from lights on resteraunts and there is noise- but we knew what to expect so it didn’t bother us. If you aren’t used to “city living” bring some ear plugs and an eye mask and you will be fine! Host was very responsive and even let us check in early as our train was scheduled earlier than we had planned. Would definitely stay again!

4.84 out of 5 average rating, 19 reviews

Old Port Studio prime location

VanceRating, 5 stars3 days ago

The unit is in a great location for exploring Portland. Everything we wanted to do was within walking distance. The unit was clean and suited our needs really well. The bed was very comfortable.