Waterfront vacation rentals in South Portland

Alluring 1 Bedroom cabin just 50ft from beach no.6

Come to relax, or be as busy as you choose and enjoy seven uninterrupted miles of sandy beaches. Nestled in a restful pine grove just a 30 second walk from Maine’s finest beach. 0.75 mile walk to the hustly & bustle of downtown Old Orchard Beach, our Cottage is situated in the peaceful residential pocket of Ocean Park - South Old Orchard Beach. Step out of your cottage and walk just a few steps until your feet hit the flat, golden sand & take in the beautiful Atlantic ocean. Do not miss sunrise!

Charming, newly remodeled space atop Munjoy Hill.

We are a 1 BR condo atop Munjoy Hill, a block from the historic 78 acre ocean side Eastern Prom Park, with its majestic homes, gourmet food trucks, grassy hills, and recreation area. Our condo is an easy, open space, renovated in 2019, with artful touches created by my woodworker husband. From here, you can grab a coffee, and muffin and hop on the Prom's paved walkway, connecting you to the seaport below. Evenings, come back to marvel at the wondrous sunset unveiled, just steps from our place.

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.

Beautiful West End Apartment

You will love staying here. Our spacious apartment feels like a treetop getaway right in the middle of Portland. Our apartment is located right on the West End on Portland's beautiful peninsula. Walking distance to the Old Port, downtown, arts district, and the rest of the peninsula, this is the perfect place to make home base for your Portland stay Explore Portland and all of Maine, work from home while your folks enjoy the area, or just chill here in Portland and "do your Maine thing."

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!

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.

Writers Cabin in the Woods with Sauna!

Nestled in the woods and on Adams Pond with new wood fired sauna! The cabin feels totally hidden away but is less than 10 minutes to Bridgton and Naples, hiking, beaches and restaurants. The woods are beautiful and peaceful and the pond is just down a mossy path. Great for couples or a weekend away. Large deck with grill and outdoor shower, firepit. There is a shared dock on the pond for swimming, fishing, or just enjoying the view as well as a canoe and 2 kayaks, and a paddle board.

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!

Bright & Cozy Beachside Cottage in Camp Ellis

HOUSE IS FULLY FUNCTIONAL - NO STORM DAMAGE. Chill with family or friends, work remotely, and/or do a whole lot of nothing at this chic, freshly renovated beach house in the best coastal neighborhood of Southern Maine. Unobstructed water view, a 1 block walk to Huot's restaurant & bar, the neighborhood beach, and a buzzing marina with wave runners and sailing trips are at your disposal. Old Orchard Beach & solid restaurant options are within 5-10 min drive.

Penthouse Two Master Waterfront Suite with Rooftop

CO2024-01785 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.

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 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 beverage in one of our comfy Adirondacks.

62 Views

Registration #2018-4090. Windows w/massive views from kitchen, dining & living areas, and private roof deck. Enjoy Portland's bustling harbor over morning joe or an evening glass of wine, stroll the Eastern Promenade, walk to excellent restaurants, the Old Port. Like to cook? Fully equipped kitchen! NOTE: Please *do not book this space* if you can't honestly live by our House Rules.