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House holiday rentals in Isle of Portland

Find and book unique houses on Airbnb

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Popular amenities for Isle of Portland house rentals

House rentals with a pool

Superhost
Home in Osmington
4.85 out of 5 average rating, 89 reviews

Large coastal cottage with spa and private pool

IanRating, 5 starstoday
Fabulous property great pool and hot tub would highly recommend to any families for holidays
Superhost
Home in Preston Road
4.84 out of 5 average rating, 113 reviews

Spacious Caravan near sea Weymouth Bay Haven

SuzanneRating, 5 stars5 months ago
This is our second time staying in this lovely caravan. It’s always pristine and lovely. I always felt like a home away from home there. The bedrooms are a good size and the extra full bathroom is a definite plus! I’d highly recommend staying here.
Guest favourite
Home in Crossways
4.95 out of 5 average rating, 40 reviews

Stunning Home with Roof Terrace at Silverlake

BarakRating, 5 stars3 weeks ago
Super comfortable and beautifully designed house, stocked with almost anything you can want The estate is beautiful and has tons to do So glad I found this place!
Superhost
Home in Charmouth
4.91 out of 5 average rating, 53 reviews

Large Airy Barn conversion, 5 bedrooms, Jurassic

SavannahRating, 5 stars2 months ago
My friends and I had such a lovely stay here over Easter! The perfect place for a city break. The house itself is airy and spacious (we were 11 and had space to ourselves!) with a big entertaining kitchen and an outdoor dining spot that catches the sunshine. Gorgeous surrounds for classic English countryside rolling hill views, and really close to towns and pubs and coastal walks. Would definitely return!
Superhost
Home in Dorset
4.88 out of 5 average rating, 8 reviews

East Creek + beach side + pool, dog Ringstead Bay

ZaraRating, 5 stars9 months ago
location was absolutely perfect for a relax and a decent walk everyday, we paddle boarded up the coast both ways and the scenery was stunning and finished most days with a swim in the pool. if you're after a close too everything place too stay this isn't the place for you but if you're looking for a break away from the world then this will tick all your boxes 🤗
Guest favourite
Home in Blandford Forum
4.98 out of 5 average rating, 55 reviews

Flint Cottage for two with indoor pool & sauna

Noelle And SamRating, 5 stars3 months ago
We had a blissful few days at Flint cottage. Wonderful kitchen to cook in, and multiple fabulous farm shops nearby. We ordered a heat and eat pie and a DIY breakfast pack for our first night, which made the start of the holiday so much more chilled out. The outdoor bath was also really special. We were so comfortable throughout we just relaxed completely. Can’t wait to come back!
Guest favourite
Home in Crewkerne
4.94 out of 5 average rating, 53 reviews

Perfect Country Home. Plenty of outdoor terraces

JadeRating, 5 stars2 weeks ago
This was the best air b and b stay I’ve had! It was so peaceful and quiet. I booked it for my mums birthday and she was blown away by the property. If you are looking to get away and relax this is the place! Everything was such high quality and felt very homely. Thank you ☺️
Top Guest favourite
Home in Buckland Newton
5 out of 5 average rating, 8 reviews

Gamekeeper's Cottage

ElizabethRating, 5 stars3 months ago
We booked Nigel and Adele's cottage very last minute and they accommodated us with no problems. The cottage is child friendly- stair gate, travel cot, high chair- everything was ready and in place when we arrived for which we were very grateful. Very impressed with the details e.g. the provision of breakfast items, homemade cake, toy basket, 2 types of pillow etc. I would highly recommend this stay if you have a toddler as the gardens are extensive and the surrounding area is great for walks and exploring!

Weekly house rentals

Guest favourite
Home in Dorset
4.83 out of 5 average rating, 29 reviews

Delimar

ChloeRating, 5 stars3 weeks ago
We loved staying here. There was a large supermarket as well as local shops and cafes within walking distance. It was easy to get around Portland and further afield from here. It had all the amenities we needed and it was clean and very welcoming. I would definitely recommend it for a stay.
Top Guest favourite
Home in Dorset
5 out of 5 average rating, 25 reviews

Wayfarers Cottage Fortuneswell Portland, UK

CarolRating, 5 stars2 days ago
What a beautiful homely cottage. Excellent layout, lovely rear garden where you get the sun most of the day. Everything you can think of you need, is there. Perfect for great walks, the SW coastal path at the bottom of the road. We had sun all week, so no need for the log burner but can imagine a winter afternoon there being all cosy. Thanks again Valerie, we all had a great time and sad to be back home.
Top Guest favourite
Home in Dorset
4.95 out of 5 average rating, 87 reviews

Charming Portland house with sea and sunset views

BenRating, 5 stars2 weeks ago
Really lovely place in the heart of Portland
Guest favourite
Home in Dorset
4.98 out of 5 average rating, 60 reviews

Stone's Throw, Portland, on the Jurassic Coast

PeterRating, 5 stars1 week ago
We've just had a wonderful stay at Stone's Throw. The property is very comfortable, clean and has everything you need for your stay with easy access to the locality and to the wider area of Dorset. The dedicated car parking space is very useful too.
Top Guest favourite
Home in Dorset
4.96 out of 5 average rating, 72 reviews

2-bed house near beach, WPNSA and marina.

TimothyRating, 5 stars3 weeks ago
Great location with lots to see and do on our first visit to Portland. Nice and modern accommodation and very useful to have an allocated parking space. Within easy walking distance of the harbour and plenty of restaurants/ pubs. Supermarkets and Weymouth beach just short drives away.
Guest favourite
Home in Dorset
4.92 out of 5 average rating, 25 reviews

Cove Cottage: Grade II listed with sea views

MartinRating, 5 stars1 week ago
Lovely location with a nice view from the top of the garden.
Guest favourite
Home in Weymouth
4.98 out of 5 average rating, 51 reviews

Wolf Cottage - Stunning Harbourside Cottage

SamanthaRating, 5 stars3 months ago
I was actually disappointed when I first arrived. I had booked a "stunning harbourside cottage" only to discover this cottage is not by the harbour. However, the stunning part is accurate. It is a really lovely property that has been lovingly made into a home-from-home. Once you get over not being by the harbour, it is in a good location that is accessible to all Weymouth has to offer. We had a fabulous stay and would absolutely go back. Tim is a delightful and dedicated host.
Guest favourite
Home in Dorset
4.95 out of 5 average rating, 20 reviews

Seaside Cottage

NoelleRating, 5 stars3 weeks ago
Great place, all in very good condition. Walking distance to the seaside. Small grocery shop (co-op) at block away. Easy to park and a lots to see around.

Private house rentals

Top Guest favourite
Home in Dorset
4.95 out of 5 average rating, 43 reviews

Beachside Cottage with Panoramic views of the sea

JohnRating, 5 stars1 week ago
We stayed here in early June and loved the place. We were slightly perturbed that the sea view overlooked the Oasis Shop/Cafe small car park but in fact this was not noisy nor did it spoil the view. It is literally a 20 yard walk to the steep pebbled beach (some sand at low tide) and half an hour's walk to Weymouth pier along the promenade. There is also a frequent bus service. The accommodation is immaculate, having the living area upstairs. Everything we needed was provided - even an electric toothbrush charger in the bathroom. We spent many an hour on the balcony with drinks watching the swimmers, surfers, sailors and spotting the commercial/navy ships which often anchored in the bay. We had many a happy days out in the Weymouth area and were able to leave the car parked outside all the ten days as we used the bus services. We hope to return in the near future.
Guest favourite
Home in Dorset
5 out of 5 average rating, 10 reviews

Islands Wrest. 2 Bedrooms. 2-3 Beds. Pet friendly.

AudraRating, 5 stars9 months ago
Mark has a lovely place and we settled in nicely. It was easy to communicate with mark and we enjoyed his place. Also ideal if you are two couples for example as each room was self contained. There is also use of a garden. Thank you
Guest favourite
Home in Easton
4.94 out of 5 average rating, 18 reviews

Hideaway House, Easton, Portland

YvonneRating, 5 stars2 weeks ago
Lovely updated house with all amenities. Centrally located with lots of takeout restaurants within easy walking distance.
Top Guest favourite
Home in Winfrith Newburgh
4.97 out of 5 average rating, 77 reviews

Jurassic coast (2 bedroom, 2 bathroom cottage

CarolineRating, 5 stars1 week ago
Beautiful cottage and garden close to the beach Penny and David were great hosts
Top Guest favourite
Home in Winfrith Newburgh
5 out of 5 average rating, 63 reviews

Cobweb Cottage, Winfrith Newburgh

ApichatRating, 5 stars1 week ago
It was great experience staying at The Cobweb cottage as it is very beautiful, nice and clean. We enjoyed our time there. I also would like say special thanks to Celia who was very proactive and responsive to our request.
Superhost
Home in Dorset
4.86 out of 5 average rating, 7 reviews

Fabulous Coastal Family Cottage - Portland, Dorset

SamRating, 5 stars3 weeks ago
Lovely house with more then enough room for large groups, also the shower pressure was excellent!
Top Guest favourite
Home in Dorset
5 out of 5 average rating, 31 reviews

Sea Pilot's Cottage | On the harbour | Sleeps 6

KarinaRating, 5 stars6 days ago
Beautiful property in an excellent location. Would highly recommend this airbnb to anyone visiting weymouth! The house is immaculate, probably the cleanest air bnbs I've ever stayed in! The view from the living room is stunning, looks directly out into the harbour, you can just sit there and watch the world go by. It was really easy to get around, all the bars and restaurants in walking distance. Parking is also 5 min walk down the road. We came with a 9 month old and the host was able to accomodate us with a cot and highchair which was really helpful. Generally, the house is very well equipped and has beautiful kitchenware if you plan on having an evening in. Overall a great stay and a lovely host who was super responsive.
Top Guest favourite
Home in Dorset
4.99 out of 5 average rating, 81 reviews

Home from home

RichardRating, 5 starstoday
A lovely private property in a quiet street. Spotlessly clean with a modern kitchen and bathroom. The town and seafront are a 30 minute walk but it's a very easy route and it was nice being away from main town. Julia and Paul were very friendly when I met them and I had a great stay

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