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Pet Friendly Holiday Rentals in Isle of Portland

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    Travellers to Isle of Portland are booking April dates now. Secure your holiday rental today, and have the perfect trip.
    22 Matching Rentals in Isle of PortlandView all 57 rentals
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    Rosa Cottage1 / 30
    (34)Very good
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Schooner Cottage - At Christmas1 / 42
    (9)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    5 Cove Park1 / 14
    (4)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Quarries Reach, rural & sea views Portland, Dorset1 / 17
    (58)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Grill
    • Cable/satellite TV
    • Wi-Fi
    • Secure Parking
    • Central Heating
    • Washer
    • Ocean Views
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    Reviewed 2 August 2018
    Perfect for our family's needs for a very enjoyable weeks stay! Plenty of room and spacious shower room, bathroom and separate toilet - not to be underestimated with a big family!
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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 +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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    Portland Hideaway1 / 8
    (11)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Washer
    • Parking
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 September 2018
    Great place to stay in, clean and everything you need like home from home,the area is lovely and bus service is exceptional had a great time.
    Reviewed 26 August 2017
    Comfortable and surprisingly spacious, kitchen adequately equipped, owners next door but very low profile.The Hideaway is a conservatory and therefore does get very warm...
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    About this property
    The Portland Hideaway is a 4* self contained self catering unit with open plan living space.It benefits from a fully equipped kitchen,separate shower room with wc & sink,open plan bedroom/lounge area with ample seating on the reclining leather sofa's & air conditioning unit for your comfort....
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    Isle of Portland, Dorset DT5 2DS
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Artist Cottage - Charming coastal cottage on Portland :-)1 / 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
    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 31 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
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    Cliff Walk Cottage1 / 22
    (3)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Wi-Fi
    • Central Heating
    • DVD Player
    • Parking
    • Washer
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 September 2018
    Really nice house has everything you need for your stay away nice quiet area good parking good base for exploring the Weymouth Portland area
    Reviewed 6 September 2018
    We were attending Weymouth and Portland sailing club for a sailing event and found this cottage perfect as only 10 min drive away and the house had everything we needed for the...
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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. The lounge / diner : smart TV, Blu...
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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
    (1)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Central Heating
    • Wi-Fi
    • Patio
    • Washer
    • Private Garden
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Central Heating
    • Patio
    • Parking
    Suitability
    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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    The Gift House, a historic Seaman's Chaplaincy1 / 22
    (3)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Cable/satellite TV
    • Private Garden
    • Central Heating
    • Ocean Views
    • Wi-Fi
    • Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 January 2018
    We stayed at the Gift House over Christmas / New Year and enjoyed staying, the accommodation was well equipped and generally well maintained.Our party consisted of two...
    Reviewed 28 September 2017
    We stayed at The Gift House for 4 nights last week and loved the house so much! It has everything you could need and is really nicely decorated with lots of quirky additions...
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    About this property
    The house is a late Georgian stone house located in the middle of island village, facing the sea. All 4 double bedrooms, the lounge and dining room are having panoramic sea view. The house is fully equipped self catering and has everything you need for an unforgettable holiday. The house has...
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    Isle of Portland, Dorset DT5 1AQ
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Cliff House1 / 8
    (4)Average
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Parking
    • Private Garden
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    Reviewed 11 November 2016
    The whole family and dog had a great time, only thing missing for me was wifi. the pool table was in good nick, bathroom had damp walls but I was renting it not buying it so...
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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
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    fishermans view1 / 11
    (21)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Ocean Views
    • DVD Player
    • Cable/satellite TV
    • Central Heating
    • Washer
    • Patio
    • Balcony
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 August 2016
    We spent a great week here lovely cottage great sea views, and the weather was amazing easy to get to Weymouth and its sandy beach.
    Reviewed 8 May 2016
    Needed a place to stay where I could relax and recharge my batteries. Fisherman's View was perfect! The cottage is cosy and has everything you could possibly need. When I saw...
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    About this property
    Cottage with sea views over beautiful famous Chesil Beach. South facing patio with sea view. Accommodates up to four . Weekly change over Saturday. Dogs welcome and most places are dog friendly. Nearest beach approximately 200 metres. Minutes from excellent bus service to Weymouth Portland Bill...
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    Isle of Portland, Dorset DT51NJ
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, 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
    • Cable/satellite TV
    • Central Heating
    • Washer
    • Patio
    • DVD Player
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 August 2015
    We loved our stay at Bayview. The back garden was definitely the best part of this property, the views were breathtaking! Lovely views from most windows too. House had lovely...
    Reviewed 29 May 2014
    My partner and I stayed here while visiting our nieces and needed a close place to stay. She was pregnant at the time and so proximity to our nieces and cleanliness were very...
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    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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    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Central Heating
    • Ocean Views
    • DVD Player
    • Wi-Fi
    Suitability
    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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    Casita del mar1 / 11
    (2)Very good
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Ocean Views
    • Grill
    • Balcony
    • Washer
    • DVD Player
    • Terrace
    • Central Heating
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 August 2017
    This cottage suited our family needs perfectly as we were able to bring our very well behaved dog with us! Susan was so helpful and ensured we were well informed about the...
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    About this property
    150 Year Old Portland Stone Fisherman's Cottage. Two leather sofas to seat six. Freeview T.V. Books. DVD's. C.D's. Games .Wifi. There is a wood burning stove for the winter months and barbeque and alfresco dining during the summer months. Vintage pine dining table and chairs to seat six. A...
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    Isle of Portland, Dorset DT5 1NJ
    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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    • Parking
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    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
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Parking
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    • Wi-Fi
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    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, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    • Wi-Fi
    • Private Garden
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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. Amenities: Sustainable eco-friendly central heating/hot water system, electric oven and hob, microwave, fridge/freezer, washing machine, tumble dryer, dishwasher, TV, Sonos wireless music player,...
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    Castletown, Isle of Portland DT5 1FG
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
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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
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    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    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
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    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
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