Cottages for large groups in South of the Island
These spacious UK getaways are perfect for reunions with friends or family get-togethers, with pools, balconies and games rooms galore. Read more
Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.We have 18 self catering cottages for a group in South of the Island
Bay View House
214Large town house in Port Erin with view of Bradda head
Bay View is a beautifully renovated six-bedroom townhouse in the heart of Port Erin, offering stylish and spacious accommodation for large families, groups of friends, and multi-ge...
Lilac House
83Nestled on the outskirts of Castletown, the breathtaking Lilac House promises an unforgettable stay
Lilac House is a premium self-catering holiday home, nestled in the serene countryside on the outskirts of Castletown. Offering seclusion, space, and luxury, this exquisite propert...
Reserve your 2027 holiday for just £40.00
Find out more
Brookville House
28A family friendly house located in rural Ballabag
Brookville House is a comfortable house set in the rural surroundings of Ballabeg, in the Isle of Man. Sleeping up to 9 people across 5 bedrooms it is perfect for families or group...
Thie Fuinnee
145Thie Fuinnee is a spacious self-catering holiday home situated in the peaceful harbour-side village
Thie Fuinnee is a spacious self catering holiday home situated in the peaceful harbour-side village of Port St Mary on the Isle of Man. The property itself is located just round th...
British Travel Awards 2025
Best company for UK holiday home rentals
Eary Cushlin
56In partnership with Manx National Heritage, we are pleased to present Eary Cushlin; a large house on
Hidden on the rugged western coastline just beneath Cronk ny Arrey Laa, sits the former home of eccentric recluse Colby Cubbon, who purchased the property hoping to escape the Germ...
Highfield
198Homestay registered property - only available for bookings during TT & MGP periods.
This beautiful property is registered with Homestay IOM Limited and is marketed exclusively through Island Escapes. Highfield is available for self-catering accommodation exclusive...
Awelon
14A premium escape located on the sought after Port Erin beach
Awelon is a premium self-catering holiday home located on the beachfront of Port Erin, with fantastic views of the beach, Port Erin Bay and Bradda Head, featuring Milner's Tower. ...
Calf of Man Bird Observatory
33Basic Self catering hostel / bunkhouse style accommodation for up to 8 visitors.
The 2026 booking season will run from early June until early September, with exact dates to be confirmed. Bookings will open at 9am on Monday 9th March 2026 on a first come fir...
Highbury House
220Luxury group getaway in the heart of historic Castletown
Set in the heart of historic Castletown, Highbury House is a beautifully renovated four-bedroom property offering stylish and spacious accommodation across three floors. Finished t...
Salt Wood
101An incredible waterfront property on the harbourside of Port St Mary, Isle of Man
There are few properties on the Isle of Man like Salt Wood. From the moment you step inside you'll feel the care and attention gone into making this a truly magical home by the ...
Be in the know… Sign up to our newsletter for holiday inspiration, offers and all things Classic.
The more the merrier, when it comes to a South of the Island holiday. So get everyone together, friends, family even the pets and spend some quality time reacquainting with each other. Holidays are when the best memories are made so make sure none of your loved ones is missed out of the fun with one of our South of the Island cottages for a large group.
