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.

5 cottages found 5 match all criteria.

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.

  • Sleeps 4
  • Bedrooms 2
  • Bathrooms 1

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 self-catering 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 lawns, a waterfall and pa...

    • Sleeps 12
    • Bedrooms 6
    • Bathrooms 6

    Relax in this large, stylish and utterly luxurious Portland quirky sea view apartment with swimming pool within the beautifully restored Pennsylvania Castle, a 19th Century Fort near Weymouth. Margaret River sleeps 8 guests within 4 sumptuously furnished bedrooms, all ensuite.

    • Sleeps 8
    • Bedrooms 4
    • Bathrooms 4

    Without a doubt, The Print Hall, a large, 5-bedroom Dorset holiday apartment with a pool in Portland, is absolutely in the luxury holiday home category. This is a beautiful and contemporary apartment in Pennsylvania Castle, a restored Georgian Fort. Whereas it was built to fend off invaders, it now ...

    • Sleeps 10
    • Bedrooms 5
    • Bathrooms 5

    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.