Holiday houses in Isle of Sheppey

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Top-rated holiday rentals in Isle of Sheppey

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite

Guesthouse in Minster on Sea

Tranquil Lodge – peaceful country stay by the sea

Tranquil Lodge is a private annexe beside our home in Minster-on-Sea, overlooking open fields where rabbits and horses are often spotted. Ideal for two (flexible for three), with a king bed and single sofa bed, plus baby items on request. Just a 10-minute walk to the cliffs + beach, with country and coastal walks from the door. Fully equipped kitchen, parking, garden, EV charging, vanity/desk, Wi-Fi + TV with Apple TV (guests sign into their own apps). A calm base for exploring Minster and Kent.

5.0 out of 5 average rating, 44 reviews

Top Guest favourite

The exterior of the annex is showcased, featuring vertical wooden slats and a glass-paneled door. A small window is visible, allowing natural light into the space. The entrance is set on a paved path, surrounded by greenery and a water storage tank nearby.

Guesthouse in Sittingbourne

Self-contained annex, with off-road parking.

Self-contained annex in Sittingbourne, perfect if you are visiting the area for work or leisure. Everything you need for a comfortable stay in your own completely private place, with driveway parking and fast WiFi. The accommodation comprises a bedroom /lounge /working room, kitchen and bathroom. The annex, especially the bedroom, is very quiet and peaceful. Located conveniently for the motorway and also easy access to the town centre, train station, shops, takeaways, restaurants and pubs.

4.93 out of 5 average rating, 305 reviews

Guest favourite

The living room features a black sectional sofa adorned with decorative pillows, complemented by a soft throw. A large artwork of white flowers hangs on the wall, while a tall lamp provides ambient lighting. Natural light flows through a nearby window, enhancing the cozy atmosphere.

Tiny home in Leysdown

Comfortable holiday home.

You’ll treasure your time at this memorable place. The chalet is on a family friendly field with other chalets. The site a clubhouse which has various entertainment at times during the season. You’re about 10 minutes from the beach and if you feel to go a bit further, you can turn left at the top of the road and follow till you come to a little cafe which sells 🍔, 🥪 and🥤. There’s free parking, where you can walk along the beach; enjoy the scenery; watch the boats go by and enjoy the peace.

4.89 out of 5 average rating, 70 reviews

Guest favourite

A tranquil outdoor space features a single reclining chair on a deck, overlooking calm waters during sunset. The sky displays shades of pink and blue, while a grassy area extends towards the water, framed by poles in the distance.

Cabin in Minster on Sea

Seaview Clifftop Caravan

Our lovely direct sea view, front row clifftop caravan is our family holiday home. The caravan is nearly new, boasts 3 bedrooms, 2 loos, is centrally heated and in good condition throughout. We are a very short drive from two of the best beaches on the island, and have easy access to some beautiful walks and nature reserves. The site itself has an indoor and outdoor pool, clubhouse and shop (March-November), outdoor play area and basketball MUGA. We very much welcome couples & small families.

5.0 out of 5 average rating, 18 reviews

Top Guest favourite

Barn in Teynham

The Bishop's Den

In a peaceful idyllic rural setting, this charming studio-style barn offers comfortable accommodation for two adults (+ a small child). Dog-friendly & perfect for a relaxing countryside escape. Sauna* Modern comfort, open-plan living, cosy furnishings and large windows frame our 2 acre garden & orchards. Off-road dog walks right from the garden & footpaths winding through orchards and marshland. Easy access to London, Faversham, Canterbury, Whitstable & the Kent coast & many other venues.

4.98 out of 5 average rating, 44 reviews

Guest favourite

A Highland cow stands by a wooden fence, surrounded by greenery under a clear blue sky. Nearby, a cluster of trees provides shade, while a few other cows are visible grazing in the background. The scene conveys a serene farm setting.

Shepherd’s hut in Minster on Sea

Daisy Dwelling at Seacliffe Staycation

We invite you to soak up this tranquil farm setting within walking distance to the seacliffes & seafront. There is a relaxing pond right by your hut and you will hear just the sounds of birds, crickets and livestock. Ideal for a break away from reality. Although the area you will be staying in is kept secluded.. there are goats, horses and sheep in nearby paddocks and Runner Ducks wandering around. We have put our whole hearts into this to create something special for our guests to enjoy!

4.92 out of 5 average rating, 113 reviews

Top Guest favourite

A balcony view is captured through bi-fold glass doors, featuring a small round table and two folding chairs. A decorative pumpkin sits at the center, with panoramic sea views of the estuary and boats in the distance, framed by a serene sunset.

Condo in Southend-on-Sea

Estuary Views Penthouse with Private Parking

A Beachfront Coastal Retreat with private driveway parking & situated in the sort after area Thorpe Bay. Boasting unspoilt Panoramic Sea Views. Central to Blue Flag Beaches, 2 mins from award winning restaurants, superb location for coastal walks, watching the seabirds & a short walk to the longest Pier in the world. Re-Designed with Bi-Folding Glass doors, bringing the Outside Inside. Intricately Designed embracing tiny details that define our property for a Luxury & cosy stay.

4.99 out of 5 average rating, 439 reviews

Top Guest favourite

Barn in Hernhill

Your next family & friends country getaway

Feel energised when you stay in this rustic gem, with a shop, cafe, summer bar and weekly events on site you won’t be short of things to do. And don’t forget the peacocks that’ll be roaming around… don’t worry they’re not scary! With the 4 bedrooms on the ground floor, two of which have French doors out to a patio, and the open plan entertaining space upstairs you’ll have plenty of bright light flooding in and access to the large deck with stunning sea views. Great for groups!

5.0 out of 5 average rating, 19 reviews

Guest favourite

A spacious outdoor deck features a textured table and seating, providing a comfortable area for relaxation. The view reveals expansive green fields stretching towards the horizon under a clear blue sky, with distant structures subtly visible.

Holiday park in Leysdown

Luxury 3 Bedroom Lodge with Spectacular views

This luxury 3 bedroom lodge is located on Harts Holiday Park. A tranquil setting, overlooking beautiful fields and the sea in the distance, this is the perfect getaway to relax and make use of the park’s amenities. The clubhouse includes children’s entertainment, bingo and evening entertainment. During the day, make the most of the on-site swimming pool, park, mini golf and children’s activities - or head down to the seafront which is moments away from the park entrance.

4.94 out of 5 average rating, 101 reviews

Superhost

An open living area features a modern gray sofa, sleek cabinetry, and a wall-mounted television. Large windows offer views of the surrounding landscape. The wooden flooring, designed in a herringbone pattern, complements the light wood paneling and cabinetry throughout the space.

Barn in Kent

Oak Lodge @ The Oaks Retreat

This memorable place is anything but ordinary. It is The Oaks Retreat, WINNER of the Paris Design awards 2024 'best hospitality interior', an architecturally inspired bespoke woodland Airbnb located in the seaside town of Whitstable. The Oak Lodge offers 2 king size bedrooms fully customized with high-end finishes which to need to be seen in person to be fully appreciated. Our Wellness area is equipped with a log burning sauna, a cold plunge and outdoor shower.

4.86 out of 5 average rating, 125 reviews

Guest favourite

A modern kitchen features sleek cabinetry and a spacious dining table surrounded by several chairs. Essential appliances, including a stove and kettle, are present. Natural light enters through a window, illuminating the countertops adorned with flowers and kitchen items.

Cottage in Borden

Cosy 3 bedroom cottage in the heart of Kent

Shillinghurst Cottage is the perfect getaway for a relaxing break for friends, couples or a family break. It is cosy, comfortable yet modern and comes with everything you would expect to make it the ideal home away from home. Set in the heart of the beautiful village of Borden, it will suit individuals who like country walks, relaxing in a peaceful surrounding or exploring the many towns and cities nearby.

4.95 out of 5 average rating, 354 reviews

Guest favourite

A barn conversion is presented with dark wooden siding and brick accents. A well-maintained lawn surrounds the building, featuring vibrant flowers along the perimeter. Large windows invite natural light, and outdoor seating is available on a patio area, creating a relaxed outdoor space.

Barn in Eastchurch

The Lodge

The Lodge is a 3 bedroom detached barn conversion on a beautiful coastal farm. Perfect for families or friends for up to 6 persons, this cottage is comfortably furnished and consists of a lounge with colour TV, a fully equipped kitchen with washing machine, a bathroom with hand basin, WC and bath & a second toilet and shower cubicle. The Lodge has 2 double bedrooms and 1 twin bedroom.

4.93 out of 5 average rating, 41 reviews