Waterfront vacation rentals in South 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!

View · Beach · TV

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.

View · Beach · Nearby

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."

Beach · View · Checkout

Two-Story, Direct Ocean Views on Eastern Promenade

You will be delighted by the direct ocean views in this 3-bedroom 2-bathroom apartment located on the Eastern Promenade. Cross the street to enjoy the 88-acre waterfront park for kayak rentals, a morning at the playground, tennis at the courts, a walk on the trails, an afternoon at the beach, or a picnic on the green. This two-story apartment offers a bathroom on each level, a side deck, washer/dryer for extended stay convenience, air conditioning and lots of windows to enjoy the views.

View · Beach · Location

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.

View · Beach · Wifi

Easy Old Port Access & Casco Bay View Craftsman

Experience classic New England charm in this beautifully restored Craftsman-style home with sweeping water views of Casco Bay and the Presumpscot River. Just minutes from Portland’s Old Port, this spacious six-bedroom, three-bath retreat offers easy access to shops, dining, and waterfront attractions. Enjoy hardwood floors, original trim, and modern updates for comfort, plus a hot tub, private patio, yard, and plenty of parking. Perfect for families, groups, and gatherings year-round.

View · Beach · Amenities

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!

River · View · Walkability

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!

View · Beach · Location

Fore River Getaway

A rich and restful oasis for a small group or family traveling through or with Portland as destination. Our second story suite features views of a waterfall and the tidal river on Casco Bay. Consider our suite the perfect calm home base for all your adventures. The “Fore River Getaway” is an expanded version of our popular "Fore River Suite" space and accommodates up to 4 guests. We hope to host people looking for peace and quiet, and will not host loud, rowdy groups.

River · Beach · Indoor spaces

East End Portland, Water Views

Perfect location! Eastern Promenade section of Portland, Maine. 4 night rental required. Will consider longer stays of 2, 3 or4 weeks. This 1885 landmark Cape, provides cozy accommodations, a fenced yard and views of Casco Bay. Just a few steps from the Prom offering trails, tennis, playground, boat launch, beach, kayak rentals, and food trucks. A short walk/bus to the bustling Old Port and downtown. No parties, pets, smoking or excessive noise at this venue, pease.

Beach · View · Checkout

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.

View · Amenities · Bathroom

Blueberry Hill

Beautiful property located on Watchic Lake in Standish Maine. Clear clean spring fed lake. 25 minutes to Portland with access to shopping, restaurants and entertainment. 45 minutes to North Conway New Hampshire. Where you wil find plenty of shopping, restaurants and winter skiing. Property includes use of Main Chalet home year round and two additional cabins each sleeping 4 are available from May-Oct. Great for extended families and friends.

Beach · View · Skiing