Vacation rentals in Isle of Sheppey

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Top-rated vacation rentals in Isle of Sheppey

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Guest favorite
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
4.94 out of 5 average rating, 266 reviews

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.

Top guest favorite
A vibrant red front door is framed by an apple tree, which extends towards the side of the dwelling. White weatherboard siding contrasts with the dark brick foundation. Multiple windows allow natural light to fill the structure, creating an inviting entryway.
Cottage in Faversham
5 out of 5 average rating, 169 reviews

A beautiful two bedroom Victorian coach house

A picturesque, newly converted Coach House in the small village of Badlesmere, high on the North Kent Downs. Set amongst rolling hills and wooded valleys, this striking conversion offers delightful accommodation, a south facing patio and use of a tennis court. Close to the market town of Faversham and the historic city of Canterbury, as well as Leeds Castle and fashionable Whitstable, it is an idyllic holiday spot or stopover on route to the continent, perfect for families or a romantic break.

Top guest favorite
An aerial view highlights a charming cottage with a red-tiled roof nestled among lush greenery. Surrounding gardens and trees create a serene outdoor setting, while a vehicle is parked by the cottage. The landscape features rolling hills in the background.
Place to stay in Selling
4.92 out of 5 average rating, 358 reviews

Character 18th Century annexe in tranquil village

Tucked away in the heart of this peaceful village that dates back to the Domesday Survey, 'Greenways' is an 18th century grade 2 listed annexe with original features. It offers a private entrance, off-road parking, a double and twin bedroom and a shower room. Tea / coffee making facilities, a mini fridge and toaster are provided - provisions for a continental breakfast are included. Perfectly situated to enjoy scenic country walks and a short drive to Faversham, Canterbury and Whitstable

Top guest favorite
The charming exterior of the cottage features dark wooden siding and a welcoming door. A gravel pathway leads to the entrance, flanked by colorful flower beds. A rustic bench is positioned near the door, offering a pleasant spot to relax among the surrounding greenery.
Cottage in Oare
4.99 out of 5 average rating, 417 reviews

Twitchers Cottage Oare - Nature on your doorstep

Twitchers Cottage at Broomfield Barn is a beautifully presented converted in 2020, one bedroom cottage. Located on the edge of Oare marshes that is an important wetland reserve with a range of bird species. This area is popular with bird watches, walkers, wildlife photographers and cyclists or anyone who wants a relaxing break away surrounded by open countryside. There is plenty to do throughout the year wether you want coast, town or countryside it’s all in easy reach for your enjoyment.

Top guest favorite
Cabin in Kent
4.98 out of 5 average rating, 235 reviews

Cosy coastal hideaway with garden sauna

A warm, stylish, peaceful retreat, perfect for a winter break, with seaside walks and cosy pubs a short stroll away. Treat yourself to a relaxing sauna with bracing cold plunge in the garden spa which is paid for separately. Enjoy Whitstable's great restaurants and cosy cafes. Alba Lodge is a double height space, designed with sustainability in mind. Drift off to sleep in the king size bed. Freshen up in the large walk in shower. Sauna and cold plunge is £30 per couple, per session.

Top guest favorite
Place to stay in Whitstable
4.99 out of 5 average rating, 159 reviews

Cosy garden cabin

Take it easy at this unique and tranquil getaway with its big cosy sofa & elegant king size bed. the cabin style is English colonial with a seaside twist. The style continues out into your own large private garden. It's an 8 minute stroll to the beach/ nature reserve and 5 to the station that has direct links to kent coastal towns & London Victoria. The popular town of Whitstable famous for its oysters, music scene & eclectic shops, pubs & restaurants is a short drive or bus ride away.

Top guest favorite
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 Thorpe Bay
4.99 out of 5 average rating, 402 reviews

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.

Top guest favorite
The exterior of a historic brick building is showcased, featuring a colonnaded façade and decorative elements. The bright blue sky provides a contrasting backdrop, enhancing the building's architectural details and its distinguished presence along the high street.
Condo in Whitstable
4.99 out of 5 average rating, 256 reviews

Boutique apartment in the heart of Whitstable

Stunning 1-bedroom apartment in an historic brick fronted and colonnaded building constructed circa 1900 and once the high street bank. Located in the very heart of vibrant Whitstable, with all of its wonderful independent bars, microbreweries, roasteries/coffee shops, restaurants, boutiques and galleries. Only a short walk from the famous harbour and beaches of this boho seaside town and only an 8 minute walk from the station with direct services to London and Canterbury.

Top guest favorite
The granary is a charming timber frame building, surrounded by lush green grass and various garden plants. The sloping roof and traditional design are highlighted under a clear blue sky, while the white door and windows provide a welcoming entry point.
Barn in Saint Margaret's at Cliffe
4.99 out of 5 average rating, 358 reviews

Beautiful bolthole near the White Cliffs of Dover

Located 5 minutes walk away from the White Cliffs of Dover, the granary is a converted timber frame building set in the garden of a 16th century Kentish farmhouse and 1 km away from the beautiful seaside village of St Margaret's-at-Cliffe. Featuring exposed beams, wattle and daub walls and many original features including staddlestones and a handcrafted spiral staircase leading to a mezzanine sleeping area, the granary has a lovely feel and is very light, warm and cosy.

Top guest favorite
The historic windmill features a distinctive white weatherboard structure, surrounded by lush greenery. Two teak steamer chairs are positioned in the foreground, inviting relaxation in the garden. A clear blue sky with soft clouds enhances the serene rural setting.
Windmill in Benenden
4.99 out of 5 average rating, 831 reviews

Old Smock Windmill in rural Kent

Old Smock Mill is a romantic place for couples. The atmosphere inside is peaceful and relaxing. Everything is designed to unwind you from the moment you walk in. It is surrounded by the lovely Kent countryside where you can ramble and refresh yourselves by perhaps ending the day in one of the great pubs cosy by a log fire in Winter or in Summer in an English garden. Guests have said how hard it is to tear themselves away, it truly is a treasure to find.

Guest favorite
A spacious wooden deck extends out from the house, featuring a wooden table and various potted plants. Large glass doors open into the living area, inviting natural light. Comfortable outdoor seating is positioned to the side, surrounded by greenery.
Bungalow in Seasalter
4.96 out of 5 average rating, 456 reviews

Seasalter Beach Chalet.

A special place. Direct beach access; wonderful views; spectacular sunsets. Beautifully converted and well equipped. A perfect retreat. A stroll from the Sportsman Restaurant, Oyster Pearl Pub and near lovely Whitstable for shops and restaurants. Perfect in summer with a safe swimming beach meters away and in winter the pleasure of of sea mist, migrating birds and walks on the shore and marshes. Afternoons with a book in front of the fire.

Top guest favorite
A charming thatched cottage is surrounded by meticulously maintained gardens featuring geometric hedges and a stone pathway. Lush greenery and trees frame the scene, while a tranquil pond reflects the clear sky above.
Cottage in Rotherfield
4.98 out of 5 average rating, 336 reviews

The Granary, Organic Vineyard stay with Pool.

Coes Farm offers 50 acres of absolute tranquillity in amongst nature, with a bit of luxury thrown in too! We have formal gardens and ornamental ponds, a large lake, plenty of woodland, open fields, an indoor saltwater swimming pool with hot tub, a tennis court and a games room which is resident in our Micro-Winery! We planted our 5 acre vineyard in Spring 2021 and extended the existing Orchard with cider varieties in 2023.

Popular amenities for Isle of Sheppey vacation rentals