Family-friendly holiday rentals in South Portland

Willard Square Charmer

Located in the center of Willard Square at 7 Pillsbury, 5 minute walk to Willard Beach. Shops restaurants and bakeries all in walking distance. Ideal for working remotely or just checking out the area. Grab a bagel and a coffee across the street from Scratch and stroll to the beach , it's a 5 minute walk.Portland Headlight is a mile away. Lots of room for remote work or a vacation . Well stocked kitchen, quality linens and space to relax after exploring the neighborhood, or visit to Portland.

Cozy South Portland studio with King bed! REG107

Welcome to our studio! Stocked with all you need! Short walk away from the green belt trail & ocean views. Just 5 minutes away from Fort Williams home to the most photographed light house in America. We are a walk away from bug light,and spring point and if you feel like a beach day Willard beach is 5 minutes away. Don't forget to stop at scratch bakery or the cookie jar for a coffee and treat. Portland's Old Port is just a 10 minute uber ride . FYI ,entrance is in back up a flight of stairs .

Cozy SoPo Condo

Welcome to this cozy one-bedroom apartment in Ferry Village, South Portland, Maine. This charming neighborhood is located just across the Casco Bay from Portland, and it's the perfect place to relax and admire the natural beauty of Maine. Enjoy a tour of our gardens and relax on the string light lit patio. The apartment is located on a quiet street, less than a mile walk from Willard Beach. Take a walk on the Greenway to Bug Light park or towards Knightville for some food and drink options.

Ocean Views, work friendly

This space is the lower level of a single family residence with separate entrance with views of the Casco Bay Ship Channel. More than simply a bedroom, there is a spacious living room with tv and computer workstation. There is a patio for relaxing as you take in the scenery. We are a short walk to Willard Beach, and we provide beach towels and chairs. There is no kitchen but we provide a coffee maker, and small fridge. Places for take out abound nearby. This is a great getaway for couples.

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.

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.

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!

Sunny Spot with Private Parking

This cozy, 1 bedroom apartment is located in the peaceful neighborhood of Knightville. The Portland Peninsula, which includes the historic Old Port and the downtown arts district, is less than a 10-minute drive across the bridge. The perfect spot for a couple or a fun friend getaway! Several excellent dining spots, coffee shops, and markets are all within walking distance from the house. Bike rentals are 2 blocks away! The local beach is a 5-minute drive /10-minute bike ride.

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.

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.

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.

Studio Apt, 7 mins to Downtown, Parking, Café

A beautiful, private studio with kitchenette and luxury bathroom in the heart of So. Portland. Although not on Portland peninsula, the Old Port is just an 7 min drive away. The apartment is five minutes to Willard Beach and 15 minutes to Scarborough beaches. Also in the building is the Second Rodeo Cafe, which serves coffee, breakfast and lunch. Enjoy our new seasonal back patio. The coffee shop is closed Wed. We are owner-operated. Lic#2764