Holiday houses in Isle of Wight

Highlands Apartment 4

Highlands takes its name from the imposing Victorian residence that stood on the cliff top site for over 100 years. Originally built for the Lord Mayor of London, Sir James Thomson Ritchie, and subsequently used by Reverend William Page Roberts, Bishop of Salisbury, for his final years, it was later owned by the McAuslane family, who turned it into a well known hotel. After its closure, it was then used by Upper Chine School for its final years. After being left for a decade, the current Highlands was then constructed, a grand and impressive mock Georgian manor house that lived up to its predecessor in terms of scale and views across Shanklin. However, it was never finished and derelict, open to the elements, for a decade. Now, after an extensive refurbishment and conversion, it is now restored into 5 spacious, luxurious apartments. Each of the apartments offer their own quirks and special features, from the penthouse’s unique roof top conservatory and balcony with its fantastic views to the annexe’s duplex apartment, the property is spread across four levels from the garden to the penthouse with annexe to side. The property benefits from spectacular panoramic sea, town and countryside views around the building, going across to Sandown Bay, Shanklin town and the Downs towards Ventnor. All of the apartments benefit from oak furniture and leather sofas, oak floored living areas with fitted kitchens with granite worktops and all your key appliances, 32″ LED TV with Freesat and DVD and free wifi. Communal gardens are available for all apartments to enjoy with seating available alongside off road parking and cycle parking bays. We are able to offer 15% discounts on car ferry services from Red Funnel from Southampton and Wightlink from Portsmouth and Lymington, so please get in touch after booking for details. For apartment 4, the property is a second floor loft penthouse apartment accessed via communal area on first floor with double and single bedrooms. There is a bathroom, kitchen/dinner and conservatory on roof living area with private balcony with views over Sandown Bay. Apartments 1, 2, 3 and 5 are also available to book individually or in any combination for larger groups. The property is found on the coastal path between Shanklin and Sandown and just down the road from National Trust land and Areas of Outstanding Natural Beauty. It is also a few minutes walk from the picturesque Old Village and its thatched cottages, plus shops, pubs, restaurants and the main town, as well as the cliff top, Esplanade and Shanklin’s beaches.

Family · Value · Beach

The View

The house name The View is so called because everyone coming in for the first time says “Oh The View”! Beautiful spacious cottage with stunning views and fabulous outside space including a summerhouse with seating on two levels. Take your choice as to where you might sit to enjoy your favourite drink. A peaceful location yet a walking distance to the award winning restaurants that Ventnor has to offer. Perfect for couples or small families with children over the age of 12. DISCOUNTED FERRY FARES

Location · Family · Check-in

The Ocean Suite, Ventnor Beach (with Sauna)

Laid back beachfront living at its best, a romantic escape - popular with many repeat guests. A cedar cabin with panoramic sea views over Ventnor beach, winner 2025 LUXLife Awards, Best Coastal Retreat, South England. 52 sq metres and open plan, with bi-fold windows/doors creating a beautiful space of just you and the ocean. With 2 private balconies, one south facing for sunbathing, the second with a private sauna, combine with a swim in the sea just a few steps away. No pets but baby welcome!

Value · Family · View

Pussy Mouse Rew, Idyllic Rural Cottage in 6 Acres

This accommodation has been specifically designed for couples looking for a tranquil break where quality and attention to detail are important factors. Ideal for romantic breaks or special occassions, surrounded by open countryside with an abundance of wildlife right outside your door. The quiet yet accessible location is a few minutes drive from various beaches perfect for cycling, walking, nature watching and exploring the IOW. See "Other details" for ferry discounts. EV charging at 40p KWH.

Location · Family · Heating

Sail Away - Ventnor apt with spectacular seaviews

Situated overlooking Ventnor with uninterrupted views of the English Channel. A bright, airy, and fully equipped one bedroom apartment with a private entrance and a small balcony area. Watch the Sun and Moon rise over the sea, see the fishing boats and cruise ships sail by, and if you're really lucky, you might spot a pod of dolphins swim past. On a dark night, you can see the Milky Way light up the sky. 20 minutes stroll to Ventnor beach and High Street with its independent and artisan shops.

Value · Family · Kitchen

Modern seaside garden apartment with sea view

Wheelers Bay Retreat is a well equipped, modern, self contained, 1 bedroom, Victorian seaside garden apartment situated within the leafy, quieter, suburbs of Ventnor, on the Bonchurch borders. Situated on the ground floor with its own private garden, Wheelers Bay Retreat enjoys an elevated south facing sunny position with breath taking panoramic sea views and is perfectly suited for couples looking for a relaxing break or for cyclists and walkers looking for a coastal or countryside adventure.

Family · Location · Walkability

Unique Boutique Retreats

Enjoy the sounds of nature when you wake up in our pine clad eco lodge. It has a fully fenced garden. Watch the sunrise over the downland with the village of Godshill and its church spire in the foreground.Take a short walk to the wildlife pond and ancient woodland within the grounds or sit on the sheltered veranda and watch the ponies grazing in the paddock, whatever the weather inside with the wood burning stove alight looking out, the view is spectacular. Pygmy goats graze in the orchard.

Location · Value · Walkability

Chalet with sunset views and ferry discount

Cliff End is a magical spot where you can truly unwind. Enjoy the breathtaking views and some of the island's most beautiful sunsets from the comfort of your stay. With extensive grounds, children will love the freedom to explore and play outside. Just a short two minute stroll will take you down some private steps to Colwell Bay, a safe swimming beach and home to the fabulous Hut Restaurant. Or venture into the historic town of Yarmouth to enjoy the boutique shops, cafes and restaurants.

Location · Family · Beach

Sandy Haven Hideaway

Sandy Haven, a stunning coastal retreat nestled in a picturesque setting with rolling hills, private garden and a short walk to the beach. Fully equipped ground floor apartment is pet friendly and offers everything you need for an unforgettable stay on the Isle of Wight. Flexible sleeping arrangements, with two kings or a king and two singles, and a set of bunk beds. Electric vehicle charging available (pre-book only) Discounted car ferry tickets are available to all our guests.

Value · Family · Bathroom

Monterey Egypt Point - Turnstone House

Beautiful newly built 5 bedroom home (summer 24) with panoramic sea views of the Solent. Situated less than 75m from the beach, this is the perfect place to relax and soak in the stunning sea views and sunsets from the decking or relax in the hot tub overlooking the gardens. Play garden games with family and friends on the large lawns or explore the local area only a stones throw from Cowes old town with its boutique shopping, restaurants, coffee bars, marinas and yacht clubs.

Family · Location · Cleanliness

Beautiful, modern chalet with stunning sea views

The Lookout is a recently renovated timber chalet which sits in an elevated position with stunning sea views. The quirky Victorian town of Ventnor with its beach and beachside cafes and restaurants is a short walk away along the promenade which is accessed by steps from the chalet. It’s also a short walk to supermarkets etc. The Lookout is ideal for adults looking for a quiet, peaceful location with stunning sea views whatever the season or weather. 15% ferry discount available.

Family · Location · Access

Waterside House

The apartment is situated in the heart of West Cowes, moments from the Red Jet, good quality restaurants, bars, yacht clubs and the sea front. The space has recently been built and is bright and modern. The bedroom has a king-size bed with luxurious Egyptian Cotton linens. There is a large walk-in shower and good quality towels. The kitchen is fully equipped and includes a Coffee Machine. The sitting area is complete with nest tables and the wall-mounted TV has Netflix.

Location · Family · Decor