Waterfront holiday rentals in Portland

4.94 out of 5 average rating, 471 reviews

A beverage sits on a small table beside a glass bottle filled with sticks. The view through a window reveals the sandy beach and calming ocean waves, with a colorful sunset casting soft hues in the sky. An American flag is partially visible in the background.

Cottage in Saco

Deja Blue~Guest Beach House

Our beach guest house is an oceanfront dream for a couple's retreat. Come relax by the sea. Listen to the waves crashing right outside your door. Disconnect or work while here we have fast WiFi for you. Enjoy this gem of a place on the coast of Maine as a year round escape. Come make some memories to cherish for a lifetime. All 4 seasons are beautiful here. Pro tip: Wake up early and observe the beautiful sunrise over the ocean. It is totally worth getting up early and will not disappoint.

4.99 out of 5 average rating, 164 reviews

The cabin's exterior is captured through a flickering flame, showcasing large glass windows that invite natural light. Surrounded by lush trees, the cozy structure features a modern design, blending seamlessly with the serene outdoors.

Home in Naples

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.

4.89 out of 5 average rating, 288 reviews

A charming coastal home is showcased with light-colored siding and a bright blue front door. Surrounding greenery includes tall trees and manicured shrubs. The property is set back from a grassy area, adding to its inviting curb appeal.

Home in Falmouth

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!

4.97 out of 5 average rating, 118 reviews

An aerial view showcases the lush greenery of the property, framed by the coastline and tranquil waters of Cape Porpoise. The landscape reveals homes, docks, and boats dotting the cove, all under a bright sky with scattered clouds.

Home in Kennebunkport

Luxurious 5 bedroom on the ocean, w/ dock & kayaks

Historic 1735 home on a spacious one-acre property overlooking the ocean. Enjoy swimming from the dock in Cape Porpoise’s protected cove. Two kayaks provided for exploring the lighthouse & picnicking on nearby islands. Stroll past picturesque lobster boats to the town pier, where restaurants serve fresh local lobster & drinks. Walk to morning coffee, pastries, a local grocery store, athe renowned Nunan’s Lobster Hut. Just two miles from Kennebunkport and a nine-minute drive to Goose Rocks Beach.

4.9 out of 5 average rating, 563 reviews

A wooden treehouse with large windows and a spiral staircase is surrounded by lush green trees. The structure is elevated, allowing for a view of the forest floor, which is covered in natural earth tones from fallen leaves and pine needles.

Treehouse in Sanford

Luxury Year-round Treehouse with private hot tub

The Canopy 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.

4.99 out of 5 average rating, 107 reviews

The image captures an aerial view of a serene landscape with lush green trees surrounding calm waters. The shoreline curves gently, leading to a private dock that extends into the water. A soft sunset glow reflects off the surface, creating a peaceful ambiance.

Home in Georgetown

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.

4.99 out of 5 average rating, 174 reviews

The cabin, designed with a modern aesthetic, features dark exterior walls and large circular windows. A cozy seating area is visible through the glass doors, which are framed by lush greenery and natural landscaping, inviting relaxation in a serene environment.

Cabin in Georgetown

Private Sauna+Near Beach+FirePit+Forest View+Pond

Relax at your own private forest retreat! * Private Cedar Glass Sauna * Minutes Reid State Park Beach & 5 Island🦞 * Private Fire Pit w/S'mores * 100% Cotton sheets/towels * Rain Shower & Heated Bathroom Floor * AC/Heat & Backup Automatic Generator * SmartTV & Record Player w/Vinyl * Fast Broadband Wifi *Pine Cabin is one of two cabins on 8 acres right down the road from one of the best beaches in Maine! The cabins are 150ft. apart and separated by a privacy screen and natural landscaping.

5 out of 5 average rating, 197 reviews

A serene waterfront scene features a small boat gliding across calm waters, reflecting the surrounding buildings. A cluster of white cottages stands on pilings, with a dock visible, under a soft pastel sky as day transitions to evening.

Cottage in Brunswick

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.

5 out of 5 average rating, 208 reviews

A modern beach house is positioned along a serene shoreline, featuring large windows that reflect the colorful sunset. The exterior showcases a blend of natural materials and white accents, with a deck that offers expansive ocean views. Rocky shores frame the property, enhancing the coastal setting.

Home in Saco

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.

Place to stay in Shapleigh

A charming red schoolhouse, dating back to 1866, is surrounded by tall trees and a well-kept grassy area. The structure features white trim, large entrance doors, and a bell tower, evoking a sense of history and nostalgia.

5 out of 5 average rating, 105 reviews

Romantic New England Historic Schoolhouse c1866

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 and tennis court.

5 out of 5 average rating, 101 reviews

An open living area is highlighted by large windows that frame scenic views of the marsh. A modern gas fireplace serves as a focal point, while a light-colored sofa and a small table with a plant create a welcoming ambiance. Bar seating for four extends to the kitchen.

Home in Higgins Beach

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.

4.97 out of 5 average rating, 539 reviews

A cozy cottage is surrounded by greenery, featuring a combination of stone and wood accents. Large windows allow natural light to enter, while a welcoming entryway is flanked by blooming shrubs. The landscaped yard offers a peaceful setting among the trees.

Cabin in Freeport

Cozy Cottage-Near Harbor & Park

Bailiwick Cottage is a cozy, private cottage that looks south down Freeport (Harraseeket) Harbor in Freeport, ME. It is a 4 season accommodation that is close to Freeport shopping, Portland eating, and the Adventure Schools of LL Bean. The cottage sits approximately 50 yards from our main house, has its own parking space and patio, and offers the ability to come and go as you wish. We have had 12 honeymoons in the cottage. Freeport Registration # STRR-2022-59

Popular amenities for Portland waterfront rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Waterfront apartment accommodation

4.92 out of 5 average rating, 171 reviews

A welcoming living area is showcased with soft furnishings in varied colors, including a green sofa and light blue armchair. A patterned area rug is placed under a coffee table. Natural light streams through a window adorned with sheer curtains, while a floor lamp and table lamp provide additional illumination.

Apartment in Richmond

Stunning Royal Richmond 2 Br Apartment Get Away!

4.96 out of 5 average rating, 509 reviews

A spacious living room is illuminated by natural light from multiple windows. A comfortable sofa and a modern chair are positioned around a low coffee table. A work desk with a lamp is situated against one wall, adding functionality to the inviting space.

Apartment in East End

Crow's Nest

Apartment in Cape Elizabeth

4.98 out of 5 average rating, 124 reviews

Beautiful Kettle Cove Apt Steps to Beaches

Apartment in Orr's Island

The exterior of a multi-unit house is displayed, showcasing a combination of gray siding and a distinctive red roof. A wooden deck is visible on the second level, connected to an open lawn area featuring grass and flowerpots. A clear blue sky enhances the setting.

4.92 out of 5 average rating, 124 reviews

Shore House, Posey Unit - Ocean Front Property

4.98 out of 5 average rating, 359 reviews

Apartment in Arundel

Cape Arundel Cottage 1 mile to downtown KPT

Apartment in Downtown Portland

A cozy living area features a comfortable gray sectional sofa and an accent chair beside large windows dressed with sheer curtains. A low coffee table sits on an ornate area rug, complemented by a modern media console with a television.

4.89 out of 5 average rating, 158 reviews

Downtown Portland ME! 4 Beds & Free Parking!

4.79 out of 5 average rating, 319 reviews

The living area features a gray couch with a decorative yellow pillow, framed by three large windows that fill the space with natural light. Two patterned armchairs are positioned opposite the couch, and a circular coffee table holds magazines, creating an inviting seating arrangement.

Apartment in East End

Parkside Retreat on Portland's Eastern Promenade

4.9 out of 5 average rating, 104 reviews

A comfortable seating area features a rust-colored couch and a light armchair, arranged around a wooden coffee table. A soft area rug lies beneath, complementing the warm light from nearby windows. The open layout connects to a kitchen in the background.

Apartment in West End

Beautiful West End Apartment

Waterfront house rentals

4.96 out of 5 average rating, 109 reviews

A bright living area features large windows providing views of the ocean and surrounding landscape. Comfortable seating options include a blue sofa and a light-colored couch. A dining table is visible, complemented by wooden beams on the ceiling, enhancing the spacious feel.

Home in Phippsburg

Newly renovated 3BR house w/ stunning ocean views

4.93 out of 5 average rating, 135 reviews

A red post and beam house is nestled among trees, featuring multiple windows and a sloped roof. A wooden deck extends from the entrance, leading to a gently sloping yard surrounded by lush greenery. Sunlight filters through the leaves overhead.

Home in Limerick

Lakefront Getaway

4.89 out of 5 average rating, 127 reviews

An aerial view captures a serene point surrounded by calm water, with lush green trees lining the rocky shore. The rocky outcrop extends into the water, providing direct access to the tidal area. The tranquil setting highlights the natural beauty of the landscape.

Home in Harpswell

Rising Tide Times - quintessential Maine cottage

4.95 out of 5 average rating, 105 reviews

A historic building stands along the river, reflecting its pastel-colored facade on the water’s surface. The surrounding landscape features vibrant autumn foliage, enhancing the scenic view. A bridge can be seen in the background, adding context to the setting.

Home in Brunswick

In Town Splendor at Castle Rock, Brunswick

4.91 out of 5 average rating, 373 reviews

A charming white cottage with a sloped roof is situated near the water's edge. Orange window boxes add a pop of color to the exterior, while a stone patio features several wooden chairs. Lush greenery surrounds the property, providing a natural backdrop.

Home in Bath

Gorgeous Studio on the Kennebec

Home in Littlejohn Island

A private balcony offers views of tranquil waters and nearby trees. A white chair is positioned against the railing, inviting relaxation while taking in the natural scenery. The landscape includes subtle reflections on the water's surface, enhancing the coastal surroundings.

4.93 out of 5 average rating, 138 reviews

Stone Isle. 8 acres next 2 little john preserve.

4.95 out of 5 average rating, 151 reviews

The exterior of a charming white house is shown, featuring green shutters and a front porch. A variety of colorful flowers, including pink blossoms, frame the yard, while a vehicle is parked nearby. The lawn is well-maintained with a mix of greenery.

Home in East End

East End Portland, Water Views

4.96 out of 5 average rating, 106 reviews

Two Adirondack chairs are positioned on a rocky area overlooking a serene waterfront. Trees frame the scene, with the sky displaying soft hues of pink and orange during sunset. The calm water reflects the natural beauty of the surroundings.

Home in Phippsburg

Private Oceanfront Home 🔆2 min to Popham ✔️Hot Tub

Waterfront condo accommodation

A sunlit sunroom features white walls and large windows adorned with bamboo shades. A blue futon is complemented by several decorative cushions. Two wicker chairs are positioned around a circular coffee table, inviting relaxation and enjoyment of the serene atmosphere.

4.87 out of 5 average rating, 67 reviews

Beautiful Updated Condo Steps from the Beach

4.99 out of 5 average rating, 115 reviews

A bright living area is revealed, featuring large windows that allow natural light to fill the space. A cozy gray sofa and matching armchair are complemented by colorful pillows. A small side table holds a plant, and a soft area rug adds warmth to the hardwood floor.

Condo in East End

Charming, newly remodeled space atop Munjoy Hill.

A wide sandy beach stretches along the coastline, with gentle waves breaking at the shore. Two figures walk along the water's edge, while a clear blue sky enhances the tranquil atmosphere of the scene.

4.89 out of 5 average rating, 118 reviews

Oceanfront Condo with Awesome Views

A modern living area features a spacious gray sofa and a flat-screen television mounted on the wall. A dining table with four chairs is positioned nearby, while a pattern rug adds texture to the floor. The open layout provides a flow towards the kitchen.

4.93 out of 5 average rating, 14 reviews

Brand new unit 45 Steps to the beach! Sleeps 4

Superhost

A cozy living area features a dark brown sofa set against a backdrop of large sliding glass doors, providing access to scenic views. A small white chair is positioned nearby, and a patterned rug adds texture to the light-colored flooring.

4.67 out of 5 average rating, 122 reviews

Oceanfront condo with Breathtaking view remodeled

A four-story oceanfront condo building features multiple balconies that overlook a sandy beach. Sunbathers and beach chairs are spread across the shoreline, with a vibrant atmosphere enhanced by people enjoying the coastal setting under a partly cloudy sky.

4.83 out of 5 average rating, 105 reviews

The Brunswick

4.98 out of 5 average rating, 59 reviews

A modern kitchen features navy blue cabinetry with gold hardware and stainless-steel appliances, including a refrigerator and oven. A neutral countertop complements the design. Kitchen utensils are organized in a basket, enhancing the functional layout.

Condo in Wells

NEW Beachside Wells Beach Condo with Pool

A bright living area features a red couch with decorative pillows and an ottoman. Two windows offer natural light and views of the surroundings. A television is placed on a white media console, while an air conditioning unit is installed above, ensuring comfort.