Holiday houses in South Portland

A spacious studio layout is visible, featuring a comfortable sectional sofa adorned with a mix of neutral and dark cushions. A large bed is situated in the background, accompanied by a soft area rug and warm wooden flooring, creating a relaxed atmosphere. Natural light enters through multiple windows.

4.98 out of 5 average rating, 162 reviews

Cozy South Portland studio with King bed! REG107

Welcome to our studio! Stocked with all you need! Short walk away from the green belt trail & ocean views. Just 5 minutes away from Fort Williams home to the most photographed light house in America. We are a walk away from bug light,and spring point and if you feel like a beach day Willard beach is 5 minutes away. Don't forget to stop at scratch bakery or the cookie jar for a coffee and treat. Portland's Old Port is just a 10 minute uber ride . FYI ,entrance is in back up a flight of stairs .

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The bedroom features a spacious bed dressed in light-colored linens, accompanied by a cozy seating area with a neutral-toned sofa. Two framed artworks are displayed on the wall, and a lamp provides soft illumination, creating a peaceful and restful environment.

4.98 out of 5 average rating, 156 reviews

Cozy SoPo Condo

Welcome to this cozy one-bedroom apartment in Ferry Village, South Portland, Maine. This charming neighborhood is located just across the Casco Bay from Portland, and it's the perfect place to relax and admire the natural beauty of Maine. Enjoy a tour of our gardens and relax on the string light lit patio. The apartment is located on a quiet street, less than a mile walk from Willard Beach. Take a walk on the Greenway to Bug Light park or towards Knightville for some food and drink options.

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Guest suite in South Portland

A serene beach scene is captured, featuring a gentle shoreline with soft sand. Small boats are anchored in the calm water, while a lush green landscape forms the backdrop under a partly cloudy sky. Sunlight reflects off the waves, creating a sparkling effect.

Apartment Walking Distance to Willard Beach

Our South Portland in-law suite is on a private floor & has its own private entrance at the back of the house. It is a 1 bedroom, 1 bathroom space with a fully stocked kitchenette and free parking. You'll love being only a 5 minute walk from Willard Beach and walking distance to 2 different lighthouses: Spring Point and Bug Light. You'll also be a 10 minute drive to Old Port. You'll have access to a shared, fenced-in backyard. South Portland Short Term Rental License #: STR2020-0022.

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4.92 out of 5 average rating, 442 reviews

4.96 out of 5 average rating, 323 reviews

Sunny Apt, 7 mins to Downtown, W/D, Café

A sunny, private, spacious, recently renovated 1 BD apartment in a quiet neighborhood in South Portland. New kitchen and 2 luxury bathrooms with shared seasonal back patio. Enjoy the new Second Rodeo Cafe next door. Minutes to the beach and downtown Portland. Enjoy Bug Light Park, the Eastern Greenway Trail, and Scratch Bakery; you are close to it all. Please note: From December through March, we have off-street parking space for only one vehicle. We are owner-operated. Lic#2764

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4.96 out of 5 average rating, 234 reviews

A cozy living area features a brown leather sofa and two woven armchairs flanking a wooden coffee table. Light flows in through two large windows with sheer curtains, creating a bright, inviting space. A decorative rug adds warmth to the floor.

Condo in South Portland

Rustic Willard Beach condo ten mins from Old Port!

Second-fl unit in historic 150-yr-old building one block from South Portland's premiere beach! Minutes away from historic Portland Head Light and Downtown Portland. Quaint, spacious and tucked away in charming Willard Square. Brand new kitchen and bathroom! Perfect for families, friends, or couples looking for a relaxing coastal retreat. World-famous Scratch Baking across the street, and the Old Port's incomparable restaurants, shopping and historic architecture across the Bay!

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A bright living area features a yellow loveseat, a gray circular chair, and a glass coffee table on a woven rug. A vibrant accent wall with colorful patterns adds a lively touch. A potted plant and a lamp complete the cozy ambiance.

4.94 out of 5 average rating, 182 reviews

Sunny Spot with Private Parking

This cozy, 1 bedroom apartment is located in the peaceful neighborhood of Knightville. The Portland Peninsula, which includes the historic Old Port and the downtown arts district, is less than a 10-minute drive across the bridge. The perfect spot for a couple or a fun friend getaway! Several excellent dining spots, coffee shops, and markets are all within walking distance from the house. Bike rentals are 2 blocks away! The local beach is a 5-minute drive /10-minute bike ride.

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A cozy sleeping area features a spacious bed dressed in a navy quilt, complemented by decorative pillows. The green walls are accented by a wooden wall art piece and hanging light fixtures. Nightstands with potted plants add a touch of greenery to the scene.

4.98 out of 5 average rating, 195 reviews

The Knightcap

Welcome to The Knightcap! Located in the wonderful area of Knightville, just across the bridge from Portland, Maine. In our neighborhood, you will find restaurants, a brewery, diner, grocery stores, and many shops. All within quick walking distances. Portland is a renowned foodie destination. We have everything here. Enjoy our beautiful working waterfront, great restaurants, shops, and the fantastic history and architecture. Or maybe have a relaxing night before a big hike.

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A bright bedroom features a queen bed with an ornate wooden headboard, flanked by two stylish wall lamps. Sliding glass doors provide access to the outdoors, while clerestory windows invite natural light. A cozy rug complements the wooden flooring, enhancing the spacious feel.

4.92 out of 5 average rating, 233 reviews

Sopo Abode

This elegantly styled garden level apartment in South Portland's crown jewel neighborhood, Sylvan Sites, is beautifully finished, spacious, and inviting. Have a sit in your private sauna, and take in the abundant birdsong of the neighborhood from your private back patio while you sip your morning coffee. Just down the road (5 minutes) to downtown Portland, Willard Beach, or Knightville, and 10-15 minutes to Scarborough and Cape Elizabeth beaches.

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5.0 out of 5 average rating, 55 reviews

The Nest

"The Nest," your serene one bedroom nestled in a quiet neighborhood just 10 minutes from downtown Portland. Owned by a local family, Ideal for solo travelers or couples seeking a peaceful getaway, "The Nest" features a generously sized bedroom, cozy living area, a fully equipped kitchenette and back deck. Whether you're here for business or leisure, "The Nest" provides a welcoming haven where you can relax after a day of exploring.

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4.94 out of 5 average rating, 84 reviews

Bright and Minimalist Home!

Stay in a sunny, cozy and colorful home, with a minimalist design concept and plenty of plants all within walking distance to Bug Light and Willard Beach. Home has easy access (by car, bike or bus) to all the amazing restaurants, coffee shops (including Second Rodeo, two doors down from our home) and beaches of the Portland area. We have a driveway for your use! This is our home, but we will be away during your stay.

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5.0 out of 5 average rating, 10 reviews

Sleeps 5 • Near Beaches-Downtown Portland -Parking

Enjoy the best of Southern Maine from this bright and comfortable first-floor apartment. Located just minutes from downtown Portland, local beaches, breweries, restaurants, and Portland Head Light, this 2-bedroom retreat comfortably sleeps up to 5 guests and includes free parking and high-speed Wi-Fi. About 2 hours from Boston and 3 hours from Acadia National Park — a great home base for exploring Maine.

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The image features a cozy hanging chair surrounded by decorative stones, set beneath a leafy structure. A beach scene is visible in the background, showcasing a sandy shoreline with umbrellas and the ocean. A simple living area is also highlighted with a neutral sofa, coffee table, and a shelf adorned with flowers.

4.91 out of 5 average rating, 280 reviews

Willard Beach–Apartment Near Portland & Parks

Many guests have remarked that this stylish, first floor apartment is much larger than it appears in the photos. Just a 4 minute walk to the beach and a ten minute drive to downtown Portland it’s the perfect home base for exploring everything the area has to offer! Jess is a fifth generation Mainer and is happy to answer any questions you may have as you plan your trip!

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Popular amenities for South Portland holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in South Portland

An aerial view captures the coastal neighborhood with a sandy beach extending along the shoreline. Classic homes and vehicles are visible, with the ocean revealing clear blue waters and scattered sailboats. The inviting beach area offers space for sunbathing and beach activities.

4.86 out of 5 average rating, 49 reviews

Willard By the Sea - 30 ft to the beach- 1st floor

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A charming two-story farmhouse is showcased, featuring a front porch with steps leading to a bright entrance. The light grey exterior complements the lush green landscaping and clear blue sky. The surrounding pathway presents ample space for parking and access to the neighborhood.

4.91 out of 5 average rating, 23 reviews

Willard Square Farmhouse

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A cozy bedroom is seen featuring a spacious bed adorned with a patterned blanket. Two large windows let in natural light, while a soft carpet covers the floor. A dresser and an open closet are present, providing ample storage, and wooden accents add warmth to the space.

4.9 out of 5 average rating, 50 reviews

The Wild Yard Home

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4.97 out of 5 average rating, 34 reviews

Charming Cottage house, 2 bedrooms & Jacuzzi tub

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4.84 out of 5 average rating, 32 reviews

Maine Coastal Getaway

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5.0 out of 5 average rating, 41 reviews

A living area is presented with a comfortable brown sofa and an accent chair, complemented by a coffee table. A television is positioned on a stand across from the seating arrangement. Large windows provide ample natural light, while a decorative rug adds texture to the hardwood floor.

Home in Cape Elizabeth

Pastoral Tranquil Walk to Trails Dining Shopping

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A welcoming living area features a leather sofa and two patterned armchairs arranged around a light-colored coffee table. Artworks are displayed on the white walls, complemented by natural light from large windows. A tall green plant adds a touch of nature to the space.

4.99 out of 5 average rating, 86 reviews

Stylish New Apartment Near Willard Beach w/ Yard

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