Isle of Wight vacation rentals

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Top-rated vacation rentals in Isle of Wight

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Guest favorite

Chalet in Isle of Wight

5.0 out of 5 average rating, 148 reviews

Rural Escape Set in 6 Acres of Gardens.

If you're looking for a bit of tranquility in an unspoilt country side setting, a few minutes drive from various beaches, Ryde, Seaview and St Helens, then come and stay with us in our detached private chalet, set in six acres of gardens. Suitable for couple getaways. Our location is perfect for cycling, walking, nature watching and exploring the IOW. A full continental breakfast is included as well as plenty of essential supplies. We look forward to welcoming you to our little slice of Eden.

Dec 29 – Jan 5

R3,400 ZAR per night

Guest favorite

Cottage in Freshwater

5.0 out of 5 average rating, 383 reviews

A beautiful country cottage, close to the sea

PREFERENTIAL FERRY RATES AVAILABLE Welcome to The Old Stables, a dog friendly, beautiful and stylish barn conversion near Freshwater Bay on the Isle of Wight. Originally forming part of the famous Farringford Estate - owned by Lord Tennyson, the world renown poet - it nestles at the foot of the downs and is located up a private lane in an Area of Outstanding Natural Beauty. It is within easy walking distance of Freshwater Bay - the local beach - nearby shops, a superb cafe/bar and friendly pub.

Oct 15 – 22

R3,623 ZAR per night

Guest favorite

Apartment in Isle of Wight

5.0 out of 5 average rating, 118 reviews

The Ocean Suite, Ventnor Beach (6ft superking bed)

The ultimate in beachfront living, a perfect romantic escape and popular with many repeat guests. A cedar cabin with panoramic sea views over Ventnor beach, winner of 22/23 LUXLife Magazine Awards, Best Luxury 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, 1 south facing for sunbathing, the other perfect for an alfresco breakfast in the morning sun. No pets but baby welcome!

Oct 17 – 24

R6,180 ZAR per night

Guest favorite

Townhouse in Isle of Wight

4.98 out of 5 average rating, 171 reviews

Beautiful Spacious Victorian Town House in Cowes

This beautiful spacious 2 bedroom town house is located on a quiet street a few minutes walk from the town centre. The whole property has been recently decorated giving a fresh light feel & furnished with a lovely seaside theme. Cowes town centre is just a few minutes walk away with its excellent selection independent shops and restaurants. Just beyond the town is the seafront which takes you along the beautiful esplanade passed the Royal Yacht Squadron and on to Gurnard famous for its sunsets

May 6 – 13

R2,399 ZAR per night

Superhost

Apartment in Isle of Wight

4.84 out of 5 average rating, 337 reviews

*Luxury Apt with stunning views over Ventnor Beach

Holiday like you are in the Mediterranean! Seacliff Self Catering apartment is a raised ground floor property in a Victorian Villa with decked verandah and unspoilt vista overlooking Ventnor Beach. Stunning seascape with outdoor seating. A private shaded courtyard to the rear. The interior is modern, stylish with a high spec finish. The property is sound proofed, with a vaulted ceiling. Adults only, no children. We are also able to provide discounted ferry travel please ask for more details.

Nov 15 – 22

R3,014 ZAR per night

Guest favorite

Apartment in Freshwater

4.93 out of 5 average rating, 307 reviews

Fully self contained, Freshwater Bay apartment

Welcome to our wonderful apartment located in an area of outstanding natural beauty, close to great beaches. Five minute stroll to Freshwater Bay at the base of Tennyson Downs, it is the perfect relaxing base for exploring the Island. The historic town of Yarmouth is 10 minutes away. The apartment is fully equipped ready for self catering holidays, long or short stays. Your own private courtyard and access to the apartment is separate from our house. Ideal for couples and plus 1 or singles.

Dec 23 – 30

R2,014 ZAR per night

Superhost

Apartment in Isle of Wight

4.81 out of 5 average rating, 259 reviews

The St Clares Hideway, Ventnor

Welcome to The St Clares Hideaway. This self contained apartment has panoramic sea views from both the bedroom and the private deck, and is only minutes from the seafront. The deck overlooks our illuminated water cascade. St Clares Hideaway is close to the town centre and easy walking distance to the seafront, restaurants, pubs, shops, bus stops, Victorian promenade, cafes and wonderful walking routes. St Clares Hideaway has its own free, private parking accessed from Kings Bay Road.

Mar 14 – 21

R1,224 ZAR per night

Guest favorite

Cottage in Isle of Wight

4.91 out of 5 average rating, 110 reviews

Harbour Cottage. cosy, romantic cottage in Cowes

Harbour Cottage - perfect romantic getaway. Close to the centre of vibrant Cowes with local independent shops, cafes, restaurants and marinas. You can leave the car at home! Minutes from Red Jet terminal, floating bridge and Shepards Marina. Generous ferry discounts enquire on booking Harbour Cottage is great for short breaks, or longer stays. Fully fitted kitchen, lounge, conservatory, bathroom and bedroom with king size bed and small sofa fold out ideal for child or small adult only

Dec 3 – 10

R1,957 ZAR per night

Guest favorite

Apartment in Isle of Wight

4.93 out of 5 average rating, 269 reviews

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.

Aug 19 – 26

R2,630 ZAR per night

Guest favorite

Hut in Isle of Wight

4.98 out of 5 average rating, 183 reviews

The Hikers' Hut, clifftop view on the Coastal Path

The Hikers' Hut at Highcliff, is a magical timber hut with stunning sea views over the east coast of the Isle of Wight. Situated on the cliff edge 100m above the shoreline between Shanklin and Ventnor, the famous Isle of Wight Coastal Path is at the front gate. The Hut borders a National Trust field and is a perfect cabin for hikers, bird watchers, beach goers and nature lovers. With its own separate entrance and garden, it sits in the apple orchard of Highcliff Estate, Luccombe.

Nov 19 – 26

R2,603 ZAR per night

Guest favorite

Tiny home in Cowes

4.95 out of 5 average rating, 134 reviews

Seaside style cabin in central Cowes

'The Cabin' sits in the heart of West Cowes, tucked away behind the high street. Very compact (and very cute!), the space is kitted out in classic holiday home style. Two bedrooms and a sofa bed. Shower room. Decked garden with dining table, BBQ and outdoor sofas. Free parking space nearby. Fast broadband (free), digital TV with DVD, washer/dryer, dishwasher, microwave. Welcome breakfast for first day included. Good for families but steep steps to access. Book today!

Jan 9 – 16

R2,166 ZAR per night

Guest favorite

Cottage in Isle of Wight

4.97 out of 5 average rating, 106 reviews

Cozy annexe with off-street parking and sea views

Our annexe sits within the conservation area of Ryde with uninterrupted views across the Solent. It forms part of a large Regency property but has an independent access and off-street parking. With it's beaches, harbour, bustling town centre and easy mainland links, Ryde has become a popular destination for many people all year round. The annexe has been recently renovated and is superbly presented with comfortable accommodation for two people.

Oct 5 – 12

R2,268 ZAR per night