Holiday rentals with outdoor seating in Portland

PRlVATE SUlTE in the Heart of East End Portland

Private Suite in the Heart of East End Portland. Sunny, elegant, Victorian studio with private entrance, bathroom and mini-kitchen area. This location is walkable to award winning restaurants, excellent cafes, the East End Beach where you can rent kayaks, ferries to the islands and more! A perfect romantic getaway close to anything you want to come to Portland to see and do, yet in the quiet, tree lined neighborhood of Munjoy Hill and the scenic East End. See guidebook included in this listing:)

Quiet West End Retreat - parking - 100% Non Smoker

Quiet, 2nd story sunny studio apartment in owner-occupied 4 unit building conveniently located in the historic West End residential neighborhood. It’s a short walk to all that Portland has to offer. Off-street parking for 1 car. Relax on the patio and soak in the summer warmth. Perfect for a single or couple traveling to the area. No complicated checkout procedures! Just leave the key in the lock on your way out and we will take care of the rest. 100% Non- smoking guests only, No Exceptions.

Lobstermen's ocean-front cottage

Be our guests & experience the life & beauty of Midcoast Maine. Relax & enjoy the views, warm up in the sauna or go for a refreshing dip. The cottage is part of an over 100 year old working lobstering, and now oyster farming property we call, Gurnet Village. Located right on historic Route 24, we are conveniently situated between Brunswick & the islands of Harpswell. All rooms have ocean views. The tidal beach & the floating dock (May-Dec) is ideal for seasonal fishing, lounging & swimming.

Dreamy Post&Beam Hideaway Near Portland & Freeport

Escape to a dreamy timber-frame cottage tucked in Maine’s woods! Soaring beams, radiant-heated floors, a king loft bed, and a crackling fire pit await. Sip coffee on one of the two decks, hike Bradbury Mountain (3 minutes away), shop Freeport (10 minutes away), or dine in Portland (20 minutes away)—then return to your cozy hideaway under the stars. Full kitchen, vaulted ceilings, radiant heat floors, private driveway, fire pit and peaceful forest views make it the perfect year-round retreat.

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.

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!

The Maine Frame | Modern A-Frame Cabin in Freeport

• Perfect for small families or couples, our signature A-Frame cabin features a modern interior gas burning fireplace, soaring ceilings, huge windows, stylish interiors, and all the comforts of home. • This cozy 1,100 square foot space comfortably accommodates up to four guests in two bedrooms (one with a King-size bed and the other with a Queen-size bed) and a shared bathroom. • 7 minute drive to downtown Freeport. • Proud to be ranked in the top 1% and voted Guest Favorite!

Sophisticated Charm at an unbeatable price!

Apartment is centrally located to all downtown amenities and transportation system. Located in the beautiful West End on a quiet residential street approximately 1 mile from the downtown area. Apartment (3rd floor) gets beautiful sun throughout and has all of the traditional charm and character of the West End homes but updated bathroom and kitchen, both recently remodeled in 2017. Rental includes access to one parking space for a small to mid size vehicle. STHR-001018-2019

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.

Cozy Rock Cabin #thewaylifeshouldbe

*As seen on Magnolia Network's 'The Cabin Chronicles'* Cozy Rock Cabin is an 800 sq ft cabin on three acres of wooded land. Carefully designed for couples and digital nomads, it has everything you'll need to explore southern Maine (#thewaylifeshouldbe) or just stay cozy in front of a fire. Follow the journey on IG at @cozyrockcabin!

Crescent Beach Gardens

Simply spectacular - panoramic ocean, beach and island views from this spacious second story apartment with shady balcony surrounded by flowers, birds and the sounds of the sea. Fifteen minutes to Portland and every beach and lighthouse in the area. Short walk through the park to the beaches and ledges of three state parks.

Charming West End Hideaway. Private Parking

Built in 1835, this historical home on the West End is just steps from the best eateries, arts and shopping the city has to offer. When you arrive, park your car in your private spot behind the house and forget about it for a while. This cozy second-floor apartment is the perfect place for a getaway!