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Waterfront vacation rentals in South Portland

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Quick stats about waterfront rentals in South Portland

  • Total vacation rentals

    Explore 30 vacation rentals in South Portland

  • Nightly prices starting at

    South Portland vacation rentals start at G$25,098 GYD per night before taxes and fees

  • Verified guest reviews

    Over 4,870 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    20 of South Portland vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across South Portland rentals

  • 4.8 Average rating

    South Portland stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated waterfront rentals in South Portland

Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.

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Guest favorite
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

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!

4.9 out of 5 average rating, 328 reviews
Top guest favorite
A serene vista showcases the city skyline reflected in calm waters, framed by lush green grass and trees. The scene captures a tranquil moment, inviting viewers to appreciate the natural beauty and urban blend surrounding the space.
Home in Portland

Top Deck - Portland Property with Views!

Views, Views, Views! 2 huge decks overlooking water and city skyline. This home is adjacent to Payson’s Park – Portland’s largest park. 5-7 min ride to downtown Portland and the Old Port’s fabulous bars and restaurants. The main floor has bedroom with bath, kitchen, and living room. The upstairs has a large bedroom with bath, open room that can be used as 2nd living room or a 3rd/4th bedroom space. Sleeps 10-12. Off street parking 6-8. Large yard. Portland License #STHR-002587-2020

4.92 out of 5 average rating, 304 reviews
Top guest favorite
A wooden treehouse with large windows and a spiral staircase is surrounded by lush green trees. The structure is elevated, allowing for a view of the forest floor, which is covered in natural earth tones from fallen leaves and pine needles.
Treehouse in Sanford

Luxury Year-round Treehouse with private hot tub

The Canopy is one of 5 luxurious tiny homes that make up Littlefield Retreat, a tranquil woodland village of 3 treehouses and 2 hobbit houses – each with its own private hot tub and dock. To see all five dwellings, click on the photo to the left of “Hosted by Bryce”, then click “Show more…”. This 15-acre forest retreat on Littlefield Pond offers our guests an experience that feels like a trip up to the woods of northern Maine, but is closer to home and to all the attractions of southern Maine.

4.91 out of 5 average rating, 601 reviews
Guest favorite
A comfortable seating area features a rust-colored couch and a light armchair, arranged around a wooden coffee table. A soft area rug lies beneath, complementing the warm light from nearby windows. The open layout connects to a kitchen in the background.
Apartment in Downtown Portland

Beautiful West End Apartment

You will love staying here. Our spacious apartment feels like a treetop getaway right in the middle of Portland. Our apartment is located right on the West End on Portland's beautiful peninsula. Walking distance to the Old Port, downtown, arts district, and the rest of the peninsula, this is the perfect place to make home base for your Portland stay Explore Portland and all of Maine, work from home while your folks enjoy the area, or just chill here in Portland and "do your Maine thing."

4.9 out of 5 average rating, 121 reviews
Top guest favorite
A serene waterfront scene captures calm waters dotted with boats gently bobbing in the harbor. Rocky shores lead to lush greenery in the background, with a clear blue sky above, creating an inviting coastal atmosphere in this Maine setting.
Apartment in Falmouth

Falmouth Waterfront Carriage House Apt

Waterviews! This 1 bedroom apt has a new “purple”mattress, above our detached garage in classic Maine waterfront neighborhood. Next door to the iconic Town Landing Market and Town Landing pier/beach. In beautiful Falmouth Foreside neighborhood. Walkable to Dockside Restaurant and marina, and 10 minute drive or bus to downtown Portland. 20 minute drive to Freeport shopping. We only accept well- behaved and house- trained dogs, no other pets are allowed for a fee of $75.00 per dog per stay.

4.96 out of 5 average rating, 198 reviews
Top guest favorite
An aerial view displays a colonial home surrounded by vibrant autumn foliage, set on an expansive lawn. The nearby Kennebunk River curves through the landscape, bordered by trees. The property includes a serene setting with open spaces and distant houses visible among the greenery.
Home in Arundel

Classic, calm river view & centrally located home

We are happy to share with you our coastal, colonial home set on eight acres along the Kennebunk River. Enjoy our quaint, warm home just 5 min to the beach and 3 minutes to Cape Arundel Golf Club. Our 4 bdrm, 2.5 bathroom suits short or long term stays. The location is ideal: 6 min from Kennebunkport, 15 min from Biddeford, and 30 min from Portland or Portsmouth! We hope to make you feel at home with the morning birds chirping and the calmness of the river just in back of the property.

4.95 out of 5 average rating, 107 reviews
Top guest favorite
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.

5.0 out of 5 average rating, 115 reviews
Top guest favorite
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!

4.96 out of 5 average rating, 228 reviews
Top guest favorite
Two windows adorned with sheer curtains frame a view of a tidal river and lush greenery. A small lamp is positioned on a round table, illuminating the space. Sunlight streams through the glass, enhancing the serene atmosphere of the room.
Home in Portland

Fore River Getaway

A rich and restful oasis for a small group or family traveling through or with Portland as destination. Our second story suite features views of a waterfall and the tidal river on Casco Bay. Consider our suite the perfect calm home base for all your adventures. The “Fore River Getaway” is an expanded version of our popular "Fore River Suite" space and accommodates up to 4 guests. We hope to host people looking for peace and quiet, and will not host loud, rowdy groups.

4.99 out of 5 average rating, 105 reviews
Top guest favorite
A modern kitchen features an island with bar stools and white shaker cabinets. Bright lighting is provided by pendant fixtures above. Large windows showcase waterfront views, while a dining area is visible, with a colorful striped rug under the table.
Apartment in Downtown Portland

Penthouse Two Master Waterfront Suite with Rooftop

CO2024-01785 Stunning penthouse suite with exposed beams, brick accents, and whitewashed poplar walls. Enjoy harbor views from the rooftop deck. Two private master suites feature custom tile showers, one with a soaking tub. The spacious kitchen offers granite countertops and modern appliances. Relax by the gas-fired stove in the inviting living room. In-unit washer/dryer and elevator access included. Please note: no animals permitted due to owner's health.

4.97 out of 5 average rating, 152 reviews
Top guest favorite
A relaxing outdoor area is shown, featuring several seating options around a fire pit. Two cabins can be seen, with one situated on a hill and the other by the water. A sun umbrella provides shade, surrounded by trees and nature.
Chalet in Standish

Blueberry Hill

Beautiful property located on Watchic Lake in Standish Maine. Clear clean spring fed lake. 25 minutes to Portland with access to shopping, restaurants and entertainment. 45 minutes to North Conway New Hampshire. Where you wil find plenty of shopping, restaurants and winter skiing. Property includes use of Main Chalet home year round and two additional cabins each sleeping 4 are available from May-Oct. Great for extended families and friends.

4.96 out of 5 average rating, 261 reviews
Top guest favorite
A spacious sleeping area features natural wood paneling and a high ceiling. A comfortable bed is dressed in light blue and white linens, accompanied by two decorative pillows. A wooden cabinet and a bedside lamp add functional elements, while a window allows soft light to fill the room.
Barn in Portland

Garrison Cove Studio

Rare, Portland waterfront studio located in the heart of the historic Stroudwater neighborhood, awaits one or two guests looking for an urban hideaway. The studio occupies a 150 year old post and beam barn situated on the banks of the Stroudwater and Fore Rivers. Enjoy morning coffee on the river swing, meditate to the soothing sound of the nearby waterfall or linger over your favorite beverage in one of our comfy Adirondacks.

5.0 out of 5 average rating, 491 reviews

Popular amenities for South Portland waterfront rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Waterfront apartment rentals

Guest favorite
A cozy living room is depicted, featuring two brown leather sofas with colorful cushions. A wooden coffee table sits center stage. Large windows adorned with patterned curtains allow natural light to fill the space, while shelves decorated with various items line the walls.
Apartment in Portland

Monument SWEET!

4.93 out of 5 average rating, 345 reviews
Guest favorite
A luxurious queen bed is adorned with intricate linens and decorative pillows. Two bedside lamps provide soft lighting, and large windows dress the space with natural light, framed by sheer curtains that enhance the overall elegance.
Apartment in Cape Elizabeth

Portland & Beach & Lighthouses! Romantic! Lovely

4.87 out of 5 average rating, 611 reviews
Top guest favorite
Apartment in Cape Elizabeth

Beautiful Kettle Cove Apt Steps to Beaches

4.99 out of 5 average rating, 134 reviews
Guest favorite
The living area features a gray couch with a decorative yellow pillow, framed by three large windows that fill the space with natural light. Two patterned armchairs are positioned opposite the couch, and a circular coffee table holds magazines, creating an inviting seating arrangement.
Apartment in Portland

Parkside Retreat on Portland's Eastern Promenade

4.8 out of 5 average rating, 358 reviews
Guest favorite
A cozy living area features a comfortable gray sectional sofa and an accent chair beside large windows dressed with sheer curtains. A low coffee table sits on an ornate area rug, complemented by a modern media console with a television.
Apartment in Downtown Portland

Downtown Portland ME! 4 Beds & Free Parking!

4.9 out of 5 average rating, 174 reviews
Top guest favorite
The exterior of a two-story building is displayed, featuring a gray facade with white trim. A wooden deck wraps around the second floor, providing multiple seating options. Stairs lead to the upper deck, where a satellite dish is visible. The clear blue sky complements the autumn foliage.
Apartment in Kennebunkport

#2Marsh Views, Cozy quiet spot on river&preserve

4.99 out of 5 average rating, 120 reviews
Top guest favorite
Apartment in Arundel

Cape Arundel Cottage 1 mile to downtown KPT

4.98 out of 5 average rating, 390 reviews
Guest favorite
The spacious living area features dark leather sofas accented with decorative pillows. A wooden coffee table is positioned in front, and a welcoming sign is displayed. Soft lighting from various sources enhances the inviting environment, while natural light enters through nearby openings.
Apartment in Portland

Casco Bay Sunrise

4.81 out of 5 average rating, 167 reviews

Waterfront house rentals

Top guest favorite
The exterior of a charming white house is shown, featuring green shutters and a front porch. A variety of colorful flowers, including pink blossoms, frame the yard, while a vehicle is parked nearby. The lawn is well-maintained with a mix of greenery.
Home in Portland

East End Portland, Water Views

4.96 out of 5 average rating, 162 reviews
Top guest favorite
An aerial view showcases the lush greenery of the property, framed by the coastline and tranquil waters of Cape Porpoise. The landscape reveals homes, docks, and boats dotting the cove, all under a bright sky with scattered clouds.
Home in Kennebunkport

Luxurious 5 bedroom on the ocean, w/ dock & kayaks

4.97 out of 5 average rating, 150 reviews
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.
Home in Saco

3 Bedroom Seaside Oasis | 3 Minute Walk to Beach

4.97 out of 5 average rating, 105 reviews
Guest favorite
Home in Naples

LUX Designer Private Waterfront Hot Tub - Secluded

4.97 out of 5 average rating, 197 reviews
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.
Home in Saco

Oceanfront w/ Stunning views and Private Deck☀️🏖

5.0 out of 5 average rating, 247 reviews
Top guest favorite
An airy living space is highlighted by tall windows that bring in natural light and showcase views of the surrounding trees. A large sectional sofa faces a flat-screen TV, complemented by a wood stove for warmth. A dining area is visible in the background.
Home in Freeport

Waterfront 5 BR Home | On Casco Bay in Freeport

4.96 out of 5 average rating, 145 reviews
Top guest favorite
An open living area features a light-filled space with high ceilings and large windows. A neutral-colored sofa offers comfortable seating, complemented by a wooden dining table with stools. A contemporary refrigerator and kitchen area are visible, along with decorative elements such as a plant and a flower bouquet.
Home in Freeport

Spacious Costal Home in Freeport, ME

4.96 out of 5 average rating, 208 reviews
Top guest favorite
The exterior of a multi-level beach house is visible, featuring a spacious deck with railings and steps leading to the sandy area by the water. The house is painted white with green accents, and tall windows allow for natural light to enter. A brick chimney is located at one end.
Home in Wells

Family Beach House, Wells Beach, Maine

4.96 out of 5 average rating, 128 reviews

Waterfront condo rentals

Top guest favorite
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 Portland

Charming, newly remodeled space atop Munjoy Hill.

4.99 out of 5 average rating, 126 reviews
Top guest favorite
Condo in Old Orchard Beach

Luxury Beach Front Condo! Prime Location!

4.92 out of 5 average rating, 511 reviews
Top guest favorite
A serene view of a sandy beach at sunset, with soft clouds painted in hues of orange and pink against a clear sky. The sun sets gently on the horizon, reflecting on calm ocean waters, creating a tranquil atmosphere.
Condo in Old Orchard Beach

Oceanfront condo, spectacular views

4.84 out of 5 average rating, 122 reviews
Guest favorite
Condo in Old Orchard Beach

Elegant 1 bedroom cabin just 50ft from the beach#2

4.79 out of 5 average rating, 168 reviews
Guest favorite
A four-story oceanfront condo building features multiple balconies that overlook a sandy beach. Sunbathers and beach chairs are spread across the shoreline, with a vibrant atmosphere enhanced by people enjoying the coastal setting under a partly cloudy sky.
Condo in Old Orchard Beach

The Brunswick

4.85 out of 5 average rating, 117 reviews
Top guest favorite
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.
Condo in Old Orchard Beach

Oceanfront Condo with Awesome Views

4.9 out of 5 average rating, 132 reviews
Guest favorite
The kitchen features modern cabinetry with a light grey finish and granite countertops. Stainless steel appliances include a refrigerator, dishwasher, oven, and microwave. A window allows natural light to illuminate the space, and oak flooring runs throughout, providing a warm atmosphere.
Condo in Wells

Two-Bedroom Condo on the Wells/Ogunquit town-line

4.85 out of 5 average rating, 227 reviews
Guest favorite
A historic brownstone building is located on a bustling street lined with shops and restaurants. The warm tones of the brick contrast with the vibrant sky at sunset. A stairway leads to the entrance of the condo, positioned above street level.
Condo in Downtown Portland

Superb Location! Heart of Old Port/Large Apt

4.96 out of 5 average rating, 97 reviews

When is the best time to visit South Portland?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$44,130 GYDG$46,431 GYDG$35,555 GYDG$41,202 GYDG$65,463 GYDG$73,201 GYDG$73,201 GYDG$65,672 GYDG$65,463 GYDG$62,535 GYDG$43,293 GYDG$47,058 GYD
Avg. temp-4°C-3°C1°C7°C13°C18°C21°C21°C16°C10°C4°C-1°C

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