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 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.

4.88 out of 5 average rating, 41 reviews

The Wild Yard Home

This is a cozy, peaceful and centrally-located place. Rustic hand finished walnut headboards, live plants, and sun drenched afternoons will settle your soul! Enjoy sitting on the sunporch or taking a nap there on the couch. Walk or bike the neighborhood, to the beach or into Portland! Feel free to grab an egg from the chicken coop or pick berries from the vines. You’ll feel like you’ve escaped into a tree fort-type hideaway. Dogs allowed with prior approval. See House Rules for details.

Superhost

4.88 out of 5 average rating, 24 reviews

Walk to Restaurants & Waterfront | 5 min Portland

Welcome to the Knightville Retreat, a stylish 3 bedroom home in the heart of South Portland’s historic Knightville neighborhood. Steps from popular restaurants, cozy cafés, local shops, and waterfront views, this inviting retreat offers the perfect mix of comfort and coastal charm. Thoughtfully designed with warm decor and relaxing spaces, each room helps you unwind and feel right at home. Enjoy easy access to Portland’s Old Port, nearby beaches, waterfront parks, and South Portland’s charm.

A charming cottage is set against a backdrop of a serene pond. The white exterior is accented by a gray roof. Trees surround the property, and a small walkway leads to the front door. A peaceful atmosphere is conveyed by the clear, early evening sky.

5 out of 5 average rating, 25 reviews

Charming Cottage house, 2 bedrooms & Jacuzzi tub

Unwind with your family at this charming cottage, where comfort meets convenience. This vibrant, newly renovated home boasts a warm, colorful interior with a cozy patio overlooking a pond. Fully furnished, it includes all utilities and offers free parking on-site. Nestled in a quiet neighborhood yet steps away from downtown, this sunny cottage offers both privacy and access to city attractions. Enjoy a peaceful retreat close to the heart of the city—perfect for a relaxing, hassle-free stay.

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, 136 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.

Guest suite in South Portland

An aerial view captures a serene coastal neighborhood with waterfront homes and manicured lawns. The ocean sparkles in the distance, and several boats can be seen on the water. A well-maintained driveway leads to a residence surrounded by lush greenery.

4.97 out of 5 average rating, 105 reviews

Ocean Views, work friendly

This space is the lower level of a single family residence with separate entrance with views of the Casco Bay Ship Channel. More than simply a bedroom, there is a spacious living room with tv and computer workstation. There is a patio for relaxing as you take in the scenery. We are a short walk to Willard Beach, and we provide beach towels and chairs. There is no kitchen but we provide a coffee maker, and small fridge. Places for take out abound nearby. This is a great getaway for couples.

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, 209 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, 420 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.

4.95 out of 5 average rating, 219 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, 159 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.

4.86 out of 5 average rating, 7 reviews

Second floor 3BR/2BA Near Willard Beach & Portland

This bright and spacious second-floor apartment features 3 bedrooms and 2 full bathrooms, comfortably sleeping up to 8 guests. Located just minutes from downtown Portland, local beaches, and Fort Williams Park—home to the iconic Portland Head Light—it’s the perfect base for exploring Southern Maine. South Portland is conveniently located about 2 hours north of Boston and Acadia National Park is also about 3 hours away for guests looking to explore more of Maine’s natural beauty.

A cozy gas fireplace is featured in a modern living space, surrounded by warm wood accents. Nearby, a comfortable sofa with decorative cushions offers a relaxing spot. The lower left corner shows a unique hanging chair, nestled in a natural environment, enhancing the tranquility of the area.

4.95 out of 5 average rating, 266 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.

Popular amenities for South Portland holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in South Portland

A comfortable living room features a teal sofa and a wooden coffee table on a patterned yellow rug. A ceiling fan circulates air, while natural light streams through large windows. A cozy armchair and a workspace with a chair are also present.

4.94 out of 5 average rating, 105 reviews

Willard Square Family Home

Superhost

A Mongolian yurt is surrounded by lush greenery, featuring vibrant plants and decorative sculptures. The yurt's exterior displays traditional designs, while a stone birdbath and seating area with cushions invite relaxation in the private outdoor space.

Yurt in South Portland

4.79 out of 5 average rating, 113 reviews

Yurtvana

Guest suite in South Portland

4.91 out of 5 average rating, 76 reviews

Studio near beaches/restaurants

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.

4.96 out of 5 average rating, 80 reviews

Willard Beach-Cute Cottage in Peaceful Community.

An open-concept living area features a comfortable sofa with colorful cushions, two accent chairs, and a light wooden coffee table. Natural light fills the space through skylights and windows, enhancing the airy atmosphere. A modern kitchen is visible in the background, along with a dining area.

4.98 out of 5 average rating, 43 reviews

Beautiful loft in Knightville, minutes to Old Port

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

An aerial view showcases a coastal neighborhood adjacent to a sandy beach. The coastline stretches along the blue waters, dotted with sailboats. Nearby structures with varying colors and sizes are visible, along with trees and vehicles on the street.