35 Best Vacation Rentals in Isle of Portland - Holiday Lettings - Cabins

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Isle of Portland

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39 Vacation rentals

(42) Excellent 

17

Vacation home rental

Dorset / Isle of Portland

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly
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. Sle  …see more

from $153 / night

$1143 - $1817 / week

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from $153 / night

(14) Very Good 

32

West Country Vacation cottage rental

Dorset / Isle of Portland

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 12 mi
  • Child friendly
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  …see more

from $108 / night

$445 - $1264 / week

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from $108 / night

(21) Very Good 

8

Vacation cottage in West Country

Dorset / Isle of Portland

3 4 7 nights min

  • 3 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Suitable for children age 5+
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 servic  …see more

from $51 / night

$356 - $737 / week

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from $51 / night

(13) Very Good 

20

Vacation cottage in West Country

Dorset / Isle of Portland

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Child friendly
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  …see more

from $96 / night

$413 - $1137 / week

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from $96 / night

(34) Excellent 

19

Home rental in West Country

Dorset / Isle of Portland

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
A contemporary, spacious house with private off-road parking. Situated in a central position on the lower part of the island, makes it ideal for guests visiting the Weymouth and Portland National Sailing Academy or the Jurrassic Coastline. Ideal for small groups, coup  …see more

from $127 / night

$966 - $1563 / week

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from $127 / night

(27) Very Good 

30

Vacation cottage rental

Dorset / Isle of Portland

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Child friendly
A beautiful restored Victorian terraced cottage, on a quiet street in the village of Fortuneswell on the Isle of Portland, only 5 minutes walk from the famous Chesil Beach and part of Dorset's glorious Jurassic Coast. 5 min drive from National Sailing Academy. This fo  …see more

from $77 / night

$375 - $966 / week

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from $77 / night

(24) Very Good 

31

Vacation studio in West Country

Dorset / Isle of Portland

Studio 2 3 nights min

  • Studio
  • Sleeps 2
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
A VERY MODERN HOLIDAY LET STUDIO APARTMENT LOCATED IN A QUIET POSITION ON THE ISLE OF PORTLAND NEAR WEYMOUTH IN THE HEART OF DORSET, ON THE COAST OF SOUTH WEST ENGLAND. SUITABLE FOR SINGLE OR DOUBLE OCCUPANCY. FACILITIES INCLUDE FLAT SCREEN TV, DVD PLAYER, MICROWAVE,  …see more

from $60 / night

$375 - $464 / week

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from $60 / night

(13) Very Good 

9

West Country Vacation home rental

Dorset / Isle of Portland

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
Pebbles view is a Victorian Portland stone built mid terrace cottage in the village of Fortuneswell Portland offering stunning panoramic sea views of the Jurassic coasts Chesil beach from all floorsThe newly refurbished cottage arranged over three floors comprises  …see more

from $89 / night

$661 - $826 / week

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from $89 / night

(7) Very Good 

6

Cottage rental in West Country

Dorset / Isle of Portland

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Ask about children
  • Car not necessary
  • Air conditioning
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  …see more

from $63 / night

$436 - $596 / week

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from $63 / night

(39) Excellent 

24

Vacation studio in West Country

Dorset / Isle of Portland

Studio 2 3 nights min

  • Studio
  • Sleeps 2
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Car not necessary
4 star studio right at the start of the new 'England Coast Path' at Church Ope Cove Portland Dorset. Spectacular view of the sea through ancient Rufus castle arch. Romantic hideaway for 2, a cosy retreat for walkers, work or leisure. Church Ope Studio is open all ye  …see more

from $68 / night

$413 - $502 / week

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from $68 / night

(11) Very Good 

20

Vacation cottage rental

Dorset / Isle of Portland

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
Seagull Cottage is a lovely holiday house ideal for sailing, beach, and outdoor activity holidays in Portland. It is located just one mile from the Weymouth and Portland National Sailing Academy (WPNSA), the 2012 Olympic Sailing venue. Chesil beach is just a few minut  …see more

from $82 / night

$559 - $883 / week

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from $82 / night

(2) Very Good 

18

West Country Vacation home rental

Dorset / Isle of Portland

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Suitable for children age 5+
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 com  …see more

from $127 / night

$889 - $1715 / week

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from $127 / night

(1) Excellent 

17

Vacation studio rental

Dorset / Isle of Portland

Studio 3 2 nights min

  • Studio
  • Sleeps 3
  • 2 nights min
  • Suitable for children age 5+
Self contained apartment base on Southwell business park , isle of Portland. A short stroll from famous Portland bill& Jurassic coastline. Come &see for yourself Towels,Linens ,Toiletries provided equipped with hair dryer,iron+board ,fridge,toaster,kettle,Microwave ov  …see more

from $101 / night

$635 / week

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from $101 / night

(9) Very Good 

8

Vacation bungalow in West Country

Dorset / Isle of Portland

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
A comfortable terraced bungalow with lounge/diner, kitchen and patio area in grounds near to Pennsylvania Castle so ideal for anyone attending functions there. Portland is a nature lovers paradise particularly of interest to birdwatching enthusiasts also to sailors as t  …see more

from $96 / night

$635 / week

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from $96 / night

(1) Very Good 

7

Vacation home in West Country

Dorset / Isle of Portland

3 5 2 nights min

  • 3 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Ask about pets
  • Private garden
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.  …see more

from $191 / night

$1334 / week

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from $191 / night

(16) Very Good 

14

Vacation cottage accommodation

Dorset / Isle of Portland

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Private garden
A charming three bedroomed character property, situated in a quiet location on the southern part of the Isle of Portland with panoramic sea views to the rear. Beautiful coastal paths and scenery close by, ideal for a chilled out relaxing break. The house has a televisi  …see more

from $115 / night

$572 - $883 / week

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from $115 / night

(6) Very Good 

22

Vacation studio in West Country

Dorset / Isle of Portland

Studio 2 2 nights min

  • Studio
  • Sleeps 2
  • 2 nights min
  • Nearest beach 3 mi
  • Suitable for children age 5+
Self contained apartment base on Southwell business park , isle of Portland. A short stroll from famous Portland bill& Jurassic coastline. Come &see for yourself Towels,Linens ,Toiletries provided equipped with hair dryer,iron+board ,fridge,toaster,kettle,Microwave ov  …see more

from $58 / night

$381 / week

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from $58 / night

(1)  

8

Vacation apartment in West Country

Dorset / Isle of Portland

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Child friendly
  • Ask about pets
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 fa  …see more

from $63 / night

$381 / week

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from $63 / night

(1) Good 

11

West Country Vacation studio accommodation

Dorset / Isle of Portland

Studio 2 2 nights min

  • Studio
  • Sleeps 2
  • 2 nights min
  • Nearest beach 3 mi
  • Suitable for children age 5+
If you are looking for the perfect place for a romantic weekend break for two, a longer get-away-from-it-all holiday or fun time with a group of friends then you've found it!Every apartment combines quality overnight comfort and en-suite facilities with mod  …see more

from $75 / night

$507 / week

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from $75 / night

11

West Country Vacation home accommodation

Dorset / Isle of Portland

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 5 mi
  • Child friendly
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  …see more

from $153 / night

$591 - $953 / week

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from $153 / night

(2) Very Good 

32

Dorset / Isle of Portland

Studio 2 3 nights min

  • Studio
  • Sleeps 2
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 11 mi
  • Child friendly

 …see more

from $58 / night

$401 / week

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from $58 / night

19

Vacation home rental

Dorset / Isle of Portland

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+
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 twin room and a family bathroom. Also in the cottage is a fitted kitchen with a dining area an  …see more

from $95 / night

$660 - $1403 / week

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from $95 / night

(1) Very Good 

34

Dorset / Isle of Portland

Studio 2 2 nights min

  • Studio
  • Sleeps 2
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 11 mi
  • Suitable for children age 5+

 …see more

from $101 / night

$699 / week

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from $101 / night

21

Vacation home accommodation

Dorset / Isle of Portland

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+
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 and a family bathroom. Also in the cottage are a fitted kitchen and a sitting room with  …see more

from $98 / night

$681 - $1424 / week

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from $98 / night

31

Vacation cottage in West Country

Dorset / Isle of Portland

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Private garden
Delimara is a charming, detached cottage set in a quiet cul-de-sac in Easton on the Isle of Portland near Weymouth. With one ground floor king-size double, plus one twin and one single set in the eaves, this cottage can sleep five people. Delimara also offers a kitchen,  …see more

from $61 / night

$422 - $961 / week

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from $61 / night

17

Dorset / Isle of Portland

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Suitable for children age 5+

 …see more

from $115 / night

$801 - $2398 / week

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from $115 / night

20

Dorset / Isle of Portland

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Suitable for children age 5+

 …see more

from $115 / night

$801 - $2398 / week

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from $115 / night

(1) Good 

6

Dorset / Isle of Portland

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Child friendly

 …see more

from $63 / night

$407 / week

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from $63 / night

(2) Excellent 

43

Dorset / Isle of Portland

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Suitable for children age 5+

 …see more

from $124 / night

$865 - $2778 / week

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from $124 / night

18

Dorset / Isle of Portland

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly

 …see more

from $85 / night

$590 - $1470 / week

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from $85 / night

(1) Very Good 

24

Dorset / Isle of Portland

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Suitable for children age 5+

 …see more

from $68 / night

$472 - $1401 / week

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from $68 / night

52

Dorset / Isle of Portland

9 20 3 nights min

  • 9 bedrooms
  • Sleeps 20
  • 3 nights min
  • Swimming pool
  • Suitable for children age 5+

 …see more

from $2178 / night

$15240 - $20320 / week

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from $2178 / night

24

Dorset / Isle of Portland

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Suitable for children age 5+

 …see more

from $115 / night

$801 - $2208 / week

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from $115 / night

14

Dorset / Isle of Portland

Studio 2 2 nights min

  • Studio
  • Sleeps 2
  • 2 nights min
  • Nearest beach 11 mi
  • Ask about children

 …see more

from $75 / night

$445 / week

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from $75 / night

39

Dorset / Isle of Portland

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly

 …see more

from $784 / night

$5487 / week

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from $784 / night

44

Dorset / Isle of Portland

6 12 3 nights min

  • 6 bedrooms
  • Sleeps 12
  • 3 nights min
  • Swimming pool
  • Child friendly

 …see more

from $1568 / night

$10973 / week

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from $1568 / night

41

Dorset / Isle of Portland

5 10 3 nights min

  • 5 bedrooms
  • Sleeps 10
  • 3 nights min
  • Swimming pool
  • Child friendly

 …see more

from $1307 / night

$9144 / week

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from $1307 / night

39

Dorset / Isle of Portland

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly

 …see more

from $1046 / night

$7316 / week

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from $1046 / night

43

Dorset / Isle of Portland

7 14 3 nights min

  • 7 bedrooms
  • Sleeps 14
  • 3 nights min
  • Swimming pool
  • Child friendly

 …see more

from $1742 / night

$12192 - $12802 / week

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from $1742 / night