South Portland vacation rentals
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Top-rated vacation rentals in South Portland
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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
Nov 28 – Dec 5
Apartment in Portland
4.78 out of 5 average rating, 304 reviewsStudio w/ Patio, Sauna & Onsite Massage
Jan 5 – 12
Apartment in Portland
4.82 out of 5 average rating, 351 reviewsSpacious and Comfortable Private Apartment
Apr 2 – 9
Apartment in Portland
4.96 out of 5 average rating, 152 reviewsCompact & Complete in residential neighborhood
Oct 30 – Nov 6
Tiny home in Portland
4.97 out of 5 average rating, 397 reviewsThe Garden Cabin Tiny Home
May 30 – Jun 6
Guesthouse in Windham
5.0 out of 5 average rating, 218 reviewsCottage on Black Brook Preserve
May 28 – Jun 4
Home in Lisbon
4.94 out of 5 average rating, 332 reviewsUnplug at a Beachy Bolthole with Classic New England Style
Jan 8 – 15
Apartment in Portland
4.88 out of 5 average rating, 379 reviewsModern East End studio, perfect Portland home base
Nov 29 – Dec 6
Other great vacation rentals in South Portland
Guest suite in Saco
4.94 out of 5 average rating, 380 reviewsBarn-Board Abode (private studio) powered by solar
Dec 18 – 25
Condo in Portland
4.96 out of 5 average rating, 164 reviews"Cornelia" Penthouse Waterfront Suite
Feb 23 – Mar 2
Condo in South Portland
4.94 out of 5 average rating, 119 reviewsRustic Willard Beach condo ten mins from Old Port!
Mar 24 – 31
Guesthouse in Portland
4.97 out of 5 average rating, 564 reviewsThe Carriage House at Libbytown
Feb 16 – 23
Apartment in South Portland
4.95 out of 5 average rating, 167 reviewsComfortable apartment near Willard Beach!
Jun 14 – 21
Apartment in Portland
4.99 out of 5 average rating, 300 reviewsQuiet West End Retreat - parking - 100% Non Smoker
Oct 15 – 22
Apartment in South Portland
4.96 out of 5 average rating, 167 reviewsBeautifully renovated spacious 2br apt in SoPo💗💗💗💗
Jan 1 – 8
Apartment in Arundel
4.91 out of 5 average rating, 126 reviewsGinger Hilltop
Jan 21 – 28
Quick stats about vacation rentals in South Portland
Total rentals
540 properties
Rentals with dedicated workspaces
280 properties have a dedicated workspace
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
150 properties allow pets
Family-friendly rentals
260 properties are a good fit for families
Total number of reviews
57K 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 5,640 vacation rentals near Portland Museum of Art, over 2,820 vacation rentals near Scratch Baking Co, and over 2,830 vacation rentals near Eventide Oyster 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 1,430 vacation rentals in Downtown Portland, over 1,550 vacation rentals in West End, and over 1,430 vacation rentals in Waterfront District.
Are there vacation rentals with a dedicated workspace in South Portland?
Yes! Work meets play with ease at over 280 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 150 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 townhouse rentals in South Portland?
Experience the best of South Portland with our townhouse rentals, starting at about $30 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 condo rentals in South Portland?
South Portland has more than 20 family-friendly condo rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do boutique hotel rentals in South Portland have air conditioning?
Absolutely! We offer over 20 boutique hotel rentals with air conditioning in South Portland. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in South Portland have a bbq area?
Absolutely! We offer over 30 apartment rentals with a bbq area in South Portland. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in South Portland have wifi?
Absolutely! We offer over 120 house rentals with wifi in South Portland. Enjoy a tailored experience with all the comforts you desire.
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