Vacation Rentals in Isle of Sheppey

127 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • stayz
  • expedia
  • hotelscom
  • tripadvisor
  • tripcom
  • agoda
  • homestay
  • tuivillas
  • hostelworld
  • hotelopia
Isle of Sheppey holiday rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

127 Holiday rentals and Airbnb in Isle of Sheppey

Best family friendly Isle of Sheppey holiday rentals

Among the 127 accommodations in Isle of Sheppey, here are the 4 best family friendly rentals

New - Luxury 3 Bedroom Townhouse - Canterbury City Centre - Isle of Sheppey
9.3 3 reviews
Isle of Sheppey
02/01 – 02/03
A$238/nighttotal: A$14042 (59 )

New - Luxury 3 Bedroom Townhouse - Canterbury City Centre

3 1
apartment , Canterbury
This 3-bedroom house in Canterbury is located a 4-minute walk from Canterbury West Train Station, 15 minutes from Canterbury East Train Station, 800 meters from Canterbury Cathedral, and 2.9 kilometers from the University of Kent.
Accommodating up to 11 guests, this property offers 94 square meters of living space with 3 bedrooms, 3 living rooms, a kitchen with a dishwasher and fridge, WiFi, and a washing machine.
Luxury Retreat Beach House - Sleeps 6 - Isle of Sheppey
9.3 85 reviews
Isle of Sheppey
17/08 – 21/08
A$502/nighttotal: A$2008 (4 )

Luxury Retreat Beach House - Sleeps 6

2 5
house , Southend-on-Sea
The Wedge is a short walk from Southend Jubilee Beach and Adventure Island, making it a great base for exploring all that Southend-on-Sea has to offer. This property has consistently received excellent ratings for location, cleanliness, and user experience.
The two-bedroom house has a floor area of 65 square metres and can comfortably accommodate up to six guests. It comes with a fully equipped kitchen, a terrace, free Wi-Fi, and a private entrance, offering everything you need for a comfortable and enjoyable stay.
Newland's - Isle of Sheppey
9.5 19 reviews
Isle of Sheppey
13/07 – 17/07
A$257/nighttotal: A$1028 (4 )

Newland's

2 2
apartment , Rochester
This apartment is located in Rochester, just a short walk from Allhallows Beach and about 16 kilometres from Rochester Castle. It has received excellent ratings for its location, cleanliness, and overall experience.
The property offers 2 bedrooms and 2 bathrooms, spanning 520 square metres and accommodating up to 6 guests. Enjoy a private garden and terrace, a fully equipped kitchen, and on-site amenities like a restaurant, bar, and swimming pool.
Historic Shop House | 6br | Ideal For Contractors - Isle of Sheppey
10 4 reviews
Isle of Sheppey
09/08 – 14/08
A$794/nighttotal: A$3970 (5 )

Historic Shop House | 6br | Ideal For Contractors

1 8
apartment , Milton Regis
This six-bedroom, four-and-a-half bathroom apartment is located on Milton Regis High Street in Sittingbourne, Kent, a 14-minute walk from Sittingbourne train station, offering easy access to central London and close proximity to local pubs and creekside walks.
The spacious property, a former shop building with original beams, sleeps twelve guests and boasts two kitchens, a garden, parking, and internet access; nearby attractions include the Light Cinema and entertainment venue in Sittingbourne.

Best Isle of Sheppey holiday rentals with a pool

Among the 127 accommodations in Isle of Sheppey, here are the 4 best rentals with a pool

Seaview Holiday Rentals - Seawall - Isle of Sheppey
8.6 36 reviews
Isle of Sheppey
14/09 – 18/09
A$281/nighttotal: A$1124 (4 )

Seaview Holiday Rentals - Seawall

2 2
house , Whitstable
Seaview Holiday Rentals 2 is a beachfront property in Whitstable, Kent, 2.1km from Herne Bay beach and 9.2km from Canterbury's train stations.
This two-bedroom, two-bathroom holiday home boasts a 45 square metre floor area, sleeps 11 guests, and includes a swimming pool, terrace, garden, restaurant, bar, free parking, and Wi-Fi.
Kentish Oast, Cottage And Barn In Stunning Private Grounds With Swimming Pool - Isle of Sheppey
9.6 4 reviews
Isle of Sheppey
02/01 – 02/03
A$902/nighttotal: A$53218 (59 )

Kentish Oast, Cottage And Barn In Stunning Private Grounds With Swimming Pool

7 1
cottage , Hollingbourne
This seven-bedroom, six-bathroom holiday home near Maidstone, Kent, is situated just over 1.6km from Leeds Castle and under 1.6km from a train station with direct links to London and Canterbury.
Sleeping up to 14 guests plus 3 pets, the property boasts a private heated swimming pool (open May-September), tennis court, and extensive landscaped grounds including lakes and orchards, alongside access to the Pilgrims Way and North Downs Way footpaths.
Host & Stay | Clearwater Willerby Lodge - Isle of Sheppey
10 1 review
Isle of Sheppey
18/10 – 28/10
A$181/nighttotal: A$1810 (10 )

Host & Stay | Clearwater Willerby Lodge

2 3
chalet , Leysdown-on-Sea
This pet-friendly seaside holiday home in Sheerness boasts stunning sea views, a 0.9km stroll from Leysdown Coastal Park and a 35.4km drive from Elmley National Nature Reserve.
The 6 square metre self-catering chalet sleeps four guests, offering two bedrooms, two bathrooms, a fully equipped kitchen, Wi-Fi, a private terrace, and access to a shared swimming pool.
Heron Barn - Isle of Sheppey
8.9 18 reviews
Isle of Sheppey
13/07 – 17/07
A$288/nighttotal: A$1152 (4 )

Heron Barn

1 2
house , Hollingbourne
Heron Barn, a delightful house in Hollingbourne, is situated 2.7km from Leeds Castle and within easy reach of other Kent attractions such as Chatham Historic Dockyard (23-29km).
This one-bedroom property, perfect for couples, boasts a swimming pool, garden, free Wi-Fi, private parking, and a fully equipped kitchen with a dishwasher; enjoy peaceful countryside living near Hollingbourne village.

Frequently asked questions about holiday rentals in Isle of Sheppey

  • What are the must-see sights on the Isle of Sheppey, United Kingdom?

    Sheppey has some great sights! The Eastchurch Manor House and its surrounding parkland are a must for history buffs. For stunning coastal views, head to Sheerness East Beach or Warden Bay. The iconic Sheerness Docks are also worth a visit, especially if you're interested in maritime history. Don't miss the fascinating Sheppey Museum, which showcases the island's rich heritage.
  • What are the best Airbnb and holiday rentals in Isle of Sheppey?

    Hogwarts Bed And Continental Breakfast, Truly Kentish Holiday Lets and Tonge Barn are the most popular Airbnb and holiday rentals in Isle of Sheppey among travellers.

  • Are there any unique natural phenomena on the Isle of Sheppey, United Kingdom?

    The Isle of Sheppey's location means it's frequently exposed to strong winds and tidal changes. The extensive mudflats exposed at low tide are a significant natural feature, and important for birdlife. The coastline itself is constantly evolving due to erosion and accretion, creating dynamic landscapes.
  • What are the most popular Airbnbs in Isle of Sheppey?

    Among the Airbnbs in Isle of Sheppey, Contemporary 2 Bed-minster - Sheppey, Georgian House - Ten Minutes From The Beach and Self Contained Annex To Rent are the most popular ones.

  • What essentials should you bring along to the Isle of Sheppey, United Kingdom?

    Pack comfortable walking shoes as you'll likely be doing a fair bit of exploring. A waterproof jacket is essential, as the weather on Sheppey can be unpredictable. Sunscreen and a hat are also wise, especially during the summer months. Don't forget a camera to capture those stunning coastal views!
  • What are the best holiday rentals with a pool in Isle of Sheppey?

  • What is the average daily budget you should plan for (accommodation, food, transportation, activities) on the Isle of Sheppey, United Kingdom?

    A daily budget of £80-£150 per person should comfortably cover accommodation, food, local transport and entry fees to attractions. This is just an estimate, and costs can vary depending on your choices of accommodation and dining.
  • What are the best rentals for families and kids in Isle of Sheppey?

  • Where can you find the best restaurants serving local dishes on the Isle of Sheppey, United Kingdom, and what are the must-try specialties?

    The island has a range of pubs and restaurants. While there aren't specific 'local' dishes unique to Sheppey, many establishments offer fresh seafood, reflecting the island's coastal location. It's best to check local reviews and menus to find places that suit your preferences.
  • What are the best rentals or Airbnbs with a jacuzzi in Isle of Sheppey?

  • What are some less-famous attractions on the Isle of Sheppey, United Kingdom that are worth a visit?

    The Oare Marshes are a beautiful area for birdwatching and nature walks. Explore the charming villages like Leysdown-on-Sea, with its traditional seaside charm. The various churches across the island, such as St. Mary's Church in Eastchurch, offer glimpses into local history and architecture.
  • What are the best activities for engaging with locals and understanding their culture on the Isle of Sheppey, United Kingdom?

    Visiting local pubs is a great way to interact with residents. Attending any local events or markets can also provide opportunities to meet people. Simply striking up conversations with shopkeepers or people you meet while exploring can offer insights into island life.
  • What unique natural landscapes and terrain features can travellers explore on the Isle of Sheppey, United Kingdom?

    Sheppey's landscape is defined by its coastline: the extensive mudflats, sandy beaches like Warden Bay, and the cliffs in certain areas. The inland areas are relatively flat, with farmland and small villages interspersed.
  • How many days are ideal for a visit to the Isle of Sheppey, United Kingdom, and what are some itinerary suggestions?

    Two or three days is sufficient to explore the main attractions. A possible itinerary could include: Day 1 – Sheerness Docks and Eastchurch Manor House; Day 2 – Warden Bay and a walk along the coast; Day 3 – exploring the villages and perhaps a visit to the Sheppey Museum. This is just a suggestion; you can adapt it based on your interests.

Nearby regions

Best Isle of Sheppey holiday rentals with a balcony

Ocean Breeze. Cosy Beachside Retreat. - Isle of Sheppey
9.0 4 reviews
Isle of Sheppey
02/01 – 01/03
A$246/nighttotal: A$14268 (58 )

Ocean Breeze. Cosy Beachside Retreat.

3 2
apartment , SOUTHEND-ON-SEA
This beachfront Southend-on-Sea apartment, situated above a Trip Advisor top-rated Chinese restaurant, offers unparalleled access to the beach and is within easy walking distance of the Southend-on-Sea Pier Museum.
Sleeping up to six guests, this three-bedroom, one-bathroom flat boasts a terrace, parking, internet, and a kitchen equipped with a fridge and microwave; enjoy sea views and proximity to Leigh Heritage Centre and Southend Marine Activities Centre.
Modern 2 Bed 2 Bath House In Sittingbourne By Splendid Stays - Isle of Sheppey
8.5 74 reviews
Isle of Sheppey
18/10 – 28/10
A$221/nighttotal: A$2210 (10 )

Modern 2 Bed 2 Bath House In Sittingbourne By Splendid Stays

2 3
house , Kent
This charming house in Kent is conveniently located just 10 miles from Leeds Castle, 14 miles from Historic Chatham Dockyard, and 15 miles from Chatham Train Station, offering easy access to popular attractions. Guests have consistently rated the property excellent for its cleanliness, location, and overall experience.
The two-bedroom, two-bathroom property spans 30 square meters and provides a comfortable and well-equipped space for a family or group of friends. Enjoy the convenience of a fully equipped kitchen with a dishwasher, washing machine, and free Wi-Fi, as well as a garden and parking for your convenience.
Chloe Cottage - Isle of Sheppey
9.5 39 reviews
Isle of Sheppey
14/09 – 18/09
A$279/nighttotal: A$1116 (4 )

Chloe Cottage

3 2
house , Whitstable
Chloe Cottage is a charming house located in Whitstable, just a short walk from the beach and within easy reach of Canterbury and its historic landmarks. The property has received excellent ratings for location, cleanliness, and user experience.
The house has 3 bedrooms and can accommodate up to 6 guests, providing ample space for families or groups of friends. This comfortable home features a fully equipped kitchen, a terrace with garden views, and a range of modern amenities, including a washing machine, free Wi-Fi, and a flat-screen TV.
Apartment ∙ 2 Bedrooms ∙ 4 Guests - Isle of Sheppey
Isle of Sheppey
18/10 – 28/10
A$199/nighttotal: A$1990 (10 )

Apartment ∙ 2 Bedrooms ∙ 4 Guests

2 3
apartment , Leysdown-on-Sea
Clearwater Willey Lodge is a pet-friendly holiday home in Leysdown-on-Sea, conveniently located a short drive (approximately 14.5km) from the Swale National Nature Reserve and 14.5km from Sheerness-on-Sea train station.
This two-bedroom, two-bathroom lodge sleeps four guests and boasts a spacious open-plan living area with a contemporary fireplace, a private decked area, and a well-equipped kitchen including a dishwasher and integrated fridge-freezer; enjoy the swimming pool and other amenities.

Best Isle of Sheppey holiday rentals with parking

Iro Properties Limited - Isle of Sheppey
8.3 33 reviews
Isle of Sheppey
09/08 – 14/08
A$474/nighttotal: A$2370 (5 )

Iro Properties Limited

4 8
apartment , Eastchurch
This beachfront home is located in Eastchurch, just 35 kilometres from Leeds Castle and 38 kilometres from Rochester Castle, offering easy access to historical landmarks and picturesque surroundings. The property has consistently received excellent ratings for its cleanliness, location, and overall user experience.
This spacious apartment, spanning 202 square metres, comfortably accommodates up to eight guests in its four bedrooms and one bathroom. Guests can enjoy a range of amenities, including a private garden with barbecue facilities, indoor and outdoor play areas, a fireplace, and a private beach area for exclusive use.
Brand New 1 Bedroom Apartments - City Centre - Isle of Sheppey
9.8 10 reviews
Isle of Sheppey
10/07 – 12/07
A$271/nighttotal: A$542 (2 )

Brand New 1 Bedroom Apartments - City Centre

1 2
apartment , Southend-on-Sea
This new one-bedroom flat offers prime city centre accommodation in Southend-on-Sea, just a 5-minute walk from Adventure Island and 549 meters from Three Shells.
Guests can enjoy a fully equipped kitchen with a fridge and microwave, free WiFi, private bathroom, and parking, with London Southend Airport located 5 kilometers away.
The Pontoon! - Pass The Keys - Isle of Sheppey
Isle of Sheppey
09/08 – 14/08
A$747/nighttotal: A$3735 (5 )

The Pontoon! - Pass The Keys

2 8
apartment , Southend-on-Sea
This unique Leigh-on-Sea houseboat, situated at Leigh Marina, offers panoramic marina views and easy access to the Estuary Bicycle Trail, Two Tree Island, and Hadleigh Farm.
The 111-square-metre floating dwelling boasts two bedrooms, one bathroom, sleeps eight guests, and includes a fully equipped kitchen with a fridge, microwave, and dishwasher, plus free Wi-Fi and parking.
Wynnstay Studio Apartments - Isle of Sheppey
8.4 367 reviews
Isle of Sheppey
27/06 – 04/07
A$164/nighttotal: A$1148 (7 )

Wynnstay Studio Apartments

1 2
studio , Southend-on-Sea
The WynnStay Studio Apartments are situated directly on the Thorpe Bay seafront, just a mile from Southend Pier and two miles from the Cliffs Pavilion Theatre, offering stunning views and a peaceful retreat. The apartments are rated very good for user experience, cleanliness, and location.
The studio apartment features a compact layout with a floor area of 12 square metres, providing a comfortable space for a single traveller. Guests can enjoy modern amenities such as a flat-screen TV, a built-in wardrobe, and a bathroom with a shower, as well as free Wi-Fi and parking, making it a convenient and comfortable base for exploring Southend-on-Sea.
©2026 cozycozy.com