Holiday rentals in Shanklin

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.

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!

Holiday flat in Shanklin, Isle of Wight

'The Courtyard', located in Shanklin's Old Village, is bright, spacious and airy throughout. Please contact us for a Wightlink 25% ferry discount linked to your booking or we may be able to offer a Red Funnel car return at a discount. Due to the convenient location of The Courtyard, it is a short walk to pubs, restaurants and tea rooms . A 10/15 minute walk to Shanklin seafront with cafes, arcades, crazy golf and sandy beaches. Shanklin town and bus links are in close proximity to the flat.

Highcliff Cottage - Clifftop Paradise

Highcliff Cottage at Luccombe is a dream holiday retreat, secluded and tranquil. A 100m high clifftop garden oasis overlooking Sandown Bay and the south of England. Relax on the deck, listen to the bird song and breathe in the fresh air. Situated between Shanklin and Ventnor, the Cottage is designed in the boathouse style with beautiful detailing inside and out, with exclusive use of a large garden and access to a spectacular cliff terrace. The Isle of Wight Coastal Path is at the front gate.

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.

Cozy cottage in a fabulous spot!

Robins Rest is a delightful cottage, 5 minutes walk from the popular Old Village in Shanklin. Walking distance to the beach, & a very good selection of restaurants/independent shops. Bedroom one has one double bed, bedroom two has a triple bunk (double bed & single on top). One bathroom with bath & shower over bath. Parking for one vehicle. Smart TV & WI FI. Perfect for families. Directly opposite a huge green/park & walking distance to all you need. Bus stop outside, great regular service.

Modern 1 bedroom apartment with patio and parking.

A stones throw away from the picturesque Old Village in Shanklin, this apartment offers a modern and tranquil setting, within walking distance of the beach and town centre. The apartment has recently been refurbished to a high standard and offers a comfortable stay with a Super King size bed and quality furnishings. A patio area will allow you to relax and unwind with a glass of wine. A private parking space is included so that you area able to explore our unique and beautiful island.

The Isley Apartment. Modern Charm in Shanklin

Contemporary and colourful flat newly renovated and furnished by a creative family. Open plan kitchen/living area with all the amenities you expect. Study room features built in desk and is stocked with vintage board games. And a relaxing, sky lit bedroom. Conveniently located, the Isley Apartment offers quick access to attractions, sights, restaurants, pubs and shopping just outside the front door. It's a ten minute walk to the beach alongside the historic Victorian Shanklin Chine.

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.

Jaw-dropping view over the English Channel

The Lawn is a semi-detached cottage with a private garden. It has been completely renovated as a stone house to create a friendly holiday home for couples and friends. The building is Grade II Listed from the 1860s with the window casements, original Victorian Conservatory and shaped roof tiles and woodwork being of historic importance. 
Relaxing and fun holidays are guaranteed at The Lawn, so it’s no wonder that many guests return year after year.

2 Bed Apartment The Priory - Panoramic Sea View

This luxury 2-bed apartment is located in a desirable area of Shanklin perched on the top of the cliff with stunning sea views. The apartment is situated on the top floor (2nd Floor) of a recently renovated Victorian gentleman’s residence dating back to 1864. The apartment has panoramic sea views with ample off street parking. Within a few minutes walk you are in the old village of Shanklin which has Tea shops, cafes, pubs

Fisherman's Loft A Unique Cottage By The Sea

Welcome to Fisherman's Loft a newly built property on the site of an original fisherman's boathouse in the heart of Wheelers Bay. We have purpose built this accommodation to comprise of open plan living space fully equipped , two double bedrooms a feature bathroom and a shower room. Views from the living room and deck are unsurpassed to the sea. The property is a level walk from the bars and restaurants that Ventnor offers.