House holiday rentals in Portland

LUX Designer Private Waterfront

Waterfront GLASS cabin with privacy professionally designed, escape to somewhere really special. Crooked river acres surrounding the house with the river wrapping around the property. Dock with direct access to Sebago lake and state park just minutes away, Outdoor shower, hot tub, hammocks, BIG walk-in shower w/ window. Heated bath floors, ac. See through Fireplace. The property has its own sandy swimming beach, pets are welcome. Come enjoy privacy and the space to run around seconds to Sebago.

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!

NewBuilt/HotTub/Great Location-4 min Kennebunkport

Follow us on IG @anchorunwind. Welcome to Mama Bear's House! Perfect girlfriends' getaway or to celebrate a special someone. Sit back and relax in our brand new and fully equipped stylish home just 5 minutes away from Kennebunkport's Dock Square. Spend time reading and sipping a fresh grounded coffee on our cozy egg chair, looking in our peaceful backyard while the sunset closes another memorable chapter of your vacation. Enjoy the firepit with hot cocoa and s'mores or fall for a cornhole game!

Oceanfront w/ Stunning views and Private Deck☀️🏖

Welcome to the Beach House on the Rocks, your very own oceanfront retreat! This beautiful, 1350 sq ft house is nestled right next to the ocean. With panoramic views and the ocean just steps away, you won’t forget this one of a kind experience. Tucked away in the hidden gem of Camp Ellis, you’ll enjoy a lively beach scene in the summer and a tranquil retreat in the off season. Just a short trip away to Old Orchard Beach and 30 min to Portland you’ll never be in need of fun activities.

Birch Ledge Guesthouse--Four Season Maine Getaway

Both rustic and elegant, the Birch Ledge Guest House offers a cozy place to relax and recharge, whatever the season. The first floor features a spacious living room (with queen sized pull-out-couch), dining area, and small kitchen. The bathroom has a walk-in shower. The second floor is a loft accessible by a spiral staircase and has a comfy queen and two twin sized beds. The guesthouse is surrounded by quiet forest and is an easy 30 minute drive to Portland.

3 bedroom house in the heart of Portland

New urban 2000 sq ft home in Portland's vibrant up and coming East End/ Munjoy Hill neighborhood. Mid-century style decor. Open concept kitchen/dining/ living area, 3 spacious bedrooms plus a quiet office/study. 2 balconies with views west to Back Cove. 2 car garage and plenty of free off street parking. There are restaurants and bars with great food and live music close by. There is a convenience store around the corner for any last minute needs.

Reno Barn w/ a lot of Charm! Breweries & Airport

** Cozy Renovated Barn w/ artist loft ** Minutes from airport and within walking distance to the Allagash Brewing Company & other breweries. Lots of hiking trails along the Presumpscot River. Short drive to downtown Portland, restaurants, music venues, beaches, lighthouses and nightlife. Barn is located in a quiet area ~ relax on the back deck with a glass of wine star gazing. Come check us out!!

Drakes Island Beach Front Breathtaking Property !

Ocean views from Kennebunkport to Cape Neddick and a gorgeous half mile sandy beach right outside your door! Watch the sunrise and the sunset over the sandy Drakes Island shores. Enjoy daily walks on the beach or take a walk on the peaceful trails nearby alongside the Rachel Carson Wildlife Refuge & Laudholm Farm, and go to town for restaurants, arcades and more fun. It doesn’t get better than this !

Modern & Sunny East End House. Private Parking!

This modern single-family home is just steps away from Portland's Eastern Promenade with its glorious views of Casco Bay and the islands. Many of the city's best restaurants, cafes, breweries & distilleries are all within a few blocks from the house. Park your car in the private parking spot behind the house and forget about it for a while and enjoy the city!