South Portland vacation rentals
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Top-rated vacation rentals in South Portland
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Cottage in Scarborough
4.85 out of 5 average rating, 279 reviewsCharming beach cottage
Pine Point is a beautiful sleepy village surrounded on three sides by water: peaceful salt marsh, river to the sea, and ocean, with an 8 mile long white sand beach, extensive sand bars at low tide (great for sand dollars!). It is the perfect spot for an unforgettable family vacation. The beach here is considered by many to be the best walking and activity beach in Maine, as well as spectacularly beautiful. Come experience an idyllic week at the beach in Pine Point. This beach is perfect for many reasons: great swimming, windsurfing, beach combing, extensive sandbars, fishing off the jetty. The cottage is located in a quaint and quiet neighborhood, just steps from the path to the beach. Spend your days reading and sunbathing, and fall asleep at night to the sounds of the ocean just outside your window. The house has an open layout downstairs with a light breezy feel, and cozy upstairs sleeping quarters. Beautiful back yard and great deck in the shade, front porch with hammock for afternoon snoozes, and all the amenities of home. 20 minutes from the great little city of Portland for added excitement.
Apr 22 – 29
Apartment in Portland
4.82 out of 5 average rating, 347 reviewsSpacious and Comfortable Private Apartment
Third floor (i.e. a few stairs) spacious apartment with a private entrance. Walking distance to Thompson’s Point, Maine Med and many other trails and attractions. The Old Port is a 5 minute drive (1.5 mi.). There is plenty of free street parking available. Space heaters warm the space in the winter, and a/c is provided in the summer. The house is shared by first floor tenants while our family occupies the second floor. Again, several stairs to navigate, but quite comfortable once you settle in!
Mar 9 – 16
Apartment in South Portland
4.89 out of 5 average rating, 199 reviewsWillard Square - The View
“So much bigger than in the photos.” A charming apartment in the Willard Beach neighborhood of South Portland, Maine. There are bakeries, ice-cream parlor and restaurants within walking distance. Easy access to Portland , Midcoast airport. The area has many local craft breweries and award winning restaurants. This apartment is the perfect spot to stay for your Maine vacation. It is a great walking neighborhood with many attractions nearby, but you might want a car for getting around the area. I
Mar 10 – 17
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for South Portland vacation rentals
Other great vacation rentals in South Portland
Apartment in South Portland
4.91 out of 5 average rating, 148 reviewsSunny and beautiful brick house apartment
Oct 29 – Nov 5
Apartment in Portland
4.97 out of 5 average rating, 475 reviewsAmazing Views! Perfect Location. Loft style feel.
Apr 4 – 11
Apartment in Portland
4.81 out of 5 average rating, 936 reviewsParking | Self-check-in | Washer+Dryer | Kitchen 5
Jan 12 – 19
Apartment in South Portland
4.95 out of 5 average rating, 167 reviewsComfortable apartment near Willard Beach!
Jun 29 – Jul 6
Guest suite in Freeport
4.96 out of 5 average rating, 193 reviewsWeather's Edge, Freeport
May 30 – Jun 6
Guest suite in Portland
4.91 out of 5 average rating, 193 reviewsGorgeous Studio 2 Blocks from Eastern Prom!
Feb 17 – 24
Apartment in South Portland
4.96 out of 5 average rating, 163 reviewsBeautifully renovated spacious 2br apt in SoPo💗💗💗💗
Aug 25 – Sep 1
Condo in South Portland
4.94 out of 5 average rating, 116 reviewsRustic Willard Beach condo ten mins from Old Port!
Nov 28 – Dec 5
Guesthouse in Windham
5.0 out of 5 average rating, 214 reviewsCottage on Black Brook Preserve
May 30 – Jun 6
Home in Lisbon
4.94 out of 5 average rating, 328 reviewsUnplug at a Beachy Bolthole with Classic New England Style
Feb 20 – 27
Apartment in South Portland
4.95 out of 5 average rating, 255 reviewsStylish Studio Apt with Parking
Jul 26 – Aug 2
Apartment in Portland
4.93 out of 5 average rating, 532 reviewsHistoric Home in the West End. Private Parking.
Nov 6 – 13
Other great vacation rentals in South Portland
Condo in Portland
4.96 out of 5 average rating, 159 reviews"Cornelia" Penthouse Waterfront Suite
Jan 12 – 19
Guesthouse in Portland
4.97 out of 5 average rating, 562 reviewsThe Carriage House at Libbytown
Aug 22 – 29
Apartment in Portland
4.82 out of 5 average rating, 310 reviewsCharming roomy in-town apartment, parking included
Apr 24 – May 1
Guest suite in Cumberland
4.92 out of 5 average rating, 108 reviewsSpringer Park! adorable guesthouse very stylish!
Jan 22 – 29
Tiny home in Portland
4.97 out of 5 average rating, 397 reviewsThe Garden Cabin Tiny Home
Jul 16 – 23
Apartment in Portland
4.82 out of 5 average rating, 426 reviewsWalk-able Portland Studio
Dec 11 – 18
Guest suite in South Portland
4.91 out of 5 average rating, 257 reviewsApartment Near Willard Beach
Aug 30 – Sep 6
Guest suite in Windham
4.93 out of 5 average rating, 149 reviewsMillers Private Studio on Highland Lake
Sep 16 – 23
Apartment in Portland
4.89 out of 5 average rating, 271 reviewsQuaint West End Flat, 1 bedroom, lots of character
Sep 14 – 21
Guest suite in Portland
4.95 out of 5 average rating, 150 reviewsJoyful Munjoy Hill Garden Suite
Apartment in Portland
4.78 out of 5 average rating, 300 reviewsStudio w/ Patio, Sauna & Onsite Massage
Oct 28 – Nov 4
Apartment in South Portland
5.0 out of 5 average rating, 40 reviewsCozy SoPo Condo
Sep 12 – 19
Quick stats about vacation rentals in South Portland
Total rentals | 560 properties |
---|---|
Rentals with dedicated workspaces | 290 properties have a dedicated workspace |
Rentals with a pool | 10 properties have a pool |
Pet-friendly rentals | 160 properties allow pets |
Family-friendly rentals | 260 properties are a good fit for families |
Total number of reviews | 56K reviews |
Your guide to South Portland
Introduction
If Portland is Maine’s Manhattan, South Portland might be its Brooklyn — at least that’s the joke among some locals. As the state’s biggest city, Portland gets the lion’s share of the media attention, but its little sister across the Fore River is worth exploring all on its own. Creative entrepreneurs have decamped across the bay to open shops and restaurants, revitalizing walkable neighborhoods like Knightville and Meetinghouse Hill. South Portland is also home to a seemingly endless array of dog-friendly parks, beaches, and trails as well as craft breweries, postcard-perfect lighthouse landscapes, and interesting museums that celebrate Maine’s military and maritime history. To get there from Portland’s West End neighborhood, just cross the Casco Bay Bridge — in a car, on a bike, or on foot. From the other shore, you’ll get a nice view of Portland Harbor, and you can continue your car-free explorations on the Greenbelt Walkway or Spring Point Shoreway.
The best time to stay in a vacation rental in South Portland
Like everywhere else in Maine, South Portland is most popular in the summer, when Mainers can finally swap their long johns for T-shirts. Expect relatively clear skies and comfortable temperatures in the upper 60s to mid-70s Fahrenheit between June and Labor Day, and more than 15 hours of daylight during the longest days of summer. If you book one of the area’s vacation rentals for fall, you’ll need to pack jackets, coats, and scarves instead of shorts and swimsuits, but you’ll be rewarded with fewer crowds and trees ablaze in gorgeous tones of crimson and gold. By January, the mercury hovers around freezing, dipping to 16 degrees overnight, and there are only around nine hours of daylight. Rain falls throughout the year in South Portland, with snow more likely in January.
Top things to do in South Portland
Fort Williams Park
This 90-acre park sits on the site of a decommissioned United States Army post that housed and trained troops during both world wars. Today, more than a million people come here each year to fly kites, ride bikes, and visit the iconic Portland Head Light and Museum, the oldest lighthouse in the state. The scenic shoreline is a popular backdrop for picnics and weddings.
Willard Beach
Locals love this relaxed, uncrowded sand-and-pebble beach, good for ocean swimming when the weather is nice. There’s a snack bar, showers, and tidepools that provide hours of entertainment for curious kids. Or just soak up the summer rays and watch the boats gently bobbing in the bay.
Spring Point Shoreway
Haven’t had your fill of lighthouses? There are two more awaiting you along this 1.6-mile pedestrian path and bikeway: the still-operational Spring Point Ledge Lighthouse, built in 1897, and the spark-plug-shaped Portland Breakwater Lighthouse, which dates back to 1875. Highlights along the way include a pair of sandy beaches and historic Fort Preble, built in 1808, where 23 captured Confederate raiders were imprisoned during the Civil War.
Frequently Asked Questions
Are there vacation rentals near South Portland's top attractions?
You're in luck! Stay at the heart of it all with our vacation rentals near South Portland's top attractions. We offer over 2,780 vacation rentals near Eventide Oyster Co., over 5,550 vacation rentals near Portland Museum of Art, and over 2,780 vacation rentals near Scratch Baking Co, and so much more! Experience the best of South Portland right on your doorstep.
Where should I stay in South Portland?
Make yourself at home in South Portland by choosing from our most frequently booked neighborhoods. We have over 1,410 vacation rentals in Waterfront District, over 1,530 vacation rentals in West End, and over 1,410 vacation rentals in Downtown Portland.
Are there vacation rentals with a dedicated workspace in South Portland?
Yes! Work meets play with ease at over 290 vacation rentals in South Portland featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in South Portland?
Four-legged friends are welcome in South Portland. Choose from more than 160 vacation rentals for guests traveling with pets.
Are there South Portland vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in South Portland, available on Airbnb. Make a splash and soak up the sun in style!
How much does it cost to stay in apartment rentals in South Portland?
Experience the best of South Portland with our apartment rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there family-friendly house rentals in South Portland?
South Portland has more than 90 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do condo rentals in South Portland have air conditioning?
Absolutely! We offer over 40 condo rentals with air conditioning in South Portland. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in South Portland have a bbq area?
Absolutely! We offer over 40 house rentals with a bbq area in South Portland. Enjoy a tailored experience with all the comforts you desire.
Do private suite rentals in South Portland have wifi?
Absolutely! We offer over 20 private suite rentals with wifi in South Portland. Enjoy a tailored experience with all the comforts you desire.
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