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, 135 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, 135 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, 104 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, 206 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.

4.91 out of 5 average rating, 241 reviews

Willard Square - The View

5 minutes to the beach , private deck , cozy apartment just a stone's throw from Scratch Bakery. Grab a bagel, or my personal fave, almond horseshoe, and relax on the deck stroll to the beach. One bedroom apartment on the third floor, fully equipped kitchen. Everything you need for a weekend or a winter rental. The stairs are steep and may not be appropriate if you have mobility issues. sloped ceilings . First response is alaways , "It's so much bigger than the photos show. Fast wifi .

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.

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, 300 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

4.95 out of 5 average rating, 217 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, 158 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.

Superhost

4.75 out of 5 average rating, 4 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.

4.94 out of 5 average rating, 144 reviews

The kitchen features modern stainless steel appliances and a spacious countertop with a light wood finish. Bright bay windows allow natural light to illuminate the area. A classic mantle adds a touch of historic charm, while overhead lighting enhances the contemporary design.

Apartment in Portland

The Margaret at Hawley Marie w/ Parking

Work + play in this modern retreat featuring original architecture with updated amenities. The sunny bay windows flood the living room with light, while the rest of the space benefits from lofty ceilings and an open floor plan. The en suite bathroom has new tiled floor and backsplash, while the kitchen features a beautiful white quartz countertop with stainless appliances. The convenient location and free, private parking is really the cherry on top of this beautiful space!

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.

Popular amenities for South Portland holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in South Portland

4.94 out of 5 average rating, 103 reviews

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.

Home in South Portland

Willard Square Family Home

4.89 out of 5 average rating, 73 reviews

Aerial view of a coastal neighborhood showcases a mix of homes surrounded by lush greenery. The nearby waterfront features boats gently bobbing in the calm water and trees lining the shore. The expansive horizon reveals a peaceful seaside atmosphere.

Condo in South Portland

Arlie's Digs! - One Block To Willard Beach!

Guest suite in South Portland

4.91 out of 5 average rating, 76 reviews

Studio near beaches/restaurants

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.

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.

4.83 out of 5 average rating, 42 reviews

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

4.87 out of 5 average rating, 38 reviews

The living room showcases a dark sofa and a large television on a white media unit. A teal accent wall provides color, while a decorative area rug lies beneath. A potted plant adds a touch of greenery, and natural light streams through the window with light-colored blinds.

Home in South Portland

Spacious Duplex in South Portland

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.