Vacation rentals in Old Port, Portland

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Top-rated vacation rentals in Old Port, Portland

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Top guest favorite

The living room features a comfortable sectional sofa and two armchairs arranged around a coffee table. A large flat-screen TV is positioned on a rustic entertainment unit. Natural light fills the space through three windows, enhancing the warm, neutral wall tones.

Apartment in East End

4.98 out of 5 average rating, 579 reviews

Amazing Views! Perfect Location. Loft style feel.

Oh the VIEW! City views and a beautiful park like old cemetery. Cozy, sunny private apartment in a quiet, Owner Occupied building. Perfect East End location for exploring all of Portland Just 2 blocks from Duckfat, Eventide and many restaurants, breweries and distilleries Comfy living room with a 55" TV and seating to take in the view. Fully equipped eat in kitchen, tile shower and a wonderful King size bed to watch the sun rise Includes Reserved Off street parking. License #STHR-000980

Guest favorite

The kitchen features modern stainless steel appliances, including a range and microwave. Granite countertops provide ample workspace, along with white cabinets for storage. A coffee maker and various utensils are neatly arranged, contributing to a functional and well-equipped cooking area.

Condo in Downtown Portland

4.87 out of 5 average rating, 428 reviews

Renovated Exchange St. Loft w/Free Parking

This renovated loft-style condo is right in the heart of the Old Port. Located on Portland's bustling Exchange Street, the loft is central to everything the Peninsula has to offer. Elevator access will take you from the apartment to the secure lobby. From there, shops, restaurants, night life and the working waterfront are just steps outside the door. Free off street parking is available for one car a few blocks away or a convenient pay-to-park garage is located next to the building.

Top guest favorite

A spacious living area features a comfortable sofa, accentuated by a decorative throw pillow. A round coffee table centers the space, while a patterned area rug adds texture. The open kitchen is visible in the background, equipped with modern appliances and ample cabinetry.

Apartment in East End

4.98 out of 5 average rating, 608 reviews

Modern* Awesome Location * With Parking

Well -appointed one bedroom in Portland’s best neighborhood, the East End. A ten-minute walk to the Eastern Prom or the restaurants of the Old Port. This first-floor apartment has a modern vibe with artwork from local artists. I pay attention to details such as cleanliness, local coffee and Brooklinen linens and towels. Bathroom Newly Renovated 2023. TV is Roku Off-street parking included. One bedroom w/a queen and a queen sleeper-sofa. This is a non-smoking and non-vaping space.

Guest favorite

An open dining area features a round wooden table surrounded by blue chairs. A comfortable living room area is visible, with a gray sofa and art on the walls. Large windows allow natural light to brighten the space, enhancing the modern design.

Apartment in East End

4.98 out of 5 average rating, 107 reviews

Harborview - Curated East End Escape w/ Parking

Harborview is a newly renovated, top-floor apartment perched on the edge of Munjoy Hill in Portland's East End. This home is a short stroll to the Eastern Promenade and the East End Beach, the Casco Bay Islands Ferry Terminal, and the historic Old Port. The apartment features a spacious open kitchen, dining, and living room floor plan adjoined by a large private deck. It's the perfect spot to gather, relax, and dine while enjoying the breathtaking views of Casco Bay!

Top guest favorite

A modern living area is designed with large floor-to-ceiling windows that provide sweeping views of the marina and cityscape. A sleek black sectional sofa and matching ottoman are paired with a cozy armchair, accented by a striped red area rug on the hardwood floor.

Condo in Downtown Portland

4.97 out of 5 average rating, 218 reviews

Waterfront Two Master Suite Penthouse with Rooftop

2023 City of Portland Registration #20185280-ST Penthouse suite w/modern amenities, exposed beams and brick, poplar walls. Rooftop deck w/views of harbor and city. Separate master suites with custom showers and one with soaking tub. Gas-fired Jotul stove in living room. Washer/dryer in unit. Easy elevator access. Spacious kitchen with granite countertops and wine cooler. Please note: animals (including assistance animals) not allowed due to owner's health.

Top guest favorite

A spacious sleeping area features a queen-sized bed with soft linens and a cozy blanket. A flat-screen television is positioned on a sleek sideboard, while large windows allow natural light to brighten the room. A small table and chair are placed near an additional seating area.

Guest suite in East End

4.92 out of 5 average rating, 303 reviews

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!

Guest favorite

A cozy sleeping area is featured, with a spacious bed adorned in neutral tones and a textured navy blanket. Exposed brick accents one wall, adding character. Soft lighting is provided by bedside lamps on wooden nightstands, while a hint of greenery is noted from the nearby curtains.

Condo in Downtown Portland

4.99 out of 5 average rating, 163 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

Guest favorite

A studio loft features exposed brick walls and wooden beams overhead. A spacious bed is positioned beside large windows with blackout shades. A cozy seating area contains a light-colored sofa and a round table. Green plants add a touch of nature to the inviting space.

Apartment in Downtown Portland

4.95 out of 5 average rating, 688 reviews

Modern Studio Loft w/ Parking in Perfect Location

This spacious and comfortable studio loft is in the heart of Portland's Arts District. Located on the quieter end of Oak Street, the studio is within walking distance of everything Portland's peninsula has to offer. Complementary parking for one car is provided in a nearby lot. 2025 City of Portland registration STHR 000854

Top guest favorite

A spacious living area displays a deep L-shaped sofa adorned with cozy throw blankets. A textured area rug anchors the seating area, while natural light pours in through the skylights. A small plant and accent tables complement the modern decor.

Apartment in Downtown Portland

4.98 out of 5 average rating, 112 reviews

Chic Portland Penthouse, 2BR

Enjoy a stylish experience at this centrally-located place. We are in the middle of all the excitement in the Old Port. Ride down the elevator and just out our front door you are steps to all the best that Portland has to offer. Shops, dining and night life all conveniently at your door step.

Top guest favorite

A light-filled living area features two sofas, one covered in white fabric and adorned with decorative pillows. A wooden coffee table sits at the center, complemented by a vase of flowers. Natural light enters through three large windows, enhancing the warmth of the pumpkin pine flooring.

Apartment in West End

4.95 out of 5 average rating, 336 reviews

AMAZING! Working waterfront views, 94 walk score!

Wow! Incredible 3 bedroom, 2 bath apartment with working waterfront views. Spacious apartment nestled in Downtown, between the Old Port, Arts District and West End, just steps away from all the highlights of the peninsula. You are truly in the heart of the City. STHR-000508-2018

Guest favorite

A bright hallway features wooden flooring and natural light filtering through large windows. Exposed wooden beams and a brick wall add character. A cozy seating area with red sofas is visible at the end, alongside a modern kitchen space. A bathroom door is located to the left.

Apartment in Downtown Portland

4.94 out of 5 average rating, 701 reviews

Extraordinary Architectural Masterpiece Downtown

Dan's place is close to nightlife, public transport, the city center, and parks. You’ll love his place because of the ambiance, the outdoors space, the light, the neighborhood, and the comfy bed. The suite is perfect for couples, solo adventurers, and business travelers.

Top guest favorite

A patio area features white Adirondack chairs facing a scenic view of the water. Colorful flowers in various pots add vibrancy to the space, while an American flag gently flutters in the breeze. The tranquil waterway is visible beyond the floral arrangement.

Guest suite in South Portland

5 out of 5 average rating, 820 reviews

Oceanfront with amazing views and private entrance

This private space has unmatched water views, a hot tub overlooking the ocean and its own entrance. We are a short drive to downtown Portland, in a quiet neighborhood that's walkable to the beach and several restaurants. It's the best of all possible worlds!