Caribbean apartment or villa with a private pool area | Holiday Lettings

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Caribbean

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4,661 Holiday homes

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

19

Holiday villa with swimming pool, golf nearby in Antigua and Barbuda

Antigua / Galley Bay

5 9 7 nights min

  • 5 bedrooms
  • Sleeps 9
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £1143 / night

£8000 / week

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from £1143 / night

(12) Excellent 

24

Caribbean holiday villa rental

Saint James Parish / Holetown

7 16 Min stay varies

  • 7 bedrooms
  • Sleeps 16
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Swimming pool

from £550 / night

£3850 / week

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from £550 / 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.
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from £205 / night

£1435 - £2688 / week

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from £205 / night

31

Maria Trinidad Sanchez Province / Rio San Juan

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden

from £35 / night

£216 - £294 / week

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from £35 / night

28

Holiday villa with swimming pool in Caribbean

Sint Maarten / Cupecoy Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool

from £307 / night

£2145 - £4683 / week

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from £307 / night

(25) Excellent 

24

Holiday villa with swimming pool in Antigua and Barbuda

Willikies / The Peninsula

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Swimming pool
“A fantastic place just what we needed” We stayed here as a couple in June 2016. This is the off season on the Island and it is very quiet and a lot of the restaurants are closed, but this is exactly what we needed as you get to experience the island w
…see more

from £171 / night

£1200 - £2600 / week

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from £171 / 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

(1) Excellent 

23

Holiday villa with swimming pool, golf nearby in Caribbean

Sint Maarten / Cupecoy Bay

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Swimming pool
“The home was perfect!” We had the best time in St Martin, we previously stayed on the French side so this time we decided to try the Dutch side. It was really great and we were so close to everything. I Loved the villa and the view.
…see more

from £738 / night

£5159 - £15080 / week

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from £738 / night

27

Holiday villa with golf nearby in Caribbean

Nevis / Charlestown

5 11 3 nights min

  • 5 bedrooms
  • Sleeps 11
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.01 km
  • Swimming pool

from £2100 / night

£14700 - £52080 / week

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from £2100 / night

24

Holiday villa with swimming pool in Caribbean

Sint Maarten / Cupecoy Bay

2 4 7 nights min

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

from £1077 / night

£7540 - £15080 / week

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from £1077 / night

(6) Very Good 

14

Holiday villa with swimming pool, golf nearby in Caribbean

Saint James Parish / Sunset Crest

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool

from £280 / night

£1960 - £2160 / week

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from £280 / night

23

Caribbean holiday apartment rental

Saint James Parish / Holetown

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 4 km
  • Swimming pool

from £1667 / night

£11667 - £18334 / week

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from £1667 / night

11

Las Terrenas / El Portillo

3 9 2 nights min

  • 3 bedrooms
  • Sleeps 9
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £104 / night

£604 / week

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from £104 / night

10

Holiday villa with swimming pool in Montserrat

Montserrat / Olveston

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Ask about pets
  • Private garden

from £184 / night

£1120 / week

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from £184 / night

10

Grande-Terre Island / Saint Francois

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Swimming pool
  • Air conditioning
  • Private garden

from £74 / night

£518 - £863 / week

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from £74 / night

(7) Very Good 

21

Holiday villa in Caribbean

Holetown / Queens Fort

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Swimming pool
“Great place to stay with fantastic hosts” 7 of us stayed at the villa for a week back in April, we were catered for perfectly by Tony and Rose who really made our trip. Tony's gravy is worth the trip alone. The villa was ideal for us, loads of outsi
…see more

from £350 / night

£2450 / week

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from £350 / night

(13) Excellent 

36

Holiday villa with swimming pool, golf nearby in Antigua and Barbuda

Antigua / Saint Mary's

4 8 Min stay varies

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

from £250 / night

£1750 - £2780 / week

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from £250 / 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 £862 / night

£6032 - £14286 / week

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from £862 / 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
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from £284 / night

£1988 / week

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from £284 / night

(1) Excellent 

11

Basse-Terre Island / Capesterre-Belle-Eau

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £44 / night

£242 - £397 / week

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from £44 / night

(2) Very Good 

26

Holiday villa with swimming pool in Caribbean

Speightstown / Heywoods

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.4 km
  • Swimming pool

from £100 / night

£600 - £750 / week

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from £100 / night

(3) Excellent 

23

U.S. Virgin Islands holiday townhouse rental

St. Thomas / St Thomas East

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 0.8 km
  • Swimming pool
  • Child friendly

from £84 / night

£584 - £2067 / week

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from £84 / night

(10) Excellent 

29

Villa rental in Caribbean with swimming pool

Samana Province / Las Galeras

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Swimming pool

from £120 / night

£600 - £1500 / week

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from £120 / night

(47) Excellent 

23

Villa rental in St. Lucia with swimming pool, golf nearby

Castries / La Toc

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Swimming pool
“It was a magical experience and we were reluctant to return home” We had a wonderful five night stay at this impressive newly built villa in a stunning location overlooking the Caribbean Sea, with the sandy beach of La Toc a short stroll away. The
…see more

from £240 / night

£1680 - £3808 / week

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from £240 / night

(3) Excellent 

41

Grande-Terre Island / Saint Francois

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Swimming pool

from £100 / night

£604 / week

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from £100 / night

(21) Excellent 

17

Holiday townhouse with swimming pool in Caribbean

Saint James Parish / Holetown

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Swimming pool
“Fantastic location, fantastic property” First visit to Barbados and we loved every minute of it. The house was fantastic, comfortable spacious and very well equipped. The bedrooms are large and each room has its own walk in shower. We really liked
…see more

from £280 / night

£1960 - £3990 / week

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from £280 / night

(1) Excellent 

16

Guadeloupe / Saint Anne

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.9 km
  • Swimming pool

from £45 / night

£311 - £518 / week

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from £45 / 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

(2) Excellent 

19

Grande-Terre Island / Saint Francois

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool

from £136 / night

£949 - £1199 / week

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from £136 / night

(1) Excellent 

31

Caribbean holiday villa rental

Saint James Parish / Holetown

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £190 / night

£1330 - £1540 / week

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from £190 / night

24

Villa rental in Caribbean with swimming pool

Saint James Parish / Lower Carlton

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 4 km
  • Swimming pool

from £1191 / night

£8334 - £16667 / week

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from £1191 / night

(7) Excellent 

13

Caribbean holiday villa rental

Bottom Bay / Apple Hall

3 6 5 nights min

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

from £150 / night

£900 - £1040 / week

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from £150 / night

(2) Excellent 

22

Arrondissement of Fort-de-France / Le Lamentin

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

from £87 / night

£604 / week

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from £87 / night

(15) Very Good 

36

Saint Francois / Anse des Rochers

Studio 4 5 nights min

  • Studio
  • Sleeps 4
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Swimming pool

from £46 / night

£311 - £432 / week

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from £46 / 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

24

Holiday villa with golf nearby in Caribbean

Antigua / Galley Bay

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £1701 / night

£11905 - £15874 / week

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from £1701 / night

(1) Excellent 

16

Holiday home rental

Saint Peter Parish / Mullins

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Swimming pool

from £214 / night

£1500 - £2656 / week

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from £214 / night

(15) Excellent 

27

Caribbean holiday villa rental

Saint James Parish / Lower Carlton

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Perfect, perfect, perfect...” We stayed here for our honeymoon and could not have asked for more. A beautiful villa, superbly maintained, in a wonderful location. We were very impressed with Andrew the property manager, but special mention must go to
…see more

from £356 / night

£2492 / week

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from £356 / 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

24

Holiday villa with swimming pool in Barbados

Saint James Parish / Lower Carlton

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 0.3 km
  • Swimming pool
  • Child friendly

from £215 / night

£1505 / week

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from £215 / night

1