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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, 337 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, 130 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, 262 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 charming two-story house is framed by vibrant yellow flowers. The white exterior features large windows that glow warmly, highlighting the inviting entrance. A manicured lawn leads to a driveway with decorative plants flanking the path, contributing to a welcoming atmosphere.

Home in Arundel

4.97 out of 5 average rating, 185 reviews

NewBuilt/HotTub/Great Location-4 min Kennebunkport

Follow us on IG @anchorunwind. Welcome to Mama Bear's House! Perfect girlfriends' getaway or to celebrate a special someone. Sit back and relax in our brand new and fully equipped stylish home just 5 minutes away from Kennebunkport's Dock Square. Spend time reading and sipping a fresh grounded coffee on our cozy egg chair, looking in our peaceful backyard while the sunset closes another memorable chapter of your vacation. Enjoy the firepit with hot cocoa and s'mores or fall for a cornhole game!

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, 127 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, 432 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.

Home in West End

4.97 out of 5 average rating, 132 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 bright corner of the cabin features a comfortable light-colored sectional sofa adorned with a decorative blanket. A wooden coffee table stands nearby, and natural light filters through large windows, highlighting the snowy landscape outside. A green potted plant adds a touch of nature to the space.

Home in Bridgton

4.99 out of 5 average rating, 112 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, 553 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!!

Vacation rentals for every style

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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, 19 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, 45 reviews

Upscale OOB Beach House | Seasonal Heated Pool

A spacious kitchen features a large granite island with four supportive stools. Large windows allow natural light to illuminate the area, showcasing the warm wood beams overhead. A festive tree adds a seasonal touch to the corner, while the open space flows into a dining area.

Home in Windham

5 out of 5 average rating, 7 reviews

Nature, Pool, Hot tub&Lakes! Mins to Sebago &More

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

4.97 out of 5 average rating, 38 reviews

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

Home in Portland

4.95 out of 5 average rating, 132 reviews

"Good Vibes" 4 Wonderful Seasons @ Portland 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, 5 reviews

Spectacular 3 Bed Resort Cottage

A classic beach house is situated amidst lush greenery, featuring a charming wraparound porch. The two-story structure is accentuated by large windows and a balcony above. A clear blue sky complements the inviting landscape, creating a serene setting just steps from the beach.

Home in Kennebunkport

4.97 out of 5 average rating, 31 reviews

Lovely Beach house in GRB - Heated pool!

Weekly house rentals

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, 12 reviews

Sophisticated 3BR Retreat in The Heart of Portland

Top guest favorite

The image showcases a restored stone ranch home surrounded by greenery, a well-maintained lawn, and a driveway. Additionally, the home features an outdoor seating area lit by string lights, enhancing nighttime gatherings. Interior areas display stylish furniture and large windows, inviting ample natural light.

4.99 out of 5 average rating, 71 reviews

Entire Home in Sunny Saco + Gym

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

4.89 out of 5 average rating, 19 reviews

My Blue Heaven Beach Cottage

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, 17 reviews

Convenient & cozy Portland home

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, 15 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

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, 15 reviews

Captain’s Quarters Seaside Cottage

Top guest favorite

The exterior of the modern guest house is showcased, featuring a spacious black facade framed by greenery. Natural light brightens the surrounding garden area, with trees and plants providing privacy. The neighboring homes are visible in the background, offering a sense of the community.

Home in East End

4.99 out of 5 average rating, 69 reviews

Modern Guest House + garden patio on Munjoy Hill

Private house rentals

A bright and airy living room features a spacious light-colored sofa adorned with decorative pillows. Natural light filters through a large window, illuminating a muted area rug on the floor. The open layout extends towards a staircase, enhancing the inviting ambiance.

Home in Westbrook

4.5 out of 5 average rating, 4 reviews

The Lori House

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, 56 reviews

Cheerful, Sunny, 3 Bedroom Island Home

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!

Top guest favorite

An open living area features a dark sofa with decorative cushions, surrounded by light wood flooring. Natural light fills the space through large windows. A dining area with a light-colored table and chairs is visible, along with decorative woven wall art enhancing the room's charm.

4.97 out of 5 average rating, 72 reviews

3 Bedroom Seaside Oasis | 3 Minute Walk to Beach

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 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, 38 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, 47 reviews

Modern Chic Home in Windham

Quick stats about house rentals in South Portland

Total rentals
130 properties
Total number of reviews
5.3K reviews
Family-friendly rentals
90 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