Waterfront holiday rentals in 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!

Portland & Beach & Lighthouses! Romantic! Lovely

Location! You get the BEACH + Portland in minutes! HUGE BEDRM Romantic canopy bed w/ lux linens Chaise lounge couch turns into twin bed TV Giant mirror for weddings etc 35’ Great Rm w/ TV Kitchen *quality pots etc New Q Sofa Bed Priv entrance Beachy Light filled tall ceilings Spacious for 2-can fit 5 pond/bridge firepit 2 decks+patio Teak Furniture Open views New bthrm A/C Parking No stairs/Garden Level All in Cape: Crescent Beach 2 Lights State Pk Portland Headlight Prtlnd 8 min! 210780

Moss House: A Modern Waterfront Cabin in the Woods

Featured in VOGUE and Maine Home + Design, this modern, handcrafted cabin offers calm Atlantic views, 150 feet of shoreline, and a private dock, perfect for morning coffee, launching a kayak, or watching seals, seabirds, and passing boats. Set among tall pines, it blends Nordic and Japanese influences in a space that is calm and composed. Interiors of wood, stone, lime plaster, and concrete form a grounded, quietly expressive, and sustainably built retreat. 1hr from Portland, but a world apart.

Historic Schoolhouse c1866 / Sauna + Hot Tub + Gym

Winner of Maine Homes Small Space Design Award 2023 We are located on the private 80-acre Shapleigh Pond in the Southern Maine, an hour from Portland and two hours from Boston. Experience a bygone era in this restored Schoolhouse circa 1866 with many original details such as oversized glass-paned windows, wood plank floors, chalkboards, tin ceiling and more. Modern amenities such as fireplace, private hot tub, fire pit, gas BBQ and access to our pool (June-Sept), pond, gym and tennis court.

Falmouth Waterfront Carriage House Apt

Waterviews! This 1 bedroom apt has a new “purple”mattress, above our detached garage in classic Maine waterfront neighborhood. Next door to the iconic Town Landing Market and Town Landing pier/beach. In beautiful Falmouth Foreside neighborhood. Walkable to Dockside Restaurant and marina, and 10 minute drive or bus to downtown Portland. 20 minute drive to Freeport shopping. We only accept well- behaved and house- trained dogs, no other pets are allowed for a fee of $75.00 per dog per stay.

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.

Penthouse Two Master Waterfront Suite with Rooftop

2023 City of Portland Registration #20185280-ST Stunning penthouse suite with exposed beams, brick accents, and whitewashed poplar walls. Enjoy harbor views from the rooftop deck. Two private master suites feature custom tile showers, one with a soaking tub. The spacious kitchen offers granite countertops and modern appliances. Relax by the gas-fired stove in the inviting living room. In-unit washer/dryer and elevator access included. Please note: no animals permitted due to owner's health.

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.

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!

Cozy log cabin on private pond, near Reid St Park!

Winter or summer, the Little River Retreat will help you step away from the world - but still be minutes from Reid State Park, Five Islands Lobster, the Georgetown General Store, and the rugged beauty of Midcoast Maine. This is our family camp, with our own books, games, and “vibe”. It is not a hotel, and some things may not be “industry standard”. We love the unique charm of this space and place, and many repeat guests do too. We hope you will treasure (and care for it) as we do!

Garrison Cove Studio

Rare, Portland waterfront studio located in the heart of the historic Stroudwater neighborhood, awaits one or two guests looking for an urban hideaway. The newly created studio occupies a 150 year old post and beam barn situated on the banks of the Stroudwater and Fore Rivers. Enjoy morning coffee on the river swing, meditate to the soothing sound of the nearby waterfall or linger over your favorite glass of wine under the splendid backyard grape arbor.