Skip to content

South Portland vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in South Portland

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

Superhost
Apartment in South Portland
Beautifully renovated spacious 2br apt in SoPo💗💗💗💗
This beautifully newly renovated sunny spot in South Portland is ready to be your home away from home on vacation! Style meets comfort in this sweet 2br apartment. Location and convenience are key to this home: minutes from downtown Portland, the hospital, beaches, the Maine Mall, Municipal Golf course and right off Rt 1, Rt 95 and Rt 295. There is a great private front porch as well as a spacious shared back yard. Plenty of off street parking in a great neighborhood. Vacationland awaits !!!!!
$84 per night
Superhost
Apartment in South Portland
Stylish Studio Near Old Port & Lighthouses
A beautiful, private studio with kitchenette and luxury bathroom in the heart of Ferry Village in So. Portland. Although not on "The Peninsula," the Old Port is just a 9 min drive. Historic Bug Light, the Liberty Ship Monument, and the Portland Headlight Lighthouse at Ft. William Park are all minutes away! The Greenway trail is just up the street. Also in the building is the Knitting Nook Café, which serves coffee, wine, beer, food, and knitting supplies. We are owner-operated. Lic#2764
$84 per night
Superhost
Guest suite in South Portland
Bright Guest Studio Near Lighthouses and Beach
This bright guest studio is steps from the Greenbelt Walkway. Walk (within 10 mins) to two lighthouses, Willard beach, Bug Light Park, Scratch Bakery, Willard Scoops ice cream and a variety of restaurants. Portland is an 8 minute drive or 20 minute bike over the bridge. The space is minimal, bright and airy with windows surrounding, an elevated bed with comfy queen mattress, fully equipped kitchen, washer/dryer and cozy couch for lounging.
$92 per night

Stay near South Portland's top sights

Portland Harbor Museum347 locals recommend
The Maine Mall86 locals recommend
DiMillo's On The Water101 locals recommend
Portland International Jetport50 locals recommend
Fort Williams Park229 locals recommend
Thompson Point28 locals recommend

Other great vacation rentals in South Portland

Superhost
Guest suite in South Portland
Top of the Hill So Po In Law
$95 per night
Superhost
Guest suite in South Portland
Apartment Near Willard Beach
$99 per night
Superhost
Apartment in Portland
Cityscape Loft. Prime Location. Walk Everywhere!
$108 per night
Superhost
Cottage in Portland
Cozy & Quiet Modern Cottage
$79 per night
Superhost
Apartment in Portland
Sophisticated Charm at an unbeatable price!
$125 per night
Superhost
Apartment in Portland
RETRO BnB in the Heart of East End Portland
$92 per night
Superhost
Condo in South Portland
Rustic Willard Beach condo ten mins from Old Port!
$166 per night
Superhost
Guest suite in Portland
Studio, Walk to everything, Parking
$78 per night
Superhost
Apartment in Portland
Charming Downtown 1BR w/ Parking, Walk to Old Port
$108 per night
Superhost
Apartment in Portland
*Serene* West End 2BR w/ Balcony: The Mermaid Cove
$98 per night
Superhost
Apartment in South Portland
Sunny and beautiful brick house apartment
$153 per night
Superhost
Apartment in Portland
Huge Dreamy urban Artist-designed loft
$96 per night

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 2,740 vacation rentals near Eventide Oyster Co., over 5,450 vacation rentals near Portland Museum of Art, and over 2,730 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 1,380 vacation rentals in Downtown Portland, over 1,500 vacation rentals in West End, and over 1,380 vacation rentals in Waterfront District.

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

    Yes! Work meets play with ease at over 270 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 140 vacation rentals for guests traveling with pets.

  • 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 townhouse rentals in South Portland?

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

  • Do serviced apartment rentals in South Portland have air conditioning?

    Absolutely! We offer over 10 serviced apartment 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 townhouse rentals in South Portland have wifi?

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

  • Do serviced apartment rentals in South Portland have a gym?

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

Destinations to explore