Holiday houses in Old Port

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Top-rated holiday rentals in Old Port

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Guest favourite
The exterior of a classic Victorian building is displayed, characterized by its wooden siding painted in muted grey. Large windows and unique architectural details enhance its charm. Surrounding greenery adds a touch of nature to the urban setting, and a gravel path leads to the entrance.
Apartment in West End
4.78 out of 5 average rating, 772 reviews

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

Top Guest favourite
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, 621 reviews

Cozy * 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. No pets.

Top Guest favourite
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, 589 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 favourite
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, 449 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 favourite
A well-lit bedroom features a spacious bed with white linens and decorative pillows. A wooden dresser and side table provide storage and surface space. Natural light filters in through two angled windows above the bed, and a door leads to a small balcony.
Apartment in West End
4.99 out of 5 average rating, 636 reviews

*Serene* West End 2BR w/ Balcony: The Mermaid Cove

The Mermaid Cove is a bright and airy two-bedroom apartment located in Portland’s historic West End. This large private apartment is serene, yet only a few minutes walk to the center of downtown and the Old Port. Each of the two separate bedrooms are outfitted with a queen-sized Casper mattress. With a fully stocked kitchen and bathroom, separate office nook, laundry, and off-street parking, The Mermaid Cove is an easy and convenient place to call home for your visit.

Top Guest favourite
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, 116 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 favourite
A bright sitting room features large windows that invite natural light and offer views of the harbor. A round table with two chairs occupies the space, alongside a built-in seating area with cushions. A door leads to an outdoor deck, enhancing indoor-outdoor connectivity.
Guest suite in West End
4.99 out of 5 average rating, 354 reviews

Sunny West End Guest Suite w/Harbor Views and Pool

Enjoy views of the working harbor from this bright, two floor guest suite in the historic West End. The space features a garden oasis and seasonal, heated saltwater pool—just a short walk from the Old Port and Arts District. The suite is attached to our home but fully private, with its own entrance. (Portland City Permit: 20185360-ST) Note: Guests agree to indemnify and hold the property owners harmless from any liability for injury or property damage.

Guest favourite
A tranquil bedroom features a spacious bed covered with a light-colored bedspread. Soft light enters through a large window adorned with sheer curtains. A decorative mirror hangs on the wall, and a small chair is positioned near the closet, creating a calm and cozy environment.
Apartment in East End
4.93 out of 5 average rating, 650 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.

Guest favourite
A welcoming living area features a light gray sectional sofa adorned with various textured pillows. A wooden coffee table sits on a neutral rug, accompanied by a dark, upholstered chair. Natural light filters through the two windows, complementing the space's relaxed ambiance.
Apartment in West End
4.97 out of 5 average rating, 194 reviews

Downtown Historical Victorian 2 BR APT

The West End is one of Portland's most historical districts. The house is within walking distance of Long Fellow Square, and the Western Promenade. It is a great home base while exploring. From its rich history rooted in the Victorian era, to its parks and restaurants, Portland's West End is consistently ranked as a favorite local hotspot. New reno located on a popular street in a neighborhood filled with historic homes.

Top Guest favourite
A bright living area features large windows that provide ample natural light. Two comfortable chairs with colorful upholstery are arranged beside a small table, while a cozy couch with red accents complements the space. A vibrant piece of artwork adorns the wall, adding a touch of color.
Apartment in West End
4.98 out of 5 average rating, 350 reviews

Beautiful West End studio, hot tub, free parking

Charming, comfortable, well-appointed studio apartment, in an historic building, just steps away from everything downtown Portland has to offer: restaurants, museums, shopping, galleries, parks, Congress Street, and the Old Port. Close to Maine Medical and Mercy Hospital, the Portland Expo, Sea Dogs stadium, and Deering Oaks Park. The studio rental includes free parking for one car and exclusive use of a hot tub.

Top Guest favourite
The spacious great room features large windows that showcase views of the sunset and Portland skyline. A wooden dining table is set beside a cozy seating area, while soft lighting from lamps creates a warm ambiance. Unique decor adds character to the inviting space.
Guest suite in East End
4.99 out of 5 average rating, 199 reviews

Sunset Suite 42

Breathtaking views, privacy, and convenient location make Sunset Suite a great place to be while visiting ME! The great room with a cathedral ceiling and skylights offers the best of natural light... day and night! The Portland skyline is all yours from your private and expansive deck as you put your feet up and reminisce about your day and plan for the next.

Top Guest favourite
The kitchen features rich wooden cabinets and countertops, complemented by green walls. A dining area with wooden chairs is visible, illuminated by natural light. A potted plant adds a touch of greenery, while kitchen appliances are neatly arranged for convenience.
Apartment in West End
4.94 out of 5 average rating, 745 reviews

Cozy West End apartment minutes from the Old Port

This spacious one-bedroom apartment is located in a restored house built in 1845. A colorful, cozy space that boasts tons of character with original honey-colored hardwood floors. With plenty of on-street parking and a 10-15 minute walk to downtown and the historic Old Port, you can park your car and forget about it for a while.

Popular amenities for Old Port holiday rentals

  1. Airbnb
  2. United States
  3. Maine
  4. Cumberland County
  5. Portland
  6. Old Port