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House vacation rentals in South Portland

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Top-rated house rentals in South Portland

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Top guest favorite

A spacious living area features two light-colored sofas arranged around a round white coffee table. A geometric rug with blue accents sits beneath the seating. Natural light floods the room through a corner window, with simple decor enhancing the serene ambiance.

Home in Portland

4.95 out of 5 average rating, 338 reviews

Explore Portland from a 18th-Century Victorian

*Covid-Clean* Cook breakfast in a bright kitchen with robust hardwood floors in this calm Victorian home. Sit down at a traditional dining table in an open-plan room featuring vivid wood-paneled walls, serene decor, and a geometric rug with pops of blue. Bright and spacious with entire top floor privacy. ** NO SHARED SPACE** This is a dedicated Airbnb apartment with no shared space whatsoever. Ultimate privacy. This apartment can be rented as (1) bedroom for up to (2) guests or as (2) bedroom for up to (4) guests. It is $50/night additional cost for the (2) bedroom. Please confirm the second bedroom is available if interested. Either option has a full bathroom with claw foot tub and shower. Full service kitchen with stove, refrigerator and microwave for your private use. Large living room with (2) couches and flat screen. The very large master bedroom with the ultra comfortable king size mattress also has cable tv. . Both the one bedroom and two bedroom option have their own private entrance, private kitchen and bath on the third floor. No shared space with anyone else with either the one or two bedroom rental options. Private entrance. Spacious one or two bedroom apartment with full kitchen, bath and living room as well as other amenities. We are available for any questions or concerns but as a rule we give the guests their privacy. The house is steps away from some of Portland’s most popular eateries including the Knotted Apron, Woodfords Bar and Grill, Bird and Co., The Treehouse, and Elsmere BBQ. Not far to the Old Port area to browse seafood markets and shops. Visit the Portland Observatory to explore a historic lighthouse. Close to all public transportation and Portland International Airport Parking in the driveway is a possibility, please ask if interested. Street parking is available, it is based on an odd /even system of the street address. You want to be parked on the same side as the date would be at 12:01 AM on any given day. You are staying at 32 Lawn Ave

The cabin's exterior is captured through a flickering flame, showcasing large glass windows that invite natural light. Surrounded by lush trees, the cozy structure features a modern design, blending seamlessly with the serene outdoors.

4.99 out of 5 average rating, 131 reviews

LUX Designer Private Waterfront

Waterfront GLASS cabin with privacy professionally designed, escape to somewhere really special. Crooked river acres surrounding the house with the river wrapping around the property. Dock with direct access to Sebago lake and state park just minutes away, Outdoor shower, hot tub, hammocks, BIG walk-in shower w/ window. Heated bath floors, ac. See through Fireplace. The property has its own sandy swimming beach, pets are welcome. Come enjoy privacy and the space to run around seconds to Sebago.

The welcoming living area includes a wooden dining table adorned with a vibrant flower arrangement. A cozy seating area features a patterned armchair and a large window allowing natural light. Exposed wooden beams enhance the warm character of the space.

Home in Falmouth

4.88 out of 5 average rating, 264 reviews

Amazing Bay View Home with Hot Tub

This enchanting 2-bedroom home is a coastal dream come true! Luxurious and well-appointed, Casco Bay House sleeps up to six, provides a five-star stay, offers all of the comforts of home AND a relaxing hot tub spa. With stunning views of the water, the house also has easy access to dining, shopping, and sightseeing in Portland's lively Old Port district (just 5 minutes away). Whether you seek quiet tranquility or want to hit the town, this waterside house is the perfect home away from home!

A cozy living room features large windows that allow natural light to fill the space. A comfortable green sofa is paired with a matching armchair, accented by soft cushions. A wooden coffee table sits in front, with warm lamps providing a soft glow in the evening.

Home in Portland

4.89 out of 5 average rating, 172 reviews

Charming Portland Home Near Back Cove & Downtown

Welcome to our inviting home, the perfect base for your Maine getaway! Nestled in a peaceful residential neighborhood near Payson Park, enjoy access to tennis courts, and the Back Cove waterfront pedestrian trail, perfect for morning jogs or evening strolls. Our home is minutes from the lively Portland peninsula, where you'll find amazing dining and shopping. Catch a ferry to explore islands or head to Freeport's outlets, local beaches, and iconic Maine lighthouses. License No STHR-001701-2019

A charming two-story home is showcased with a striking red exterior. Large windows allow natural light to flood in, while well-maintained landscaping features lush greenery and a stone wall lining the front yard. The inviting porch adds a welcoming touch.

Home in Portland

4.9 out of 5 average rating, 128 reviews

Charming Portland Colonial, In Town

Beautiful, well-appointed, family friendly 3 bdrm 2 bath home with fenced in backyard and attached garage in the heart of centrally located Deering Highlands & Rosemont neighborhoods, situated on the corner of Brighton Ave. Blocks from law school & USM, Close to downtown, walkable to Rosemont market, coffee shops & restaurants. Fully equipped, kitchen, bonus sunroom, fantastic backyard with gas grill/firepit, Roku TV/WiFi. Excellent oasis in the heart of Portland. Perfect for family getaways

Top guest favorite

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.

5 out of 5 average rating, 182 reviews

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.

Top guest favorite

The Birch Ledge Guest House is a two-story structure nestled among trees, featuring a rustic exterior with a metal roof. A small patio with two chairs is positioned at the entrance, and a staircase leads to the loft area. Lush greenery surrounds the home.

4.99 out of 5 average rating, 433 reviews

Birch Ledge Guesthouse--Four Season Maine Getaway

Both rustic and elegant, the Birch Ledge Guest House offers a cozy place to relax and recharge, whatever the season. The first floor features a spacious living room (with queen sized pull-out-couch), dining area, and small kitchen. The bathroom has a walk-in shower. The second floor is a loft accessible by a spiral staircase and has a comfy queen and two twin sized beds. The guesthouse is surrounded by quiet forest and is an easy 30 minute drive to Portland.

Top guest favorite

A living area features a light-colored sofa paired with a leather armchair. A large mirror hangs on the wall, reflecting the space. Decorative art pieces are framed and displayed. A blue side table complements the warm wood flooring.

4.97 out of 5 average rating, 137 reviews

2 bed house w/king bed, pets & off-street parking!

Welcome to the 1840s Farm Hand’s House 800sqft West End house • off-street parking directly behind house (plz confirm car size) • King bed in primary bedroom • 90 walk score • dog friendly! (fee applies) • fast wifi • 3 min drive to S. Portland • 10 min drive to beaches • 5 min walk to renowned restaurants & coffee • 10 min walk to Old Port • Free W/D in first floor • Residential street • 1840s house with some quirks Max 3 adults unless you message ahead

Top guest favorite

A modern cabin exterior is framed by tall trees, featuring a large window that invites light into the interior. A spacious wraparound deck is present, enhanced by warm, glowing string lights. Comfortable outdoor seating is arranged on the deck, creating an inviting atmosphere.

Home in Bridgton

4.97 out of 5 average rating, 115 reviews

Wren Cabin + Wood fired Sauna

We built the Wren Cabin to be a serene space filled with light and art and with lots of cozy details. Lofted ceilings, a spiral staircase and large open concept with lofted bedroom. The cabin also has a gorgeous wood-fired sauna for those colder days. Wren cabin has a large wraparound deck for relaxing and an outdoor fire pit, as well as shared access to Adams Pond. The space is modern Scandinavian, light and aery, and filled with thoughtful details.

A spacious bed is centered in the room, adorned with a neutral blanket and a decorative pillow featuring floral patterns. A bedside lamp complements the wooden furniture, which includes a dresser. A doorway leads to a separate area, hinting at additional living space.

Home in Portland

4.88 out of 5 average rating, 155 reviews

Grandma's 2 Bedroom Bungalow with loft

Step back in time and enjoy the original features of this 1929 Craftsman gem in the North Deering neighborhood minutes from the Old Port. This is Grandma's house with modern comforts of this newly remodeled home. The original hardwoods floors, trim and built in are shining like new. The kitchen boosts a deep porcelain bowl which will take you back in time. A fenced in backyard with a fire pit or the cozy loft are special places to relax and retreat.

A charming multi-story house is surrounded by vibrant flower beds featuring yellow and purple blooms. A well-maintained front yard is bordered by a white picket fence, and a welcoming front porch leads to a bright orange door.

Home in Portland

4.91 out of 5 average rating, 355 reviews

House Your Group - 5 Minutes to Everything!

Our goal is to ensure our guests have a comfortable place to stay so they can focus on making the most of their visit. With four bedrooms, a large living room for everyone to gather, and an eat-in kitchen, this house is the ideal place to host your group. The kitchen is stocked with the essentials: dishes, cooking basics, and plenty of coffee. In addition, you can enjoy the private back deck and fenced in yard. Dogs are welcome as well!

A dining area features a round wooden table with black dining chairs set atop a textured area rug. The kitchen is equipped with white cabinetry, modern appliances, and a spiral staircase leading to an upper loft. Natural light enters through the window, accented by light green curtains.

Home in Westbrook

4.9 out of 5 average rating, 554 reviews

Reno Barn w/ a lot of Charm! Breweries & Airport

** Cozy Renovated Barn w/ artist loft ** Minutes from airport and within walking distance to the Allagash Brewing Company & other breweries. Lots of hiking trails along the Presumpscot River. Short drive to downtown Portland, restaurants, music venues, beaches, lighthouses and nightlife. Barn is located in a quiet area ~ relax on the back deck with a glass of wine star gazing. Come check us out!!

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Popular amenities for South Portland house rentals

Free parking on premises

Air conditioning

House rentals with a pool

The spacious indoor pool area features a large heated swimming pool with a smooth surface. Natural wood paneling adorns the ceiling and walls, providing a warm ambiance. Abundant light enters through multiple windows, enhancing the inviting atmosphere of the space.

4.95 out of 5 average rating, 20 reviews

Willow Creek Homestead Indoor Pool Lake Access

The living area features a spacious sectional sofa complemented by a matching ottoman. Light wood flooring contrasts with a large area rug displaying a star motif. Artwork depicting coastal scenes adorns the walls, while windows let in natural light, illuminating the adjacent dining table.

Home in Old Orchard Beach

4.96 out of 5 average rating, 47 reviews

Upscale OOB Beach House | Seasonal Heated Pool

Aerial view of a spacious home surrounded by lush green trees, showcasing a private in-ground pool and outdoor seating area. The structure features a natural roof and large windows, enhancing the connection with nature. The scene conveys a sense of privacy and seclusion.

Home in Windham

5 out of 5 average rating, 8 reviews

New Listing! Pool, Hot tub & Lakes! Mins to Sebago

Top guest favorite

A spacious deck features a hot tub with a privacy screen and comfortable seating arrangements. The outdoor furniture includes a sectional sofa and a low coffee table, all set under a large orange umbrella. Lush greenery surrounds the area, providing a sense of seclusion.

Home in Biddeford

4.98 out of 5 average rating, 41 reviews

Pool|HotTub|1Acr FencedYard|Firepit|Garden|PETS OK

Home in Portland

4.96 out of 5 average rating, 134 reviews

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

An aerial view captures a spacious community area featuring a large swimming pool surrounded by lounge chairs. Lush greenery envelops the setting, enhancing the tranquil atmosphere. A small pond reflects the landscape, with walking paths guiding residents between the pool and neighboring homes.

Home in Arundel

5 out of 5 average rating, 10 reviews

Maritime Meadows – Charming Resort-Style Home!

A two-story home is presented, featuring a yellow exterior and dark blue shutters. A welcoming front porch is adorned with decorative elements. Lush green grass and various shrubs frame the entrance, while a driveway leads to a garage on the left side.

Home in Portland

4.82 out of 5 average rating, 112 reviews

There's No Place Like Home

A spacious living room features a large sectional sofa with colorful accent pillows. A wooden coffee table sits in the center. Natural light fills the space through multiple windows, while a spiral staircase leads to an upper level. A mounted television is positioned above the fireplace.

Home in Arundel

5 out of 5 average rating, 6 reviews

Spectacular 3 Bed Resort Cottage

Weekly house rentals

An open living area features exposed wooden beams and a circular dining table with four white chairs. A comfortable couch is positioned near a television and a modern fireplace. Large windows offer natural light and views of the surrounding beach area.

5 out of 5 average rating, 37 reviews

"Beachfront/Ocean Front” Cottage NEW!

The airy living space features hardwood floors and a cozy couch. The kitchen area is visible, showcasing a breakfast bar with seating, a variety of appliances, and a window allowing natural light to fill the room. Decorative elements include a lamp and wall art.

Home in Scarborough

4.9 out of 5 average rating, 20 reviews

My Blue Heaven Beach Cottage

Top guest favorite

A dining space features a large wooden table paired with four chairs, set on a decorative area rug. A bright green wall provides a cheerful backdrop, complemented by a charming fireplace. Natural light enters through an adjacent window, enhancing the inviting atmosphere.

Home in Downtown Portland

5 out of 5 average rating, 20 reviews

Sweet Home Near Food & Old Port

Top guest favorite

An aerial view captures the coastal neighborhood, highlighting sandy beaches stretching along the shoreline. The residential area features a mix of homes with greenery interspersed. The clarity of the view showcases the proximity to the ocean, inviting exploration of nearby beach areas.

Home in Scarborough

5 out of 5 average rating, 20 reviews

Lobster Boats & Harbor View Pine Point Home

A cozy living area features a light gray sofa and two armchairs, set on a colorful area rug. A coffee table sits in the center, while a decorative fireplace and unique lamp add character to the space. Large windows provide natural light.

Home in Portland

4.95 out of 5 average rating, 97 reviews

comfy cozy house with yard and central location

The exterior of the residence features a deck with a round metal table and six matching chairs. A rainbow flag is displayed prominently, and warm light emanates from the windows, creating a welcoming ambiance. Lush greenery surrounds the area, enhancing the natural setting.

Home in East End

4.98 out of 5 average rating, 46 reviews

Tiny Mansion - whole house in the heart of Munjoy!

Top guest favorite

A bright living area is furnished with a leather sofa, a glass coffee table, and a pair of armchairs. A well-lit space features a fireplace with a modern television mounted above, while light curtains frame a window, enhancing the room’s open feel.

Home in Falmouth

5 out of 5 average rating, 16 reviews

Captain’s Quarters Seaside Cottage

Top guest favorite

A bright and spacious living area is featured, showcasing large windows with views of the marsh. A comfortable gray sofa and two accent chairs are arranged around a glass coffee table. The kitchen island offers seating options, and the space is complemented by indoor plants.

Home in Scarborough

5 out of 5 average rating, 95 reviews

Higgins Beach *New* Beach Home & Private Offices

Private house rentals

The front exterior of the bungalow is shown, featuring a light-colored facade and a welcoming entrance with a decorative wreath. A set of steps leads up to the front door, flanked by a flowering tree and a bench for seating. The yard is landscaped with gravel and mulch.

Home in Portland

4.84 out of 5 average rating, 57 reviews

Cute Craftsman Bungalow home w/ fenced in yard

Top guest favorite

An inviting home exterior is illuminated in the evening light, showcasing multiple large windows. A spacious deck is visible, along with a circular fire pit area surrounded by adirondack chairs in the yard. Lush greenery enhances the setting, creating a serene outdoor atmosphere.

Home in Peaks Island

4.96 out of 5 average rating, 57 reviews

Cheerful, Sunny, 3 Bedroom Island Home

Top guest favorite

A spacious dining area features a wooden table surrounded by black chairs, positioned in front of a well-equipped kitchen. The kitchen includes white cabinetry, modern appliances, and a brick accent wall. A warm light fixture hangs above the table, enhancing the inviting ambiance.

Home in Portland

5 out of 5 average rating, 13 reviews

Sophisticated 3BR Retreat in The Heart of Portland

The home’s exterior features a modern grey facade with white trim, framed by a well-maintained garden. A front porch with steps leads into the house, surrounded by greenery and a wooden fence, providing a sense of privacy and charm.

Home in Portland

4.94 out of 5 average rating, 18 reviews

Convenient & cozy Portland home

The exterior of a modern cabin is presented, surrounded by tall trees and a grassy area. A fire pit with Adirondack chairs is visible in the foreground, while the cabin features multiple windows and a deck overlooking the landscape.

Home in Falmouth

4.95 out of 5 average rating, 40 reviews

Modern Maine Lake House near Portland

An open living space showcases sleek flooring and neutral-toned walls. A modern television is mounted above a wooden sideboard. Light streams in from the kitchen area, which features contemporary appliances, while decorative plants enhance the inviting atmosphere.

Home in Windham

4.98 out of 5 average rating, 49 reviews

Modern Chic Home in Windham

A well-lit living room features two comfortable sofas adorned with decorative pillows. A wooden coffee table sits on a patterned rug, and large windows provide natural light and views of the outdoors. A floor lamp adds additional illumination to the space.

Home in Scarborough

4.89 out of 5 average rating, 37 reviews

BigHome10MinsToPortland&Beaches|2KingBeds|FirePit

A serene coastal view emerges during sunset, featuring soft reflections on the water. A mailbox is positioned in the foreground, partially obscured by lush green foliage, while boats rest gently on the horizon against a backdrop of calm waters.

Home in Biddeford

4.94 out of 5 average rating, 35 reviews

The Blowfish - Oceanside Escape

Quick stats about house rentals in South Portland

Total rentals
130 properties
Total number of reviews
4.9K reviews
Family-friendly rentals
100 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with dedicated workspaces
60 properties have a dedicated workspace
Wifi availability
130 properties include access to wifi

Destinations to explore