Holiday rentals with outdoor seating 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, 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 .

4.92 out of 5 average rating, 676 reviews

A cozy living and dining area features comfortable seating, including a pair of light-colored armchairs and a round dining table. Soft lighting illuminates the space, and decorative accents, such as art and plants, create a welcoming atmosphere.

Flat in Cape Elizabeth

Portland + Cape Elizabeth + Beaches + luxurious!

Permit210780 •Luxurious 3 rm apt with 1322 5* reviews! Only a mi to the beach & 4.4 mi to Portlnd - Location! •1st flr Great Rm to dine & relax: microwave, fridge, toaster, Keurig, TV, cooktop •2nd flr huge bathrm & bedrm for 2 w/ another sitting rm + a 2nd bdrm w/ 1 Q & 2 twins •More than 2 people? Alter reservation #’s for additional cost •2 people wanting 2 bedrms? Only add a $50 cleaning fee for 2nd bdrm •luxurious furnishings & superior bedding! •I am known for thinking of EvErYtHiNg ;-l

4.96 out of 5 average rating, 164 reviews

A private pool area features a colorful inflatable parrot floating in clear water. Surrounding the pool are several lounge chairs arranged for relaxation. Lush trees provide shade, and a fence ensures privacy for the space, which is brightly illuminated by natural sunlight.

Home in Portland

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

Your crew will be close to everything when you stay at this centrally-located place with a pool and spacious yard! Enjoy the home and it is a quick 10 minute uber to downtown Portland to the most popular shops and restaurants. This home is located perfectly to explore greater Portland from beautiful parks/trials to the shopping outlets not far away. This is a family neighborhood and out of respect for my neighbor’s, no loud partying after 10 pm. City of Portland License #: STHR-004465-2022

4.98 out of 5 average rating, 397 reviews

A bright studio apartment features a spacious bed with neutral bedding, complemented by a plush area rug in a geometric pattern. Large windows offer natural light and a view of the outside. A small dining area with two stools is visible in the background next to the kitchen.

Flat in West End

Quiet West End Retreat - parking - 100% Non Smoker

Quiet, 2nd story sunny studio apartment in owner-occupied 4 unit building conveniently located in the historic West End residential neighborhood. It’s a short walk to all that Portland has to offer. Off-street parking for 1 car. Relax on the patio and soak in the summer warmth. Perfect for a single or couple traveling to the area. No complicated checkout procedures! Just leave the key in the lock on your way out and we will take care of the rest. 100% Non- smoking guests only, No Exceptions.

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.

5 out of 5 average rating, 115 reviews

An open living area is highlighted by large windows that frame scenic views of the marsh. A modern gas fireplace serves as a focal point, while a light-colored sofa and a small table with a plant create a welcoming ambiance. Bar seating for four extends to the kitchen.

Home in Higgins Beach

Higgins Beach *New* Beach Home & Private Offices

Custom designed contemporary at the beach. Perfect for a relaxing getaway, visiting family and friends or working remotely. Chef's kitchen w/ high end appliances, granite countertops, enclosed porch grill area. 3 bedrooms and 2 private offices Huge windows and amazing views from all of the rooms highlight the natural beauty of high tides, sun rises and sun sets. Wonderful beachfront walks and beautiful surroundings inside and out. Easy proximity to Portland's Old Port.

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, 299 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

Apartment in South Portland

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.

4.96 out of 5 average rating, 216 reviews

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 seating area is featured with an orange sofa and a blue chair. Modern cabinetry lines the wall beside a kitchenette. Large windows allow natural light and provide a view of the private outdoor seating area, which includes a small table and chairs.

5 out of 5 average rating, 207 reviews

Private Garden Retreat on Munjoy Hill

This well-appointed, new space is located on first floor of a modern, new home on Munjoy Hill - Portland’s most charming neighborhood. This convenient suite has a separate, private entrance with a private outdoor seating area. The location is perfect for walking - just minutes to excellent restaurants, coffee shops, gourmet market, Eastern Promenade, St. Lawrence Arts Center and Washington Avenue. Portland’s Old Port and bustling harbor is just a 10 - 15 minute walk down the Hill.

Popular amenities for outdoor seating rentals in South Portland

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

4.97 out of 5 average rating, 230 reviews

The kitchen features modern stainless steel appliances, a spacious countertop, and white cabinetry. Bar stools provide seating at the side counter, while a large clock hangs prominently on the wall. Ample natural light enters through windowed areas, enhancing the airy design.

Home in Kennebunkport

The Trolley House - Close to Goose Rocks Beach

4.89 out of 5 average rating, 614 reviews

Home in Westbrook

Cozy Maine Cottage • Near Jetport & Coast

4.97 out of 5 average rating, 157 reviews

Home in Saco

Seaside Serenity: 4-BR Oceanfront Escape!

Home in Old Orchard Beach

A spacious living area features a large sectional sofa adorned with patterned throw pillows. A wooden coffee table sits nearby, complementing the light wood flooring. Natural light fills the room through large windows, with a mounted television and decorative wall art enhancing the modern aesthetic.

4.96 out of 5 average rating, 218 reviews

Luxury Home w/HOT TUB & Fire Pit

4.98 out of 5 average rating, 175 reviews

A lofted bedroom features a spacious bed adorned with a vibrant striped blanket. Light filters through a window, highlighting the sloped whitewashed ceilings and simple artwork on the walls. Warm wood accents complement the soft, neutral tones throughout the room.

Home in Bridgton

Wren Cabin + Wood fired Sauna

4.98 out of 5 average rating, 187 reviews

The cabin exterior is showcased with large glass walls, allowing natural light to fill the interior. A wooden deck is lined with outdoor lights, leading to a hot tub. Surrounded by trees, the peaceful setting is visible, creating a serene outdoor atmosphere.

Home in Naples

LUX Designer Private Waterfront Hot Tub - Secluded

4.89 out of 5 average rating, 246 reviews

An aerial view captures a coastal neighborhood with sandy beach access visible in the foreground. Buildings are spread out, showcasing residential homes and their proximity to the shoreline. The sun reflects off the water, creating a serene atmosphere under a partly cloudy sky.

Home in Scarborough

Adorable Beach House Across the Street From Beach!

4.95 out of 5 average rating, 127 reviews

Home in Portland

comfy cozy house with yard and central location

Apartment rentals with outdoor seating

4.92 out of 5 average rating, 631 reviews

A cozy living area features a light-colored sectional sofa adorned with decorative pillows. A wooden coffee table sits in front, displaying books and a small plant. Natural light fills the space through large windows, with a sliding glass door leading to the adjacent bedroom.

Flat in West End

Sophisticated Charm at an unbeatable price!

Natural light fills the cozy living area, which features a large woven rug and hardwood floors. Two brown armchairs are positioned by the windows, and a small white table with books stands near a mirror. A subtle beach-themed artwork is displayed on the wall.

4.85 out of 5 average rating, 314 reviews

Stunning 2BR Airbnb on Portland’s Back Bay

4.99 out of 5 average rating, 302 reviews

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.

Flat in Cape Elizabeth

Cape Elizabeth Garden Apt+Beach+Close to Portland!

4.92 out of 5 average rating, 121 reviews

A cozy kitchen area features a gray countertop and green cabinetry. Three barstools are positioned at the counter. Lush plants adorn the sloping ceiling, accompanied by a small dining table and vibrant flower arrangements. A comfortable seating area with decorative pillows completes the space.

Flat in Saco

Welcome to our BoHo Treehouse! Beaches/Portland

Flat in Downtown Portland

4.97 out of 5 average rating, 116 reviews

Sunny West End Apartment With Private Courtyard

A serene bedroom is furnished with a comfortable queen bed dressed in neutral linens and accent pillows. Warm tones are complemented by decorative wall hangings, while a large mirror and plants enhance the light-filled space. A cozy chair and woven basket add to the inviting atmosphere.

4.89 out of 5 average rating, 148 reviews

Portland Back Cove Hideaway-1 BR- With Patio

A welcoming living space features a comfortable gray sofa adorned with decorative cushions. A wooden media console supports a 50-inch television, complemented by a coffee table displaying decorative items. Soft lighting creates a cozy atmosphere, while a potted plant adds a touch of greenery.

4.91 out of 5 average rating, 113 reviews

Spacious 3BR with Parking, Walk to Thompson Point

Flat in Downtown Portland

4.93 out of 5 average rating, 260 reviews

Hidden Garden Apartment in Portlands West End

Apartment rentals with outdoor seating

A bright living area is revealed, featuring large windows that allow natural light to fill the space. A cozy gray sofa and matching armchair are complemented by colorful pillows. A small side table holds a plant, and a soft area rug adds warmth to the hardwood floor.

4.99 out of 5 average rating, 115 reviews

Charming, newly remodeled space atop Munjoy Hill.

A comfortable living room is showcased with a grey sofa adorned with colorful cushions and a stylish armchair. Light streams through large windows, illuminating a coral-patterned area rug. A coffee table sits in the center, accompanied by decorative items and a small air conditioning unit near the window.

4.91 out of 5 average rating, 102 reviews

Beach Breeze

Superhost

A sandy pathway bordered by lush grass leads to a tranquil beach, with gentle waves reflecting soft colors of the sky at dusk. The horizon showcases a gradient of pastel shades, creating a serene landscape inviting relaxation.

4.77 out of 5 average rating, 289 reviews

Modern Industrial Beach Cottage

Superhost

A bright living area features two dark leather sofas and a patterned area rug. Natural light enters through large windows adorned with sheer curtains. A coffee table is positioned in the center, and a piece of wall art enhances the space. A plant and floor lamp provide additional warmth.

4.94 out of 5 average rating, 147 reviews

Penthouse, Walk To The Old Port & The Beach!

A warm wooden interior features a cozy seating area with a light-colored couch and decorative pillows. Floating shelves display various items, and the kitchen is visible in the background, showcasing essential appliances and a stylish design. Natural light filters through a skylight above.

4.96 out of 5 average rating, 408 reviews

Cozy condo by the beach!

The exterior of a two-story building is shown, featuring multiple windows and a front porch adorned with potted plants. A well-maintained lawn surrounds the property, and trees provide shade along the yard. The pathway is bordered by manicured grass.

4.95 out of 5 average rating, 131 reviews

Top Of The Line Stay!

Superhost

A cozy living area features wooden beams and paneling, with a comfortable sofa and an ottoman. Natural light enters through the windows, highlighting decorative shelves and a compact kitchen area. A small table and lamp add functionality to the space.

4.95 out of 5 average rating, 301 reviews

Comfy condo with loft by the beach!

A cozy living room features a large sectional sofa and a circular coffee table at the center. Natural light enters through multiple windows, casting a bright atmosphere. A small dining area with two chairs is visible in the corner, and area rugs add subtle texture to the hardwood floor.