Vacation Condo Rentals By Owner In Portland, ME

$443.99

Quiet Family Vacation Home in Portland, Maine 7 minutes to the Old Port

Portland, Maine, United States

7 minutes from downtown Old Port, accommodating 4 guests in comfort with 2 bedrooms, a/c, wifi, full bath, half bath, kitchen, living room, dining areas, office, gas grill, outdoor patio seating and more, this private single family home offers ~1,300 sq ft in a quiet neighborhood of Portland, Maine.

2

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1

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6

Sleeps

$377.52

/ Nightly

Private Vacation Home

Cozy Coveside Island Retreat

Portland, Maine, United States

Coveside Island Retreat | 2BR Duplex with Sauna & Pool AccessbrbrUnplug and unwind at this cozy two-bedroom, one-and-a-half-bath apartment on beautiful Great Diamond Island — part of a peaceful duplex just steps from the water. Ideal for families or small groups, this island getaway offers a perfect mix of comfort, charm, and exclusive resort-style amenities.brInside, you’ll find a queen bed in the primary bedroom and two twin beds in the second, with an additional full bed and TV in the finished basement—perfect for extra guests or movie nights. You’ll also enjoy a private sauna, a washer and dryer, and a fully equipped kitchen that opens to a bright living area.brOut back, relax on the fenced-in deck with a BBQ grill and take in the quiet surroundings or head to the open-air front deck with rocking chairs and a wraparound lawn — a perfect spot for morning coffee or sunset drinks.brbrA short walk brings you to the Crown Jewel Restaurant and the island general store, while your stay includes access to exclusive Coveside amenities:br- Heated swimming pool (with pool bar access)br- Six private beachesbr- Tennis & pickleball courtsbr- Duckpin bowling alley & indoor basketball courtsbr- Fitness center & yoga studiobr- Waterfront dining at Diamond's Edge Restaurant & MarinabrbrWhether you're swimming, strolling, playing, or just relaxing in the sauna, this is the island escape you've been dreaming of.brbrCome get away. Your island retreat awaits.

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Sleeps

$686.03

/ Nightly

Private Vacation Home

Wonderful Portland Waterfront Home

Portland, Maine, United States

Wonderful cottage style home with spectacular views and direct access to your own waterfront. Perfect for kayaking, SUP, fishing or enjoying the abundant birdlife. 3 minutes to downtown Portland's Old Port, restaurants, galleries, museums, micro brews. Walking distance to Mackworth Island State Park, rocky beaches, neighborhood restaurants and groceries. Relax on the deck with friends for breakfast, cocktails or dinner. Enjoy coffee from second floor deck off master bedroom. Nicely landscaped, always a cool breeze with off street parking. Built in 1915, the home has new on demand hot water system, lighting and original artwork throughout.brRecent renovations include hardwood kitchen flooring and new master bath. While new to VRBO, I have rented my home in the past and all of the guests loved their stay. Slate Pool Table, stereo, HD TV, WIFI included. Simply furnished, with two bedrooms, p living room, billiard room and two full baths. Nicely equipped kitchen with DW, microwave, coffee maker, toaster and new stainless refrigerator. Water views abound including Portland Headlight. brThere are less than 25 homes in the city of Portland with waterfront property. This is one of them.brBTW, Coffee and chilled bottle of Prosecco await new guests!

2

Bed

2

Bath

4

Sleeps

$609.97

/ Nightly

Apartment

One Bedroom Loft in Portland's Historic Old Port

Portland, Maine, United States

Immerse yourself in the culture of the Old Port at your luxury loft hosted by The Docent’s Collection. Enjoy this spacious open-concept floor plan featuring a full-sized kitchen and one bedroom with soft luxurious linens and cozy pillows for your comfort. Admire the tapestry of a curated collection of local artists and enjoy five-star service from our local hospitality team. brbrWoven into the fabric of the Old Port’s historic architecture, cobblestone streets and salty ocean air, each private loft in the collection has been thoughtfully placed within steps of a vibrant arts community, local boutiques, and nationally recognized cuisine.brbrThis local culture permeates throughout each loft, with bespoke interior design and locally crafted exhibits from Maine artists.brbrThe kitchen is fully equipped with everything you need to prepare a delicious meal at any time of the day. We recommend taking a stroll to visit local markets, such as Portland Co-Op or Harbor Fish Market for the freshest of ingredients to stock your kitchen and pantry. brbrEvery loft features a welcome gift featuring local specialties and delights, such as a medium roast Coffee by Design’s select Old Port blend roasted locally for The Docent’s Collection. brbrGet settled in. Your luxury loft features ample storage for everything you brought along and picked up along the way. With everything in its place and after a long day of exploring Portland’s eclectic culture, you’ll be ready for a blissful slumber on lush linens and soft cozy pillows. brbrThere are multiple layouts of one-bedroom lofts featured throughout the building. Our team will assign a specific loft when you arrive. We are always happy to take requests, which are not guaranteed, for specific units. brbrThe Docent’s Collection - Thompson Block brbrState of Maine Lodging License # 28352

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$872.0

/ Nightly

Condo

50 Exchange Street Portland 3A

Portland, Maine, United States

Step into the timeless allure of Portland, Maine, with this exquisite 2-bedroom, 2-bathroom residence nestled within a beautifully restored 1868 building in the historic Old Port district. A perfect fusion of classic charm and modern convenience, this home invites you to experience the best of Portland's waterfront.brThe spacious interior boasts two bedrooms, providing comfort and privacy. Each bathroom is a sanctuary of relaxation, featuring modern fixtures and thoughtful design. Original architectural details have been lovingly preserved, creating an ambiance that speaks to the rich history of the building.brAs you explore the surrounding neighborhood, you'll find yourself immersed in the vibrant culture of the Old Port. Indulge in the eclectic array of shopping options, from quaint boutiques to artisanal markets. Discover a culinary paradise with renowned restaurants serving up the freshest seafood and local flavors. Galleries and art studios dot the streets, showcasing the creativity that thrives in this historic community.brCome evening, experience the heartbeat of Portland with entertainment options just moments away. Whether you're seeking a quiet evening stroll along the waterfront or the energy of a night out, Old Port has it all.brWith its prime location, historic charm, and proximity to everything the city has to offer, this 1868 gem is an opportunity to embrace the coastal lifestyle in a place where history and modernity coalesce seamlessly. Don't miss the chance to call this piece of Portland home.br

2

Bed

2

Bath

4

Sleeps

$677.44

/ Nightly

Private Vacation Home

Harmony House/Walk to Downtown/Parking/Balcony

Portland, Maine, United States

Welcome to Harmony House- your Portland retreat-where comfort, convenience, and city charm come together. This thoughtfully designed home offers an inviting living space just minutes from Portland’s vibrant waterfront, arts scene, and dining hotspots. Whether you're visiting with family, working remotely, or exploring Maine’s coastal beauty, this home is the perfect place to recharge after a day of adventure.brbr 5 min-Back Cove Trailbr 8 min-Old Port br10 min-Museum of Artbr10 min-Victoria MansionbrbrLicense Number: STHR-003971-2022brbr→ Sleeps 8 | 3 Bedrooms | Queen Bedsbr→ 2 Full Bathrooms with shower/tub combosbr→ Fully equipped kitchen with full-size appliancesbr→ Dining table seating 8br→ Dedicated workspace for remote workbr→ Smart TV + High-speed Wi-Fibr→ Washer & dryer in unitbr→ Mini-split heating & AC in every roombr→ High chair for familiesbr→ Free on-site parking + free street parking nearbybr→ Private balcony off the main living areabrbr☆☆ BEDROOMS ☆☆brbrOur three bedrooms are designed as serene retreats, blending coastal-inspired decor with modern comfort. Each room features premium bedding and thoughtful lighting, ranging from the nautical charm of the first room with its blue accents and individual climate control, to the sophisticated warmth of the second bedroom, which offers ample storage and a stylish workspace vibe.brbrWith queen-sized setups, the rooms provide flexible sleeping arrangements for all guests. You will find elegant touches throughout, such as full-length mirrors, designer rugs, and curated artwork, ensuring a restful and high-end experience that makes you feel right at home.brbr☆☆ BATHROOMS ☆☆brbrEach bathroom offering a unique aesthetic that ranges from contemporary chic to classic elegance. Guests can choose between refreshing glass-enclosed walk-in showers featuring custom mosaic tiling or unwind in full bathtubs equipped with sliding glass doors. Premium finishes are evident throughout, including marble countertops, sleek pedestal sinks, and high-end fixtures in varied finishes like matte black, polished chrome, and vintage brass.brbrDesigned for both comfort and style, these spaces are bright and airy, with windows that invite natural light to bounce off the crisp white subway tiles and intricate floor patterns. Thoughtful touches such as large mirrors, curated artwork—ranging from floral prints to coastal landscapes—and ample storage space ensure a boutique hotel experience. A convenient half-bath with a modern vanity rounds out the facilities, ensuring plenty of space for everyone to get ready with ease.brbr☆☆ KITCHEN & LIVING AREA ☆☆brbrNaturally bathed in sunshine, the social heart of this property features an expansive open-concept layout that seamlessly connects the fully equipped kitchen with the main living areas. Each kitchen is designed with a modern, high-end aesthetic, showcasing sleek charcoal or white cabinetry paired with premium stainless steel appliances and spacious islands that double as breakfast bars. These bright culinary hubs flow effortlessly into the dining spaces, where a grand wooden table for eight serves as a central point for shared meals and gatherings under elegant coffered ceilings.brbrThe living areas are similarly flooded with natural light, highlighting the plush sectional seating and sophisticated décor. With dual lounge spaces available, the home offers flexibility for large groups to either congregate together or find a quiet corner to relax. Every detail, from the ambient integrated lighting to the large windows and direct access to the private balcony, is designed to create a warm, inviting, and airy atmosphere throughout the day.brbr☆☆ LOCATION ☆☆brbrStay close to everything while enjoying the comfort of a residential neighborhood.brbrArts District (10 min) – Explore museums, galleries, local cafés, and creative energy along Congress Street.brbrState Theatre (10 min) – A historic venue hosting concerts and live performances.brbrOld Port & Eastern Promenade (10 min) – Cobblestone streets, waterfront views, boutiques, and top restaurants.brbrPayson Park (8 min) – A large green space with sports fields, walking areas, and outdoor recreation.brbrFort Allen Park (12 min) – Scenic coastal views over Casco Bay and historic landmarks.brbrGuests have full private access to the home, including all three bedrooms, two full bathrooms, the spacious living area, fully equipped kitchen, dining space, and dedicated workspace. Enjoy the convenience of in-unit laundry, Smart TV, high-speed Wi-Fi, and mini-split heating and air conditioning in every room. A high chair is also available for families.brbrFree on-site parking is available for one vehicle, with additional free street parking nearby. Entry is easy and secure via smart lock, and exterior security cameras provide added peace of mind. The home’s central location offers quick access to Portland’s restaurants, waterfront, arts scene, parks, and local attractions.brbrBy booking, you accept responsibility for any damage or extra cleaning they may be required during the stay.brbrSchena Group Properties, LLC, guests are automatically protected by the Waivo® damage protection program. The program offers the industry’s broadest protection. It’s damage protection done right.

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Sleeps

$203.23

/ Nightly

Condo

50 Exchange Street Portland 2B

Portland, Maine, United States

Step into timeless allure at this 1-bed, 1-bath gem in Portland's Old Port. This meticulously restored 1868 building seamlessly blends classic charm with modern luxury. The open floor plan features a King-size bed, an elegant walk-in shower and a pull-out sofa for flexible accommodations. The location immerses you in the Old Port's historic charm. Balancing history with comfort, this residence offers a stylish and sophisticated experience, inviting you to savor Portland's enduring allure.

1

Bed

1

Bath

2

Sleeps

$98.1

/ Nightly

Apartment

The Boat Berth on Peaks Island

Portland, Maine, United States

Feels like you have set sail-small bedroom with a balcony from the room in private home with adjacent bath. Steps from ocean and conservation land trail system. Small frig and microwave in room. Approx. hourly ferry service to Portland. Quiet,quiet…

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$217.38

/ Nightly

Condo

50 Exchange Street Portland- 3B

Portland, Maine, United States

Discover the timeless allure of Portland, Maine, in this exquisite 2-bedroom, 2-bathroom residence within a beautifully restored 1868 building in the historic Old Port district. The spacious interior features two bedrooms with private bathrooms, blending classic charm with modern comfort. Original architectural details evoke the rich history of the building, creating an ambiance that invites you to experience the best of Portland's waterfront.brImmerse yourself in the vibrant culture of the Old Port, where renowned restaurants offer the freshest seafood, galleries showcase local creativity, and eclectic boutiques line the streets. Come evening, enjoy the heartbeat of Portland with entertainment options just moments away. Whether you seek a quiet waterfront stroll or the energy of a night out, Old Port has it all.br

2

Bed

2

Bath

4

Sleeps

$465.72

/ Nightly

Apartment

Stylish Brownstone Downtown Free St|Perfect Getaway for 2

Portland, Maine, United States

Imagine strolling among the brownstones of the Arts District and Old Port admiring the vibrant history and architecture, just steps from your home base in this completely restored late 1800s brownstone 2nd-floor apartment.brbrAs you enter, you’re greeted by a warm and inviting space. The exposed brick and hardwood floors add a touch of history, while modern furnishings and appliances create a comfortable and stylish atmosphere. You’re drawn to the spacious living area with floor-to-ceiling glass overlooking Congress Street. It’s the ideal place to relax with a cup of fresh brewed coffee or your favorite glass of wine and watch the world go by. Your fully equipped kitchen is perfect for whipping up a snack using the freshest seafood from the local purveyor down the street. brbrAfter a fun filled day browsing the many local boutiques and galleries or cruising the bay there’s nothing better than pampering yourself in the roomy glass shower and toweling off with the plush white towels. Then it’s time to head out to experience the city’s diverse culinary masters, thriving nightlife and music scene of Portland.brbrA quick walk brings you back for a relaxing sleep in your new queen bed, finished with fresh luxe linens, in your eclectic and comfortable bedroom with large east-facing windows overlooking the Portland Museum of Art and views out to Casco Bay. As you drift off to sleep, you listen to the faint sounds of the city below. The hum of traffic, laughter of people still enjoying the evening and an occasional gull guarding its dinner. brbrThough this is a new apartment, we are not new to hosting. We have over 100 5 Star reviews showcasing our properties. This is the place to stay and have a wonderful time exploring the city of Portland. Don’t wait to book your stay!brbrSo beautiful and clean!! Spacious newly renovated apartment located in an 1890s brownstone in the center of the Arts District of Portland. Main entry into the brownstone is through a street-level door with keyless access to the shared stairwell. Your 2nd-floor walk-up apartment also has keyless access. There is no parking at your building as it is in a row of historic brownstones. On-street parking is free from 6pm-9am, free on Sunday, and major holidays. Otherwise, on-street parking is metered with a max of 2 hrs. A better solution is a nearby parking garage with 24 hr access for a fee of $19 per 24 hrs on weekdays and $28 on weekends, which is affordable in the city. I am here for you during your stay, but our level of interaction is up to you. I`m only a phone call/message away. you will be able to self check-in upon arrival.brbr*Walk-up apartment with stairs br*No parking br*No Smoking br*No Pets

1

Bed

1

Bath

2

Sleeps

$76.3

/ Nightly

Apartment

Peaks Island Retreat adjacent to miles of trails and steps from the ocean.

Portland, Maine, United States

Large, light and cozy upstairs studio apt with separate small space with door, perfect for a child or night owls :-). brLocated at the tiptop of the island with gorgeous starry nights and the sound of ocean waves to soothe you. Adjacent to conservation land and steps from the ocean. Efficiency kitchen with appliances (no oven), Full bath with tub and shower.brTelevision but no cable. Wireless internet.brbrFerry from Portland approx every hour @ 20 minute ride. Please check rates for passengers and cars at Casco Bay Ferry. Taxi on island, bike and golf cart rentals available. Large and well stocked grocery store open 7 days a week. In season restaurants. Public beaches. Tennis and pickleball courts with short term club membership.brIsland life is quiet and laid back with little traffic and lots of lovely oceanside and woods walking opportunities. Close to all that Portland has to offer, restaurants, museums and shops.

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Bath

Sleeps

$204.06

/ Nightly

Apartment

Beautiful Back Cove Area/ Maine the Way Life Should Be

Portland, Maine, United States

.*PLEASE READ ENTIRE DESCRIPTION* br Back Cove a beautiful area with an ocean inlet has a 3.5 mile bike & walking path. Close to Mackworth Island, City Center, Old Port Area, Restaurants, Shopping, Night Life, Music & Cultural Events. Wide variety of great restaurants & microbreweries. You’ll love this place because of the privacy and location. Portland's Working Waterfront w/ Ferry Excursions to Casco Bay Islands. Swimming, Boating, Fishing /30 min drive to Sebago Lake or Old Orchard Beach... br Our cozy studio apartment is a cute daylight basement walkout.. of a single family ranch.. in a very quiet & safe residential neighborhood just a stones throw from Back Cove, with three double hung windows and its own entry with motion sensor lighting by the door and security camera covering yard & walkway areas only. Motion sensor lighting covering the off street driveway parking. There is a deck just above apt entry that is part of the upper living area. Shower and toilet are raised about 3 inches to accommodate plumbing flow (pictured in photo) The bedroom has a brand new queen size DreamCloud Premier Hybrid Mattress with individually pocketed coils, several layers of memory foam... with the top layer infused with a cooling gel.... all covered with a plush cashmere Euro Top. We use 400 thread count ultra soft sheets. There is also a double high self inflating/deflating air bed w/linen... available if more then two people will be staying (extra guests $30/person/night) ... set up in living room. ( A raised twin air bed w/linen also available if requested for 2nd guest of 2 @ $15/night). Check in 3-5pm with a grace period up to 9pm. *After 9pm a $50 surcharge for late arrival . Check in takes about 15 minutes, Air conditioned in summer.. baseboard heat for cooler nights. Living room has two leather loveseats and lift top coffee table... great for enjoying take out while watching a movie, 55 TCL Roku wall mounted Flat Screen Smart HD TV, WIFI internet connection (with download speeds up to 300 mbs), , Netflix & Peacock for enjoying free movies & Alexa for your music listening enjoyment. Kitchen area has brand new full size refrigerator, microwave, new Keurig coffee brewer, frozen drink blender along with plates, bowls cups, glasses and utensils. (no stove in unit...this keeps cooking odors and safety issues in check for all upcoming guests). However ... there are many extraordinary restaurants in the area. Bathroom has toilet, vanity and shower ( due to height limitations shower stall is about 6 ft tall with new multi spray head) ** 10% Discount for bookings of 7 days or more!br.....We also offer a Personal 3 hr Boat Tour of pristine Sebago Lake & State Park or Casco Bay with it's many Islands, w/water views of Portland Headlight and Portland's working waterfront. Soft Drinks, Snacks, personal flotation devices & fuel provided. $125/pp (3rd person just $50 more)brbr*** (Check out Dan's Guide for great info on local restaurants and watering holes) brDan's Guidebook Maine the way life should bebrbrFood scenebrDiMillo's On the WaterbrGreat food, exceptional experience...seating available overlooking Portland Harbor (Free Parking....make sure to get your parking ticket validated) Reservations requiredbrbrStreet & CobrUnique dining experience....everything cooked fresh in saute pans... nothing fried... served directly to you in saute pan. Reservations requiredbrbrFore Street RestaurantbrJames Beard award winnerbrbrRí Rá Irish Pub & RestaurantbrUpstairs dining overlooks Casco BaybrDown stairs lounge comfortable sofas and relaxed atmospherebrbrJoe's Boathouse CateringbrGreat home style food... a must see ...popular with fisherman to lawyers try the blueberry pancakes with maine maple syrupbrbrStandard Baking CobrBest Bakery hands down... My personal favorite....Outstanding pastries and breads try a morning roll (buttery caramel roll), spectacular scones or lemon curd tart-let...you can't go wrong with any choice you make!brbrThe Great Lost BearbrCheck out this link http://www.greatlostbear.com/about.htmlbrbrLuke's Lobster Portland PierbrGreat place for any of your seafood desires. Located on Portland Pier overlooking Casco Bay.brbrThe Lobster Shack at Two LightsbrLocated by Two Lights Light House a great place to experience Maine's Rock Bound Coast and enjoy some of your favorite seafood dishes.brbrMekong Asian BistrobrGreat lunch specials under $10brbrBayou KitchenbrGreat place for Cajun style breakfast... just around the corner..delicious home fries and blueberry corn breadbrbrThe Porthole Restaurant & PubbrWaterfront casual restaurant with largest out side deck in city right on the water. Two lobster special. Music most weekends in summerbrbrFlatbread CompanybrWonderful wood fired pizza place on the waterfront with unusual combinationsbrbrBissell BrothersbrTip back a tall one Food available everyday but TuesdaybrbrThe Sinful KitchenbrVery popular breakfast eatery with a special gluten free menu as well.brbrMaine MallbrEverything you need for the holidays and more!brbrBoone's Fish House & Oyster Roombra landmark seafood restaurant on Portland Harbor since 1898 — featuring the original baked stuffed lobster, oysters and other local favorites. Boone’s has two spacious decks overlooking Portland HarborbrbrCasa NovellobrDelicious Italian Food reasonable pricesbrbrBack Cove BBQ & PizzeriabrA warm friendly atmosphere this Back Cove Eatery offers Comfort Food at its best!brbrBecky's DinerbrA Portland Landmark alon the waterfront great place for breakfast a real experience Fisherman 5am lawyers 8 am LOLbrbrNeighborhoodsbrBack CovebrInlet from Casco Bay with 3.5 mile path great for walking, jogging & bicycling. Part of Baxter Blvd Closed to vehicles on Sundays so families can use the space to playbrbrOld PortbrThe center of activity for Portland area. Great restaurants, pubs, shopping & night life.brbrEastern PromenadebrHighest point in the city ...Over looking Casco BaybrbrCity/town informationbrFreeportbrHome to LL Bean's Flagship Store just 20 minutes from home.brbrBoothbay HarborbrQuaint coastal town with a myriad of local restaurants and shops Home of Windjammer DaysbrbrOld Orchard BeachbrCool off at the beach take in surf sand and wavesbrbrSightseeingbrMackworth Island State Parkbr10 minute drive to put you on the coast of Casco Bay... Great Island hiking and exploringbrbrbrbrPortland Head Lightbr134 locals recommendbrbrDeering Oaks ParkbrHuge oak trees in a beautiful downtown park...complete with it's own duck pondbrbrSebago Lake State Park Beach or CampgroundbrEntire waterfront on sand bar all the way out in the lake...Crystal clear water... plenty of room to stretch out ... picnic tables and permanent charcoal grillsbrbrPeaks IslandbrTake Casco Bay Ferry over for a hike around the island and stop in for lunch, dinner or drinks at The Cock Eyed Gull or Island Lobster.brbrPortland Museum of ArtbrSeasonal Free Friday Admission 4-8pmbrbrDeering OaksbrBeautiful Park in the center of Portland that hosts many events and Saturday Morning Farmers MarketbrbrCasco Bay LinesbrTake a beautiful ride and bring a lunch if you like and explore the beautiful waters of Casco Bay on Casco Bay Ferry Mail Boat which goes twice a day to deliver mail to all the major islands on casco bay about 2 hour round trip reasonably priced inside and outside seating onboard ferrybrbrLocal Sport VenuesbrHadlock FieldbrIf you are a baseball fan then you'll enjoy watching the Portland Seadogs while enjoying a hotdog and cold brewbrbrEastern Trail ScarboroughbrThe Eastern Trail is a scenic 65 +- mile signed bike route that starts at the Piscataqua River in Kittery (at the New Hampshire border) and ends in South Portland, Maine. Great for cycling or hiking.brbrHadlock FieldbrCatch a afternoon game at the ball park

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$463.7

/ Nightly

Cottage

Ocean front cottage with private beach.

Portland, Maine, United States

Beautiful Maine cottage with extra large porch with rocking chairs and 200 degree views of Casco Bay. Charming 2 bedroom with one bath. Sun room with pull out couch for 3rd sleeping area. Fully equipped kitchen. Abutting sister cottage at 61 Evergreen Landing.

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$2,132

/ Nightly

Private Vacation Home

Steps from Old Port. New, Beautifully Appointed Home. Sleeps up to 11.

Portland, Maine, United States

Brand New Listing! Experience the best of Portland, Maine in this stunning, newly built home just steps from the working waterfront, world-class restaurants, boutique shops, and everything that makes Portland one of New England's most beloved destinations.brbrThoughtfully designed for groups up to 11, this spacious home offers an effortless blend of comfort, style, and function across three floors. The heart of the home is a chef's dream kitchen featuring a six-burner Wolf range, two dishwashers, and generous counter space — perfect for everything from a leisurely breakfast to an elaborate dinner party. This house is equipped with an elevator. The open-concept first floor flows seamlessly from kitchen to dining to living, creating an inviting space for gathering. Step outside to a deck with a gas grill that leads to a covered porch — ideal for morning coffee or evening cocktails in any weather.brbrFour bedrooms | 4.5 baths Two en-suite bedrooms offer private retreats, with an additional full bath serving the remaining bedrooms on the second floor. The open floor plan finished third floor provides flexible bonus space with its own full bath.brbrArriving by car No problem. The street level garage accommodates 3–4 vehicles — a rare luxury in Portland.brbrWhether you're planning a romantic escape, a family reunion, a friends' getaway, or a working retreat with colleagues, this home delivers an experience that's hard to match.

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Bath

Sleeps

$388.59

/ Nightly

Apartment

East End Guesthouse

Portland, Maine, United States

Newly renovated in 2023! brbrThe East End guesthouse is a stylish 1 bedroom apartment located parkside directly at the top of Portland’s Historic Munjoy Hill. Featuring designer and handmade furnishings, the 3rd floor loft has been thoughtfully redesigned for a serene and upscale stay.brbrFeaturing a large furnished deck overlooking the roofs of Munjoy Hill, a warm and inviting open living room and kitchen – recently renovated with all new appliances – and air conditioning. Off-street parking for 1 car is included.brbrThe location is quiet, safe, and very walkable. Only a 5-10 minute walk to either the Eastern Promenade Beach or the restaurants and shops on Washington Avenue, and a 20 minute walk to the Old Port.brbrThe guesthouse has 1 bedroom but can accommodate 4 guests with the use of an air mattress we are happy to provide.

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$267.05

/ Nightly

Private Vacation Home

Cozy, Quiet and Convenient

Portland, Maine, United States

This Portland house boasts 1 inviting bedroom with 1 king bed on the second floor. A sleeping loft with 1 queen bed with no door to access the bedroom you walk through the loft area. While there is laundry available access to the basement is a very steep set of stairs with a vey low ceiling. The 1st floor bath comes equipped with a hair dryer for your convenience. Step inside this adorable retreat and feel right at home. Relax in the cozy living space or whip up a delicious meal in the fully equipped kitchen. Book now and enjoy everything this house has to offer.

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$2563.32

/ Nightly

Private Vacation Home

Historic 1849 Sea Cpt. Mansion; Weddings, Groups

Portland, Maine, United States

Summary:brEnjoy the flexibility of 3 condos in this 1849 mansion that can accommodate up to 18 guests. Off street parking for 6 cars, private patio and 10 minute walk to Old Port.brbrLicense# STHR-004723-2022 & STHR-005205-2023brbrThe Space:brEnter through the historic front entry of the 1849 Cpt. Ingraham into the foyer. To the left, is unit one which features 2 bedrooms and 1.5 bathrooms and can accommodate 6 guests. At the top of the stairs, you will find two units that together provide 3.5 bathrooms, 4 bedrooms each with a queen bed and two sofa beds with additional sleeping for 4 guests. brbrbrUNIT ONE: Two Queen bedrooms w/queen sofa bed. (6 guests)brbrThe unit is uniquely divided between the first floor and lower level. Up the side stairs, you will enter through a private entrance.br brYou will enter into the kitchen area, which features a full kitchen stocked with everything you would need to prepare a meal in house. A full bathroom with in unit washer/dryer is off of the kitchen. Around the corner you will find a large office for working from home as well as a queen pull out sofa. On the right side of the entry, is a spacious living room with a fireplace (non-working). brbrOn request, the living room in this unit can be set up for dining with banquet tables and seats 12.brbrDown a set of stairs from the kitchen are the bedrooms. Each bedroom has a queen bed with premium mattresses and bedding. There is plenty of hanging storage and space to relax. One bedroom features a half bath. There is also a walk out door to the parking area for easy access to bring in luggage. br brbrUNIT TWO: One Queen Bedroom w/ full couch bed (4 guests)brbrThe second unit is on the second floor and to the right of the home. It features black and white accents and newly remodeled space. Step into a living room and well equipped kitchen space with high end appliances. The bathroom features a classic black and white mosaic floor and subway tile with duel rainfall and adjustable shower heads. It also features a grohe smart control. A stacked LG ThinQ washer/dryer finishes the space. brbrUNIT THREE: 3 Queen Bedrooms w/ 2 Queen sofa beds (10 guests)brbrThe third unit, features navy blue accents, skylights, historic brick walls, and wood beamed bedrooms. It encompasses the left side of the second floor and the entire third floor. The unit features a large living room with sectional. A bar table has seating for 8 and flows into a kitchen space with high end appliances and a half bath. Off of the kitchen is a private office space with a door that offers a queen pull out sofa and desk. brbrUp a second set of stairs, you will find 3 bedrooms and two full baths. The primary bedroom has a queen pull out sofa with en suite full bath. The other two bedrooms share a hallway full bath with a dual vanity, shower and washer/dryer.

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$554.45

/ Nightly

Apartment

Great 2 bedroom apartment on Munjoy Hill! Private backyard - walk everywhere!

Portland, Maine, United States

Beautiful 2 bedroom, sunny, modern apartment. Deck with gorgeous view of Casco Bay. Private,peaceful, beautiful yard with lawn furniture for your relaxation. Apartment is roomy and comfortable with touches of local art. All the amenities of home, toiletries, pots and pans, kitchen gadgets to superb linens. Walking distance to stores, restaurants and the Eastern Promenade and beach. Laundry in building... Parking available upon request. Short term (min 2 nights) or long term rentals available.brbrPlease email for better pictures... Will be upgrading waiting on photographer...

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$426.19

/ Nightly

Apartment

Fresh East End Apartment Walkable to Downtown Portland

Portland, Maine, United States

Kick back on the glossy green Chesterfield at this sunlit, loft-style retreat in Munjoy Hill with open shelving bursting with books and eclectic ornaments. Climb the ladder to the cozy mezzanine bedroom for an afternoon nap, then head out to explore.brbrMunjoy Hill is a safe, quiet area with beautiful water views, walkable to nearly anywhere on the peninsula. The gorgeous Eastern Prom park is a few blocks away, and a short walk or Uber ride will reach Portland's Old Port, restaurants, and breweries.brbrThis stylish, sunny apartment is fresh and new, and beautifully outfitted with finest linens and towels, glassware and all the comforts you would want. There’s a kitchenette with a small refrigerator and convection cooktop, microwave, toaster and coffee maker. But while the place is super comfy, this spot is best suited as a launching pad to go explore Portland. Set in the heart of Munjoy Hill, on Portland’s East End it’s just a few blocks to the gorgeous Eastern Prom park with the most stunning views of the water, and a trail system that winds down to East End Beach, a scenic waterfront park including walking trails, boat launch, kayak and stand up paddle board rentals. A short walk up the street will put you in the East End’s sweet little downtown, Belleville (exquisite bakery), Hilltop Coffee, Lolita Vinoteca & Asador, The Blue Spoon restaurant, and Rosemont Market & Bakery. One half mile away, about a 10-15 minute walk to the stretch of Washington Avenue that has several of Portland’s best restaurants and bars including Drifter’s Wife, Minato, Cong Tu Bot, Terlingua, The Shop by Island Creek Oysters, and Oxbow Brewing & Bottling, Maine Craft Distilling, Hardshore Distilling Company, and Maine Mead Works tasting rooms. The apartment’s location is also just a short walk or Uber ride to Portland's Old Port, and greater Portland’s remarkable restaurant scene, breweries, boutiques and galleries. This stylish, sunny apartment is fresh and new, and beautifully outfitted with finest linens and towels, glassware and all the comforts you would want. There’s a kitchenette with a small refrigerator and convection cooktop, microwave, toaster and coffee maker. But while the place is super comfy, this spot is best suited as a launching pad to go explore Portland. Set in the heart of Munjoy Hill, on Portland’s East End it’s just a few blocks to the gorgeous Eastern Prom park with the most stunning views of the water, and a trail system that winds down to East End Beach, a scenic waterfront park including walking trails, boat launch, kayak and stand up paddle board rentals. A short walk up the street will put you in the East End’s sweet little downtown, Belleville (exquisite bakery), Hilltop Coffee, Lolita Vinoteca & Asador, The Blue Spoon restaurant, and Rosemont Market & Bakery. One half mile away, about a 10-15 minute walk to the stretch of Washington Avenue that has several of Portland’s best restaurants and bars including Drifter’s Wife, Minato, Cong Tu Bot, Terlingua, The Shop by Island Creek Oysters, and Oxbow Brewing & Bottling, Maine Craft Distilling, Hardshore Distilling Company, and Maine Mead Works tasting rooms. The apartment’s location is also just a short walk or Uber ride to Portland's Old Port, and Portland’s remarkable restaurant scene, breweries, boutiques and galleries.

Bed

Bath

Sleeps

$1199.0

/ Nightly

Apartment

Superb Location! Heart of Old Port-Spacious Apartment

Portland, Maine, United States

Come explore the beautiful, historic and vibrant Old Port District when you stay at this stunning walk-up loft apartment situated at the epicenter! Just steps from the award winning restaurants, eclectic boutiques and exciting nightlife while breathing in the salty sea breeze from Casco Bay—this is the ideal getaway for family/group vacations, celebrations or business professionals who are looking to stay in the middle of the action. Enjoy the vaulted ceilings, original wood beams and exposed brick that tell tales of eras past. Your apartment is appointed with luxe linens, modern urban decor, lavish amenities and sleeps 9 guests. Complete with 3 bedrooms, each with an en-suite bathroom, fully equipped kitchen and spacious living area—what a way to experience the beautiful Old Port District!brbrPlease be advised your apartment is at the epicenter of the Old Port which is known for its nightlife and there will be outside noise from the restaurants and bars especially in the evenings and on weekends. We provide earplugs for your comfort if you may be retiring early and/or are noise sensitive.brbrThere is no dedicated parking for the apartment as it is right downtown in a row of brownstones. However, on-street parking is permitted free of charge from 6pm-9am, free all day Sunday and major holidays. Otherwise, is metered with a 2 hr max. Also, there is a parking garage directly across the street for a fee, as well as several other parking garages throughout the Old Port. brbrLooking for more space Sleep up to 16 by combining this listing with sister condo across the hall. In addition, if you’re interested in a more serene atmosphere, we own 3 gorgeous newly renovated apartments in the Old Port that can accommodate up to 14. Message me for details!brThere is a high probability of noise in the warmer months, especially on the weekend.

3

Bed

3

Bath

9

Sleeps

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