Waterfront holiday 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!

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

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."

Luxury Year-round Treehouse with private hot tub

Skyframe 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.

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.

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!

Rustic, cozy cabin on Sebago Lake. A hidden gem.

Step out of the screened in patio to lakeside relaxation. Dive into crystal waters, snorkel or float with a cool beverage. Kayak or canoe out to Turtle Cove and enjoy the wildlife in this natural waterway teeming with birds to include our resident Blue Heron, ducks, geese, and loons who make this place their home. We have the fortune of bald eagles in several tall pines. Turtles sunning on doting rocks and lily pads in bloom greet us each day. It is a natural water landscape.

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.

Luxury Beach Front Condo! Prime Location!

⚠️ Special rate June 15! ✨ Encourage reserving multiple nights to bring down the cost per night ✨ Minimum stay varies, typically 2 to 3 nights ✨ If you see a longer minimun, it’s likely to prevent the reservation from leaving a single night open. Just select different start date. ✨ Much appreciated if guests book trips connected to other guest trips ✨ Unless the trip is within the next few weeks, please don't book a trip that leaves a single night open ✨

Wren Cabin + Wood fired Sauna

We built the Wren Cabin to be a serene space filled with light and art and with lots of cozy details. Lofted ceilings, a spiral staircase and large open concept with lofted bedroom. The cabin also has a gorgeous wood-fired sauna for those colder days. Wren cabin has a large wraparound deck for relaxing and an outdoor fire pit, as well as shared access to Adams Pond. The space is modern Scandinavian, light and aery, and filled with thoughtful details.

Beautiful large studio on the ocean.

Our large, light, 2nd floor studio is airy and modern with a deck overlooking the garden, ocean and sunrise. We love to welcome guests so if you'd like to book please introduce yourselves and let us know who is coming. We are caring, unobtrusive hosts who value getting to know our guests a little beforehand. We think we have the best of both worlds here - the peace and beauty of Casco Bay, yet 5 minutes to the center of town.