
Waterfront holiday rentals in South Portland
Find and book unique waterfront accommodation on Airbnb
Quick stats about waterfront rentals in South Portland

Total holiday rentals
Explore 30 holiday rentals in South Portland

Nightly prices starting at
South Portland holiday rentals start at $83 AUD per night before taxes and fees

Verified guest reviews
Over 4,890 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
30 of South Portland holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across South Portland rentals

4.7 Average rating
South Portland stays receive an average rating of 4.7 out of 5 from guests
Top-rated waterfront accommodation in South Portland
Guests agree: These waterfront accommodation options are highly rated for location, cleanliness and more.

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

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.

Cottage style home 2 blocks from the beach!
Comfortable Cottage style home with 3 bedrooms, private baths. Many amenities. Two living areas for everyone's comfort, a beautiful kitchen, a large private outdoor patio with multiple seating, a fire pit and a gas grill. Backyard is partially shared. We are close to the Portland nightlife, airport, shopping, restaurants and family-friendly activities. We are in a community that offers biking , running routes, parks and History. Warm, welcoming home. In law attached with private entrance.

Spacious 2 bedroom cabin, 50ft from the beach no.8
This spacious, charming cottage features two bedrooms. One bedroom has a queen bed and one has two bunk beds, for a total of 6 people maximum. The open kitchen, dining, living room area has cathedral ceilings. The bathroom offers his & her sinks, shower and whirlpool tub. Relax with the whole family at this peaceful place to stay. Fully equipped efficiency kitchenettes, with dishes, utensils, paper towels, and coffee provided Individually controlled heat & air conditioning All linens provided

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."

Falmouth Waterfront Carriage House Apt
Waterviews! This 1 bedroom apt has a new “purple”mattress, above our detached garage in classic Maine waterfront neighborhood. Next door to the iconic Town Landing Market and Town Landing pier/beach. In beautiful Falmouth Foreside neighborhood. Walkable to Dockside Restaurant and marina, and 10 minute drive or bus to downtown Portland. 20 minute drive to Freeport shopping. We only accept well- behaved and house- trained dogs, no other pets are allowed for a fee of $75.00 per dog per stay.

Beautiful Kettle Cove Apt Steps to Beaches
This sunny, 1 BR ground-floor apartment in Cape Elizabeth has seasonal water views and is nestled between Kettle Cove, Crescent Beach, and Two Lights State Parks. Fields, forests, beaches and ponds are a stroll away, while downtown Portland is an easy 15-minute drive. The apartment is a great base for exploring Southern Maine and an equally great place to simply soak in the restorative water and air of coastal Maine. Get one free sauna session in Kettle Cove Sauna, subject to availability.

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!

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.

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.
Popular amenities for South Portland waterfront rentals
Waterfront apartment accommodation

Shore House, Leona Unit - Ocean Front Property

62 Views

Old Port Gem- 2 BR Loft/418 Fore St

#2Marsh Views, Cozy quiet spot on river&preserve

Beachside Penthouse Paradise on Old Orchard Beach

Modern Waterfront Apt with Bay Views

Willard By the Sea - 30 ft to the beach- 1st floor

Beach Front, Waterfront, Ferry Beach
Waterfront house rentals

Easy Old Port Access - Casco Bay Views Craftsman

Maine Vacation Home on the Water

Ocean Paradise Sunrise/Sunset Peaks Portland

Lobster Boats & Harbor View Pine Point Home

Cozy Lakefront Cabin-Private Dock-Kayaks-Firepit

Cozy Camp on the lake

Home on Historical Island and Saco River (+ Gym)

The Blowfish - Oceanside Escape
Waterfront condo accommodation

Luxury Beach Front Condo! Prime Location!

Charming, newly remodeled space atop Munjoy Hill.

Oceanfront Condo with Awesome Views

Brand new unit 45 Steps to the beach! Sleeps 4

*GRAND VICTORIAN*MODERN *OCEAN VIEWS* 3 BEDRM

Oceanfront condo with Breathtaking view remodeled

Kings Wharfe Riverside Kennebunkport

The Brunswick
When is the best time to visit South Portland?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $293 AUD | $308 AUD | $236 AUD | $264 AUD | $331 AUD | $406 AUD | $486 AUD | $436 AUD | $435 AUD | $415 AUD | $287 AUD | $312 AUD |
| Avg. temp | -4°C | -3°C | 1°C | 7°C | 13°C | 18°C | 21°C | 21°C | 16°C | 10°C | 4°C | -1°C |
Destinations to explore
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- Family-friendly rentals South Portland
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- Rentals with outdoor seating South Portland
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- Fitness-friendly rentals South Portland
- Rentals with a washing machine and dryer South Portland
- Rentals with a hot tub South Portland
- Rentals with pools South Portland
- Rentals with a fire pit South Portland
- Private suite rentals South Portland
- Pet-friendly rentals South Portland
- Rentals with beach access South Portland
- Rentals with a patio South Portland
- House rentals South Portland
- Rentals with a fireplace South Portland
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- Waterfront rentals Cumberland County
- Waterfront rentals Maine
- Waterfront rentals United States
- Sebago Lake
- Ogunquit Beach
- Wells Beach
- Long Sands Beach
- Popham Beach, Phippsburg
- Scarborough Beach
- York Harbor Beach
- Popham Beach State Park
- Pemaquid Beach
- Willard Beach
- Pemaquid Point Lighthouse
- East End Beach
- Short Sands Beach
- Cape Neddick Beach
- King Pine Ski Area
- Gooch's Beach
- Coastal Maine Botanical Gardens
- Crescent Beach State Park
- Wolfe's Neck Woods State Park
- Footbridge Beach
- Funtown Splashtown USA
- Pleasant Mountain Ski Area
- Palace Playland
- Hills Beach





