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

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Caribbean

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6,142 Holiday homes

Filters applied: Private pool

(13) 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

(7) Very Good 

23

Holiday villa with swimming pool in Caribbean

Saint James Parish / Weston

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Definitely the place to stay.” We spent an amazing, relaxing week at this beautiful beach villa in St. James. The house is tucked away behind an electronic gate down a private drive. The beach is on your door step and the views from the veranda are br
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from £749 / night

£5237 / week

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from £749 / night

(12) Excellent 

29

Caribbean holiday villa rental

Jolly Harbour / Jolly Harbour Villas

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool
“The best holiday ever” Coco House was the perfect place to stay with everything we could have wished for. Very spacious but homely and the pool a must. The villa was very well equipped and comfortable. Shops, bars and restaurants all within easy re
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from £170 / night

£1190 / week

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Responds fast!
avg. 1 hour 56 minutes

from £170 / 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 £276 / night

£1930 / week

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from £276 / night

(24) 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
“If you really want to feel at home on holiday, look no further.” After a fantastic stay last year we returned here for 2 weeks in April/May (this time 5 of us). Yet again despite its size and very modern feel we immediately felt at home – definitely a
…see more

from £280 / night

£1960 - £3990 / week

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Responds fast!
avg. 3 hours 35 minutes

from £280 / night

(48) 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 £237 / night

£1654 - £3749 / week

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from £237 / night

(5) Very Good 

24

Caribbean holiday villa rental

Porters / Porters Gate

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.4 km
  • Swimming pool
“Amazing, brilliantly appointed villa in one of the best locations in Barbados” This villa was awsome. My wife and I and two kids (18 and 12) have just returned from a fantastic two weeks at this super villa. The interior decorating has clearly been
…see more

from £129 / night

£903 / week

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from £129 / night

(21) Excellent 

35

Holiday apartment with swimming pool in Caribbean

Saint Peter Parish / Mullins

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Swimming pool
“Fantastic - paradise by the sea!” What an amazing place to stay! We went for Christmas with our 7 year old and can't wait to go back. Ive been to Barbados 7 times before and this is simply the best holiday Ive ever had. The apartment was spacious, b
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from £165 / night

£1150 - £2475 / week

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Responds fast!
avg. 3 hours 2 minutes

from £165 / 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 £119 / night

£596 - £1489 / week

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from £119 / night

(26) 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
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from £171 / night

£1200 - £2600 / week

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from £171 / night

(7) Excellent 

16

Villa rental in Caribbean with swimming pool, golf nearby

Punta Cana / Bavaro Beach

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Swimming pool

from £237 / night

£1575 - £2638 / week

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from £237 / night

(14) 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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Responds fast!
avg. 1 hour 56 minutes

from £250 / night

(14) Very Good 

23

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

Cap Estate / Rodney Bay Heights

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Swimming pool

from £115 / night

£790 - £1725 / week

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from £115 / night

(24) Excellent 

24

Holiday villa with swimming pool in Caribbean

Porters / Porters Gate

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Swimming pool
“The perfect location for chilling out and enjoying local hospitality” Actually this was my second trip to the property, I love being near to Hole Town's excellent shops and night life ( especially Friday night and Sundays on 2nd Street). I feel the
…see more

from £150 / night

£1050 - £2500 / week

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Responds fast!
avg. 3 hours 53 minutes

from £150 / night

(2) Excellent 

19

Villa rental in Caribbean with swimming pool, golf nearby

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 £138 / night

£965 - £1220 / week

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from £138 / night

18

Holiday villa in Antigua and Barbuda

Saint John Parish / St. John's

3 6 7 nights min

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

from £203 / night

£1418 - £1733 / week

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from £203 / night

(2) Excellent 

26

Holiday villa with swimming pool, golf nearby in Caribbean

Nevis / Charlestown

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Beyond Expectations” This villa met all our expectations when booking a villa with the Four Seasons! From the ferry transfers (that docks at the pier at the resort) to the top-quality staff- it truly was an amazing week. The villa was spotless and ha
…see more

from £745 / night

£5209 - £8819 / week

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from £745 / night

36

Caribbean holiday villa rental

Grande-Terre Island / Sainte-Anne

4 7 7 nights min

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

from £157 / night

£1097 - £1746 / week

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from £157 / night

(3) Very Good 

8

Martinique holiday bungalow rental

Arrondissement of Saint-Pierre / Le Carbet

2 6 2 nights min

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

from £176 / night

£1141 / week

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from £176 / night

(7) Very Good 

21

Holiday villa in Caribbean

Holetown / Queens Fort

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • 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 £300 / night

£2100 - £3500 / week

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from £300 / night

(10) Excellent 

16

Holiday townhouse with swimming pool in Caribbean

Enterprise / Cottonbay

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 1 km
  • Swimming pool
  • Child friendly
“Repeat guest - many times over” This holiday villa has been our yearly destination for 6 years in a row. After our first encounter we knew we've found the right destination for our young family. What drew us to the property was the safety for our to
…see more

from £115 / night

£800 - £950 / week

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from £115 / night

(3) Very Good 

20

St. Maarten-St. Martin holiday villa rental

Sint Maarten / Oyster Pond

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Swimming pool

from £172 / night

£1198 - £2426 / week

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Responds fast!
avg. 2 hours 29 minutes

from £172 / night

(20) Excellent 

33

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

(15) Excellent 

24

Holiday villa with swimming pool in Guadeloupe

Grande-Terre Island / Sainte-Anne

3 6 7 nights min

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

from £107 / night

£746 - £1316 / week

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Responds fast!
avg. 3 hours 31 minutes

from £107 / night

(11) Excellent 

21

Antigua and Barbuda holiday villa rental

Saint Phillip Parish / Long Bay

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Swimming pool
“A fantastic holiday destination, where nothing more can be asked for” Brightside is an amazing place to stay on holiday - clean, spacious, wonderful views and perfect for a relaxing time away. I stayed out there with some friends and we had an excelle
…see more

from £450 / night

£3150 - £4961 / week

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from £450 / night

(41) 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
“Lovely family holiday villa” We stayed at Beija Flor for 10 nights in April 2017. We had a lovely holiday. The villa did not disappoint. The kitchen is well equipped. The pool is a reasonable size and in full sun all day - there is a light, welcoming
…see more

from £205 / night

£1435 - £2688 / week

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from £205 / night

(8) Excellent 

28

Holiday villa in Dominican Republic

Maria Trinidad Sanchez Province / Rio San Juan

4 10 1 night min

  • 4 bedrooms
  • Sleeps 10
  • 1 night min
  • Nearest beach 4 km
  • Swimming pool
  • Child friendly

from £162 / night

£1130 / week

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Responds fast!
avg. 2 hours 14 minutes

from £162 / night

(9) 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
“Impressive villa with stunning views” We have just returned from a fabulous holiday at Silk Cotton House. The villa owner was extremely responsive from the outset and clearly has considered everything to ensure guests have a comfortable stay.The villa
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from £286 / night

£2000 - £4000 / week

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Responds fast!
avg. 1 hour 45 minutes

from £286 / night

(15) Excellent 

21

Holiday lodge in Caribbean

Great Exuma / George Town

3 8 5 nights min

  • 3 bedrooms
  • Sleeps 8
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £331 / night

£2315 / week

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Responds fast!
avg. 3 hours 8 minutes

from £331 / night

29

Holiday home with swimming pool in Caribbean

Arrondissement of Le Marin / Le Diamant

5 10 5 nights min

  • 5 bedrooms
  • Sleeps 10
  • 5 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £176 / night

£1229 - £1930 / week

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from £176 / night

(2) 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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Responds fast!
avg. 1 hour 30 minutes

from £190 / night

(29) Excellent 

Certificate of Excellence

20

Barbados holiday villa rental

Bottom Bay / Apple Hall

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“5 minutes to an amazing beach” We stayed at Sunrise Villa for 12 days in March. The weather was brilliant, some rain but on the whole it was in the 80's. The villa had everything you could want for a self catering holiday, well equipped kitchen, washi
…see more

Certificate of Excellence

from £75 / night

£459 - £1015 / week

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Responds fast!
avg. 1 hour 17 minutes

from £75 / night

(2) Excellent 

24

Villa rental in Barbados with swimming pool

Saint James Parish / Paynes Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Swimming pool
“Lovely Property” We thoroughly enjoyed our stay in this lovely property. We found the location to be really central. It was our first time to Barbados. The beach did occasionally get quite busy but Coral Cove always had sunbeds for us. The view f
…see more

from £630 / night

£4686 - £11024 / week

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from £630 / night

30

Holiday villa with swimming pool in Caribbean

Martinique / Sainte Anne

3 6 Min stay varies

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

from £141 / night

£983 - £1492 / week

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from £141 / night

(25) Very Good 

26

Holiday villa with swimming pool, golf nearby in Caribbean

Tobago / Prospect, Tobago

4 12 2 nights min

  • 4 bedrooms
  • Sleeps 12
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Swimming pool
“A fabulous relaxing holiday in a spectacular part of the world.” Villa in fabulous elevated private location, with fantastic views out over the Atlantic Coast line during the day time, and constantly changing night time views of the low lands. The vi
…see more

from £220 / night

£1400 / week

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Responds fast!
avg. 1 hour 31 minutes

from £220 / night

(2) Average 

13

Holiday studio with swimming pool in Dominica

Saint Luke Parish / Pointe Michel

Studio 3 1 night min

  • Studio
  • Sleeps 3
  • 1 night min
  • Nearest beach 15 km
  • Swimming pool
  • Child friendly

from £62 / night

£430 / week

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from £62 / night

20

Holiday apartment with swimming pool, golf nearby in Caribbean

Saint Peter Parish / Mullins

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Swimming pool

from £150 / night

£1050 - £1722 / week

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Responds fast!
avg. 3 hours 10 minutes

from £150 / night

(9) Very Good 

32

Holiday villa with swimming pool, golf nearby in Trinidad and Tobago

Tobago / Mount Irvine

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Swimming pool
“Tranquility in Paradise” I have stayed at Eternity Villa on my last two trips to Tobago. I consider it home away from home. On both occasions I brought my family and the house was more than accomodating for everyone. Located in Mt Irvine and amazin
…see more

from £189 / night

£1260 - £1969 / week

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from £189 / night

(8) Very Good 

22

Holiday villa with swimming pool, golf nearby in Caribbean

Cap Estate / Villas on the Green

3 6 3 nights min

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

from £150 / night

£1048 / week

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from £150 / night

24

Holiday villa with swimming pool, golf nearby in St. Kitts and Nevis

Nevis / Charlestown

4 9 3 nights min

  • 4 bedrooms
  • Sleeps 9
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Swimming pool

from £1328 / night

£16260 - £48504 / week

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from £1328 / night

1