Hosts to the London 2012 Olympic sailing and connected to the Dorset resort of Weymouth by a causeway, Portland is a small Island offering a handful of beautiful holiday homes for rent. Its limestone coastline is beautiful as well as being perfect for sailing and diving. With an interesting stretch of sand that runs adjacent to the main road running from Weymouth to Portland it also branches out beyond the land leaving a sandy strip further out to sea which eventually joins the land at Portland.

8 cottages found 8 match all criteria.

Pennsylvania Castle is a dream come true. The luxurious castle in Portland, Dorset, glows with opulence and sophistication and offers magnificent grounds with a waterfall, a swimming pool and stunning ocean views, as well as a grand interior featuring regal elegance and trappings fit for royalty.

View The Old Higher Lighthouse, an unusual Portland Bill holiday cottage with sea views near Weymouth in Dorset offering a sensational and unique holiday home, once the dwelling place of Marie Stopes, this converted Jurassic Coast Lighthouse sleeps 4 in 2 bedrooms.

Sea Pinks Cottage is a fine example of a traditional Portland stone-built fisherman's cottage built around 1860. Now lovingly restored to create a contemporary coastal holiday cottage near Weymouth, it sleeps 6 in 3 bedrooms and welcomes pets. Pets welcome.

Half Moon is a large, luxury holiday apartment with a swimming pool in a beautifully restored 19th Century fort over-looking the sea on the Isle of Portland in Dorset. Sleeping 12 in 6 bedrooms, all ensuite, guests also have use of beautifully maintained gardens with a waterfall and sea views.

Boasting spectacular sea views, the aptly named Chesil View House gives guests the scenic Dorset coast getaway of their dreams. The family-friendly three-bedroom restored fisherman’s cottage is located on Portland Island in close proximity to Chesil Beach and Weymouth. Pets welcome.

Shearwater is an eco-friendly cottage situated just moments from the sea in Portland, Dorset. The pet-friendly cottage is a designated Passivhaus with a low carbon footprint and boasts a sun-drenched patio plus sea views and joyful decor. Guests can also enjoy use of a beach hut at Church Ope Cove.

Jurassica House is a stunning eco-sustainable townhouse featuring crisp modern lines, a relaxing garden and sweeping views of the ocean. Situated in the heart of Portland, large Weymouth holiday cottage is within reach of many aquatic activities, beautiful beaches and the attractions of Dorset.

9 Sidon Mews is a light and airy seaside cottage offering sleek stylish design and a log burning stove as well as views to Portland Harbour. The modern cottage in Portland also boasts a sun-drenched courtyard and proximity to Portland and the coast of Dorset, making it ideal for family getaways.

The harbour is one of the largest on the south coast of England and is constantly in use from pleasure boats to cross channel ferries. From a map Portland looks like its own secluded island, with tall cliffs lining its perimeter and a stretch of beautiful golden sand. With Weymouth a hop and a skip down the road, the potential for indulging in a spot retail therapy is irresistible. After a long day browsing, the local cuisine is beautifully fresh with seafood bistros dotted along the coast ready awaits your pleasure.