Isle of Portland Vacation Rentals & Homes - 434 Rentals Available
434 Vacation rentals
OLD HIGHER LIGHTHOUSE BRANSCOMBE LODGE, family friendly, character holiday
Isle of Portland House
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 3 nights min
- Swimming pool
- Child friendly
$203.00
from $203.00 / night
Old Higher Lighthouse Stopes Cottage, Portland bill
Isle of Portland House
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 3 nights min
- Swimming pool
- Child friendly
$203.00
from $203.00 / night
Quarr Cottage, Wakeham, Portland
Weston Cottage
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 3 nights min
- Private garden
$196.00
from $196.00 / night
ALPEN ROSE COTTAGE, private parking, two dogs, three bedrooms on Isle of
Weston Cottage
- 3 bedrooms 3
- 1 bathroom
- sleeps 5 5
- 3 nights min
- Child friendly
- Pet friendly
$236.00
from $236.00 / night
The Old Council Chamber, Fortuneswell
Castletown Apartment
- 1 bedroom 1
- 1 bathroom
- sleeps 2 2
- 3 nights min
- Child friendly
- Pet friendly
$167.00
from $167.00 / night
AMMONITE COTTAGE, WiFi, two bedrooms, courtyard on Isle of Portland.
Castletown Cottage
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 3 nights min
$206.00
from $206.00 / night
CHARLTON HOUSE, beautiful portland cottage, sleeps 6, slipper bath, close to
Weston Cottage
- 3 bedrooms 3
- 1 bathroom
- sleeps 6 6
- 3 nights min
- Child friendly
- Pet friendly
$212.00
from $212.00 / night
SUNSET LODGE, modern apartment, sleeps 6, sea views, WiFi, Portland
Castletown Cottage
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 3 nights min
- Child friendly
$252.00
from $252.00 / night
JURASSIC COAST HOUSE, Sleep 8, modern olympic athletes house, Close to Chesil
Castletown Cottage
- 4 bedrooms 4
- 2 bathrooms
- sleeps 8 8
- 3 nights min
- Child friendly
- Pet friendly
- Private garden
$377.00
from $377.00 / night
Little Lodge, Wakeham, Portland
Weston Bungalow
- 1 bedroom 1
- 1 bathroom
- sleeps 2 2
- 3 nights min
- Child friendly
- Private garden
$229.00
from $229.00 / night
THE OLD PORTLAND COURTHOUSE, sleeps 8, historic building, four poster bed
Castletown Cottage
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- 3 nights min
- Private garden
$471.00
from $471.00 / night
UNICORN, cute cottage, sleeps 4, sea glimpses, cottage garden, Portland
Castletown Cottage
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 3 nights min
- Child friendly
- Pet friendly
- Private garden
$215.00
from $215.00 / night
OSPREY HOUSE, contemporary house, sleeps 7, Rooftop balcony with views, WiFi
Castletown Cottage
- 4 bedrooms 4
- 2 bathrooms
- sleeps 8 8
- 3 nights min
- Child friendly
$286.00
from $286.00 / night
Panoramic View, Castletown, Portland
Castletown Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 3 nights min
$215.00
from $215.00 / night
For your view only, Portland Bill
Weston Apartment
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 3 nights min
- Child friendly
- Pet friendly
$243.00
from $243.00 / night
ST JOHNS VIEW, contemporary house, sleeps 4, off road parking, Wifi, Portland
Castletown Cottage
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 3 nights min
- Child friendly
- Private garden
$215.00
from $215.00 / night
BOWMAN'S COTTAGE, Traditional stone cottage, sleeps 4, close to walks, Portland
Castletown Cottage
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 3 nights min
- Private garden
$200.00
from $200.00 / night
Cove Lodge, Wakeham
Weston Chalet
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 3 nights min
- Child friendly
- Pet friendly
$366.00
from $366.00 / night
LANGHAM COTTAGE, Terraced cottage with sea views, Sleeps 4, Log Burner, WiFi
Castletown Cottage
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 3 nights min
- Child friendly
- Pet friendly
$206.00
from $206.00 / night
Pitt Hayes Cottage, Fotrtuneswell
Castletown Cottage
- 4 bedrooms 4
- 2 bathrooms
- sleeps 8 8
- 3 nights min
- Child friendly
- Pet friendly
$395.00
from $395.00 / night
Neptune Cottage, Fortuneswell
Castletown Cottage
- 3 bedrooms 3
- 2 bathrooms
- sleeps 5 5
- 3 nights min
- Child friendly
- Pet friendly
$222.00
from $222.00 / night
QUARRY TRAILS, Sleeps 5, Close to coast walks, WiFi, Parking, Portland
Castletown Cottage
- 3 bedrooms 3
- 2 bathrooms
- sleeps 5 5
- 3 nights min
- Child friendly
- Private garden
$252.00
from $252.00 / night
THE VIEW, beautiful sea views, sleeps 6, Walk to chesil beach, Portland.
Castletown Cottage
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 3 nights min
$303.00
from $303.00 / night
Pennsylvania Castle, Wakeham, Portland
Weston Cottage
- 9 bedrooms 9
- 11 bathrooms
- sleeps 20 20
- 3 nights min
- Swimming pool
- Child friendly
$2,845.00
from $2,845.00 / night
OLYMPIC COTTAGE, Sleep 4, Original olympic althlete house, WiFi, Contemporary
Castletown Cottage
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 3 nights min
- Child friendly
- Pet friendly
- Private garden
$233.00
from $233.00 / night
Cove Chalet, Wakeham, Portland
Weston Bungalow
- 2 bedrooms 2
- 1 bathroom
- sleeps 3 3
- 3 nights min
- Child friendly
- Pet friendly
- Private garden
$186.00
from $186.00 / night
Spring Rose Cottage, Fortuneswell
Castletown Cottage
- 3 bedrooms 3
- 1 bathroom
- sleeps 8 8
- 3 nights min
- Child friendly
- Pet friendly
- Private garden
$203.00
from $203.00 / night
Telltales, Fortuneswell
Castletown Cottage
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 3 nights min
- Child friendly
- Pet friendly
- Private garden
$227.00
from $227.00 / night
The Shambles, Fortuneswell
Fortuneswell Cottage
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 3 nights min
- Child friendly
$244.00
from $244.00 / night
Pebbles View, Wyke Regis
Castletown Cottage
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 3 nights min
- Child friendly
- Pet friendly
- Private garden
$263.00
from $263.00 / night
Boatswain's Watch, Fortuneswell
Fortuneswell Cottage
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 3 nights min
- Child friendly
- Pet friendly
$204.00
from $204.00 / night
Jurassica House, Fortuneswell
Castletown House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 8 8
- 3 nights min
- Child friendly
- Private garden
$390.00
from $390.00 / night
Smallmouth Cottage, Wyke Regis
Castletown Cottage
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 3 nights min
- Private garden
$219.00
from $219.00 / night
21 Court Barton, Weston, Portland
Weston Cottage
- 3 bedrooms 3
- 1 bathroom
- sleeps 5 5
- 3 nights min
- Child friendly
- Pet friendly
- Private garden
$186.00
from $186.00 / night
The Old Police Station, Fortuneswell
Fortuneswell House
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- 3 nights min
- Child friendly
- Private garden
$413.00
from $413.00 / night
Jay Cottage, Weymouth
Castletown Cottage
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 3 nights min
- Child friendly
- Pet friendly
- Private garden
$166.00
from $166.00 / night
Sunrise Hill, Castletown, Portland
Castletown Apartment
- 1 bedroom 1
- 1 bathroom
- sleeps 2 2
- 3 nights min
$169.00
from $169.00 / night
Portland View, Portland Bill
Weston Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 3 nights min
- Child friendly
$222.00
from $222.00 / night
Tidal Drift, Wyke Regis
Castletown Cottage
- 3 bedrooms 3
- 1 bathroom
- sleeps 5 5
- 3 nights min
- Child friendly
- Pet friendly
- Private garden
$223.00
from $223.00 / night
Schooner Cottage, Fortuneswell
Fortuneswell House
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- 3 nights min
- Child friendly
- Pet friendly
$234.00
from $234.00 / night
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