Waterfront vacation rentals in Isle of Portland

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Isle of Portland

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

%{current} / %{total}1 / 1
Top guest favorite
An open plan kitchen and living area is showcased, featuring a modern kitchen island with three high bar stools. The living space includes a comfortable sofa accented with several cushions, while large windows allow natural light to fill the room.
Condo in Dorset
4.91 out of 5 average rating, 510 reviews

1 Bed home near Sailing academy Portland, Weymouth

The home is located in Portland near to a Port and 5 miles to Weymouth also 10 min walk to sailing academy The area is noted for diving,windsurfing,fishing,sailing,extensive coastal walks,rock climming, cycle routes It is a one bedroom apartment.There is a small Beach and it’s a short walk to shops,cafe's and restaurants.Includes an open plan kitchen,living room and en-suite bathroom with electric showerThere is a sofa bed on request Parking is nearby but free parking is available in the street

Guest favorite
A balcony with panoramic sea views is highlighted by a small dining set featuring four yellow chairs and a matching table. Sunlight illuminates the area, enhancing the inviting space for relaxation or meals.
Townhouse in Dorset
4.91 out of 5 average rating, 124 reviews

Bright & beautiful 4 bedroom house with sea views

We're very excited to have installed a large balcony overlooking the sea, we hope you'll fall in love with Coastguard's Vantage as much as we have. Many of the rooms have sea views A 3min walk from Chesil Beach, it's the perfect base for experiencing the world famous walks We'll give you a guide about all the free parking spaces within 2mins walk from the house A utility room with washing machine & dryer has space to store boards, sails etc It's also close to the National Sailing Academy.

Guest favorite
A serene outdoor seating area is highlighted, featuring two wicker armchairs with soft cushions and a glass-topped table. Beyond, the tranquil Fleet Lagoon reflects sunlight, providing picturesque views, while colorful flowers add a touch of warmth to the setting.
Chalet in Weymouth
4.95 out of 5 average rating, 218 reviews

Summer Lodge

The Summer Lodge boasts uninterrupted views of the Fleet Lagoon and world famous Chesil Beach from its elevated position on the South West Coast Path (Jurassic Coast). Located just one mile from the Isle of Portland, the home of the 2012 Olympic sailing events and a short drive from Weymouth town centre and harbour, our stunning holiday home is perfectly situated for anyone wanting a coastal escape. Our sea view lodge sleeps 6 people. There are 2 double bedrooms and a small double sofa bed.

Guest favorite
A large window presents a stunning view of the beach and sea, illuminated by natural light. The light curtains gently frame the window, while a television stands on a dresser nearby. The serene coastal scenery offers a glimpse of a sandy beach and distant hills.
Condo in Weymouth
4.91 out of 5 average rating, 462 reviews

Stunning Beachfront apartment overlooking the sea

A brand new apartment just 50 steps from the beach with free parking in the heart of Weymouth directly on the Esplanade with panoramic sea views of the award winning beach. Well equipped and nestled amongst shops and restaurants . Just minutes walk to bars , the harbour and train station. Fully fitted kitchen with family size fridge freezer, oven, microwave, toaster, kettle, cutlery, crockery, dishwasher, washing machine, flat screen TV's, Wifi, Hand, bath and beach towels provided.

Guest favorite
A living room is presented with a navy blue feature wall and elegant chandeliers. A plush blue sofa and floral upholstered chairs provide seating around a central coffee table. A decorative mirror and artwork enhance the space, complemented by a non-working fireplace.
Apartment in Dorset
4.92 out of 5 average rating, 148 reviews

Esplanade: Beach front, Regency flat with parking

Alexandra House, Esplanade is on the seafront overlooking Weymouth’s glorious sandy beach and close to the bandstand, Pavilion theatre, harbour and town centre. This stunning Grade II listed property retains many of its original features and has a modern kitchen, new bathroom and free parking at the rear of the property for one car. This ground floor flat has been refurbished to a very high standard - step into luxury on the seafront and enjoy the uplifting view over Weymouth Bay.

Top guest favorite
A variety of fishing boats and yachts are anchored in the calm harbor waters, with the historic row of buildings in the background featuring distinct thatched roofs. The clear blue sky reflects on the water, enhancing the serene coastal scene.
Apartment in West Bay
4.97 out of 5 average rating, 316 reviews

Jurassic View, Pier Terrace

Pier Terrace, one of many listed buildings within the historic harbour area of West Bay, enjoys a stunning location on the UNESCO World Heritage designated Jurassic Coast. 'Jurassic View', our cosy top-floor harbourside apartment offers beautiful sea and coastal views from every window. Just a short stroll from the beach and within easy reach of local shops, pubs and restaurants, the apartment is ideally situated for a relaxing stay in this breathtakingly scenic part of Dorset.

Top guest favorite
A scenic view of a calm harbor features various boats moored along the waterfront. Buildings with a mix of architectural styles line the opposite bank, displaying warm colors under a partly cloudy sky. A bird is seen flying overhead, adding to the tranquil atmosphere.
Townhouse in Dorset
4.94 out of 5 average rating, 117 reviews

Sailor's Watch: A beautiful home by the sea...

A spacious Grade 2 Listed Dutch Style harbourside merchant house which has been split into two homes. You will be renting our home which spans across the first and second floors. It has been recently refurbished and has wonderful views of the harbour. There is a garden out the back with table and chairs. Close to the main town, beach and amenities of Weymouth. Dogs will be charged at £20 each per booking, please let me know if you are bringing your dog with you.

Guest favorite
Apartment in Weymouth
4.89 out of 5 average rating, 449 reviews

Flat One The Beaches

***Flat one the Beaches is in a central position & can be noisy in the evenings especially at the weekends***Recently converted Grade II listed building on Weymouth seafront. The apartment is one of four located off a private inner courtyard on the first floor. well equipped apartment across the road from Weymouth’s award winning beach and nestled a stones throw away from Weymouth town with its great choice of harbour side restaurants and bars.

Top guest favorite
A bright and inviting area features a large window draped with sheer curtains, allowing natural light to flood in. A small wooden table with two chairs is positioned near the window, complemented by decorative items on the wall and a plant on the table.
Tiny home in Weymouth
4.9 out of 5 average rating, 242 reviews

Cosy Sail Loft on the harbour.

This special place is close to everything, making it easy to plan your visit. With your own parking space, own entrance, bedroom / lounge, own kitchen and Bathroom, you can be fully self sufficient or enjoy all the local pubs and restaurants on your door step. Literally right on the harbour front and only a minute away from the beach, this cosy property allows you to enjoy all of this seaside town within a few minutes.

Top guest favorite
The image shows a beachfront restaurant with a large awning displaying the name 'ROCKFISH.' Multiple outdoor tables are visible on a balcony above. The building's facade features light-colored walls and large windows, contributing to a welcoming atmosphere by the sea.
Apartment in Weymouth
4.93 out of 5 average rating, 254 reviews

Central, beach front apartment - with own balcony

Watch the sun rise and night fall over the bay from this charming, central Esplanade, Georgian first floor apartment with free parking permit. Looking directly onto Weymouth's award winning beach and just minutes from Weymouth's picturesque harbour and town. A comfortable, light and airy living space offering a large sea and beach view balcony with seating. Ideal for couples. Superfast Sky WiFi.

Top guest favorite
A spacious deck overlooks the tranquil Fleet Lagoon, featuring a glass-topped table surrounded by four wicker chairs. A cushioned seating area is positioned nearby, inviting relaxation under the expansive sky filled with scattered clouds.
Place to stay in Weymouth
4.94 out of 5 average rating, 273 reviews

Pebble Lodge

Pebble Lodge is a stylish, modern and luxury home from home for four guests (plus one infant). Situated on the five star Chesil Beach Holiday Park, Pebble Lodge boasts an uninterrupted view of the Fleet Lagoon and Chesil Beach, infamous parts of the Jurassic Coast. Beautiful accommodation, finished with some personal touches really makes Pebble Lodge the perfect coastal escape in all seasons.

Top guest favorite
The hut is visible through a natural frame of green foliage, overlooking a serene pond. The tranquil water reflects surrounding trees and blue sky, while a glimpse of the hut's wooden structure adds a sense of retreat in nature.
Hut in Toller Porcorum
4.96 out of 5 average rating, 272 reviews

Isolated off-grid self-contained cabin

The perfect escape, come and enjoy the private facilities in an idyllic location. The hut is situated in a 22 acre woodland at the heart of our family farm. Surrounded by nature, sit back and enjoy the sights and sounds of our local wildlife. On sunny evenings relax on the veranda overlooking the pond or snuggle up in front of the wood burner after a day of exploring.

Popular amenities for Isle of Portland waterfront rentals