South Portland vacation rentals

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Popular amenities for South Portland vacation rentals

Stay near South Portland's top sights

Old Port223 locals recommend
Willard Beach135 locals recommend
Portland Museum of Art412 locals recommend
Hannaford Supermarket280 locals recommend
Eventide Oyster Co.271 locals recommend
Rosemont Market & Bakery222 locals recommend

Other great vacation rentals in South Portland

Superhost
Home in Old Orchard Beach
4.88 out of 5 average rating, 25 reviews

Walk to beach, shuffleboard, and bunk room

IsaacRating, 5 stars2 months ago
The place was great! It was just as described and Nina responds very quickly and was very sweet! We had a great time!
Guest favorite
Home in Limerick
4.93 out of 5 average rating, 122 reviews

Lakefront Getaway

MarieRating, 5 stars1 week ago
We LOVED our weekend on Arrowhead Lake! Great house for families. We have three teenagers and loved having separate spaces for everyone, as well as places we could all gather together, inside or out! There was something for everyone! Perfectly set up for those who love to cook, fish, kayak, walk or just read a book outside! Nearby we enjoyed the farm stands, our first attempt at disc golf, my son's first catch of a small mouth bass and shopping at the Limerick Grocery Store (very well stocked!). We hope to return again soon!! Elizabeth was a wonderful and attentive host!
Guest favorite
Home in Harpswell
5 out of 5 average rating, 6 reviews

The Hideaway, In Harpswell Maine

NikkiRating, 5 stars7 months ago
We had a great long weekend at The Hideaway! The house was clean and very comfortable for 5 adults. There is a fire pit in the backyard, but plan ahead for firewood as the closest market does not sell it (we found some at Zach's Country Store in Brunswick). It's a great location with beautiful views and great restaurants nearby. We would definitely stay here again!
Top guest favorite
Home in Gray
4.97 out of 5 average rating, 63 reviews

cozy 3 bedroom ranch with deck and screen porch

MichaelRating, 5 stars4 months ago
The house is lovely and, if it’s not new, it sure feels that way. In a very quiet area with tons of outdoor space yet just a mile or two from more main roads. Had a lovely white Christmas/Hanukkah with fresh snow on the 24th. Diana was a great host, always answering questions promptly and rolling with some last minute travel issues. Would love to stay here in warmer months to take advantage of the outdoors and the lovely sun porch.
Top guest favorite
Apartment in Orr's Island
4.92 out of 5 average rating, 120 reviews

Shore House, Posey Unit - Ocean Front Property

JessicaRating, 5 stars6 months ago
We had such a nice stay at this lovely house. The house had everything we needed with a fantastic view. Plenty of things to see and do nearby.
Top guest favorite
Home in Old Orchard Beach
4.98 out of 5 average rating, 89 reviews

Woods Lane Golf and Beach Vacation

MarjorieRating, 5 stars7 months ago
Our group of 5 adults were so pleased we chose to stay at Jason’s house in Old Orchard Beach. We first looked at places in Portland, but Jason’s spacious house offered a quieter setting, with parking and more amenities, at a better price. Comfortable beds, immaculate throughout. Very thoughtfully appointed, with nightstands on both sides of the beds, and superior blackout blinds in the bedrooms. And we ended up spending less time in Old Port, because we enjoyed exploring the towns south of Portland: Old Orchard Beach, Saco, Biddeford, and we found good restaurants (including Holy Donuts!) nearby. We had no issues: we contacted Jason to confirmed our arrival/departure and he responded within minutes. We highly recommend!
Guest favorite
Home in Windham
4.93 out of 5 average rating, 14 reviews

Sebago Lake Beach Paradise

Jan & DebRating, 5 stars4 months ago
Mike & Jess’s home is beautiful! We were celebrating our family Christmas, and this was the perfect location! The kitchen was well stocked and easy to prepare Christmas dinner. The living room was cozy and inviting. The primary bedroom is spacious and mattress was very comfortable. The kids loved the bunk room, and had so much fun hanging out there. It was so cold outside, but we never felt the chill indoors.
Guest favorite
Cottage in Wells
4.94 out of 5 average rating, 147 reviews

Cozy Cottage with Ocean Views, Wells Maine

SarahRating, 5 stars5 months ago
This was a great spot for a fall terrific lady weekend. The surroundings are beautiful and the house is comfortable. We had everything we needed and really enjoyed our stay. Of note, you can't really access the beach from the house; a short drive is required.

Quick stats about vacation rentals in South Portland

  • Total rentals

    550 properties

  • Total number of reviews

    65K reviews

  • Family-friendly rentals

    260 properties are a good fit for families

  • Pet-friendly rentals

    170 properties allow pets

  • Rentals with dedicated workspaces

    300 properties have a dedicated workspace

  • Wifi availability

    540 properties include access to wifi

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 2,730 vacation rentals near Scratch Baking Co, over 5,450 vacation rentals near Portland Museum of Art, and over 2,740 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 1,470 vacation rentals in West End, over 1,360 vacation rentals in Downtown Portland, and over 1,360 vacation rentals in Waterfront District.

  • Are there vacation rentals with a dedicated workspace in South Portland?

    Yes! Work meets play with ease at over 300 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 170 vacation rentals for guests traveling with pets.

  • How much does it cost to stay in boutique hotel rentals in South Portland?

    Experience the best of South Portland with our boutique hotel rentals, starting at about $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do boutique hotel rentals in South Portland have air conditioning?

    Absolutely! We offer over 30 boutique hotel rentals with air conditioning in South Portland. Enjoy a tailored experience with all the comforts you desire.

  • Do boutique hotel rentals in South Portland have wifi?

    Absolutely! We offer over 30 boutique hotel rentals with wifi in South Portland. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly hotel rentals in South Portland?

    South Portland has more than 10 family-friendly hotel rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • 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 house rentals in South Portland have a gym?

    Absolutely! We offer over 10 house rentals with a gym in South Portland. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore