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.

Sep 23 – 30

G$40,016 GYD per night

Guest favorite

Cottage in Freshwater

5.0 out of 5 average rating, 385 reviews

A beautiful country cottage, close to the sea

PREFERENTIAL FERRY RATES AVAILABLE Welcome to The Old Stables a beautiful and stylish barn conversion near Freshwater Bay on the Isle of Wight - Dog Friendly. 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 2 – 9

G$39,476 GYD per night

Guest favorite

Apartment in Isle of Wight

5.0 out of 5 average rating, 119 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!

Sep 22 – 29

G$67,346 GYD per night

Guest favorite

Chalet in Isle of Wight

5.0 out of 5 average rating, 205 reviews

Seaglass. Beautiful cabin, fantastic sea views

A beautifully remodeled chalet situated in a tranquil setting with no passing footfall or traffic so it's a very private location. Seaglass is perfectly positioned to explore Ventnor, a quirky Victorian seaside town set in fantastic scenery. There is a decked garden area with brick bbq overlooking the sea in Wheelers Bay. You are a short walk away from the seafront and also to the town. The accommodation is cosy and beautifully decorated in a coastal style. 15% ferry discount codes available.

Mar 6 – 13

G$34,271 GYD 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.

Nov 1 – 8

G$22,069 GYD per night

Guest favorite

Cottage in Isle of Wight

4.91 out of 5 average rating, 112 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

Feb 12 – 19

G$21,329 GYD per night

Guest favorite

Apartment in Isle of Wight

4.93 out of 5 average rating, 270 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.

Oct 24 – 31

G$20,482 GYD per night

Guest favorite

Hut in Isle of Wight

4.98 out of 5 average rating, 184 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.

Jan 14 – 21

G$28,369 GYD per night

Guest favorite

Cottage in Isle of Wight

4.96 out of 5 average rating, 211 reviews

A charming little wooden house by the sea

This quirky attractive vintage little cottage is perfect for getting away from it all and relaxing in idyllic surroundings. Just a few metres from the lovely pebbly Gurnard beach, this fully refurbished historical little wooden building is set back from the road and tucked away behind our wild garden. It is accessed from its own car parking space via a little path. At the rear, a small stream goes to the sea and a large oak tree provides shelter to birds and a relaxing swing seat.

Sep 28 – Oct 5

G$30,622 GYD 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!

Apr 1 – 8

G$24,110 GYD 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.

Sep 18 – 25

G$28,105 GYD per night

Guest favorite

Condo in Isle of Wight

4.99 out of 5 average rating, 166 reviews

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

Jan 30 – Feb 6

G$32,470 GYD per night