Family-friendly holiday rentals in East Cowes

4.97 out of 5 average rating, 318 reviews

The exterior of the barn features a mix of natural stone and brick, illuminated by warm outdoor lighting. A woven willow screen offers privacy, surrounding the well-maintained garden that extends alongside the structure.

Barn in Isle of Wight

Chapel Road Barn, I.O.W Ferry discount available

Chapel Road Barn is a lovingly restored Victorian out-building which is an ideal place for a couple to stay whilst exploring the Isle of Wight. Beautifully furnished and cozy.... 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 have partnered with both Red Funnel and Atlas ferries to offer generaous ferry discounts from both Portsmouth and Southampton

4.83 out of 5 average rating, 196 reviews

The living area features a large flat-screen TV positioned on a media unit. Two gray sofas are complemented by decorative pillows, and a vibrant yellow rug adds a pop of color. A coffee table rests in the center, while natural light enters through the window.

Flat in Isle of Wight

Central Cowes -Luxury Spacious Flat with Sea Views

Spacious Modern Apartment, Located in the heart of Cowes, on the High Street (very quiet!). Bright and airy, newly re-furbished, well equipped, furnished flat. Sleeps 4, one Double Bed and Two singles. Wi-Fi, 65" TV plus Sky TV inc Sky Sports and Sky Cinema, sound bar. Spectacular views over the Harbour/Solent. One minute walk to Red Jet fast link from Southampton, Shops, Pubs and bars and many restaurants - all within walking distance - as too are the Yacht Clubs, and Marinas. A Cut above!

A private patio area is depicted, featuring a small round table and two chairs. The space is surrounded by brick borders and is paved with light-colored tiles. The entrance to the cottage is showcased, with double doors framed by windows, and greenery visible in the background.

4.96 out of 5 average rating, 212 reviews

Albert’s Dairy Cottage, Whippingham

Albert’s Dairy Cottage is a beautifully converted one bedroom cottage situated adjacent to open countryside. The contemporary design offers spacious accommodation, is finished to a high specification and offers the perfect environment for couples looking for a relaxing break away. Conveniently situated less than 10 mins from both the Red funnel and Wightlink car ferry terminals, the property is ideally located for exploring the Island, is close to the River Medina and popular waterside pubs.

A cozy open plan living area features a deep red leather sofa adorned with decorative cushions. A colorful rug lies on the light-colored wooden floor, complemented by a coffee table and a dining area with bright chairs. Framed coastal artwork adorns the walls.

4.93 out of 5 average rating, 115 reviews

A unique 2 bedroom retreat in the heart of Cowes

Yachters is a snug hideaway in central Cowes nestled amongst vibrant and popular restaurants & bars. Sleeping up to 5 guests in comfortable accommodation, it is the perfect base for exploring the island, or as a bolt hole for those whose passion lies on water rather than dry land. A few minutes walk away from the Red Jet terminal and within 100 metres of Cowes Yacht Haven. There is a frequent bus service to all parts of the island and plentiful parking close by. FERRY DISCOUNTS AVAILABLE

Superhost

A cozy lounge area features a navy blue sofa with decorative cushions, complemented by a light rug. In the background, a fully equipped kitchen can be seen. A spiral staircase, showcasing intricate metalwork, ascends to the upper level of the cottage.

4.89 out of 5 average rating, 194 reviews

Harbour Cottage Your Romantic Getaway 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

Townhouse in Isle of Wight

Cringle Cottage

Comfortable Victorian town cottage on three floors. Fully furnished and equipped for up to six people (please note, however, that there is only one bathroom). Walking distance from town centre and ferries, but on a quiet side street with very little passing traffic. A great place to feel part of the yachting life of Cowes, to have walking-distance access to Cowes-based organisations including UKSA and the Ellen MacArthur Foundation or as a base to explore the beautiful Isle of Wight.

4.87 out of 5 average rating, 124 reviews

4.96 out of 5 average rating, 295 reviews

A charming vintage cottage is set amidst lush greenery, featuring a slate roof and blue exterior. The structure is accented by white trim and has a welcoming porch with large windows, allowing natural light to filter inside.

Cottage in Gurnard

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.

A charming brick building is seen nestled among lush greenery, with a gravel driveway leading to the entrance. The surrounding countryside features gently rolling hills under a cloudy sky, creating a serene and natural setting.

4.99 out of 5 average rating, 211 reviews

Converted barn perfect for families and couples

At the base of Rowridge Valley in the heart of the Isle of Wight countryside. You will find The Piglet, a great place to stay, relax and use as a base to explore the island. A cosy building with a sunny aspect and a private garden to the rear that overlooks the neighbouring countryside. Due to its location most of the island is accessible from here within a short drive. Explore the heritage castles & monuments, the beaches & surf, and family friendly parks throughout the island.

A view from the window captures the tranquil scene of Cowes Harbour with boats gently bobbing in the water. Lush green grass and a well-maintained garden are visible in the foreground, with a distant shoreline lined by trees and buildings.

4.97 out of 5 average rating, 150 reviews

Cozy cottage with sea views and off street parking

Built in 1882, our lovely cottage is a former coastguard cottage located in a row of 14. The inside of the cottage is very well appointed and very cozy. The west facing garden deck provides a good size outdoor area to sit and take in the fantastic views of Cowes harbour, the Solent beyond and the amazing sunsets. You will have access to a dedicated off street parking space. Two bedrooms - one with a double bed and one which can be made with two single beds or one king size.

Superhost

A charming collection of upside-down houses is situated along the water's edge, showcasing a mix of modern and traditional designs. The clear water reflects the sunlight, while the shoreline features a rocky outcrop leading to the properties, with greenery visible along the pathway.

Townhouse in East Cowes

Riverside Mews is ideally located with sea views.

Riverside Mews, 5 Seymour Court is right on the River Medina with far reaching views across the Solent. The floating bridge is steps away from the front door and you can hop on it for a few pennies to reach West Cowes. Here you will find a plethora of shops and restaurants all busy with tourists and sailors. Cowes is a mecca for the sailing community and yachts can be seen at all times of the year. Seals have also been seen bobbing up and down just outside the house !

4.79 out of 5 average rating, 218 reviews

4.98 out of 5 average rating, 149 reviews

The Watch House is viewed from a garden path lined with blooming flowers, leading down to the beach. The white exterior of the cottage is highlighted against a clear blue sky, while the tide is low, revealing a sandy shore.

Home in Lepe

Iconic Beach Front Stay | The Watch House, Lepe

A standout seafront landmark on Lepe Beach, The Watch House is a lovingly restored former lifeboat and coastguard station, once used to combat smuggling across the Solent. With original features, a modern kitchen, wood burner, cosy window seat over the water, and views to the Isle of Wight, it’s a guest favourite—“an iconic beachfront stay” and “perfect relaxing getaway.” Pet-friendly with parking for two, perfect for families, couples, or friends.