Approached through a tunnel carved into the rock, this three-bedroom hideaway, sleeping six, is grand without being stuffy... Photograph: PR
Inside, it is all contemporary furnishings and period details, while outside it has a large terrace and a private path leading from the garden to the beach. It is also close to a decent pub, the Bonchurch Inn, and the sophisticated Pond Café for a splurge.
• 07816 901396, undermountbonchurch.co.uk. From £750 per week Photograph: PR
A modernist cedar-and-glass retreat on a wooded cliff above Gurnard Bay (part of the beach below is privately owned by the house), this contemporary, four-bedroom property, sleeping eight, has simple, chic decor, with white walls and bare wood floors... Photograph: PR
Several rooms have glass doors that open on to a wraparound terrace, leading to a large garden with views of the sea and the New Forest. The Cowes yachting centre is a 25-minute stroll along the seafront.
• 0797 4315684, houseblue.eu. From £1,350 per week Photograph: PR
A former cricket pavilion in the grounds of Osborne House, Queen Victoria's retreat on the island, this elegant cottage, sleeping four, belongs to English Heritage (guests get free access to the big house)... Photograph: David Oliver /English Heritage
Sit on the verandah with a book or take a short stroll for a paddle off what was once the queen's private beach.
• 0870 333 1187, english-heritage.org.uk. From £458 for three nights Photograph: Nigel Corrie/English Heritage
Couples in search of a retro lovenest can live out the dream in Little Chert... Photograph: PR
This Thunderbirds-esque property, built in the 1970s, is styled with exposed brick, mosaic tiling and a turquoise-and-orange colour scheme. The garden has dazzling sea views.
• 0844 800 2070, nationaltrustcottages.co.uk. From £183 for two nights Photograph: PR
Heritage fans will appreciate the refurbished English Rose kitchen at this 1960s chalet, a 10-minute walk from the sea, near Ventnor. The kitchens were produced after the war in the same factories that had made parts for the Spitfire fighter aircraft... Photograph: PR
The cottage, which sleeps six adults and two children, also has a collection of early 20th-century bevelled mirrors. Modern comforts include a washing machine and iPod dock, but there's no Wi-Fi so you've got the perfect excuse to do nothing but cloud-spot from the lawn.
• 07802 758113, vintagevacations.co.uk. From £120 for two nights Photograph: PR
