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A Perfect Pairing: Separate Properties for Big Groups

29 September 2025
Holly Price

When you holiday as a large group – or even as two couples – it doesn’t necessarily mean you have to look for a single home that will accommodate all of you. If you want to get away as a group while also enjoying your own space, you can opt to book neighbouring or closely located properties instead!  

We’re lucky enough to work with a variety of lovely property owners across different areas of Kent, and so we have a collection of houses and cottages that are close to each other. For group trips to Whitstable, Kingsdown and Deal, here are the ‘perfect pairings’ with convenient proximity to each other.    

Neighbouring holiday cottages in Kent 

If you want a relaxing break with all of your own private amenities coupled with the experience of holidaying with friends or family, these three pairings are quite literally next-door neighbours. Based in Whitstable, Deal and Kingsdown, each duo offers a coastal break for a larger group.   

 

Ravenscourt & Flamingo House, Whistable 

Sleeps 8 & 8 | Pet-Friendly | Stylish Interiors 

Both stunning terraces with deceptively spacious interiors and private gardens, Ravenscourt and Flamingo House can accommodate a combined total of 16 people. Flamingo House is a great choice for those bringing along little ones, with toys, books and all of the essentials for smaller guests. The street leads almost all the way down to the shingle beach, where you’ll find popular beachfront pub The Old Neptune waiting for you on the shoreline. 

 

Seapink & Rumbosun, Kingsdown 

Sleeps 5 & 4 | Pet-Friendly | Beachfront Location

Traditional fishermen’s cottages, Seapink and Rumbosun are quaint, charming and full of character. So close to the shoreline that you can fall asleep to the soundtrack of the sea, the cottages are an idyllic antidote to modern life. Wedged between two pubs and perfectly placed for long coastal walks, this is a perfect pairing for up to 9. 

 

 The Writer’s Cottage and The Crow’s Nest, Deal 

Sleeps 4 & 3 | Pet-Friendly | Enclosed Gardens 

Ideally situated for discovering Deal’s bustling Georgian high street, The Writer’s Cottage and The Crow’s Nest are both spread out over three floors and can accommodate up to four and three, respectively. Great for those looking to sample the foodie scene in Deal, they are also located just a short distance from the beach – just what the doctor ordered. 

Holiday cottages in Deal on the same street

Recently featured in The Sunday Times ‘Best Coastal Towns to Live in the UK’ & Time Out’s ‘20 Best Day Trips From London,’ Deal is a hot topic right now. If you’re looking to beat the crowds and experience it for yourself, here are our perfect pairings for a large group stay… 

 

Ivy House & Fig Tree House, College Street, Deal  

Sleeps 8 & 5 | 1 Pet Allowed at Fig Tree House | Character Properties 

Situated just over the street from one another, Ivy House and Fig Tree House are teeming with stunning Georgian character. Offering spacious interiors, log burners and private outdoor spaces, they are a fantastic getaway to enjoy in any season. 

 

Riley Cottage & Skimming Stone, Middle Street, Deal

Sleeps 4 & 4 | Pet-Friendly | In Conservation Area 

Want to combine oodles of character, proximity to the beach and elegant interiors? Riley Cottage and Skimming Stone are the ideal combination, sleeping up to a total of 8, but also offering a luxurious experience for two couples wanting their own space. Situated just a few doors down from each other, they sit at the heart of Deal’s conservation area. 

 

Saltwater Cottage & The Pink House, Middle Street, Deal

Sleeps 4 & 8 | Pet-Friendly | In Conservation Area

Located along the meandering Middle Street, with its gorgeous Grade-Listed properties and quick access to the sea, Saltwater Cottage and The Pink House are the perfect combination for a group of up to 12 and three four-legged friends. Located within a few steps of one another, both properties have stunning interiors and charming outdoor courtyards.   

Large group holiday cottages in Kingsdown 

Rugged and romantic with miles of beach stretching out ahead of you, Kingsdown is the perfect choice for a milestone celebration or relaxing getaway. With beautiful architecture, stunning interiors and sea views as far as the eye can see, the below could make for a captivating combination.  

Victory at Cliffe & Oldestairs, Kingsdown

Sleeps 8 & 10 | Special Stays | Clifftop Setting

A charming duo located on the same stunning stretch of road, Victory at Cliffe and Oldestairs house are some of our top choices for those celebrating something special. Victory at Cliffe brings romance and drama with shuttered windows and a wrap-around veranda, while Oldestairs is a quintessential coastal pile with exquisite interior decor. 

Need space for an extra 12? The grand Bowden Lodge is at the top of the road, too. 

Group stays by the sea in Whitstable 

We love Whistable for many reasons. The oysters, the short distance to Canterbury and the sunsets are just three great reasons to head here with your nearest and dearest. We have two roomy cottages right by the beach, which can accommodate a total of 14.   

 

Peace Cottage & Sea View Cottage, Whitstable

Sleeps 6 & 8 | Pet-Friendly | Steps from the Sea 

Situated within ambling distance of Whitstable’s famous The Old Neptune pub, both of these stunning coastal boltholes are comfortably equipped for a large group stay. Each cottage also allows one dog, which is great news for those already planning their early morning beach walkies.

Allow us to plan your perfect large group stay in Kent

Still searching for the perfect property? Allow us to assist you – every single member of the Keepers Cottages team is a local, and so we know exactly how to help you get the most out of your stay. From the best restaurants within walking distance to which beaches you should visit, our team is on hand to help. Get in touch with us on 01304 382044.

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About Holly Price

Holly is a Freelance Copywriter who joined the Keeper's Cottage marketing team in 2025. Passionate about good food, good wine, good books and good beaches, she's keen to highlight the very best spots to explore and enjoy throughout Kent.

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