We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Pet Friendly Holiday Rentals in Isle of Portland

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Location
    Any Distance
    from
    Price
    per night
    AU$143 Average
    |||
    |||
    AU$0AU$1,000+
    Suitability
    More filters
    Travellers to Isle of Portland are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    20 Matching Rentals in Isle of PortlandView all 55 rentals
    Sort by:
    Default
    Quarries Reach, rural & sea views Portland, Dorset1 / 17
    (58)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    other travellers have booked this property
    Certificate of Excellence
    Check in Check out
    Show Prices
    Payment Protection
    Rosa Cottage1 / 30
    (34)Very good
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    other travellers have booked this property
    Certificate of Excellence
    Check in Check out
    Show Prices
    Payment Protection
    Schooner Cottage - At Christmas1 / 42
    (9)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Portland Hideaway1 / 8
    (11)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other travellers have booked this property
    Certificate of Excellence
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Washer
    • Parking
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 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...
    See all reviews
    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....
    View all property information
    Location Information
    Isle of Portland, Dorset DT5 2DS
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    The Gift House, a historic Seaman's Chaplaincy1 / 22
    (3)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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...
    See all reviews
    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...
    View all property information
    Location Information
    Isle of Portland, Dorset DT5 1AQ
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    5 Cove Park1 / 14
    (4)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • DVD Player
    • Central Heating
    • Ocean Views
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 December 2017
    Just leaving Portland after having a smashing Christmas and break at this delightful bungalow. It was just perfect for myself and my mum. So warm and cosy and very well equipped...
    Reviewed 30 June 2017
    Had a great stay in this lovely bungalow. Lots of home comforts and the kitchen was well equipped.Home from home. Loved the view from the veranda and the dogs enjoyed the garden.
    See all reviews
    About this property
    PET Friendly! A two-bedroom bungalow set in a unique coastal park offering total relaxation and fantastic sea views. The site is ideal for a place to rest your head after a day on the water or if you are looking for a relaxing quiet break by the sea. This holiday home features all the essentials...
    View all property information
    Location Information
    Isle of Portland, Dorset DT5 1HU
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    Artist Cottage - Charming coastal cottage on Portland :-)1 / 12
    (4)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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...
    See all reviews
    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...
    View all property information
    Location Information
    Isle of Portland, Dorset DT5 1NQ
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    Cliff Walk Cottage1 / 22
    (3)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other travellers have booked this property
    Certificate of Excellence
    Check in Check out
    Show Prices
    Payment Protection
    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...
    See all reviews
    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...
    View all property information
    Location Information
    Isle of Portland, Dorset DT5 2LZ
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    Ted's House1 / 11
    (1)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    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...
    See all reviews
    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...
    View all property information
    Location Information
    Isle of Portland, Dorset DT5 1AG
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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...
    View all property information
    Location Information
    Isle of Portland, Dorset DT5 1NJ
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    Save time - get the best Isle of Portland rentals sent straight to your email!
    Get the List
    Cliff House1 / 8
    (4)Average
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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...
    See all reviews
    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...
    View all property information
    Location Information
    Isle of Portland, Dorset DT5 1AW
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
    Make Enquiry
    fishermans view1 / 11
    (21)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Ocean Views
    • DVD Player
    • Cable/satellite TV
    • Central Heating
    • Washer
    • Patio
    • Balcony
    • Wi-Fi
    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...
    See all reviews
    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...
    View all property information
    Location Information
    Isle of Portland, Dorset DT51NJ
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    Bayview1 / 22
    (5)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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...
    See all reviews
    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...
    View all property information
    Location Information
    Isle of Portland, Dorset DT5 1HE
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Make Enquiry
    Shearwater located in Portland, Dorset1 / 36
    (4)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    The house was lovely with everything you needed down to cling film, take away menus, local interests and a beach hut. The area was great with a Tesco’s, small coop and great...
    Reviewed 5 January 2014
    We rented this house for a family holiday in October 2013, and couldn't of been happier with the accommodation.The house was clean, well laid out and had everything you could...
    See all reviews
    About this property
    Shearwater is a newly built three bedroom house, set over three floors, designed by an award-winning team and located on the east coast of Portland. It offers superb views of Pennsylvania Castle and out to the sea. The property is a highly energy efficient ‘Passivhaus' eco-home, operating on a low...
    View all property information
    Location Information
    Isle of Portland, Dorset DT5 1FJ
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Casita del mar1 / 11
    (2)Very good
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Ocean Views
    • Grill
    • Balcony
    • Washer
    • DVD Player
    • Terrace
    • Central Heating
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 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...
    See all reviews
    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...
    View all property information
    Location Information
    Isle of Portland, Dorset DT5 1NJ
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You'll be sure to enjoy your time whilst staying at Cornerstone. This well-appointed home from home, complete with period features, offers ample accommodation for up to six guests, looking to enjoy a holiday in coastal Dorset. The modern kitchen is fully-equipped with a breakfast bar, which makes...
    View all property information
    Location Information
    Castletown, Isle of Portland DT5 1LD
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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...
    View all property information
    Location Information
    Isle of Portland, Dorset DT5 1LX
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
    Make Enquiry
    Chesil View House located in Portland, Dorset1 / 15
    (2)Very good
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 August 2017
    Just back from a lovely week here. The house is beautiful and the views from the top floor are amazing. Yes it's on a steep hill but so are most houses on Portland! Parking...
    Reviewed 18 January 2017
    The little house on St Martins Road is very sweet. It is on a tremendous hill and parking can be a problem but once inside it is very well appointed. The living/dining room is a...
    See all reviews
    About this property
    Chesil View House offers stylish accommodation that was originally a fisherman's cottage in the beautiful village of Fortuneswell, nestled amongst the hills of Portland. Internally the property is furnished to a high standard with spectacular views from the top of the house of Chesil Beach, Lyme...
    View all property information
    Location Information
    Isle of Portland, Dorset DT5 1JY
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    Sea Pinks Cottage located in Portland, Dorset1 / 13
    (3)Average
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 April 2017
    This booking was made on behalf of my daughter and her young family, and friends of hers. The owner was very helpful when I was making the arrangements. Overall my family were...
    Reviewed 7 November 2016
    Upon arrival we weren't overly surprised at the lack of parking in Mallams. It is very narrow. Yes, you can stop in the vicinity to unload, but then have to drive down to a free...
    See all reviews
    About this property
    Sea Pinks Cottage was built around 1860 and is a fine example of a traditional fisherman's cottage built with Portland stone. The property has been refurbished to a high standard with the bedrooms offering views either towards Portland, Lyme Bay or Chesil Beach. Externally, the property boasts a...
    View all property information
    Location Information
    Isle of Portland, Dorset DT5 1NJ
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    Elizabethan House located in Portland, Dorset1 / 24
    (4)Average
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 July 2018
    Lovely old house, walls very thick so nice and cool in the hot weather. Typical stairs for an old property loved it. The free car park opposite does get busy as is the road that...
    Reviewed 3 October 2017
    The house was perfect for our visit, everything we needed. Close to the beach and also local pub. The dogs enjoyed it too!
    See all reviews
    About this property
    Elizabethan House is 17th Century Grade II listed property located in Portland, situated just 500 yards from Chesil Beach and within a short walk from the National Sailing Academy. Internally, the property has been refurbished whilst retaining a character style with exposed stone walls, stripped...
    View all property information
    Location Information
    Isle of Portland, Dorset DT5 1AP
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
    Make Enquiry
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    List your property
    Owner log in