Holiday rentals with outdoor seating in Portland

A serene garden area is depicted, featuring a gently flowing stream bordered by smooth stones. Lush greenery and colorful flowers, including irises and daylilies, create a vibrant atmosphere. Stepping stones lead through the grass, inviting exploration of the tranquil landscape.

4.96 out of 5 average rating, 634 reviews

Peaceful Oasis on Munjoy Hill -2nd flr/3BR+parking

Spacious, light-filled 3 Bedroom/1 bath 2nd-floor apartment with tasteful art, contemporary furnishings, + a well-appointed kitchen. Fantastic location! -A 5-minute walk to the Eastern Promenade with its food trucks, beach & scenic trails -Nearby are bakeries, cafes, world-class restaurants and popular breweries -Relax in the serene garden w/ outdoor seating -A 15-minute walk takes you to the Old Port. Discover the best of Portland, then return to A Peaceful Oasis, a place to truly call home.

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.

4.98 out of 5 average rating, 383 reviews

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.

A well-lit living area features oversized bay windows that provide ample natural light. A large, brown leather couch is complemented by a brown armchair and a plush ottoman. A coffee table made of wood is centered on a decorative area rug, while bookshelves display a variety of colorful books.

4.94 out of 5 average rating, 123 reviews

Sunny West End Gem • parking, courtyard & walkable

Welcome to The Kerry! Stay in style in this eclectic space with boho touches inside a charming historic building. Great for a quick jaunt, family getaway or extended work-from-anywhere stay. 🛏️ 2 bedrooms — king & queen beds 📍 Central peninsula,. West End 🚘 Off-street parking (nearby) 🧺 Laundry 🖥️ Workstations 🏠 2nd-floor unit 🍼 Portable crib 🔥 Courtyard 👩‍🍳 Steps to Tandem, State Theatre, Chaval & more 🦞 Walk to Downtown, Arts District, Old Port & East End ⛱️ Quick drive to beaches

The spacious dining area features a black and white checkered floor, complemented by red walls. A rustic wooden table with four black chairs is placed centrally, while a vintage mirror reflects the room. Natural light filters through windows adorned with floral curtains, enhancing the cozy atmosphere.

4.96 out of 5 average rating, 525 reviews

RETRO BnB in the Heart of East End Portland

Retro BnB in The Heart of Portland's East End offers a combination of 70's mod charm with a vibrant comfortable style. Sunny, first floor back apartment with private entrance, one hybrid coil/thermarest queen bed overlooking yard with lovely perennial garden, bathroom with central, well appointed kitchen/dining room. This space is perfect for one couples looking for a cozy home base hideaway. A short walk to gourmet restaurants, cafes, East End beach and all Portland peninsula has to offer!

4.99 out of 5 average rating, 448 reviews

The exterior of a post and beam cottage is shown, featuring a light wood facade and a brown shingled upper section. Two black Adirondack chairs are placed on a wooden deck, accompanied by potted plants. Large windows offer a view of the forested surroundings under a partly cloudy sky.

Cottage in Pownal

Dreamy Post&Beam Hideaway Near Portland & Freeport

Escape to a dreamy timber-frame cottage tucked in Maine’s woods! Soaring beams, radiant-heated floors, a king loft bed, and a crackling fire pit await. Sip coffee on one of the two decks, hike Bradbury Mountain (3 minutes away), shop Freeport (10 minutes away), or dine in Portland (20 minutes away)—then return to your cozy hideaway under the stars. Full kitchen, vaulted ceilings, radiant heat floors, private driveway, fire pit and peaceful forest views make it the perfect year-round retreat.

5 out of 5 average rating, 217 reviews

A modern beach house is positioned along a serene shoreline, featuring large windows that reflect the colorful sunset. The exterior showcases a blend of natural materials and white accents, with a deck that offers expansive ocean views. Rocky shores frame the property, enhancing the coastal setting.

Home in Saco

Oceanfront w/ Stunning views and Private Deck☀️🏖

Welcome to the Beach House on the Rocks, your very own oceanfront retreat! This beautiful, 1350 sq ft house is nestled right next to the ocean. With panoramic views and the ocean just steps away, you won’t forget this one of a kind experience. Tucked away in the hidden gem of Camp Ellis, you’ll enjoy a lively beach scene in the summer and a tranquil retreat in the off season. Just a short trip away to Old Orchard Beach and 30 min to Portland you’ll never be in need of fun activities.

Apartment in South Portland

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, 194 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, 108 reviews

The exterior of the A-frame cabin is showcased, featuring a unique wooden facade and metal roof. Sunlight streams through tall triangular windows, illuminating the surrounding wooded area. A gravel path leads to the entryway, enhancing the cabin's connection to nature.

Cabin in Freeport

The Maine Frame | Modern A-Frame Cabin in Freeport

• Perfect for small families or couples, our signature A-Frame cabin features a modern interior gas burning fireplace, soaring ceilings, huge windows, stylish interiors, and all the comforts of home. • This cozy 1,100 square foot space comfortably accommodates up to four guests in two bedrooms (one with a King-size bed and the other with a Queen-size bed) and a shared bathroom. • 7 minute drive to downtown Freeport. • Proud to be ranked in the top 1% and voted Guest Favorite!

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.

4.91 out of 5 average rating, 616 reviews

Sophisticated Charm at an unbeatable price!

Apartment is centrally located to all downtown amenities and transportation system. Located in the beautiful West End on a quiet residential street approximately 1 mile from the downtown area. Apartment (3rd floor) gets beautiful sun throughout and has all of the traditional charm and character of the West End homes but updated bathroom and kitchen, both recently remodeled in 2017. Rental includes access to one parking space for a small to mid size vehicle. STHR-001018-2019

4.89 out of 5 average rating, 142 reviews

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.

Apartment in Back Cove

Portland Back Cove Hideaway-1 BR- With Patio

Our quiet residential Back Cove neighborhood is your perfect retreat from a busy day exploring Portland. Take a short drive to the center of the city, or enjoy the waterfront walking and biking trail which loops around the cove. Dine at Tipo or Woodford F&B, two neighborhood favorites. Come home to this newly renovated space and relax on the patio! Our space can accommodate four guests. Great for a family, or close friends! We look forward to hosting you!

4.96 out of 5 average rating, 223 reviews

The tiny home is set in a snowy wooded area, with its natural wood exterior complementing the surrounding environment. A fire pit and seating area are visible in front, surrounded by a blanket of snow, indicating a tranquil retreat in winter.

Tiny home in Biddeford

Tiny house near the beach!

Enjoy a wooded retreat just minutes from Maine's stunning Fortune's Rocks beach. This newly constructed tiny home welcomes you for a memorable stay near the coast. We strive to offer a thoughtful balance between modern amenities and a natural setting. This space is perfect for two guests, with a maximum of four who are comfortable sharing tiny accommodations. We are pet friendly for an additional fee - one dog maximum per reservation.

4.95 out of 5 average rating, 523 reviews

The cozy cabin is illuminated by soft outdoor lights, enhancing its charming facade. The front porch features a seating area, with potted flowers adding a touch of nature. The surrounding grassy area includes stone steps leading towards the entrance, promoting a welcoming atmosphere.

Tiny home in Portland

The Garden Cabin Tiny Home

Curious about tiny homes? Love dogs, gardens, pine trees, campfires, and birds? Hate cleaning fees? Our private 128 sqft cozy cabin is for you! On the spectrum between camping and a hotel room, it's a chill place to call home while visiting Portland. Enjoy our garden while sipping a beverage from your own deck or around the campfire. Heat and A/C in the cabin. Please, no smokers, kids under 7, or guest pets. STHR-000718-2018

Popular amenities for Portland outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with Outdoor Seating

4.89 out of 5 average rating, 158 reviews

A fire pit is positioned near the water's edge, surrounded by two adirondack chairs. The setting sun reflects off the river, casting warm hues across the sky and water. Green trees frame the tranquil scene, creating a peaceful atmosphere.

Home in West Bath

Oak Leaf

4.98 out of 5 average rating, 163 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

4.95 out of 5 average rating, 355 reviews

Home in Acton

The LOTUS welcomes you, stay a while

4.9 out of 5 average rating, 111 reviews

Home in Auburn

The Loons' Nest: Lakefront oasis w/ private dock

4.96 out of 5 average rating, 153 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 North Deering

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

4.96 out of 5 average rating, 108 reviews

Two Adirondack chairs are positioned on a rocky area overlooking a serene waterfront. Trees frame the scene, with the sky displaying soft hues of pink and orange during sunset. The calm water reflects the natural beauty of the surroundings.

Home in Phippsburg

Private Oceanfront Home 🔆2 min to Popham ✔️Hot Tub

4.9 out of 5 average rating, 299 reviews

A charming coastal home is showcased with light-colored siding and a bright blue front door. Surrounding greenery includes tall trees and manicured shrubs. The property is set back from a grassy area, adding to its inviting curb appeal.

Home in Falmouth

Amazing Bay View Home with Hot Tub

5 out of 5 average rating, 108 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

Apartment rentals with outdoor seating

The open kitchen and dining area is designed with modern finishes and natural light. A white table with four chairs is positioned next to a large window. The kitchen features stainless steel appliances, including an oven and refrigerator, with sleek cabinetry and a decorative wall clock.

4.92 out of 5 average rating, 280 reviews

Oceanside Open Concept 2BR- East End/ Downtown

Apartment in Old Orchard Beach

A covered patio area features a black wooden dining table surrounded by six matching chairs. Bright pink flowers are planted along the edge, enhancing the space. The patio is bordered by a white picket fence and has a pebble-strewn pathway leading from the entrance.

4.91 out of 5 average rating, 195 reviews

Breezy Beach Bungalow on Old Orchard Beach

Apartment in Ferry Village

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, 129 reviews

Cozy South Portland studio with King bed! REG107

A well-appointed bedroom features a spacious bed adorned with a floral patterned duvet and coordinating throw. A bedside lamp provides soft lighting, while French doors lead to a hallway. Hardwood flooring complements the room's elegant design, offering a fresh and inviting atmosphere.

4.91 out of 5 average rating, 432 reviews

Renovated 1 BR Downtown Apt w/backyard

A bright living area features large windows that provide ample natural light. Two comfortable chairs with colorful upholstery are arranged beside a small table, while a cozy couch with red accents complements the space. A vibrant piece of artwork adorns the wall, adding a touch of color.

4.98 out of 5 average rating, 370 reviews

Beautiful West End studio, hot tub, free parking

4.98 out of 5 average rating, 365 reviews

Apartment in Arundel

Cape Arundel Cottage 1 mile to downtown KPT

A common area is depicted, featuring a spacious couch adorned with yellow pillows. A light wood coffee table is centered on a striped rug. Natural light flows through large windows, illuminating a dining table with several wooden chairs, complemented by a cozy décor.

4.96 out of 5 average rating, 498 reviews

Bright and cozy Munjoy Hill neighborhood apartment

4.94 out of 5 average rating, 217 reviews

The living area features a red sofa and a black armchair, arranged around a wooden coffee table. A vibrant area rug adds color to the hardwood floor. Natural light enters through a window with blinds, and artwork is displayed on the walls, contributing to a welcoming atmosphere.

Apartment in Parkside

Garden Apartment Close to Everything

Condo rentals with outdoor seating

4.99 out of 5 average rating, 115 reviews

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.

Condo in East End

Charming, newly remodeled space atop Munjoy Hill.

Condo in Old Orchard Beach

A wide sandy beach stretches along the coastline, with gentle waves breaking at the shore. Two figures walk along the water's edge, while a clear blue sky enhances the tranquil atmosphere of the scene.

4.89 out of 5 average rating, 122 reviews

Oceanfront Condo with Awesome Views

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.

Condo in Scarborough

4.77 out of 5 average rating, 287 reviews

Modern Industrial Beach Cottage

4.95 out of 5 average rating, 129 reviews

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.

Condo in Portland

Top Of The Line Stay!

4.96 out of 5 average rating, 294 reviews

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.

Condo in Scarborough

Comfy condo with loft by the beach!

Superhost

Condo in East End

4.77 out of 5 average rating, 278 reviews

Direct Ocean View on the Eastern Promenade

4.96 out of 5 average rating, 209 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 Willard Square

Rustic Willard Beach condo ten mins from Old Port!