Holiday rentals with outdoor seating in South Portland

Amazing Bay View Home with Hot Tub

This enchanting 2-bedroom home is a coastal dream come true! Luxurious and well-appointed, Casco Bay House sleeps up to six, provides a five-star stay, offers all of the comforts of home AND a relaxing hot tub spa. With stunning views of the water, the house also has easy access to dining, shopping, and sightseeing in Portland's lively Old Port district (just 5 minutes away). Whether you seek quiet tranquility or want to hit the town, this waterside house is the perfect home away from home!

Willard Square Charmer

Located in the center of Willard Square, a short trip into Portland, but also a vibrant neighborhood in its own right. Bakeries, restaurants,breweries, a short walk away. 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 cozy place in winter with plenty of room to relax after some exploring. We have installed whole house generators, so we've got you covered no matter what the weather brings .

Cottage style home 2 blocks from the beach!

Comfortable Cottage style home with 3 bedrooms, private baths. Many amenities. Two living areas for everyone's comfort, a beautiful kitchen, a large private outdoor patio with multiple seating, a fire pit and a gas grill. Backyard is partially shared. We are close to the Portland nightlife, airport, shopping, restaurants and family-friendly activities. We are in a community that offers biking , running routes, parks and History. Warm, welcoming home. In law attached with private entrance.

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.

Quiet Neighborhood Apt – Clean, Safe, w/ Parking

Your cute, cozy one bedroom apartment is close to all that Portland has to offer! Your home away from home, you have 1 GBPS Wifi, the fastest Portland offers along with a comfortable desk to work from. Centrally located, the space it is a short drive to all of the great restaurants, bars, shops, parks and more! It is close to the 295-N ramp (Freeport outlet shopping is just a few exits down).Our location blends city living with that “just-off-the-beaten-path” feel that offers pleasant rest.

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.

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

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!

*Serene* West End 2BR w/ Balcony: The Mermaid Cove

The Mermaid Cove is a bright and airy two-bedroom apartment located in Portland’s historic West End. This large private apartment is serene, yet only a few minutes walk to the center of downtown and the Old Port. Each of the two separate bedrooms are outfitted with a queen-sized Casper mattress. With a fully stocked kitchen and bathroom, separate office nook, laundry, and off-street parking, The Mermaid Cove is an easy and convenient place to call home for your visit.

Cape Elizabeth Garden Apt+Beach+Close to Portland!

Bright, airy, two-story, 1000 sf apartment, with view of gardens. Off-street parking and private entrance. First floor living area with kitchenette, and sofa-bed, for additional guests. Second floor king bedroom with full bath. Ideally located a short walk to Kettle Cove Beach, and just minutes from Two Lights State Park, Crescent Beach, Higgins Beach and Robinson Woods Trail. Portland - voted the best restaurant city in the US - is a 10 minute drive. STR Permit #210701.

The Roost - lovely one bedroom efficiency unit

Staying at the Roost means you will be 15 minutes to the ocean, the airport and to the Old Port; 10 minutes to nearby lakes and rivers; 5 minutes to everything downtown Westbrook has to offer, including many restaurants, parks, live music venues, shopping and a movie theater: what you are looking for is nearby! Kick back and relax in this calm, stylish space with a queen-sized bed, kitchenette, dining/work area, excellent wifi, a full bathroom and a big yard.

Beautiful large studio on the ocean.

Our large, light, 2nd floor studio is airy and modern with a deck overlooking the garden, ocean and sunrise. We love to welcome guests so if you'd like to book please introduce yourselves and let us know who is coming. We are caring, unobtrusive hosts who value getting to know our guests a little beforehand. We think we have the best of both worlds here - the peace and beauty of Casco Bay, yet 5 minutes to the center of town.