Villas with a pool Isle of Wight | Apartments to rent with swimming facilities | Holiday Lettings

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Isle of Wight

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34 Holiday homes

Filters applied: Swimming pool (34)

Travellers going to Isle of Wight are booking June dates now. Secure your holiday home today and have the perfect trip.

(28) Excellent 

26

Holiday caravan/mobile home with shared pool in Thorness Bay

Cowes / Thorness Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Swimming pool
“A charming experience” The Salisbury was a wonderful place to stay, it was well equipped with utensils, tea equipment and more. The living area was great with sky tv and a charming little electric fire place which gives the property great character.  …see more

from £65 / night

£375 - £865 / week

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from £65 / night

(17) Excellent 

23

Seaview holiday home rental

Isle of Wight / Seaview

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Swimming pool
“coastal seclusion” I stayed at Lebrel Lodge with friends for a winter weekend - I think there were about seven of us, mostly couples. It was extremely well appointed and immaculately clean. The weekend was a typical English winter one and so we someti  …see more

from £150 / night

£1045 - £1495 / week

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from £150 / night

(13) Excellent 

22

St Helens holiday lodge rental

Isle of Wight / St Helens

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Swimming pool
“Fantastic stay!!” We (4 adults and one baby) stayed here for a week in february and thoroughly enjoyed every minute. The accommodation was brilliant. Everything you could need was there and the place was spotless. A definite home from home. Will g  …see more

from £65 / night

£395 - £1295 / week

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from £65 / night

(12) Excellent 

24

Godshill holiday cottage rental

Godshill / Roud

4 6 7 nights min

  • 4 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 6 km
  • Swimming pool
“Mrs Jan walton” Really lovely cottage tucked away in the most peaceful of locations, set in a beautiful garden with gingerbread house over looking a pond perfect for afternoon tea. As the cottage is towards the centre of the island it is a good locati  …see more

from £79 / night

£550 - £995 / week

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from £79 / night

(37) Excellent 

23

Holiday log cabin with indoor pool in Ryde

Isle of Wight / Ryde

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Swimming pool
“Brilliant Holiday” We have just returned from our first family holiday on the Isle Of Wight with our two children aged 9 and 6. The Cabin is an amazing place to stay for a holiday, very clean and has everything you need. The swimming pool seemed bigge  …see more

from £93 / night

£650 - £1400 / week

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from £93 / night

(16) Excellent 

18

Holiday caravan/mobile home with shared pool in Bembridge

Isle of Wight / Bembridge

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Excellent” Stayed here for 4 nights, what a lovely clean and well equiped caravan. The bedrooms were lovely and comfortable and the 2 bathrooms were excellent. So big, and the lovely decked patio made this a really enjoyable stay. The personal touches  …see more

from £60 / night

£420 / week

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from £60 / night

(18) Excellent 

12

Holiday chalet with shared pool, golf nearby in Gurnard

Isle of Wight / Gurnard

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Decorated to a high standard and spotless” We booked this chalet for one week, we stay on the Island every year in self catering accommodation and this was by far the best we have stayed in. The chalet is decorated to a high standard, it was absolutel  …see more

from £80 / night

£350 - £850 / week

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from £80 / night

(15) Very Good 

22

Cottage rental in Whippingham with golf nearby

Isle of Wight / Whippingham

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Swimming pool
“Superb!” This is a real hidden gem, as are the the owners! From start to finish they made us feel most welcome and nothing was too much trouble for them. The cottage was absolutely delightful and the 30ft. swimming pool was immaculately clean and warm  …see more

from £114 / night

£795 - £1500 / week

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from £114 / night

(6) Very Good 

26

Holiday apartment letting

Isle of Wight / Sandown

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool
Comfortable, spotlessly clean, hot tub all towels including beach towels, and all linen, bedding and tea towels included free of charge.Central heating and hot water included.The sandy beach is a ten minute walk.  …see more

from £35 / night

£200 - £380 / week

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from £35 / night

(3) Excellent 

13

Caravan/mobile home rental in Bembridge with shared pool

Isle of Wight / Bembridge

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“A home from home” A lovely homely place to stay, comfortable clean everything you need for the perfect getaway, incredibly well presented in a lovely location, will be back again for sure.  …see more

from £45 / night

£315 / week

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from £45 / night

(4) Excellent 

16

St Helens holiday caravan/mobile home rental

Isle of Wight / St Helens

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
The Retreat is a privately owned three bedroom static caravan set in the St Helens Holiday Park which is child friendly and car free and features a heated outdoor pool, games room, launderette and play areas. The Retreat is double glazed with full gas central heating an  …see more

from £26 / night

£182 / week

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from £26 / night

(13) Very Good 

15

Chalet letting in Cowes with shared pool

Cowes / Gurnard Pines

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Lovely chalet, good facilities.” A lovely home from home. We stayed for 4 nights over the weekend of the Isle of White Festival. We didn't want to camp at the festival & this chalet was the perfect alternative on a budget. With 4 adults and a 5 month  …see more

from £80 / night

£300 - £600 / week

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from £80 / night

(17) Excellent 

12

Holiday caravan/mobile home rental

Isle of Wight / Bembridge

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
“Title says it all it is Luxury Caravan” Finished to very high standards, clean, cosy and excellent views. Everything you want was available. Very much enjoyed our short stay and son loved the place he was not very happy to leave. Would definitely reco  …see more

from £45 / night

£315 / week

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from £45 / night

(13) Excellent 

23

Sandown holiday apartment rental

Isle of Wight / Sandown

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool
“A first rate holiday with first rate accommodation” We were made to feel very welcome from the very first phone call. Everything pre-arrival was handled extremely well, and when we arrived there was somebody to meet and greet us, and there was somebod  …see more

from £35 / night

£200 - £380 / week

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from £35 / night

(8) Very Good 

22

Thorness Bay holiday caravan/mobile home accommodation

Cowes / Thorness Bay

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Perfect” Comfortable ,clean everything we needed was provided children loved the pool & park and a wander down to the beach ,clubhouse & resturant great ,children joined in all the fun & the food was excellent ,will definatly be back  …see more

from £40 / night

£310 - £595 / week

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from £40 / night

(2) Excellent 

8

Holiday caravan/mobile home in St Helens

Isle of Wight / St Helens

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Nearest beach 0.5 km
  • Swimming pool
  • Child friendly
Privately owned static caravan on St Helens Holiday Park. Comfortable accommodation sleeps 6/8 people. 3 bedrooms (1 double bedroom, 2 twin bedrooms plus double pull out bed in lounge. Fully equipped with central heating, double glazing, electric shower, Freeview TV. Th  …see more

from £59 / night

£413 / week

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from £59 / night

(5) Excellent 

24

Thorness Bay holiday caravan/mobile home rental

Cowes / Thorness Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Greenwood 46 is situated at Thorness Bay Holiday Park, on the Isle of Wight. We also have the caravan Greenwood 48 which is two doors up from Greenwood 46. We were asked a few times last year if we had two caravans close together so that a large family or a group of f  …see more

from £40 / night

£310 - £595 / week

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from £40 / night

(2) Very Good 

11

Cowes holiday caravan/mobile home rental

Isle of Wight / Cowes

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
“Fantastic holiday” We had a wonderful stay at thorness bay, well situated to get around the island with good facilities on site. We will be coming back again next year!  …see more

from £50 / night

£300 - £450 / week

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from £50 / night

25

Shanklin holiday home rental

Isle of Wight / Shanklin

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Copsegate Lodge is a beautiful home aimed at the 5 star market. This home has 4 bedrooms 31/2 bathrooms. Heated pool ( fee £150 per week heating), large private gardens, Hot Tub (£150 per week) , 3 living room areas. Large flat smart tvs throughout living ar  …see more

from £286 / night

£2000 - £3000 / week

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from £286 / night

(2) Very Good 

21

Holiday home with golf nearby in Ryde

Isle of Wight / Ryde

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Westridge House is a one of the most exclusive homes on the island comfortably sleeping up to 10 people. The house holds 5 bedrooms, consisting of 3 double bedrooms and 2 twin bedrooms. Stunning garden, lawns and swimming pool found on the outskirts of Ryde and Seaview.  …see more

from £600 / night

£1995 - £4695 / week

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from £600 / night

24

Holiday home in Woodside Beach

Isle of Wight / Woodside Beach

8 16 Min stay varies

  • 8 bedrooms
  • Sleeps 16
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 7 km
  • Swimming pool
Oak Cliff Place is a magnificent Victorian detached house, wonderfully private with stunning uninterrupted views over the Solent to Portsmouth. Light-filled, high-ceilinged and spacious, it is set in an elevated position within five acres of land including its o  …see more

from £325 / night

£2272 - £5061 / week

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from £325 / night

(9) Excellent 

23

Cowes holiday caravan/mobile home rental

Isle of Wight / Cowes

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.25 km
  • Swimming pool
Newly refurbished for 2016. Modern 3 bedroom caravan with 1 double bedroom, 2 twin bedrooms and pull out in lounge area. Full central heating and double glazing throughout. Shower room, and additional separate WC. Caravan facilities include fully equipped kitchen with i  …see more

from £70 / night

£365 - £750 / week

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from £70 / night

13

Caravan/mobile home rental in St Helens

Isle of Wight / St Helens

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
Privately owned static caravan on St Helens Holiday Park. Comfortable accommodation sleeps 6/8 people. 3 bedrooms (1 double bedroom, 2 twin bedrooms plus double pull out bed in lounge. Fully equipped with central heating, double glazing, electric shower, Freeview TV. Th  …see more

from £59 / night

£413 / week

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from £59 / night

(4) Very Good 

10

Shanklin holiday caravan/mobile home rental

Isle of Wight / Shanklin

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 1 km
  • Swimming pool
  • Child friendly
Superbly appointed mobile home, 3 bedrooms, one double, 2 twin rooms and a double bed sofa in the lounge, sleeps a max of 6. Has fully fitted open plan kitchen/ diner including microwave, gas cooker, fridge and separate freezer also a washing machine. A lovely l  …see more

from £70 / night

£290 - £760 / week

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from £70 / night

5

Shanklin holiday log cabin rental

Isle of Wight / Shanklin

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Private garden
Lyon Court is a beautiful country house in a lovely countryside setting, tastefully converted into individual apartments. It overlooks Shanklin Down, yet is close to bus & train routes, and only 10 minutes walk to the town centre or Shanklin Old Village. The beach  …see more

from £135 / night

£640 / week

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from £135 / night

(1) Excellent 

9

Holiday caravan/mobile home in St Helens

Isle of Wight / St Helens

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Swimming pool
  • Child friendly
“Amazing” The caravan and site were both great. It was a really good base to see the island from. The caravan was very clean and tidy and had everything that you could need. The swimming pool was heated, so it was a pleasure. The only thing that I woul  …see more

from £100 / night

£600 - £880 / week

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from £100 / night

(9) Average 

9

Holiday bungalow with shared pool in Gurnard

Isle of Wight / Gurnard

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Brillant” We visited gurnard pines for a weeks holiday,such a lovely week fantastic weather. Appartment/chalet was clean, had everything we needed especially for having children which was great! There is a huge bit of green for kids to play out on, be  …see more

from £60 / night

£420 / week

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from £60 / night

(1) Excellent 

19

Holiday home in Bembridge

Isle of Wight / Bembridge

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
'Willow House' is the perfect home from home! A substantial modern detached family residence with spacious accommodation, it's particularly well maintained throughout and provides the ideal holiday retreat for parties of all sizes, with a heated swimming  …see more

from £180 / night

£775 - £1845 / week

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from £180 / night

8

Shanklin holiday apartment rental

Isle of Wight / Shanklin

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Swimming pool
  • Child friendly
Orchardcroft, located in a leafy avenue on the fringe on Shanklin, is a one bedroom apartment its own entrance and is light, airy and comfortably furnished throughout. It comprises of a twin bedroom with a door to a small balcony; an open plan living/dining room & k  …see more

from £94 / night

£375 - £600 / week

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from £94 / night

(1) Excellent 

19

Isle of Wight / Yarmouth

2 4 Min stay varies

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

 …see more

from £47 / night

£329 - £1223 / week

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from £47 / night

20

Isle of Wight / Sandown

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Suitable for children age 5+

 …see more

from £105 / night

£734 - £2356 / week

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from £105 / night

23

Isle of Wight / Ryde

8 16 Min stay varies

  • 8 bedrooms
  • Sleeps 16
  • Min stay varies
  • Swimming pool
  • Child friendly

 …see more

from £570 / night

£2840 - £5061 / week

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from £570 / night

36

Isle of Wight / Shanklin

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly

 …see more

from £58 / night

£402 - £1432 / week

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from £58 / night

13

Isle of Wight / Shorwell

8 16 3 nights min

  • 8 bedrooms
  • Sleeps 16
  • 3 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Pet friendly

 …see more

from £481 / night

£3361 / week

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from £481 / night

Top Destination reviews

Luxury Cowes Penthouse
Excellent place to stay loved it

Well worth the money.... We have recommend this to our family and friends. if you have small children some of the fine ornements are only to be looked at.... The large outside area is lovly in the sunshine. … see more
"TOP DECK" - STUNNING SEASIDE APARTMENT
Another fantastic stay at 'Top Deck'

Top Deck has everything needed for a relaxing holiday/break in Ventnor -great location, stunning views, good facilities and a lovely welcome pack. Everything from washing-up liquid and kitchen roll to shower gel and toilet roll is also provided, mak … see more
Seaspray Chalet
Great Walks

WE had a great time. Chalet was clean and comfortably. Walking distance to sandown beaches and town.15 min by to car to Ryde. … see more
Stickey Wicket
Fantastic place

Would give it 110% so clean and tidy and peaceful. There's everything you need in the chalet. Beautiful walks and scenery Looking forward to returning there again. … see more
The Mill House
We couldn't have found a better property on the island

We were expecting a welcome pack based on the reviews we read before our arrival but it exceeded our expectations - the hot cross buns were great and the selection of Easter chocolate was a lovely surprise. We felt very much at home straight away. … see more
Luxurious Park Side Apartment - The Carisbrooke
A perfect stay in a great apartment in a great location

Lovely apartment, comfortably and beautifully fitted out in a great location: ideal for the Botanic Garden and coast walks, and equally easy to walk the other way through the park and along the coast into town for some good meals out. … see more