Pet-friendly holiday rentals in Isle of Sheppey

Rural Cottage in grounds of Grade II* Farmhouse

Mark & Paul would love to welcome you to our rural 2 bedroom cottage, close to the North Kent coast in the grounds of 14th Century Frognal Farmhouse. The triple glazed cottage provides comfortable accommodation and is just over an hour away from SE London by car, or by train straight into Teynham station from London Victoria, (1 hr 6m). We are 10 mins walk from Teynham railway station. Faversham & Sittingbourne are 10 minutes away. We have released all availabilty through to end of December 2026

Pets · Walkability · Barbecue

Mediterranean inspired home/garden opposite beach

Indulge in seaside bliss at our Mediterranean-styled retreat, moments away from the beach. Ideal for couples and families, this pet-friendly haven is local to Southchurch Park and trendy eateries like Cameilla Hotel and Ocean Beach. Also, a short 10-minute walk brings you to the mile long Southend Pier, offering many local amusements. Complete with FREE roadside parking and freshly redecorated interiors; this charming sanctuary offers a unique getaway, our beautiful garden is perfect to chill.

Pets · Outdoor spaces · Cleanliness

The Cosy Cottage, with heated swimming pool !

Take it easy at this unique getaway, sleeps 4 woodland walks, local pub/restaurant ,Micro brewery and much more to make your time away a memorable one. Relax in the countryside or take a short drive to the local town/Beach. Spend some private time relaxing in our heated swimming pool, and then retire to your own comfort of the "Cosy Cottage" for that long earned rest. Herne Bay,Whitstable towns and the city of Canterbury just 15 mins by car. Local buses run frequently in both directions Enjoy.

Outdoor spaces · Pets · Hiking

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 small 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

Walkability · Outdoor spaces · Layout

Sunflower Stay 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 tent 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!

Walkability · Pets · Cleanliness

Adorable 4 bedroom annex with hot tub

Welcome to 'The Annex' a super hidden gem, tucked away in a rural location but only 11 miles to Southend seaside with 'Adventure Island', 8 miles to Leigh-on-sea and only 33 miles from London. Nestled between the A13 and A127. 'The Annex' is the perfect setting for special occasions, birthdays, families, contractors, hens, stags, holidays, treat yourself time. Take time to relax in the bubbly hot tub. It's important to look at 'other details to note' for rules on events and celebrations.

Walkability · Pets · Family

Luxury 5-BedRm • Hot Tub • Games Room • Sleeps 12

Kent Downs AONB • Newly renovated 5‑bed group house (sleeps 12 + 2 infants) for friends and family get‑togethers, birthdays and wedding weekends. Flexible sleeping arrangements, private year‑round Hot Tub with views, big games room (pool/TT/foosball + 86" TV + sofa‑bed), Kamado Joe BBQ patio, superfast Wi‑Fi (1gb fibre) + Ethernet, luxury hotel‑quality linen & towels, parking for 7 cars + EV charger. Great for midweek offsites. Easy M20/M2/A249 access + Bearsted train station nearby.

Pets · Walkability · Sleep quality

The Midnight Express; Magical Bus, Hot Tub+ Views!

Probably the most magical bus stay in the UK, inspired by the romance of the Orient Express & Harry Potter ✨ Set in peaceful countryside near Canterbury, with epic views, the Midnight Express is a one-of-a-kind converted double-decker bus for couples, families, and small groups seeking a cosy, playful stay. With a hot tub, gaming area in the driver’s seat, cinema snug, log burner, private garden, and separate First Class Waiting Room, it feels like a magical little world of its own.

Pets · Outdoor spaces · Location

Gather&Unwind: Gardens, Woodland & Tennis Cottages

Two charming 3-bedroom cottages with private en-suite bathrooms, set within 2.5 acres of Kentish gardens and woodland. Enjoy a tennis court, children’s play area, walking trails and an in-house ice cream parlour stocked with local Taywell Kentish ice cream. Make your own old-fashioned candyfloss and buttery cinema-style popcorn. Perfect for families, friends and wedding guests. Dog-friendly, with historic Yalding village nearby and London just 45 minutes away by train.

Walkability · Outdoor spaces · Quiet

Acorn 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 Acorn Lodge is a bespoke 1 king size bedroom retreat fully customized with high-end finishes. It must be seen in person to be fully appreciated. Our Wellness area is equipped with a log sauna, a cold plunge and outdoor shower.

Walkability · Pets · Comfort

Seabird Cottage

Beautifully restored 3 bedroom cottage on quaint, quiet street moments from the high street's bars, restaurants and quirky shops; and just 2 minutes from the sea! Light and airy open planned living and dining space with access to landscaped garden. Modern design with contemporary art and travel books to enjoy. We recently fitted a brand new kitchen which is fully equipped for proper cooking and dining. The house has recently been re-decorated and painted.

Outdoor spaces · Walkability · Checkout

2 bedroom Georgian cottage on Island Wall

A beautiful 2 bedroom cottage in the most wonderful location - steps away from the beach and a few minutes walk to the centre of Whitstable. This fisherman’s cottage dates back to 1810, is full of period charm, and sympathetically decorated with antique, comfortable furniture. The cottage has a mature garden with side access, and is set down several steps meaning it feels nice and private. The cottage has steep stairs and some low ceilings.

Pets · Outdoor spaces · Comfort