Holiday houses in South Portland

A spacious dining area is illuminated by natural light from large windows. A simple wooden table is set with a decorative pumpkin and surrounded by four light-colored chairs. Green plants are placed on the table and near the windows. A woven basket adds a touch of warmth to the room.

4.94 out of 5 average rating, 136 reviews

Willard Square Charmer

Located in the center of Willard Square at 7 Pillsbury, 5 minute walk to Willard Beach. Shops restaurants and bakeries all in walking distance. Ideal for working remotely or just checking out the area. Grab a bagel and a coffee across the street from Scratch and stroll to the beach , it's a 5 minute walk.Portland Headlight is a mile away. Lots of room for remote work or a vacation . Well stocked kitchen, quality linens and space to relax after exploring the neighborhood, or visit to 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, 131 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 .

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.

4.99 out of 5 average rating, 133 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.

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.

4.93 out of 5 average rating, 205 reviews

Sopo Abode

Welcome to your garden oasis. Your home away from home. This elegantly styled garden level apartment in South Portland's crown jewel neighborhood, Sylvan Sites, is spacious, calm, 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.

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.

4.92 out of 5 average rating, 417 reviews

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.

A modern kitchen is highlighted by sleek cabinetry and a dark countertop. A black refrigerator, microwave, and stove are visible. Natural light enters through two windows, illuminating a vase of sunflowers beside a small potted plant. A textured area rug adds warmth to the space.

4.96 out of 5 average rating, 297 reviews

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

4.96 out of 5 average rating, 216 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!

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, 156 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.

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, 176 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.

4.89 out of 5 average rating, 111 reviews

Home in West End

Mary J. Eastburn House-Eastburn Suite

City of Portland Reg. No. : STHR-002888-2021 Perched on a quiet street corner on Portland's Western Promenade, this historic residence enjoys what Longfellow called the "rarefied air of this little town by the sea," spectacular sunsets, and commanding views of the White Mountains. Built in 1891, the Mary J. Eastburn House now offers 3 private and exclusive guest suites for those who enjoy the grandeur of the past, updated with the luxuries and technology of the present.

A serene ocean view is captured at dusk, with a bright full moon reflecting on the water's surface. The shoreline is lined with smooth rocks, while distant lights from a coastal town softly illuminate the horizon beneath a cloudy sky.

4.95 out of 5 average rating, 264 reviews

Willard Beach: Cozy Apartment with a King Size Bed

This luxurious first floor apartment is filled with sunshine all day long and on chilly nights the gas fireplace provides a warm ambiance. We think you’ll especially enjoy sinking into the velvet covered king size bed at night and stepping into the spacious shower that includes a rainfall shower head along with a handheld ... use either or both, as you please! The kitchen is equipped with quartz countertops, solid cherry cabinets and high end stainless steel appliances.

The kitchen and living area feature warm wooden floors and reclaimed beams. A central island offers seating at two bar stools, while a round dining table with four chairs provides additional space. Large windows allow ample sunlight, highlighting the colorful decor and brick wall.

4.9 out of 5 average rating, 219 reviews

Sunny and beautiful brick house apartment

This beautiful and cozy apartment was renovated by our own hands, with energy efficiency and craft in mind. The space is an opened kitchen/living room with 2 bedrooms. Reclaimed beams and old wood mix with fun colors and gorgeous full sunlight. A lush organic garden surrounds the house with backyard chickens. Set on a quiet street, walking distance to Willard Beach & Scratch bakery, 5 minutes to Portland Headlight and 10 minutes to Portland's Old Port.

Popular amenities for South Portland holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in South Portland

A cozy living area features a beige sofa adorned with colorful pillows, complemented by a small white coffee table. A work desk is positioned nearby, illuminated by natural light streaming through the large windows. A potted plant adds a touch of greenery.

4.87 out of 5 average rating, 31 reviews

Quiet Work/Stay Space near Beaches & Old Port

4.96 out of 5 average rating, 80 reviews

The exterior of the home is framed by a colorful garden filled with various flowers and greenery. A winding gravel path leads to the front door, bordered by vibrant blooms, creating a welcoming entrance. Sunlight illuminates the scene, enhancing the natural colors.

Home in South Portland

Willard Beach-Cute Cottage in Peaceful Community.

Guest suite in Scarborough

4.92 out of 5 average rating, 61 reviews

Poet's Nook: Cozy and Private 1BR Apartment

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, 72 reviews

Stylish New Apartment Near Willard Beach w/ Yard

The charming exterior of the apartment features a red facade with large windows. A welcoming entrance door is flanked by flowering shrubs and greenery. A brick pathway leads up to the entrance, creating an inviting approach to the property.

4.98 out of 5 average rating, 50 reviews

Vista Views Apt

Apartment in Downtown Portland

A spacious living area features exposed brick walls and large windows, providing ample natural light. A comfortable sofa and two accent chairs are arranged around a stylish coffee table. A chandelier hangs above, and a television is positioned on a console in view.

4.94 out of 5 average rating, 54 reviews

Old Port Loft - 301

5 out of 5 average rating, 68 reviews

A comfortable living area features a gray sofa adorned with orange cushions, complemented by a wooden coffee table. A wall-mounted TV is positioned above a modern fireplace, with large windows allowing natural light. An expandable dining table is set against the wall, with a simple bowl as decor.

Tiny home in Scarborough

Southern Maine Tiny Home Cottage