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Isle of Portland Villas

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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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    65 Fortuneswell - 180o Sea Views from Balcony1 / 19
    (37)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    5 Cove Park1 / 14
    (2)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pitt Hayes Cottage1 / 14
    (10)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Garden
    • Wi-Fi
    • Central Heating
    • Washer
    • Ocean Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    4 Sea View offers the best of modern comforts with period character in a cottage just a short walk from the splendors of Chesil Beach & Cove on the Isle of Portland Dorset. Offering a fabulous kitchen and comfortable accommodation. A character cottage designed to sleep six in three bedrooms in a...
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    Isle of Portland, Dorset DT5 1AA
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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
    • Parking
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    Pet friendly
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    Smoking allowed
    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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    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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    About this property
    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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    Dory Cottage1 / 9
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Private Garden
    • Patio
    • Ocean Views
    • Wi-Fi
    • Washer
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Three bedroom Portland Stone cottage over three floors with fabulous views over Chesil Beach and The Fleet. Just a short walk from Chesil Beach. Divers, sailors, walkers and families will love this cottage. WiFi and TV included but you will be busy watching the sunset! Three bedroom cottage...
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    Isle of Portland, Dorset DT5 1JJ
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    Fishermans Cottage1 / 38
    (20)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Grill
    • Central Heating
    • DVD Player
    • Ocean Views
    • Hot Tub
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fishermans Cottage is a charming detached 18th century cottage on the edge of Southwell, with excellent sea views. Recently renovated with full central heating throughout and Wi Fi. On the ground floor there is a lounge / diner with sea view, a reception room, a fully equipped kitchen, a...
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    Isle of Portland, Dorset DT5 2EF
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Pebble Reef1 / 21
    (18)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Balcony
    • DVD Player
    • Grill
    • Central Heating
    • Wi-Fi
    • Terrace
    • Washer
    Suitability
    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. 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 floor...
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    Isle of Portland, Dorset DT5 1HR
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Quarries Reach, rural & sea views Portland, Dorset1 / 17
    (48)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    • Central Heating
    • DVD Player
    • Ocean Views
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ideal for small groups, couples & families - fabulous rural and sea views. A contemporary spacious detached house with a safe, secluded and walled garden. Situated in a prime position with spectacular rural and sea views looking towards Dorset's Jurassic Coast. Sleeps up to 8 +2 comfortably in...
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    Isle of Portland, Dorset DT5 2DL
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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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
    Jurassica House is part of our Olympic legacy, home to the Swedish sailing team during the sailing events in 2012. A great location for water sports enthusiasts, walkers, cyclists, rock climbing, bird watching and of course, perfect for simply for relaxing. Internally, the spacious living areas are...
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    Isle of Portland, Dorset DT5 1AU
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, 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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    The Porthole located in Portland, Dorset1 / 24
    (3)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    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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    Mermaid Cottage1 / 8
    (1)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Grill
    • DVD Player
    • Private Garden
    • Washer
    • Central Heating
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Whether you are looking for that relaxing break, or here to sail or just time with the family this charming cottage would suit your needs. Nestled off Wakeham, you will agree this cottage is a real find. A charming cottage nestled just behind Wakeham, backing on to open land. This spacious...
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    Isle of Portland, Dorset DT5 1HS
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Sea Cat1 / 6
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Central Heating
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    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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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    About this property
    Set on the ever-popular Isle of Portland, Ashlar Cottage is the perfect home from home for that family escape to Dorset. With a traditional feel throughout that makes you feel instantly at home, this two bedroom property has traditional features and a cosy décor. One of our favourite things about...
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    Isle of Portland, Dorset DT5 1HP
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Artist Cottage1 / 12
    (4)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Terrace
    • Shared Garden
    • Balcony
    • Ocean Views
    • Central Heating
    Suitability
    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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    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
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • 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, 2 Bathrooms, Sleeps 4
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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
    Kid friendly
    Smoking allowed
    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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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Central Heating
    • DVD Player
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    Pet friendly
    Kid friendly
    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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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Central Heating
    • Patio
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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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    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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    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Central Heating
    • Ocean Views
    • DVD Player
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Wavecrest is in the village of Fortuneswell, overlooking Chesil Beach and close to the Weymouth and Portland Sailing Academy and Windsurfing Centre. Perfectly located for sailors, windsurfers, divers, walkers and cyclists with storage for boards, sails, bikes and wetsuits as well as a 72 hour free...
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    Isle of Portland, Dorset DT5 1LX
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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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
    • Cable/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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    1 Bedroom, 1 Bathroom, Sleeps 1 Quick View
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    • Washer
    • DVD Player
    • 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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