Vacation rentals with outdoor seating 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.

4.97 out of 5 average rating, 113 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 .

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, 127 reviews

Willard Square Charmer

Located in the center of Willard Square, a short trip into Portland, but also a vibrant neighborhood in its own right. Bakeries, restaurants,breweries, a short walk away. 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 cozy place in winter with plenty of room to relax after some exploring. We have installed whole house generators, so we've got you covered no matter what the weather brings .

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.

5 out of 5 average rating, 109 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, 101 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.

4.94 out of 5 average rating, 159 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.

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, 255 reviews

Luxury Apt, 7 min to Old Port, W/D, Street Parking

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, 190 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!

Apartment in Downtown Portland

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.

4.99 out of 5 average rating, 615 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.

Apartment in Cape Elizabeth

The airy living area features a neutral-toned sofa, complemented by two stylish chairs and a round glass coffee table. Soft light enters through two windows, and a vibrant abstract painting is displayed on the wall. Decorative lamps add subtle illumination.

4.99 out of 5 average rating, 274 reviews

Cape Elizabeth Garden Apt+Beach+Close to Portland!

Bright, airy, two-story, 1000 sf apartment, with view of gardens. Off-street parking and private entrance. First floor living area with kitchenette, and sofa-bed, for additional guests. Second floor king bedroom with full bath. Ideally located a short walk to Kettle Cove Beach, and just minutes from Two Lights State Park, Crescent Beach, Higgins Beach and Robinson Woods Trail. Portland - voted the best restaurant city in the US - is a 10 minute drive. STR Permit #210701.

4.98 out of 5 average rating, 107 reviews

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

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!

4.99 out of 5 average rating, 339 reviews

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

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.