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Pet Friendly Holiday Rentals in Isle of Portland

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    Travellers to Isle of Portland are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    27 Matching Rentals in Isle of PortlandView all 75 rentals
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    Rosa Cottage1 / 30
    (33)Very good
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Schooner Cottage ** New 2018 **1 / 40
    (12)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Portland Hideaway1 / 8
    (16)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    A new eco-home with views out to sea and a beach hut in the local cove.. <strong>Ground Floor:</strong> <strong>Kitchen/dining room: </strong>With double electric oven, electric hob, microwave, fridge, freezer and dishwasher. <strong>Utility room:</strong> With washer/dryer. <strong>Bedroom...
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    Weston, Isle of Portland DT5 1HT
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Ocean Views
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    Smoking allowed
    About this property
    A Grade II listed four bedroom house situated just 500 yards from the famous Chesil Beach.. <strong>Step to entrance.</strong> <strong>Ground Floor:</strong> <strong>Living/dining room: </strong>With wood burner, 43' Freeview TV, DVD player, iPod dock, wooden floor and beams. <strong>Kitchen:...
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    Castletown, Isle of Portland DT5 1AP
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
    Cliff House1 / 8
    (6)Average
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Reviewed 6 June 2019
    It was very good, my family liked it too. the mattress is comfortable. I hope to get vacancies when I come back. Thank you.
    Reviewed 21 June 2018
    Large rooms basic accommodation with no frills. This is reflected in the price. Owners friendly & accommodating. Beach & parking behind property. Suited our needs for a...
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    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
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    About this property
    Many outdoor activities can be enjoyed from this 200 year old cottage and walks on the coastal path nearby should not be missed.. <strong>Ground Floor:</strong> <strong>Living/dining room:</strong> With wood burner, TV, DVD player, CD player, beams and oak floor. <strong>Kitchen: </strong>With...
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    Castletown, Isle of Portland DT5 1NH
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
    Artist Cottage - Charming coastal cottage on Portland :-)1 / 12
    (5)Average
    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
    Reviewed 18 April 2017
    We stayed with friends on New Years Eve in this beautiful terraced cottage. The experience was amazing: Portland Bill seems to exist in a time warp and I will always remember...
    Reviewed 30 March 2017
    We have stayed here 3 or 4 times and always had a lovely time. The house is a very pretty old traditional Portland Stone building. It is in a no through road so very quiet...
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    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
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    This semi-detached property is in an ideal location for watersport enthusiasts or those who wish to stroll along the beach. Situated in Weston in the heart of Portland, this semi-detached holiday home for four is ideally suited for exploring this scenic area, along with Weymouth and Dorchester...
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    Weston, Isle of Portland DT5 2BZ
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Cliff Walk Cottage with hot tub1 / 34
    (6)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
    • Central Heating
    • Private Garden
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    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 June 2019
    Lovely cottage ,clean ,bright and comfortable ,with large garden ,and off road parking ,well equipped ( though teacups or smaller mugs would be nice for us oldies !!),otherwise...
    Reviewed 19 February 2019
    Lovely clean house nice and warm good area with lots of great walks.would stay here again .All homes owened by amanda are first class thankyou wendy and peter.
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    About this property
    Cliffwalk Cottage is a modern two bedroom house, which can sleep up to 4 people. The Property has WiFi and full gas central heating throughout. At the rear of the house there is a enclosed garden with patio and BBQ area with garden furniture and a clothesline. Hot Tub will be installed by July...
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    Isle of Portland, Dorset DT5 2LZ
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Ted's House1 / 11
    (4)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 September 2019
    We found the property to be very clean, spacious and comfortable. Fairly well equipped, apart from no iron & ironing board. We did have a issue with the shower flooding as a...
    Reviewed 2 June 2018
    Just arrived home after staying for the Whitsun Week at Teds House and enjoyed our stay very much. Chesil Beach just down the road and 4 local pubs within walking distance, we...
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    About this property
    This lovely holiday home sits in the heart of Fortuneswell, Portland a short stroll from the Jurassic Coast. 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 offers...
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    Isle of Portland, Dorset DT5 1AG
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Tompot Cottage - Character cottage by the sea1 / 14
    (5)Very good
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Central Heating
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    Just back after a wonderful stay at Tompot cottage, there was everything we needed in a lovely little place. Location was fantastic with the sea and coastal walks right on the...
    Reviewed 4 weeks ago
    Nice cottage ,well equipped with all amenities you could need,far more than logged on Airbnb. Beds were comfy with nice quality bedding. Plenty of room for our group of 5 and a...
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    About this property
    A character cottage by the sea, 400 years old with beams, steep stairs, quirky walls and creaky floors, just a stone’s throw from the world famous Chesil Beach and Portland Harbour, sleeping seven in three bedrooms. Based in the iconic sailing location with access to water sports, walks and outdoor...
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    Isle of Portland, Dorset DT5 1AP
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 7
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    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
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Gather up the kids, the crab nets and the wetsuits and get down to Wavecrest, our homely Dorset retreat just minutes from the sea. Its location is perfect for watersports enthusiasts, walkers and cyclists alike. Alive with activity, the Weymouth and Portland Sailing Academy and Windsurfing Centre,...
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    Castletown, Isle of Portland DORSET
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Central Heating
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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
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Ocean Views
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    Smoking allowed
    About this property
    A beautiful stone house which can sleep six people in three bedrooms situated in the Isle of Portland in Dorset.Charlton House situated on the Isle of Portland near Weymouth in Dorset can sleep six people in three bedrooms, 2 x double and 1 x twin and a family bathroom. The cottage has a fully...
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    Weston, Isle of Portland DT5 1BS
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This apartment property rests in Portland Bill and can sleep four people in two bedrooms.For your view only is a superb apartment resting within Portland Bill. It comes with a super-king-size bed with en-suite shower, a double and a twin, together sleeping up to six and serviced by a shower room...
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    Weston, Isle of Portland DT5 2NA
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    THE PALMS, sleep 4 bungalow, pet friendly, close to amenities, 2 miles to1 / 27
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Smoking allowed
    Reviewed 23 March 2019
    Stayed at the Palms for a week best place we ever stayed in home from home very clean and modern we go away 3 times a year and this is the best yet location is good
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    About this property
    This stylish bungalow on the Isle of Portland near to Weymouth in Dorset and can sleep 4 people in 2 bedrooms.The Palms is a stylish modern bungalow situated on the Isle of Portland near to the town of Weymouth in Dorset and benefits from accommodation all on one floor. The bungalow can sleep 4...
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    Castletown, Isle of Portland DT5 2BZ
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Washer
    • Ocean Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Portland stone semi-detached cottage is in Fortuneswell, Portland in Dorset and can sleep 8 people in 4 bedrooms.Pitt Hayes Cottage is a Portland stone semi-detached cottage situated in Fortuneswell in Portland in Dorset boasting stunning sea views and conservatory. The cottage can sleep 8...
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    Castletown, Isle of Portland DT5 1LQ
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Ocean Views
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    Pet friendly
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    Smoking allowed
    About this property
    This traditional Portland cottage is in the village of Fortuneswell, Portland, Dorset and can sleep 5 people in 3 bedrooms.Neptune Cottage is a traditional Portland cottage situated in Fortuneswell, Portland, Dorset and benefits from its location on Chesil Beach. The cottage can sleep 5 people in 1...
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    Castletown, Isle of Portland DT5 1AP
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Smoking allowed
    About this property
    This traditional terraced cottage is in the village of Fortuneswell , Portland, Dorset and can sleep 4 people in 2 bedrooms.Langahm Cottage is a traditional terraced cottage situated in Fortuneswell, Portland, Dorset and benefits from beautiful sea views. The cottage can sleep 4 people in 1 Super...
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    Castletown, Isle of Portland DT5 1AB
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Smoking allowed
    About this property
    This contemporary residential cottage is in the Fortuneswell in Portland in Dorset and can sleep 4 people in 2 bedrooms.Olympic Cottage is a contemporary residential cottage situated in Fortuneswell, Portland in Dorset close to the beach and welcomes 1 dog. The cottage can sleep 4 people in...
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    Castletown, Isle of Portland DT5 1FH
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Balcony
    • Washer
    • Central Heating
    • Wi-Fi
    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This lovely first floor apartment is based in Fortuneswell, Dorset, on the Isle of Portland and can sleep two people in one bedroom.Officers Retreat is a spacious apartment based in Fortuneswell, Dorset, on the Isle of Portland. All rooms are on the first floor. It has one king-size double bedroom,...
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    Castletown, Isle of Portland DT5 1FH
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    • Ocean Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This modern 3 storey house is in Fortunewell, Portland, Dorset and can sleep 8 people in 4 bedrooms.Jurassic Coast House was originally built to house 2012 Olympic athlete’s and is a modern house situated in Fortuneswell , Portland, Dorset. The cottage can sleep 8 people in 1 x king-size double...
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    Castletown, Isle of Portland DT5 1FG
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    This traditional terraced cottage is in Fortuneswell on the Isle of Portland in Dorset and can sleep 4 people in 2 bedrooms.Unicorn is a traditional terraced cottage situated in Fortuneswell on the Isle of Portland in Dorset and is a short walk from Chesil Beach. The cottage can sleep 4 people in...
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    Castletown, Isle of Portland DT5 1NH
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    About this property
    Alpen Rose Cottage is a restored terraced fisherman’s cottage on the Isle of Portland and can sleep five people in three bedrooms.Alpen Rose Cottage is a terraced fisherman’s cottage on the Isle of Portland, near Weymouth, Dorset. The property comprises of 1 x king-size, 1 x twin and 1x single...
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    Weston, Isle of Portland DT5 1HQ
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
    Quarries Reach, rural & sea views Portland, Dorset1 / 20
    (60)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Cable/satellite TV
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    • Grill
    • Central Heating
    • Washer
    • Ocean Views
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 February 2019
    This is a great house for a big family to stay in we have just had a long weekend away to Portland,The house has everything you need.The location is great with amazing views.
    Reviewed 16 October 2018
    This house was just what we needed for a get together with friends. The three storey property worked really well for us. Even thought the property is next to a road it was quiet...
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    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 comfortably in 4...
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    Isle of Portland, Dorset DT5 2DL
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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