Waterfront vacation rentals in South Portland

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in South Portland

Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Cottage in Saco

4.93 out of 5 average rating, 313 reviews

Deja Blue~Guest Beach House

Our beach guest house is an oceanfront dream for a couple's retreat. Come relax by the sea. Listen to the waves crashing right outside your door. Disconnect or work while here we have fast WiFi for you. Enjoy this gem of a place on the coast of Maine as a year round escape. Come make some memories to cherish for a lifetime. All 4 seasons are beautiful here. Pro tip: Wake up early and observe the beautiful sunrise over the ocean. It is totally worth getting up early and will not disappoint.

Oct 19 – 26

R7,797 ZAR per night

Guest favorite

Cottage in Topsham

4.95 out of 5 average rating, 212 reviews

Cozy waterfront home on Merrymeeting Bay.

Our cozy cottage is the perfect romantic getaway or quiet retreat in any season. Located on a private rd with scenic waterfront view. Guests can enjoy sitting on the dock (May- October) or the jetty, watch the eagles and Osprey, use our kayaks, do some fishing, walking or biking. Sit by the propane fueled fireplace on a chilly night. Brunswick, home of Bowdoin College and a # of great restaurants and unique shops is just 5 mi. Travel by bus or train to/from Boston. Portland is @ 30 min away.

Mar 8 – 15

R3,036 ZAR per night

Guest favorite

Apartment in South Portland

4.93 out of 5 average rating, 109 reviews

Willard Square Charmer

Located in the center of Willard Square, a short trip into Portland, but also a vibrant neighborhood in its own right. Bakeries, restaurants,breweries, a short walk away. Ideal for working remotely or just checking out the area. Grab a bagel and a coffee across the street from Scratch and stroll to the beach . It's a cozy place in winter with plenty of room to relax after some exploring. We have installed whole house generators, so we've got you covered no matter what the weather brings .

Jan 6 – 13

R5,092 ZAR per night

Guest favorite

Home in South Portland

4.9 out of 5 average rating, 102 reviews

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.

Jan 19 – 26

R7,052 ZAR per night

Guest favorite

Tiny home in Windham

4.98 out of 5 average rating, 132 reviews

Private riverside retreat

Private tiny house situated on the Pleasant river in Windham Maine surrounded by woods and nature! River is stocked with brook trout and lots of bass. Canoes are available for guest use to explore the river. The camp is located behind the main property ~500ft down a dirt road. 4X4 is recommended or you can park at the main house and it's a 3 minute walk. House is very comfortable with modern amenities. Running hot water, electricity, smart TV, wifi , firepit, outdoor shower, king sized bed.

Mar 11 – 18

R2,969 ZAR per night

Guest favorite

Guesthouse in Bath

5.0 out of 5 average rating, 113 reviews

Waterfront Sunrise Cove Cottage

Unwind and enjoy spectacular sunrises from this sunny waterfront cottage on a tidal cove in the Kennebec River! Less than 30 minutes to Popham Beach, this is the perfect home base for a midcoast Maine getaway. The cottage has a post-and-beam design, cozy furnishings, and expansive views across the field, pond, and cove. Bald eagles and osprey soar overhead, sturgeon leap in the river, and nights are full of stars. Best for 2 adults or a small family. Owners live on property with small dog.

Oct 18 – 25

R3,109 ZAR per night

Guest favorite

Home in Saco

5.0 out of 5 average rating, 124 reviews

Oceanfront w/ Stunning views and Private Deck☀️🏖

Welcome to the Beach House on the Rocks, your very own oceanfront retreat! This beautiful, 1350 sq ft house is nestled right next to the ocean. With panoramic views and the ocean just steps away, you won’t forget this one of a kind experience. Tucked away in the hidden gem of Camp Ellis, you’ll enjoy a lively beach scene in the summer and a tranquil retreat in the off season. Just a short trip away to Old Orchard Beach and 30 min to Portland you’ll never be in need of fun activities.

Apr 3 – 10

R9,128 ZAR per night

Superhost

Cottage in Harpswell

4.9 out of 5 average rating, 124 reviews

Classic Maine Cottage - dock, sauna & kayaks

The Perfect Maine Cottage! On the edge of the ocean, carefully preserved with traditional details. Charming, open floor plan, with a wall of windows to the ocean. Sunny large wrap-around deck and screen porch creates beautiful outside spaces to enjoy. Perfect for listening to waves and watch lobstermen pull up their traps. Cathedral ceilings and Scandinavian design gives the cottage an exclusive feeling. Gentle stairs lead to the private deep water dock for all kinds of boating.

Oct 3 – 10

R9,282 ZAR per night

Guest favorite

Cabin in Freeport

4.98 out of 5 average rating, 470 reviews

Cozy Cottage-Near Harbor & Park

Bailiwick Cottage is a cozy, private cottage that looks south down Freeport (Harraseeket) Harbor in Freeport, ME. It is a 4 season accommodation that is close to Freeport shopping, Portland eating, and the Adventure Schools of LL Bean. The cottage sits approximately 50 yards from our main house, has its own parking space and patio, and offers the ability to come and go as you wish. We have had 12 honeymoons in the cottage. Freeport Registration # STRR-2022-59

Oct 2 – 9

R3,434 ZAR per night

Guest favorite

Condo in South Portland

4.94 out of 5 average rating, 121 reviews

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. Ideal 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!

Sep 19 – 26

R8,384 ZAR per night

Guest favorite

Guesthouse in Richmond

4.9 out of 5 average rating, 137 reviews

The Studio

Welcome to our 2.5 acre haven! This studio is full of life with color that will bring your spirits up. It is a little over 400 sq. ft. with your own private entrance from the garage and above apartment, on the first floor, your own parking and not too far from the city. Richmond is a small town that sits near the Kennebec River and Swan Island where you can enjoy outdoor adventures. * Space not equipped for children *

Apr 4 – 11

R1,974 ZAR per night

Guest favorite

Guest suite in Windham

4.92 out of 5 average rating, 152 reviews

Millers Private Studio on Highland Lake

If you're looking for a quiet, cozy getaway with private Highland Lake access this is the place for you. Private deck to enjoy your morning coffee, close to everything but in a country setting. 15 minutes from 95, Portland ME and Sebago Lake Region. Small boat launch available, Swimming & Fishing . Large back yard and a great window view of the lake. Wifi 100(mbps) for a work from home atmosphere.

Aug 23 – 30

R2,867 ZAR per night