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

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11,289 Holiday homes

Filters applied: Swimming pool

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

(11) Excellent 

14

Apartment rental in Antigua and Barbuda with shared pool, golf nearby

Antigua / Friars Hill

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary
“Great place to stay” Nice and easy transfer by taxi to the accommodation complex. Friendly reception staff on arrival. Very attractive and clean appartment, with a lovely balcony with sun loungers, table and chairs. Just a few hundred yards from a lo  …see more

from £100 / night

£700 - £1100 / week

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from £100 / night

(2) Excellent 

18

Condo letting in Caribbean with shared pool, golf nearby

Tobago / Lowlands

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 1 km
  • Swimming pool
  • Child friendly

from £144 / night

£1008 / week

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from £144 / night

(3) Excellent 

16

Maria Trinidad Sanchez Province / Cabrera

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Swimming pool
  • Child friendly

from £52 / night

£302 / week

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from £52 / night

(17) Excellent 

16

Arrondissement of Le Marin / Sainte-Luce

Studio 2 7 nights min

  • Studio
  • Sleeps 2
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Air conditioning

from £52 / night

£302 - £345 / week

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from £52 / night

(20) Excellent 

20

Home rental in Caribbean with swimming pool

Saint Peter Parish / Maynards

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool
“Lovely Villa, great location” Our party of family and friends had a lovely time at Palm Villa. The facilities are excellent, it was plenty big enough for all ten of us and Beverley was helpful and went out of her way to make our stay comfortable. We  …see more

from £125 / night

£875 - £2555 / week

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from £125 / night

(9) Excellent 

19

Caribbean holiday apartment rental

Saint Peter Parish / Gibbes

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Swimming pool

from £151 / night

£800 - £960 / week

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from £151 / night

(2) Very Good 

15

Holiday apartment in Caribbean

Saint James Parish / Weston

3 6 7 nights min

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

from £100 / night

£700 - £1037 / week

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from £100 / night

(7) Excellent 

24

Caribbean holiday villa rental

Antigua / Dickenson Bay

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Swimming pool
“Perfect for a very chilled out holiday” Stunning views, amazing sunset, all amenities within 5 mins car ride. Dickinson Bay very close. Villa furnished to a very high spec and well maintained including pool. A very relaxing and chilled out stay. Would  …see more

from £286 / night

£2000 - £4000 / week

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from £286 / night

31

Holiday apartment in Caribbean

Christ Church Parish / St. Lawrence Gap

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

from £220 / night

£1540 / week

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from £220 / night

17

Grande-Terre Island / Saint Francois

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool

from £51 / night

£357 - £773 / week

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from £51 / night

(4) Excellent 

29

Grande-Terre Island / Sainte-Anne

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Air conditioning

from £65 / night

£432 / week

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from £65 / night

(3) Very Good 

16

Arrondissement of Le Marin / Riviere-Salee

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £35 / night

£242 / week

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from £35 / night

(17) Very Good 

23

Holiday townhouse with shared pool in Caribbean

Saint James Parish / Fitts

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.25 km
  • Swimming pool
“Lovely accommodation in a quiet, well maintained complex close to the beach.” Fitts is a small quiet village with a lovely beach between Bridgetown and Holetown both of which are easily accessed by frequent buses, There is a well stocked supermarket,  …see more

from £70 / night

£490 - £590 / week

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from £70 / night

(12) Very Good 

23

Holiday villa with swimming pool, golf nearby in St. Lucia

Cap Estate / Rodney Bay Heights

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Swimming pool

from £115 / night

£790 - £1620 / week

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from £115 / night

37

Holiday home in Caribbean

Warrens / Arthur Seat

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Swimming pool

from £80 / night

£450 - £490 / week

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from £80 / night

(1) Excellent 

6

St. Barts / Anse des Cayes

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Nearest beach 2 km
  • Swimming pool
  • Ask owner if suitable for children

from £87 / night

£604 / week

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from £87 / night

(11) Excellent 

18

Holiday villa with swimming pool in Caribbean

Bottom Bay / Apple Hall

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Swimming pool
“Will Definitely Be Returning” This was my first time visiting Barbados and staying at Cou Cou~ I will definitely be returning!!!!. Cou Cou is a well maintained and tastefully decorated villa with even the smallest of amenities thought of which assist  …see more

from £120 / night

£840 / week

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from £120 / night

(3) Average 

42

Samana Province / Las Terrenas

1 4 90 nights min

  • 1 bedroom
  • Sleeps 4
  • 90 nights min
  • Nearest beach 0.6 km
  • Swimming pool
  • Child friendly

from £23 / night

£152 - £208 / week

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from £23 / night

(4) Very Good 

8

Arrondissement of Le Marin / Trois-Ilets

1 2 Min stay varies

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

from £35 / night

£233 - £259 / week

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from £35 / night

25

Basse-Terre Island / Deshaies

2 6 7 nights min

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

from £111 / night

£776 - £1035 / week

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from £111 / night

(8) Excellent 

19

Holiday apartment with shared pool in Barbados

Saint Peter Parish / Gibbes

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Perfect holiday, perfect place - relaxation, sun and calm” We spent 2 weeks at Ashanti, staying in one of the larger 3 bed appartments. Our lift from the airport had been arranged with Collis, the fantastically helpful site manager, so the transfer wa  …see more

from £115 / night

£800 - £960 / week

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from £115 / night

(22) Excellent 

25

Holiday apartment with shared pool in Caribbean

Speightstown / Mount Brevitor

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Swimming pool
“Beautiful apartment on quiet, delightful complex” Four of us stayed here for 2 weeks in late February and there was plenty of room without us getting under each other's feet. The apartment is perfectly situated on a hill 10 minutes outside Speightstow  …see more

from £100 / night

£700 - £756 / week

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from £100 / night

(8) Very Good 

20

Holiday villa with shared pool, golf nearby in Caribbean

Jolly Harbour / Jolly Harbour Villas

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Swimming pool
“a dream holiday” Really lovely villa well situated with nice beaches on the doorstep,there are lots of restaurants to choose from at Jolly Harbour and the golf buggies are great fun. The villa itself is very well equipped with excellent air conditio  …see more

from £80 / night

£550 - £700 / week

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from £80 / night

(15) Excellent 

16

Holiday apartment with swimming pool in Caribbean

Mullins / Beacon Hill

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Swimming pool
“Condo is kept at a very high specification and standard” Had a very relaxing 9 days in a lovely garden apartment with pool. John & Sheila who own it helped a great deal before we went. Kerry the local manager was also very professional & helpful, as  …see more

from £150 / night

£1050 - £2295 / week

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from £150 / night

(4) Very Good 

21

Holiday villa rental

Saint James Parish / Holetown

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £112 / night

£778 - £1556 / week

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from £112 / night

8

Saint-Martin / Marigot

1 4 5 nights min

  • 1 bedroom
  • Sleeps 4
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

from £78 / night

£483 - £733 / week

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from £78 / night

(13) Very Good 

18

Holiday villa rental

Saint Philip Parish / Bottom Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Swimming pool
“Excellent” My boyfriend and I had the privilege of staying at Edna's Court on two occasions. Our first experience was back in December 2015 and based on that made us return for the second time in December 2016 into January 2017. Our stay on both occas  …see more

from £100 / night

£833 - £1183 / week

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from £100 / night

(2) Average 

23

Holiday studio in Saint Ann Parish

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

(17) Excellent 

20

Caribbean holiday villa rental

St. Kitts / Frigate Bay

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool
“Beautiful place and view!!!” Beautiful place - one of the best places we have stayed at - location was great!! We would go go back! One concern was that there was no hot water ion the kitchen until the last day.  …see more

from £343 / night

£2400 - £3160 / week

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from £343 / night

(46) Very Good 

21

Grande-Terre Island / Saint Francois

1 3 Min stay varies

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

from £74 / night

£397 - £496 / week

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from £74 / night

(9) Very Good 

24

Holiday home in Caribbean

Bottom Bay / Apple Hall

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Swimming pool
“A million dollar view” This was an excellent villa with all the amenities you could need. The location is very quiet but not for those hoping for a bustling night life. For us it was the perfect vacation and the view from the villa is stunning. Both t  …see more

from £65 / night

£450 - £690 / week

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from £65 / night

(18) Very Good 

22

Self-catering villa with private pool in Bottom Bay, Barbados

Bottom Bay / Apple Hall

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Swimming pool
“Lovely Villa, quiet location” Hideaway was a lovely villa to stay in for a week. It is new, so in very good condition, everything you need is provided and the manager is on hand for anything you require. Only drawback for some may be it's relatively r  …see more

from £97 / night

£675 - £843 / week

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from £97 / night

(7) Excellent 

23

Holiday villa with swimming pool in St. Kitts and Nevis

Nevis / Barnes Ghaut

4 6 1 night min

  • 4 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 4 km
  • Swimming pool
“Large spacious house with beautiful scenery” The house for just beautiful, great scenery and what a view! The staff was wonderful. The road is horrible and it is getting worse everyone says. Pretty dangerous in some spots. It takes 15 minutes to get t  …see more

from £192 / night

£1320 - £1440 / week

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from £192 / night

(3) Very Good 

24

Marie-Galante / Capesterre

3 6 3 nights min

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

from £173 / night

£1207 - £1690 / week

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from £173 / night

(4) Excellent 

22

Holiday villa with indoor pool in Caribbean

Saint George Parish / St. George's

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Swimming pool
“What a Gem!” My husband and I stayed in this lovely Villa for three weeks in March, the weather was glorious. We had a wonderful time.The Villa is located at Lance Aux Epines in a residential area surrounded by other lovely properties. It is a beautif  …see more

from £135 / night

£875 - £1400 / week

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from £135 / night

(37) Excellent 

15

Holiday villa with swimming pool in Barbados

Saint James Parish / Holetown

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.7 km
  • Swimming pool
“Mrs.” Had the BEST 1st visit!! The house was very accomodating. Will be returning to Barbados in the near future.  …see more

from £205 / night

£1435 - £2688 / week

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from £205 / night

(1) Excellent 

25

Holiday apartment with swimming pool in Caribbean

Saint James Parish / Prospect

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“A Great Condon” What a great condo. It really lived up to our expectations. We loved the fact that the decor was really contemporary and the House Keeper Miss Sophia keeps it spotless. She also did our laundry which we felt was a great help. We  …see more

from £880 / night

£6160 - £12320 / week

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from £880 / night

(7) Very Good 

29

Villa rental in Antigua and Barbuda with swimming pool, golf nearby

Saint John Parish / St. John's

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Swimming pool
“stunning” we stayed for 10 days in this villa and the first thing that delighted us was the stunning view over the bay. the villa itself was very roomy and well equiped and had been refurnished recently to make it very pleasant and comfortable. it  …see more

from £284 / night

£1988 / week

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from £284 / night

(2) Excellent 

20

Holiday villa in Caribbean

North Caicos / Horse Stable Beach

3 7 3 nights min

  • 3 bedrooms
  • Sleeps 7
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+

from £440 / night

£3080 / week

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from £440 / night

(6) Excellent 

16

Grande-Terre Island / Sainte-Anne

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Nearest beach 3 km
  • Swimming pool
  • Child friendly

from £52 / night

£363 / week

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from £52 / night

1