Holiday rentals in Scarborough

Sunny Scarborough Apartment - Longmeadow Retreat

Relax in this bright 1BR/1BA second-floor apartment just south of Portland. Enjoy a full kitchen, dining area, living room, and spacious bedroom for two. Located 10 minutes from beaches and shopping, with direct access to an interconnected network of walking trails right outside your door. Private unit attached by mudroom, owner onsite for assistance if needed. Whether you’re here to unwind, explore, or need a convenient base near Portland, this retreat offers a comfortable and memorable stay.

Pine Point Beach Lookout

Kick back & relax in this calm, beach themed space with a private deck that overlooks the marsh for morning coffee. 1/2 mile to Pine Point beach, golfing, hiking, kayaking, outdoor activities, shopping, restaurants local breweries, and 5 minutes to OOB Private 1 queen bedroom, full kitchen and living room space with all the amenities of home including washer and dryer in unit. Private entrance - parking available. Backyard with grill and patio table. 20 minute drive to downtown Portland, ME.

Luxury Year-round Treehouse with private hot tub

Skyframe is one of 5 luxurious tiny homes that make up Littlefield Retreat, a tranquil woodland village of 3 treehouses and 2 hobbit houses – each with its own private hot tub and dock. To see all five dwellings, click on the photo to the left of “Hosted by Bryce”, then click “Show more…”. This 15-acre forest retreat on Littlefield Pond offers our guests an experience that feels like a trip up to the woods of northern Maine, but is closer to home and to all the attractions of southern Maine.

Bright, clean, private cottage near Higgins Beach!

Nestled amongst the trees and located just 2 miles from beautiful Higgins Beach and just 5 miles to Portland, this recently renovated, sparkling clean, bright, private, stunning cottage is waiting just for you! Your private entrance is just steps away from your parked car. The cottage is 16 x 20 so it's super cozy! We live on the property (so we're here if you need us) but you are 100 feet from us, way out in the backyard. (It's private!) Our location is perfect for your Maine vacation!

Higgins Beach *New* Beach Home & Private Offices

Custom designed contemporary at the beach. Perfect for a relaxing getaway, visiting family and friends or working remotely. Chef's kitchen w/ high end appliances, granite countertops, enclosed porch grill area. 3 bedrooms and 2 private offices Huge windows and amazing views from all of the rooms highlight the natural beauty of high tides, sun rises and sun sets. Wonderful beachfront walks and beautiful surroundings inside and out. Easy proximity to Portland's Old Port.

Southern Maine Tiny Home Cottage

This newly built stand alone cottage leaves a BIG impression! With high ceilings, a full-size kitchen, generous shower, W/D in unit, King-size bed, queen-size pullout, coffee table that converts to a desk and expandable dining table, it feels like your staying in a much larger home. Cool off with summer air conditioning, or have a cozy winter beverage by the fireplace. Take day trips to every kind of imaginable recreation. Enjoy great beaches and Portland dining only 10 minutes away.

Tiny Pine Point Beach Pad - comfy, cozy surf shed

Fondly referred to as “The Barnacle” this tiny beach pod is the perfect place to eat, sleep & shower. This efficient apartment is PERFECT for those who want to try tiny living! Call this home as you explore the beach, take a hike, enjoy day trips around the coast or check out the vibrant culture in Portland. Super comfy bed, Fully functional kitchen and bathroom have everything you need to prepare simple meals, take shelter from the elements and rest comfortably on vacation!

Pet-Friendly Coastal Studio | Beaches + Portland

This private coastal studio in Scarborough offers a peaceful retreat near Maine’s most beautiful beaches, including Scarborough Beach, Higgins Beach, Ferry Beach, and Pine Point. Downtown Portland is less than 20 minutes away. Perfect for couples, solo travelers, and pet owners. Enjoy a private entrance, full bathroom, kitchenette, and access to a fully fenced yard. Nearby restaurants, shops, and the Eastern Trail make this an ideal home base for relaxation and adventure.

Cozy Tiny Cottage • 9mi Portland • 6mi Beach

Escape the everyday in this charming, brand-new tiny cottage in Scarborough, Maine. The Greenhouse proves you don’t need a lot of square footage to live in style — just the right details. Wake up in a king bed, cook in a fully stocked kitchen, and unwind by the electric fireplace. When evening falls, string lights set the perfect mood for a quiet Maine night. Portland’s restaurants and breweries are 9 miles away. The beach is 6. Come home whenever you’re ready.

Adorable Beach House Across the Street From Beach!

Time for a beach vacation! Cozy home right across the street from Pine Point! Stroll the seven miles of quiet, sandy, residential beach, or bring your bike for a quick ride to the Pier at Old Orchard Beach. Located within a block are several restaurants and a gift shop. Just 20 minutes drive to the heart of Portland, you won't want to miss the local breweries and shopping in Old Port. Kayak rental nearby. Be sure to check out our other listings!

Updated Studio Across From Beach!

Modern beach cottage with a funky industrial vibe. Located across the street from the beach, just about a 2 minute walk to reach the sand. Quick drive (15 miles) to Portland and walk or bike to Old Orchard Beach. Our unit is located across the street from the beach, making it the ideal location for your next beach vacation! Located 2 doors away from the local market and deli, grab a sandwich and head to the quiet local stretch of Pine Point beach.

Poet's Nook: Cozy and Private 1BR Apartment

Close to the Jetport, a number of spectacular local beaches, and downtown Portland, our Poet's Nook is ideally situated. Our place has a country feel while being close to the action. This comfortable and unique apartment has a separate entrance, free parking, and great views of the Maine sky. There are horses across the street and lots of flowers. We're also within driving distance of several amazing beaches.