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.

Guest favorite

Cottage in Scarborough

4.85 out of 5 average rating, 279 reviews

Charming 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

G$23,492 GYD per night
Superhost

Apartment in Portland

4.82 out of 5 average rating, 347 reviews

Spacious 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

G$13,691 GYD per night
Guest favorite

Apartment in South Portland

4.89 out of 5 average rating, 199 reviews

Willard 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

G$37,800 GYD per night

Popular amenities for South Portland vacation rentals

Stay near South Portland's top sights

The Maine Mall86 locals recommend
Portland International Jetport50 locals recommend
Fort Williams Park229 locals recommend
Thompson Point28 locals recommend
Portland Museum of Art412 locals recommend
Portland Harbor Museum347 locals recommend

Other great vacation rentals in South Portland

Guest favorite

Apartment in South Portland

4.91 out of 5 average rating, 148 reviews

Sunny and beautiful brick house apartment

Oct 29 – Nov 5

G$43,408 GYD per night
Guest favorite

Apartment in Portland

4.97 out of 5 average rating, 475 reviews

Amazing Views! Perfect Location. Loft style feel.

Apr 4 – 11

G$28,533 GYD per night
Superhost

Apartment in Portland

4.81 out of 5 average rating, 936 reviews

Parking | Self-check-in | Washer+Dryer | Kitchen 5

Jan 12 – 19

G$20,583 GYD per night
Guest favorite

Apartment in South Portland

4.95 out of 5 average rating, 167 reviews

Comfortable apartment near Willard Beach!

Jun 29 – Jul 6

G$89,849 GYD per night
Guest favorite

Guest suite in Freeport

4.96 out of 5 average rating, 193 reviews

Weather's Edge, Freeport

May 30 – Jun 6

G$18,325 GYD per night
Guest favorite

Guest suite in Portland

4.91 out of 5 average rating, 193 reviews

Gorgeous Studio 2 Blocks from Eastern Prom!

Feb 17 – 24

G$21,295 GYD per night
Guest favorite

Apartment in South Portland

4.96 out of 5 average rating, 163 reviews

Beautifully renovated spacious 2br apt in SoPo💗💗💗💗

Aug 25 – Sep 1

G$48,226 GYD per night
Guest favorite

Condo in South Portland

4.94 out of 5 average rating, 116 reviews

Rustic Willard Beach condo ten mins from Old Port!

Nov 28 – Dec 5

G$56,573 GYD per night
Guest favorite

Guesthouse in Windham

5.0 out of 5 average rating, 214 reviews

Cottage on Black Brook Preserve

May 30 – Jun 6

G$26,503 GYD per night
Guest favorite

Home in Lisbon

4.94 out of 5 average rating, 328 reviews

Unplug at a Beachy Bolthole with Classic New England Style

Feb 20 – 27

G$13,862 GYD per night
Guest favorite

Apartment in South Portland

4.95 out of 5 average rating, 255 reviews

Stylish Studio Apt with Parking

Jul 26 – Aug 2

G$42,095 GYD per night
Guest favorite

Apartment in Portland

4.93 out of 5 average rating, 532 reviews

Historic Home in the West End. Private Parking.

Nov 6 – 13

G$33,403 GYD per night

Other great vacation rentals in South Portland

Guest favorite

Condo in Portland

4.96 out of 5 average rating, 159 reviews

"Cornelia" Penthouse Waterfront Suite

Jan 12 – 19

G$87,915 GYD per night
Guest favorite

Guesthouse in Portland

4.97 out of 5 average rating, 562 reviews

The Carriage House at Libbytown

Aug 22 – 29

G$35,936 GYD per night
Superhost

Apartment in Portland

4.82 out of 5 average rating, 310 reviews

Charming roomy in-town apartment, parking included

Apr 24 – May 1

G$28,043 GYD per night
Guest favorite

Guest suite in Cumberland

4.92 out of 5 average rating, 108 reviews

Springer Park! adorable guesthouse very stylish!

Jan 22 – 29

G$31,252 GYD per night
Guest favorite

Tiny home in Portland

4.97 out of 5 average rating, 397 reviews

The Garden Cabin Tiny Home

Jul 16 – 23

G$35,539 GYD per night
Guest favorite

Apartment in Portland

4.82 out of 5 average rating, 426 reviews

Walk-able Portland Studio

Dec 11 – 18

G$27,847 GYD per night
Guest favorite

Guest suite in South Portland

4.91 out of 5 average rating, 257 reviews

Apartment Near Willard Beach

Aug 30 – Sep 6

G$64,146 GYD per night
Guest favorite

Guest suite in Windham

4.93 out of 5 average rating, 149 reviews

Millers Private Studio on Highland Lake

Sep 16 – 23

G$24,113 GYD per night
Superhost

Apartment in Portland

4.89 out of 5 average rating, 271 reviews

Quaint West End Flat, 1 bedroom, lots of character

Sep 14 – 21

G$28,372 GYD per night
Guest favorite

Guest suite in Portland

4.95 out of 5 average rating, 150 reviews

Joyful Munjoy Hill Garden Suite

G$18,911 GYD per night
Superhost

Apartment in Portland

4.78 out of 5 average rating, 300 reviews

Studio w/ Patio, Sauna & Onsite Massage

Oct 28 – Nov 4

G$32,584 GYD per night
Guest favorite

Apartment in South Portland

5.0 out of 5 average rating, 40 reviews

Cozy SoPo Condo

Sep 12 – 19

G$30,444 GYD per night

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.

Destinations to explore