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Isle of Portland Holiday Rentals

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    Travellers to Isle of Portland are booking January dates now. Secure your holiday rental today, and have the perfect trip.
    All 48 Rentals in Isle of Portland
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Cove Holiday Park1 / 7
    (3)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Sea Cat1 / 12
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Central Heating
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    Pet friendly
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    Smoking allowed
    About this property
    A charming Portland Stone Cottage in the heart of Fortuneswell. Tastefully decorated and furnished it offers cosy accommodation, for four people. Public parking close by and you are just a short stroll from Chesil Beach, if you turn in the other direction and head up the hill you will arrive at the...
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    Isle of Portland, Dorset DT5 1AH
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Wi-Fi
    • Ocean Views
    • Central Heating
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Charming three bedroom cottage ticked away a pebble's throw from Chesil Beach. Coral Cove is found between Sea View and Coastguard Cottages at the north end of the island. Ideal as a base for sailing, walking, diving and exploring the island and the rest of the county of Dorset. Vibrant night...
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    Isle of Portland, Dorset DT5 1AD
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    Stonecleave located in Portland, Dorset1 / 42
    (2)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
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    Stonecleave is part of a very special group of properties owned by Pennsylvania Castle Estate (www.*************) providing luxury accommodation on the island. A bright and inviting home where you’ll find yourself in the perfect position for exploring Portland. Inside, the house has been newly...
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    Isle of Portland, Dorset DT5 1HN
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    The Porthole located in Portland, Dorset1 / 24
    (3)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
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    About this property
    Set in a prime position for exploring the picturesque island of Portland is The Porthole, a bright and modern third floor apartment with two spacious bedrooms. When you step inside, you’ll find yourself in a light, contemporary and fresh living area with leather sofas and a flatscreen TV, perfect...
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    Isle of Portland, Dorset DT5 1EF
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Cliff House1 / 7
    (2)Average
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Parking
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    Pet friendly
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    Smoking allowed
    About this property
    Portland Stone detached house backing onto Chisel Beach. 3 bedrooms, gas central heating, large bathroom on the first floor, and ample parking for two cars. Ideal for sailing holidays, dog walkers, in fact anyone who wants to make use of all that Portland has to offer. The property also has a...
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    Isle of Portland, Dorset DT5 1AW
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    Pebble View1 / 9
    (18)Very good
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Private Garden
    • Central Heating
    • DVD Player
    • Satellite TV
    • Washer
    • Wi-Fi
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Pebbles view is a Victorian Portland stone built mid terrace cottage in the village of Fortuneswell Portland offering stunning panoramic sea views of the Jurassic coasts Chesil beach from all floors<BR>The newly refurbished cottage arranged over three floors comprises of the lounge with wooden...
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    Isle of Portland, Dorset DT51NW
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
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    Pet friendly
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    Smoking allowed
    About this property
    This centuries-old cottage is in Easton, a village at the heart of the peaceful island of Portland. Easton has a good selection of shops, friendly pubs, cafes and a children's play area. Dunsubbin is a short walk from the atmospheric Church Ope Cove with its 'smuggler's' graveyard. Portland is...
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    Isle of Portland, Dorset DT5 1HG
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Bayview1 / 22
    (5)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Wi-Fi
    • Balcony
    • Satellite TV
    • Central Heating
    • Washer
    • Patio
    • DVD Player
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bayview has beautiful sea and coastal views in all directions. There are extensive coast and country walks from the door and a number of local coves and beaches with safe swimming, in particular Weymouth. Portland Harbour is famed for its water sports and was the venue for the last Sailing...
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    Isle of Portland, Dorset DT5 1HE
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Artist Cottage1 / 24
    (4)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Terrace
    • Shared Garden
    • Balcony
    • Ocean Views
    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Built in the 1800's, this sweet little original Portland stone Fisherman's cottage promises a lovely holiday experience.Artist Cottage sleeps four people in two bedrooms and has been delightfully restored.The cottage is found in Fortuneswell just five minutes from the National Sailing Academy and a...
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    Isle of Portland, Dorset DT5 1NQ
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Lyndhurst is a four bedroomed house opposite Victoria Gardens and a short walk from Chesil Beach. Downstairs you will find two family rooms, one with a TV and the other for quiet moments. The kitchen, which overlooks the outside decking area, is spacious and sports a large dining table - ideal...
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    Isle of Portland, Dorset DT5 1AH
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 7
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Private Garden
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This lovely holiday home sits in the heart of Fortuneswell, Portland a short stroll from Chesil Cove. Sea views can be seen from the property where in the evening the rear windows provide lovely sunset viewing. The owners of the property have made this holiday property a home and it offers...
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    Isle of Portland, Dorset DT5 1AT
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    9 Bedrooms, 10 Bathrooms, Sleeps 20 Quick View
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    • Grill
    • Balcony
    • Parking
    • Washer
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Opulence reigns at this modernized castle in Dorset. Chandeliers swing above you, and the blue English Channel beckons below. Though it was built 200 years ago of Portland stone, this castle is far from old school. The furnishings exhibit classic lines in sophisticated neutral colors, full of...
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    Isle of Portland, Dorset DT5 1AA
    Holiday Rental House - 9 Bedrooms, 10 Bathrooms, Sleeps 20
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    When you’re looking for an escape with the beauty of Portland Harbour on your doorstep, look no further that 9 Sidon Mews. With stylish and modern interiors and a bright and sunny garden, you will find plenty of space for everybody to unwind. This contemporary house is especially well suited to...
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    Isle of Portland, Dorset DT5 1FG
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Hot Tub
    • Washer
    • Ocean Views
    • Sauna
    • Shared Indoor Pool
    • Patio
    • Central Heating
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This luxury 7th floor apartment at 199 Atlantic House is part of the prestigious Ocean View complex in Portland, Dorset. The apartment has been rated as 4* by the AA and overlooks Weymouth Bay and Portland Marina and is less than a mile from the National Sailing Academy, venue of the 2012 Olympics...
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    Isle of Portland, Dorset DT5 1FB
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Ocean Studio Apartments OSA9- Portland Dorset1 / 11
    (1)Average
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
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    Pet friendly
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    Smoking allowed
    About this property
    If you are looking for the perfect place for a romantic weekend break for two, a longer get-away-from-it-all holiday or fun time with a group of friends then you've found it! Every apartment combines quality overnight comfort and en-suite facilities with modern self-catering kitchenette. The Ocean...
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    Isle of Portland, Dorset DT5 2NT
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Ocean Studio Apartments OSA11A-Southwell, Portland1 / 22
    (8)Excellent
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
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    • Ocean Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Self contained apartment base on Southwell business park , isle of Portland. A short stroll from famous Portland bill& Jurassic coastline. Come &see for yourself Towels,Linens ,Toiletries provided equipped with hair dryer,iron+board ,fridge,toaster,kettle,Microwave oven. Tesco & co-op & local...
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    Isle of Portland, Dorset DT5 2NT
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Central Heating
    • Patio
    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A sea side cottage situated a short stroll from Chesil beach and the Cove Inn, at the heart of Fortuneswell within a short distance of the Jurassic Coastline and National Sailing Academy at Portland Harbour. At the front of the property is an ideal place to relax with a cocktail under your own...
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    Isle of Portland, Dorset DT5 1NJ
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    1 Bow & Arrow Cottages1 / 18
    (2)Very good
    4 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Grill
    • Satellite TV
    • Wi-Fi
    • Washer
    • Private Garden
    • DVD Player
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This lovely family house is located in a perfect spot to offer the best of both worlds, a semi detached Edwardian cottage down a quiet lane leading to the beach and cliffs and just 10 minutes walk away from shops, cafes and other amenities. The ground floor offers comfortable, spacious open plan...
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    Isle of Portland, Dorset DT5 1JA
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 8
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    50 Ocean Views, Portland located in Portland, Dorset1 / 18
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy contemporary living in a beautiful setting at 50 Ocean Views. This bright, open plan apartment is found on the second floor of the Ocean Views development in Portland, and with a spacious design and an onsite swimming pool and fitness centre, it’s the perfect place for a relaxing family...
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    Isle of Portland, Dorset DT5 1DT
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Ocean Studio Apartment OSA11- Portland,Dorset1 / 8
    (2)Terrible
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Internet Access
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    Pet friendly
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    About this property
    Studio Apartment situated on 2nd Floor , Maritime House, Southwell Business Park, Portland .(ex mod building converted to living accommodation with kitchenette & en-suite bathroom) . Local amenities are within 5-10 mins driving distance. Approx 10 minutes walks from famous Portland Bill Lighthouse...
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    Isle of Portland, Dorset DT5 2NT
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    OLD HIGHER LIGHTHOUSE STOPES COTTAGE, family friendly, character holiday1 / 16
    (5)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
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    Pet friendly
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    About this property
    This semi detached cottage is located on the tip of Portland Bill in Dorset and can sleep four people in two bedrooms. Stopes Cottage is a semi detached cottage next to a lighthouse on the tip of Portland Bill near to Weymouth in Dorset. The cottagesleeps four people in one double bedroom, one...
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    Isle of Portland, Dorset DT5 2JT
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    TREE TOPS, woodburning stoves, pet-friendly, sea views, Portland, Ref 9342911 / 19
    (1)Excellent
    4 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
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    This detached cottage is in the small hamlet of Wakeham near Portland and sleeps six people in four bedrooms. Tree Tops is a detached cottage in the small hamlet of Wakeham near Portland. The cottage sleeps six people in four bedrooms which are a second floor super king-size double (zip/link, can...
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    Isle of Portland, Dorset DT5 1JA
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 6
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    OLD HIGHER LIGHTHOUSE BRANSCOMBE LODGE, family friendly, character holiday1 / 20
    (3)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
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    Pet friendly
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    About this property
    This detached cottage is located on the tip of Portland Bill in Dorset and can sleep four people in two bedrooms. Brancombe Lodge is a detached cottage next to a lighthouse on the tip of Portland Bill near to Weymouth in Dorset. The cottage sleeps four people in one double bedroom, one twin room...
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    Isle of Portland, Dorset DT5 2JT
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 1 Quick View
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    • Washer
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Well suited single occupancy rooms, possibly suitable for a couple with an additional fee providing access to communal living room, kitchen & utility room. On the ground floor there is communal living room, kitchen & one bedroom. On the first floor there are two bedrooms & a utility room & on the...
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    Isle of Portland, Dorset DT5 1JQ
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 1
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    Pebble Reef1 / 21
    (18)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Satellite TV
    • Balcony
    • DVD Player
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    • Terrace
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Pebble Reef is a traditional Quarryman's Cottage, full of character but lovingly renovated to include all the modern comforts you need.<BR><BR> The cottage sleeps up to six people in 3 comfortable bedrooms. Upstairs there's one double with en-suite shower room, a twin bedroom, and on the ground...
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    Isle of Portland, Dorset DT5 1HR
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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