Pet-friendly vacation rentals in South Portland

Luxury Year-round Hobbit House w/ private hot tub

Fern Hollow 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.

Portland + Cape Elizabeth + Beaches + luxurious!

Permit210780 •Luxurious 3 rm apt with 1322 5* reviews! Only a mi to the beach & 4.4 mi to Portlnd - Location! •1st flr Great Rm to dine & relax: microwave, fridge, toaster, Keurig, TV, cooktop •2nd flr huge bathrm & bedrm for 2 w/ another sitting rm + a 2nd bdrm w/ 1 Q & 2 twins •More than 2 people? Alter reservation #’s for additional cost •2 people wanting 2 bedrms? Only add a $50 cleaning fee for 2nd bdrm •luxurious furnishings & superior bedding! •I am known for thinking of EvErYtHiNg ;-l

Large Loft—Walk to Breweries— Coffee Bar—King Bed

Located on outer Forest Avenue in Portland, Maine, Forest Loft is an impressive, custom built, 1 bedroom / 2 bathroom apartment with vaulted ceilings and plenty of space. Due to its close proximity to the breweries on Industrial Way, Forest Loft commonly welcomes craft beer fans from all over the world. Enjoy the proximity to popular amenities while only a short ride from downtown Portland. MAINE'S TOP HOST OF 2022 https://news.airbnb.com/celebrating-our-top-new-hosts-in-each-us-state-for-2022

Luxury One Bedroom Loft in Portland’s Old Port

Immerse yourself in the culture of the Old Port at your luxury loft. A top choice for travelers, The Docent's Collection was most recently awarded Condé Nast Readers' Choice (2025) and Tripadvisor Travelers' Choice (2025). Enjoy this spacious open-concept floor plan featuring a full-sized kitchen and bedrooms with soft luxurious linens and cozy pillows for your comfort. Admire the tapestry of a curated collection of local artists and enjoy five-star service from our local hospitality team.

LUX Designer Private Waterfront Hot Tub - Secluded

Escape to a luxurious, privately designed glass-walled waterfront cabin on 3+ secluded acres along the Crooked River in Naples, Maine. The river wraps around, offering total privacy, your own sandy beach, dock with direct Sebago Lake access, and state park minutes away. Unwind in the year-round hot tub, outdoor shower, hammocks, or by the see-through fireplace. Luxe bath with heated floors, huge walk-in shower w/ scenic window. AC, pets welcome. Perfect peaceful retreat—come recharge!

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.

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.

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!

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.

Bright and cozy Munjoy Hill neighborhood apartment

Bright and cozy apartment in Portland's Munjoy Hill neighborhood with private backyard deck. Short walk (like a minute!) to neighborhood bagels, coffee, breweries, beach, playgrounds, restaurants and 15 minute walk to the Old Port & Downtown. Ample/free street parking available. Our family of four lives upstairs, our home is surrounded by flower gardens and located on the Portland Trail system. We welcome all folks of all backgrounds to our home and neighborhood!

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.

Tiny house near the beach!

Enjoy a wooded retreat just minutes from Maine's stunning Fortune's Rocks beach. This newly constructed tiny home welcomes you for a memorable stay near the coast. We strive to offer a thoughtful balance between modern amenities and a natural setting. This space is perfect for two guests, with a maximum of four who are comfortable sharing tiny accommodations. We are pet friendly for an additional fee - one dog maximum per reservation.