Villas with a pool Jamaica | Apartments to rent with swimming facilities | Holiday Lettings

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1,261 Holiday homes

Filters applied: Swimming pool

Travellers going to Jamaica are booking July dates now. Secure your holiday home today and have the perfect trip.

(6) Excellent 

33

Holiday townhouse rental

Westmoreland Parish / Negril

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £160 / night

£1400 - £2856 / week

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from £160 / night

(2) Excellent 

29

Villa rental in Jamaica with swimming pool, golf nearby

Saint James Parish / Montego Bay

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £684 / night

£4788 - £10800 / week

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from £684 / night

26

Holiday villa rental

Saint Ann Parish / Discovery Bay

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly

from £869 / night

£6080 - £14400 / week

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from £869 / night

(6) Very Good 

21

Villa rental in Negril Beach with shared pool

Negril / Negril Beach

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Swimming pool

from £52 / night

£320 - £616 / week

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from £52 / night

(2) Average 

23

Holiday studio in Ocho Rios

Saint Ann Parish / Ocho Rios

Studio 2 1 night min

  • Studio
  • Sleeps 2
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £46 / night

£299 / week

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from £46 / night

(3) Average 

18

Holiday condo with shared pool in Negril

Westmoreland Parish / Negril

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £80 / night

£400 - £680 / week

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from £80 / night

27

Holiday villa rental

Montego Bay / St James, Montego Bay

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £1029 / night

£7200 - £17640 / week

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from £1029 / night

(10) Very Good 

42

Runaway Bay holiday apartment rental

Saint Ann Parish / Runaway Bay

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool
“Perfect Vacation!” Awesome!! If you need a perfect vacation spot, Dreamy Haven is the place to stay. It was very clean and well-equipped with everything you could ever need. The shower worked perfectly, I did not want to end my showers! The place is q  …see more

from £56 / night

£392 / week

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from £56 / night

(3) Very Good 

11

Holiday villa in Runaway Bay

Saint Ann Parish / Runaway Bay

4 6 3 nights min

  • 4 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £150 / night

£1050 / week

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from £150 / night

(1) Excellent 

44

Ocho Rios holiday apartment let

Saint Ann Parish / Ocho Rios

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Swimming pool

from £70 / night

£390 - £630 / week

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from £70 / night

24

Holiday home rental

Saint Ann Parish / Discovery Bay

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £1052 / night

£7360 - £15920 / week

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from £1052 / night

(28) Very Good 

19

Holiday apartment with shared pool in Ocho Rios

Saint Ann Parish / Ocho Rios

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“lovely clean spacious apartment” Had a lovely time staying here and Jacquie the owner so friendly and accommodating as was her housekeeper Annette. Central to everything, shops and nightlife. Good place to rent as a base. Well equipped and comfy. W  …see more

from £80 / night

£560 / week

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from £80 / night

24

Villa letting in Jamaica with swimming pool, golf nearby

Saint James Parish / Montego Bay

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £1388 / night

£9711 - £12718 / week

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from £1388 / night

(1) Excellent 

24

Holiday villa rental

Saint James Parish / Montego Bay

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £748 / night

£5228 - £8028 / week

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from £748 / night

(1) Excellent 

21

Holiday villa in Ironshore

Montego Bay / Ironshore

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £583 / night

£4077 - £5332 / week

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from £583 / night

(2) Very Good 

24

St. Ann's Bay holiday home rental

Saint Ann Parish / St. Ann's Bay

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £100 / night

£700 / week

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from £100 / night

13

Holiday home with shared pool in St. Ann's Bay

Saint Ann Parish / St. Ann's Bay

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Nearest beach 13 km
  • Swimming pool
  • Child friendly

from £80 / night

£480 / week

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from £80 / night

(3) Average 

36

Ocho Rios holiday apartment rental

Saint Ann Parish / Ocho Rios

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Swimming pool

from £100 / night

£590 - £690 / week

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from £100 / night

(8) Excellent 

26

Holiday villa with shared pool in Ocho Rios

Saint Ann Parish / Ocho Rios

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool

from £93 / night

£651 / week

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from £93 / night

(11) Excellent 

40

Runaway Bay holiday bungalow rental

Saint Ann Parish / Runaway Bay

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 2 km
  • Swimming pool
  • Child friendly

from £64 / night

£443 / week

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from £64 / night

(2) Very Good 

35

Holiday apartment with shared pool in Ocho Rios

Saint Ann Parish / Ocho Rios

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Swimming pool

from £80 / night

£390 - £560 / week

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from £80 / night

(1) Very Good 

26

Ocho Rios holiday studio rental

Saint Ann Parish / Ocho Rios

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Nearest beach 1 km
  • Swimming pool
  • Car not necessary

from £40 / night

£250 - £315 / week

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from £40 / night

(1) Excellent 

62

Villa rental in St. Ann's Bay with shared pool

Saint Ann Parish / St. Ann's Bay

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £116 / night

£760 / week

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from £116 / night

(10) Very Good 

25

Holiday studio with shared pool in Ocho Rios

Saint Ann Parish / Ocho Rios

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool
“wish you was there with me” make shore you dont have a lot off running around to do and you have lots off refreshment and snacks to enjoy whilst you relax in the pool. Bring your laptop with you it saved me a lot off trouble contacting people around  …see more

from £37 / night

£240 - £300 / week

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from £37 / night

20

Holiday villa with swimming pool in Silver Sands

Trelawny Parish / Silver Sands

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Air conditioning

from £260 / night

£1820 / week

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from £260 / night

(3) Very Good 

38

Holiday apartment rental

Saint Ann Parish / Ocho Rios

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Swimming pool

from £70 / night

£390 - £560 / week

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from £70 / night

(1) Excellent 

29

Mammee Bay holiday apartment rental

Saint Ann Parish / Mammee Bay

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Swimming pool

from £80 / night

£500 / week

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from £80 / night

(4) Excellent 

12

Holiday bungalow with shared pool, golf nearby in Portmore

Saint Catherine Parish / Portmore

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 10 km
  • Swimming pool
“CANNOT WAIT TO GO BACK!!!” This house is so beautiful, a wonderful modern home. The community is nice and peaceful with excellent security and location is great for getting around as it is close to the toll road. The aircon was a well needed touch and  …see more

from £55 / night

£330 / week

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from £55 / night

(1) Very Good 

5

Holiday apartment with shared pool in Ocho Rios

Saint Ann Parish / Ocho Rios

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Swimming pool
  • Air conditioning

from £32 / night

£160 / week

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from £32 / night

(10) Very Good 

14

Ocho Rios holiday apartment rental

Saint Ann Parish / Ocho Rios

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Swimming pool
“Best apartment in Sandcastles” This is my 2nd time staying in this apartment, 2012 was the first and i had to come back and stay. Everything still works perfect, wifi, cooker, tv's, shower etc i was happy. As always it was easy to book the apartment  …see more

from £96 / night

£560 / week

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from £96 / night

(6) Very Good 

10

St James, Montego Bay holiday condo rental

Montego Bay / St James, Montego Bay

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 0.6 km
  • Swimming pool

from £112 / night

£784 / week

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from £112 / night

(18) Very Good 

25

Holiday villa with swimming pool in Ocho Rios

Saint Ann Parish / Ocho Rios

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Swimming pool
“the amazing almond tree villa” stayed 11 nights in February. it was an amazing experience! the villa was large, spacious clean and tidy. The pool area was lovely! the villa is located in a quiet street and is a short and cheap taxi ride to the town ce  …see more

from £80 / night

£500 - £896 / week

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from £80 / night

(1) Very Good 

20

Ocho Rios holiday apartment rental

Saint Ann Parish / Ocho Rios

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Nearest beach 1 km
  • Swimming pool
  • Ask owner if suitable for children

from £45 / night

£300 / week

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from £45 / night

(8) Excellent 

49

Ocho Rios holiday apartment rental

Saint Ann Parish / Ocho Rios

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Swimming pool
“Modern Gem in Ocho Rios” I stayed at Serenity in Sandcastles in August 2016 and i must say its one of the nicest apartments in the complex. It has everything you want with a lovely ocean view to the rear. Sandcastles is very peaceful and quiet, you ar  …see more

from £75 / night

£525 - £630 / week

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from £75 / night

(5) Excellent 

23

Holiday studio in Ocho Rios

Saint Ann Parish / Ocho Rios

Studio 2 2 nights min

  • Studio
  • Sleeps 2
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Swimming pool

from £80 / night

£480 / week

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from £80 / night

(6) Very Good 

27

Negril holiday villa rental

Westmoreland Parish / Negril

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £560 / night

£3920 / week

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from £560 / night

(1) Excellent 

10

Apartment rental in Tower Isle with shared pool

Saint Mary Parish / Tower Isle

3 6 3 nights min

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

from £80 / night

£560 - £1400 / week

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from £80 / night

(33) Very Good 

77

Holiday villa with swimming pool, golf nearby in Ocho Rios

Saint Ann Parish / Ocho Rios

3 10 1 night min

  • 3 bedrooms
  • Sleeps 10
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Swimming pool
“WISH WE COULD HAVE STAYED LONGER... LOVED THIS PLACE!” We arrived on January 31/17 and reluctantly departed on February 22/17. What an amazing place. The pool was beautiful, clean and refreshing and the beach was a 5 minute walk away with a lovely res  …see more

from £150 / night

£900 / week

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from £150 / night

(6) Excellent 

15

Apartment rental in Ocho Rios with shared pool

Saint Ann Parish / Ocho Rios

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool
“Would definitely come back to Turtle beach towers!!! Great stay” Stayed at TBT in April 2014. It was a fantastic stay and Janet the Housekeeper was one of the reasons why. Janet is warm , friendly and very welcoming. she made our stay very comfortab  …see more

from £80 / night

£560 / week

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from £80 / night

(3) Very Good 

24

Holiday condo with shared pool in Ocho Rios

Saint Ann Parish / Ocho Rios

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £60 / night

£390 - £488 / week

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from £60 / night

1