Vacation rentals in Isle of Wight

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Top-rated vacation rentals in Isle of Wight

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Guest favourite

Cottage in Freshwater

5.0 out of 5 average rating, 388 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.

Nov. 30 – Dec. 7

$231 CAD per night

Guest favourite

Chalet in Isle of Wight

5.0 out of 5 average rating, 150 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.

Nov. 26 – Dec. 3

$264 CAD per night

Guest favourite

Apartment in Isle of Wight

5.0 out of 5 average rating, 121 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!

Jan. 8 – 15

$445 CAD per night

Guest favourite

Chalet in Isle of Wight

5.0 out of 5 average rating, 207 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.

Nov. 1 – 8

$212 CAD per night

Guest favourite

Guesthouse in Isle of Wight

4.97 out of 5 average rating, 129 reviews

Cosy Chalet With Private Hot tub - No Cleaning Fee

Modern purpose built self contained chalet, next to the house but with its own private entrance and private pergola area with canvas sides complete with cosy seating & lighting plus hot tub! Situated in East Cowes. The house was part of the Osborne estate so we are situated right next to Osborne House, also a 2 minute drive or 15 minute walk from East Cowes Red Funnel. We are also on a main bus route to Newport or Ryde. There is private access & your own parking space. It is an ideal location.

Sep. 13 – 20

$233 CAD per night

Guest favourite

Apartment in Freshwater

4.94 out of 5 average rating, 308 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. 10 – 17

$145 CAD per night

Guest favourite

Cottage in Isle of Wight

4.91 out of 5 average rating, 115 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

Nov. 18 – 25

$151 CAD per night

Guest favourite

Apartment in Isle of Wight

4.93 out of 5 average rating, 271 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.

Nov. 6 – 13

$165 CAD per night

Guest favourite

Tiny homes in Downsway, Blackbridge Road

4.96 out of 5 average rating, 102 reviews

Secluded garden cabin in Freshwater Bay

The Bird Hide is ideal for singles or couples (max 2 people) interested in exploring the local area with its own garden and separate access. A comfortable double bed, seating area and with it's own dining and inbuilt kitchen, it offers all you need for a short stay. It has a separate bathroom, as well as on outside decking area to catch the evening sun. The Bird Hide is 5 minutes walk from Freshwater Bay, even closer to footpaths to the Downs and the local village via the SSSI trail.

Jan. 20 – 27

$111 CAD per night

Guest favourite

Tiny homes 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!

Mar. 14 – 21

$190 CAD per night

Guest favourite

Barn in Isle of Wight

4.97 out of 5 average rating, 175 reviews

Chapel Road Barn Isle of Wight

Chapel Road Barn is a lovingly restored Victorian out-building which had a variety of uses at the start of the 20th Century. We are a 5 minute drive from the car ferry or a 25 minute walk to Ryde Pier. The number 9 bus stop is 2 minutes away and we have a variety of country walks and lovely cycles on hand....... We can offer a 15% or 20% Red Funnel ferry discount code or Tesco vouchers are accepted by Wightlink.

Nov. 19 – 26

$147 CAD per night

Guest favourite

Tiny homes in Cowes

4.9 out of 5 average rating, 119 reviews

The Garden Room, West Cowes

The Garden Room is the latest addition to my portfolio and has been lovingly restored to provide private, comfortable and fully equipped accommodation. The Garden Room has its own secure access and is located opposite Shepards Wharf Marina being a great location for sailing and training opportunities. Please check out my reviews on my existing accommodation ‘seagull cottage’ Cowes.

Mar. 11 – 18

$88 CAD per night