Holiday rentals in South Portland

4.94 out of 5 average rating, 142 reviews

Sopo Abode

Welcome to your garden oasis. Your home away from home. This elegantly styled garden level apartment in South Portland's crown jewel neighborhood, Sylvan Sites, is spacious, calm, and inviting. Have a sit in your private sauna, and take in the abundant birdsong of the neighborhood from your private back patio while you sip your morning coffee. Just down the road (5 minutes) to downtown Portland, Willard Beach, or Knightville, and 10-15 minutes to Scarborough and Cape Elizabeth beaches.

4.9 out of 5 average rating, 225 reviews

Willard Square - The View

5 minutes to the beach , private deck , cozy apartment just a stone's throw from Scratch Bakery. Grab a bagel, or my personal fave, almond horseshoe, and relax on the deck stroll to the beach. One bedroom apartment on the third floor, fully equipped kitchen. Everything you need for a weekend or a winter rental. The stairs are steep and may not be appropriate if you have mobility issues. sloped ceilings . First response is alaways , "It's so much bigger than the photos show. Fast wifi .

4.92 out of 5 average rating, 344 reviews

Apartment Walking Distance to Willard Beach

Our South Portland in-law suite is on a private floor & has its own private entrance at the back of the house. It is a 1 bedroom, 1 bathroom space with a fully stocked kitchenette and free parking. You'll love being only a 5 minute walk from Willard Beach and walking distance to 2 different lighthouses: Spring Point and Bug Light. You'll also be a 10 minute drive to Old Port. You'll have access to a shared, fenced-in backyard. South Portland Short Term Rental License #: STR2020-0022.

4.96 out of 5 average rating, 232 reviews

Luxury Apt, 7 min to Old Port, W/D, Street Parking

A sunny, private, spacious, recently renovated 1 BD apartment in a quiet neighborhood in South Portland. New kitchen and 2 luxury bathrooms with shared seasonal back patio. Enjoy the new Second Rodeo Cafe next door. Minutes to the beach and downtown Portland. Enjoy Bug Light Park, the Eastern Greenway Trail, and Scratch Bakery; you are close to it all. Please note: From December through March, we have off-street parking space for only one vehicle. We are owner-operated. Lic#2764

Apartment in South Portland

4.95 out of 5 average rating, 179 reviews

Rustic Willard Beach condo ten mins from Old Port!

Second-fl unit in historic 150-yr-old building one block from South Portland's premiere beach! Minutes away from historic Portland Head Light and Downtown Portland. Quaint, spacious and tucked away in charming Willard Square. Brand new kitchen and bathroom! Perfect for families, friends, or couples looking for a relaxing coastal retreat. World-famous Scratch Baking across the street, and the Old Port's incomparable restaurants, shopping and historic architecture across the Bay!

Top guest favourite

4.98 out of 5 average rating, 123 reviews

The Knightcap

Welcome to The Knightcap! Located in the wonderful area of Knightville, just across the bridge from Portland, Maine. In our neighborhood, you will find restaurants, a brewery, diner, grocery stores, and many shops. All within quick walking distances. Portland is a renowned foodie destination. We have everything here. Enjoy our beautiful working waterfront, great restaurants, shops, and the fantastic history and architecture. Or maybe have a relaxing night before a big hike.

4.96 out of 5 average rating, 221 reviews

Willard Beach: Cozy Apartment with a King Size Bed

This luxurious first floor apartment is filled with sunshine all day long and on chilly nights the gas fireplace provides a warm ambiance. We think you’ll especially enjoy sinking into the velvet covered king size bed at night and stepping into the spacious shower that includes a rainfall shower head along with a handheld ... use either or both, as you please! The kitchen is equipped with quartz countertops, solid cherry cabinets and high end stainless steel appliances.

4.89 out of 5 average rating, 192 reviews

Sunny and beautiful brick house apartment

This beautiful and cozy apartment was renovated by our own hands, with energy efficiency and craft in mind. The space is an opened kitchen/living room with 2 bedrooms. Reclaimed beams and old wood mix with fun colors and gorgeous full sunlight. A lush organic garden surrounds the house with backyard chickens. Set on a quiet street, walking distance to Willard Beach & Scratch bakery, 5 minutes to Portland Headlight and 10 minutes to Portland's Old Port.

Superhost

Flat in West End

4.78 out of 5 average rating, 577 reviews

Downtown Studio, Walk Everywhere, Parking

The state of Maine requires all reservations must abide by current state travel restrictions. Please review before booking with us. You will love the location - just park at your reserved spot and forget about it! Great restaurants, bars, coffee shops, museums, Old Port, and Art Districts are all within 20 min walk. Fresh linens, towels, shampoo, french press, an insanely comfortable bed, and warm hospitality are provided, only bring your curious self!

Top guest favourite

5 out of 5 average rating, 254 reviews

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.

4.92 out of 5 average rating, 282 reviews

Guest suite in East End

Gorgeous Studio 2 Blocks from Eastern Prom!

Located in Portland's trendy East End and within walking distance to the Old Port and Downtown, this beautiful studio is only 2 blocks from the Eastern Promenade and Casco Bay! You will have the Unit entirely to yourself with its own entrance, air conditioning, kitchenette, queen sized bed and an additional pull out single. Easily walk to all of the cool breweries, great restaurants, coffee shops, and night life! Welcome to Portland!

4.92 out of 5 average rating, 255 reviews

Top of the Hill So Po In Law

Lovely In law apartment in desirable Meeting House Hill area of South Portland .We were recently the hottest real estate market in the country .Conveniently located , 10 minutes to Portland , and on the doorstep of local beaches, State parks , restaurants ,unique boutique shops ,amazing bakeries and coffee , lunch and antiquing .All you need for a home away from home . Your going to love this neighborhood !

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Popular amenities for South Portland holiday rentals

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Wifi

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Free parking on premises

Air conditioning

Other great holiday rentals in South Portland

5 out of 5 average rating, 25 reviews

So. Po. Sweet Spot

EilidhRating, 5 stars10 months ago

The pictures don't do this lovely place justice - it is incredibly spacious and thoughtfully decorated (I loved all the cabinetry too!). Linda was very communicative and personable and I appreciate the book with clear instructions and local recommendations. We didn't use the kitchen much in our short stay but I noticed it was very well equipped so great if you're looking to cook at home. We found some great spots to eat locally and Portland is a short drive/cheap Uber away if you fancy it. Would definitely stay with Linda again!

5 out of 5 average rating, 4 reviews

Charming Victorian Getaway With Private Patio

LorieRating, 5 stars2 days ago

We immediately felt right at home. This apartment was the perfect stay for our time exploring the Portland and South Portland area. Colleen was a fantastic host! She made sure we had everything needed and more. The entire home was spotless and the beds were extremely comfortable. The next time I’m in this area I will definitely stay here again. Highly recommended!

Guest house in Scarborough

5 out of 5 average rating, 5 reviews

North Coast Retreat | New Luxury Near Beaches

ShanroyRating, 5 stars3 weeks ago

Leading up to my stay we started communicating to know everything I need to know for check in. Cindi was very flexible with the check in seeing I was on my motorcycle on a road trip and needed to get out the cold 🥶. Went inside and wow took my breath away. The home was perfectly laid out everything was there you needed. I would literally stay there forever lol. Very clean comfortable and just homey. I highly recommend this host and property 5 star rating all the way. Thank you Cindi for allowing us to stay in your home.

4.79 out of 5 average rating, 38 reviews

Newly Renovated Private Suite

EricRating, 5 stars8 months ago

Patrick’s place is perfect for anyone looking to stay near Portland, but still a quick ride away - to have some peace and quiet come night time. It has everything you need for a comfortable stay. Patrick was very responsive and checked in on us during our stay to make sure we were finding everything well. We would recommend this to anyone looking for a quick visit to Portland!

Superhost

Hotel room in Downtown Portland

4.87 out of 5 average rating, 463 reviews

Eateries, nightlife, galleries – walk to it all

JackieRating, 5 stars4 days ago

Our stay at the Aloft was amazing! Location was great and walking distance to so many restaurants, bars, shops. All the staff were very nice! Would love to stay here again

Private room in South Portland

4.89 out of 5 average rating, 374 reviews

Airy Room in Antique Victorian - SOPO

HenriqueRating, 5 stars3 weeks ago

I thought it was great! It was exactly what the pictures and descriptions said it would be. The only thing I would watch out for is if you get the AIRY room it does face the street so you can hear cars passing by. I didn’t wake up at night because of it but I’m also not a light sleeper so it might be different for you. But like I said. This was probably the most accurate depiction of any place I’ve ever stayed at. So if it looks good to you on the app it’ll look good to you in person.

4.89 out of 5 average rating, 38 reviews

Willard By the Sea - 30 ft to the beach- 2nd floor

LisaRating, 5 stars3 weeks ago

We loved our long weekend at Kathy’s place on Willard Beach! It was easy to find and access, clean and comfortable, and full of character and charm. It was a quiet little place to land after exploring Portland that was very walkable and close to cute shops and restaurants. We traveled with our 3 year-old and 1.5 year-old, and it was easy to “toddler-proof.” Kathy was very responsive and helpful to recommend activities for us when our plans were foiled by rain. Would love to come back and stay again!