Waterfront holiday rentals in Southport

4.99 out of 5 average rating, 120 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, 211 reviews

A cozy living area is viewed through large glass sliding doors. A wooden coffee table is placed in front of a dark seating area, complemented by two plush pillows. A colorful piece of wall art adds vibrancy to the light-toned walls, enhanced by natural light from the outdoors.

Cabin in Georgetown

Sauna+Near Beach+Pond+Outdoor Shower+Fire Pit

Relax at your own private forest retreat! * Private Cedar Glass Sauna * Minutes Reid State Park Beach & 5 Island🦞 * Private Outdoor Shower * Private Fire Pit w/S'mores * 100% Cotton sheets/towels * Rain Shower & Heated Bathroom Floor * AC/Heat * 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.

4.84 out of 5 average rating, 261 reviews

A glamping Geodome stands elevated against a twilight sky, illuminated by warm lights. A small fire burns in a metal pit near a seated figure. Surrounding trees add greenery to the serene outdoor setting, creating a calming atmosphere.

Dome in Buckfield

StreamSide Getaway- HOT TUB / AC/ Wi-Fi

The Streamside Getaway offers a luxurious glamping experience in a new solar and wind-powered Geodome. Equipped with custom furniture, new hot tub,luxury appliances, free high speed wifi, AC/Heat Unit and modern bathroom and kitchen facilities, guests can enjoy a homely and comfortable stay in nature. A glamping site built in 2022 offers a contactless check-in process with a custom key code. Additionally, we have added archery, axe throwing, and kayaks to enhance your outdoor activity!

4.98 out of 5 average rating, 184 reviews

The cabin exterior is showcased with large glass walls, allowing natural light to fill the interior. A wooden deck is lined with outdoor lights, leading to a hot tub. Surrounded by trees, the peaceful setting is visible, creating a serene outdoor atmosphere.

Home in Naples

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!

4.93 out of 5 average rating, 114 reviews

The image captures a serene riverside scene along the New Meadows River during sunset. Calm waters reflect the clear blue sky, while trees line the banks. Nearby, natural elements like rocky shores and patches of snow create a peaceful outdoor setting.

Cottage in West Bath

Coastal Waterfront Cottage in West Bath

***Please Message me to ask about possible discounts and length of stay minimums.*** 4 season home right on the waters edge on New Meadows River in West Bath sits this newly remodeled home. Fully furnished and includes a Minisplit Heat Pump/ AC, and Propane fireplace. Great location as it is on a dead end road that is just minutes to shopping, restaurants, etc. Incredible spot to watch the boats come and go as Sawyer park boat launch as well as the town boat launch are right in view.

4.88 out of 5 average rating, 154 reviews

A cozy cabin is nestled within a forest, featuring a spacious covered porch and steps leading up to it. Seating is arranged around a fire pit in the foreground, with several black Adirondack chairs placed on a gravel surface, surrounded by lush greenery.

Cabin in Georgetown

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!

4.95 out of 5 average rating, 364 reviews

A treehouse structure is perched on stilts among the trees, surrounded by lush greenery. A cozy screened-in porch with rockers is visible, along with a private wood-fired cedar hot tub on the deck. Steps lead down to the wooded area below.

Treehouse in Georgetown

Modern Treehouse with hottub + Water Views

Experience the airiness of life up among the pines. This unique tree dwelling, with its own private attached wood-fired cedar hot tub, is perched atop a 21-acre wooded hillside sloping to beautiful water views. Enjoy the view from the wood-fired cedar hot-tub or the king size bed--through a wall of windows. This treehouse is cozy all year round, especially in winter. Located in a classic coastal Maine village with Reid State Park's beaches and the famed Five Islands Lobster Co.

The front entrance showcases a vibrant red door framed by two sconces, inviting guests inside. Steps lead up to a spacious deck, which is flanked by decorative flower pots. The house features a classic shingle exterior, accented by charming dormer windows.

4.92 out of 5 average rating, 159 reviews

Renovated home with amazing waterfront views

Welcome to Dancing Pines Cottage! We are located across from West Harbor Pond with beautiful water views in each room. Relax on the deck or bbq on the patio or take a short drive into charming Boothbay Harbor town for lobster rolls. We have three bedrooms and a den/office and 2 full bathrooms and can accommodate up to 7 guests. The house is private and has ample parking. One week rentals for June, July, and August (Saturday-Saturday). We accept either one dog or one cat.

A modern kitchen is illuminated by a rustic light fixture with exposed bulbs, enhancing the open layout. Quartz countertops extend through the space, complemented by stainless steel appliances. A vase of mixed flowers sits on the counter, with a scenic view of the ocean visible through large windows.

5 out of 5 average rating, 103 reviews

Pinkham Cove - Water Front Cottage

Authentic oceanfront Maine home, with stunning views and amazing sunsets. Located on Pinkham Cove at the mouth of Boothbay Harbor. Experience the village of BBH , hiking trails, Botanical Gardens and explore the tranquility of Maine. This is the perfect getaway cottage. Enjoy the deck and beach access. The home was recently remodeled. The kitchen is a gem with quartz countertops and Bosch appliances. Curl up by the cozy fireplace, enjoy the amazing harbor view!!

Cottage in South Thomaston

An open-concept great room features high wooden ceilings with exposed beams. Large windows provide ample natural light and views of the surroundings. A comfortable seating area includes a sofa and coffee table, while a dining space with chairs is positioned near the kitchen.

4.96 out of 5 average rating, 203 reviews

Timeless Tides Cottage

This comfortable 2 bedroom, one bathroom, A-frame pine cottage is set on its own private point with 350 feet of waterfront! Cook out on the grill, lounge on the deck or dock while taking in the wildlife on a beautiful tidal river. Watch nesting Bald Eagles and Great Blue Herons fishing! There is plenty of sight-seeing in this picturesque area. Rockland is just 10-minutes away where you can enjoy shopping, restaurants, museums, galleries, lighthouses and festivals.

Apartment in Boothbay Harbor

A welcoming living space features two comfortable armchairs and a soft couch, with a wooden coffee table at the center. Large windows provide abundant natural light and views of the water. A well-equipped kitchen is visible in the background, along with light-colored cabinetry.

5 out of 5 average rating, 136 reviews

Sail Loft: Oceanfront Apartment on a Pier.

Experience a one-of-a-kind waterfront escape at the Sail Loft in Boothbay Harbor! This unique 1-bedroom apartment is located directly over the water in a working marina, offering stunning panoramic views from every window. It feels like being on a private yacht. Perfect for a couple's getaway, you're just a short walk from all the downtown shops and restaurants. Enjoy a truly memorable stay with free parking included.

5 out of 5 average rating, 174 reviews

A spacious waterfront view captures the serene Kennebec River, adorned with small islands and surrounded by lush green trees. The sky is bright blue with scattered clouds, reflecting a tranquil natural setting.

Guesthouse in Bath

Waterfront Sunrise Cove Cottage

Unwind with spectacular sunrises from this sunny waterfront cottage on a tidal cove in the Kennebec River! This is the perfect home base for a midcoast Maine getaway. The post-and-beam cottage has cozy furnishings and expansive views across a field, pond, and cove. Bald eagles and osprey soar overhead, sturgeon leap in the river & nights are full of stars. Owners live on property with small dog.

Popular amenities for Southport waterfront rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment accommodation

Apartment in Orr's Island

The exterior of the multi-unit house is shown, featuring a light gray facade and a red roof. An expansive wooden deck is visible on the second level, overlooking the green lawn. Bright flowers adorn the entrance, adding a touch of color to the outdoor space.

4.94 out of 5 average rating, 108 reviews

Shore House, Leona Unit - Ocean Front Property

4.95 out of 5 average rating, 174 reviews

The private roof deck offers stunning views of Portland's bustling harbor. The wooden deck features a railing for safety and is furnished with a comfortable outdoor seating area, perfect for enjoying the scenery or relaxing in the sun.

Apartment in Portland

62 Views

4.97 out of 5 average rating, 109 reviews

A serene view of Penobscot Bay is framed by lush green foliage and a rustic wooden fence. Boats are visible in the distance, and the calm water reflects the clear blue sky, creating a tranquil coastal scene.

Apartment in Belfast

Coastal Loft Apartment with Beach Access

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!

4.98 out of 5 average rating, 113 reviews

Apartment in Belfast

Parisian apartment in downtown Belfast, Maine

Apartment in Damariscotta

4.87 out of 5 average rating, 113 reviews

Cottrill House on Damariscotta River #2

Apartment in Downtown Portland

A modern kitchen features an island with bar stools and white shaker cabinets. Bright lighting is provided by pendant fixtures above. Large windows showcase waterfront views, while a dining area is visible, with a colorful striped rug under the table.

4.96 out of 5 average rating, 140 reviews

Penthouse Two Master Waterfront Suite with Rooftop

4.94 out of 5 average rating, 109 reviews

A wooden dining table is set by large windows, offering views of the water and surrounding trees. A blue bowl sits at the center, complemented by placemats in soft blue tones. Natural light fills the space, highlighting the warm wooden floor.

Apartment in Wiscasset

Panoramic Water Views on the Sheepscot

Waterfront house rentals

4.92 out of 5 average rating, 130 reviews

Two wooden chairs are situated on a dock overlooking a calm pond surrounded by dense trees. The water reflects the sky and greenery, creating a serene backdrop. A sense of tranquility is conveyed through the peaceful atmosphere of the natural setting.

Home in Oxford

Mirror Pond Cottage

4.91 out of 5 average rating, 439 reviews

Home in Bath

Beautiful Summer River Retreat

4.89 out of 5 average rating, 166 reviews

A fire pit is positioned near the water's edge, surrounded by two adirondack chairs. The setting sun reflects off the river, casting warm hues across the sky and water. Green trees frame the tranquil scene, creating a peaceful atmosphere.

Home in West Bath

Oak Leaf

A charming two-story cottage with a yellow exterior and a slate roof is surrounded by lush greenery. The inviting front porch features intricate white detailing. A gravel driveway leads to the entrance, while scenic views of the water are visible in the background.

4.97 out of 5 average rating, 30 reviews

Town’s End Cottage

An aerial view of the Harbourside cottage is displayed, highlighting its proximity to the Boothbay Harbor waterfront. The surrounding area includes various buildings and a parking lot, with boats visible in the water. Ample greenery frames the cottage, enhancing the welcoming ambiance.

4.91 out of 5 average rating, 77 reviews

Cheerful Harbourside Cottage

5 out of 5 average rating, 17 reviews

Home in Southport

Southport, ME Waterfront- (Boothbay region)

4.96 out of 5 average rating, 110 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

4.97 out of 5 average rating, 113 reviews

The exterior of the guest house is shown, featuring a light-colored facade with large front windows. A wooden deck is accessible via steps on one side, while two garage doors are visible at the ground level. Surrounding greenery and a well-maintained lawn contribute to the inviting environment.

Home in South Bristol

Hermit Thrush House

Waterfront condo accommodation

4.91 out of 5 average rating, 500 reviews

Luxury Beach Front Condo! Prime Location!

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 Portland

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.

4.9 out of 5 average rating, 127 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

5 out of 5 average rating, 5 reviews

Condo in Edgecomb

Coastal Sunrise Condo 2 bd (1 king,1 twin) Balcony

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.

4.84 out of 5 average rating, 115 reviews

The Brunswick

4.98 out of 5 average rating, 40 reviews

A serene waterfront scene captures a dock curving toward a hazy sunrise over the water. Soft clouds scatter in the sky, reflecting gentle hues of orange and yellow, while a bridge is visible in the distance. Green grass and reeds frame the tranquil setting.

Condo in Edgecomb

Waterviews|Sunsets|Boothbay Harbor

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.