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

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11,927 Holiday homes

Filters applied: Swimming pool (11,927)

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

(5) Excellent 

1 / 27

Home rental in Mamora Bay with swimming pool

Saint Paul Parish / Mamora Bay

7 12 7 nights min stay

House / 7 bedrooms / sleeps 12 / 7 nights min stay

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from £695 / night

£4865 / week

Book

from £695 / night

(1) Excellent 

1 / 99

Holiday villa with swimming pool in Marigot Bay

Castries Quarter / Marigot Bay

6 12 Min stay varies

Villa / 6 bedrooms / sleeps 12 / Min stay varies

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from £280 / night

£2038 - £4611 / week

Book

from £280 / night

(8) Excellent 

1 / 17

Holiday home with swimming pool in Willikies

Willikies / The Peninsula

3 6 5 nights min stay

House / 3 bedrooms / sleeps 6 / 5 nights min stay

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from £175 / night

£1775 - £1995 / week

Book

from £175 / night

Featured properties

(6) Excellent 

1 / 32

Holiday villa in Eagle Beach

Aruba / Eagle Beach

3 10 Min stay varies

Villa / 3 bedrooms / sleeps 10 / Min stay varies

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from £166 / night

£1545 - £1835 / week

Book

from £166 / night

(3) Excellent 

1 / 16

Saline Point holiday villa accommodation

Cap Estate / Saline Point

2 4 Min stay varies

Villa / 2 bedrooms / sleeps 4 / Min stay varies

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from £320 / night

£2240 - £2625 / week

Book

from £320 / night

(3) Excellent 

1 / 38

Holiday villa rental

Aruba / Noord

3 8 3 nights min stay

Villa / 3 bedrooms / sleeps 8 / 3 nights min stay

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from £111 / night

£749 - £1183 / week

Book

from £111 / night

(19) Excellent 

1 / 32

Villa letting in Montego Bay with swimming pool, tennis court

Saint James Parish / Montego Bay

6 12 Min stay varies

Villa / 6 bedrooms / sleeps 12 / Min stay varies

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from £739 / night

£5173 - £9656 / week

Book

from £739 / night

(3) Very Good 

1 / 14

Holiday villa in Punta Cana

La Altagracia Province / Punta Cana

3 6 Min stay varies

Villa / 3 bedrooms / sleeps 6 / Min stay varies

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from £172 / night

£1379 / week

Book

from £172 / night

(6) Excellent 

1 / 45

Villa rental in Las Terrenas with swimming pool

Samana Province / Las Terrenas

13 33 1 night min stay

Villa / 13 bedrooms / sleeps 33 / 1 night min stay

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from £173 / night

£1242 - £4042 / week

Book

from £173 / night

(2) Excellent 

1 / 12

Holiday villa rental

Puerto Rico / Rio Grande

2 6 5 nights min stay

Villa / 2 bedrooms / sleeps 6 / 5 nights min stay

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from £276 / night

£1932 - £2621 / week

Book

from £276 / night

(2) Very Good 

1 / 41

Malmok Beach holiday villa rental

Aruba / Malmok Beach

3 6 3 nights min stay

Villa / 3 bedrooms / sleeps 6 / 3 nights min stay

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from £414 / night

£2414 / week

Book

from £414 / night

(3) Excellent 

1 / 44

Holiday villa with shared pool in Montego Bay

Saint James Parish / Montego Bay

16 32 1 night min stay

Villa / 16 bedrooms / sleeps 32 / 1 night min stay

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from £56 / night

£373 - £7856 / week

Book

from £56 / night

1 / 27

Holiday villa with swimming pool in Bavaro

Punta Cana / Bavaro

2 6 2 nights min stay

Villa / 2 bedrooms / sleeps 6 / 2 nights min stay

Add to shortlist

from £276 / night

£1738 / week

Book

from £276 / night

1 / 12

Holiday b&b with swimming pool in Noord

Aruba / Noord

4 12 2 nights min stay

B&B / 4 bedrooms / sleeps 12 / 2 nights min stay

Add to shortlist

from £56 / night

£387 - £2776 / week

Book

from £56 / night

1 / 71

Holiday apartment with shared pool in Montego Bay

Saint James Parish / Montego Bay

3 8 2 nights min stay

Apartment / 3 bedrooms / sleeps 8 / 2 nights min stay

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from £345 / night

£2069 / week

Book

from £345 / night

(2) Excellent 

1 / 41

Holiday villa with shared pool in Bavaro

Punta Cana / Bavaro

5 10 Min stay varies

Villa / 5 bedrooms / sleeps 10 / Min stay varies

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from £100 / night

£1035 - £4483 / week

Book

from £100 / night

(3) Excellent 

1 / 17

Grace Bay holiday home rental

Providenciales / Grace Bay

5 10 Min stay varies

House / 5 bedrooms / sleeps 10 / Min stay varies

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from £552 / night

£3863 - £7932 / week

Book

from £552 / night

(3) Very Good 

1 / 41

Holiday villa with swimming pool in Soto

Curacao / Soto

4 9 Min stay varies

Villa / 4 bedrooms / sleeps 9 / Min stay varies

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from £187 / night

£1303 - £3528 / week

Book

from £187 / night

(22) Excellent 

1 / 85

Villa rental in Montego Bay with swimming pool, golf nearby

Saint James Parish / Montego Bay

6 12 Min stay varies

Villa / 6 bedrooms / sleeps 12 / Min stay varies

Add to shortlist

from £725 / night

£5069 - £6518 / week

Book

from £725 / night

(1) Excellent 

1 / 48

Cupecoy Bay holiday b&b rental

Sint Maarten / Cupecoy Bay

5 10 3 nights min stay

B&B / 5 bedrooms / sleeps 10 / 3 nights min stay

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from £690 / night

£4138 / week

Book

from £690 / night

(7) Excellent 

1 / 19

Holiday villa in Vieux Fort

Vieux Fort Quarter / Vieux Fort

2 6 Min stay varies

Villa / 2 bedrooms / sleeps 6 / Min stay varies

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from £242 / night

£1690 - £3863 / week

Book

from £242 / night

1 / 33

Apartment letting in Punta Cana with swimming pool

La Altagracia Province / Punta Cana

2 6 2 nights min stay

Apartment / 2 bedrooms / sleeps 6 / 2 nights min stay

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from £242 / night

£1352 / week

Book

from £242 / night

(3) Excellent 

1 / 29

Villa letting in Cul de Sac with swimming pool

Saint-Martin / Cul de Sac

4 8 Min stay varies

Villa / 4 bedrooms / sleeps 8 / Min stay varies

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from £235 / night

£1329 - £6250 / week

Book

from £235 / night

(22) Excellent 

1 / 18

Gros Islet holiday apartment rental

Gros Islet Quarter / Gros Islet

1 3 Min stay varies

Apartment / 1 bedroom / sleeps 3 / Min stay varies

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from £107 / night

£749 / week

Book

from £107 / night

(4) Excellent 

1 / 33

Cruz Bay holiday villa rental

St. John / Cruz Bay

4 8 Min stay varies

Villa / 4 bedrooms / sleeps 8 / Min stay varies

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from £297 / night

£2076 - £5297 / week

Book

from £297 / night

(2) Very Good 

1 / 8

Holiday guest house rental

Puerto Rico / Yabucoa

7 16 1 night min stay

Guest house / 7 bedrooms / sleeps 16 / 1 night min stay

Add to shortlist

from £100 / night

£630 - £10430 / week

Book

from £100 / night

(4) Good 

1 / 14

Holiday villa rental

Punta Cana / Bavaro

4 8 3 nights min stay

Villa / 4 bedrooms / sleeps 8 / 3 nights min stay

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from £207 / night

£1380 - £1621 / week

Book

from £207 / night

1 / 10

Villa rental in Saint Francois with swimming pool, golf nearby

Grande-Terre Island / Saint Francois

4 10 Min stay varies

Villa / 4 bedrooms / sleeps 10 / Min stay varies

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from £198 / night

£1388 - £2481 / week

Book

from £198 / night

(3) Very Good 

1 / 50

Holiday home with swimming pool in Oyster Pond

Saint-Martin / Oyster Pond

6 12 7 nights min stay

House / 6 bedrooms / sleeps 12 / 7 nights min stay

Add to shortlist

from £296 / night

£2069 - £10518 / week

Book

from £296 / night

1 / 23

Villa letting in Fajardo with shared pool

Puerto Rico / Fajardo

3 10 Min stay varies

Villa / 3 bedrooms / sleeps 10 / Min stay varies

Add to shortlist

from £287 / night

£1897 - £2414 / week

Book

from £287 / night

(9) Good 

1 / 10

Holiday villa with shared pool, golf nearby in Montego Bay

Saint James Parish / Montego Bay

11 24 1 night min stay

Villa / 11 bedrooms / sleeps 24 / 1 night min stay

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from £104 / night

£725 - £16656 / week

Book

from £104 / night

(1) Excellent 

1 / 15

Eagle Beach holiday villa rental

Aruba / Eagle Beach

3 6 Min stay varies

Villa / 3 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £190 / night

£1207 - £1725 / week

Book

from £190 / night

1 / 27

Holiday villa rental

Las Terrenas / Las Ballenas

7 16 Min stay varies

Villa / 7 bedrooms / sleeps 16 / Min stay varies

Add to shortlist

from £483 / night

£2897 - £8621 / week

Book

from £483 / night

(3) Excellent 

1 / 29

Holiday apartment rental

Punta Cana / Bavaro

2 4 2 nights min stay

Apartment / 2 bedrooms / sleeps 4 / 2 nights min stay

Add to shortlist

from £241 / night

£1310 / week

Book

from £241 / night

(4) Excellent 

1 / 50

Holiday apartment with shared pool in Seven Mile Beach

Grand Cayman / Seven Mile Beach

2 6 3 nights min stay

Apartment / 2 bedrooms / sleeps 6 / 3 nights min stay

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from £94 / night

£652 - £2221 / week

Book

from £94 / night

1 / 4

Holiday home with swimming pool in San Juan

Puerto Rico / San Juan

8 18 1 night min stay

House / 8 bedrooms / sleeps 18 / 1 night min stay

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from £759 / night

£5311 / week

Book

from £759 / night

(1) Excellent 

1 / 25

Providenciales holiday villa let

Turks and Caicos Islands / Providenciales

4 10 Min stay varies

Villa / 4 bedrooms / sleeps 10 / Min stay varies

Add to shortlist

from £397 / night

£2759 - £5518 / week

Book

from £397 / night

1 / 12

Rodney bay, Gros Islet holiday home rental

Gros Islet / Rodney bay, Gros Islet

3 6 Min stay varies

House / 3 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £138 / night

£869 - £1787 / week

Book

from £138 / night

(3) Excellent 

1 / 18

Santo Domingo holiday villa rental

Santo Domingo Province / Santo Domingo

6 20 1 night min stay

Villa / 6 bedrooms / sleeps 20 / 1 night min stay

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from £466 / night

£3259 / week

Book

from £466 / night

(2) Excellent 

1 / 24

Holiday apartment with swimming pool, golf nearby in Bavaro Beach

Punta Cana / Bavaro Beach

2 4 3 nights min stay

Apartment / 2 bedrooms / sleeps 4 / 3 nights min stay

Add to shortlist

from £200 / night

£1200 - £1304 / week

Book

from £200 / night

(9) Excellent 

1 / 61

Holiday villa with swimming pool in Soto

Curacao / Soto

4 9 6 nights min stay

Villa / 4 bedrooms / sleeps 9 / 6 nights min stay

Add to shortlist

from £211 / night

£1477 - £1860 / week

Book

from £211 / night

1 / 28

Holiday home with shared pool in Eagle Beach

Aruba / Eagle Beach

3 8 Min stay varies

House / 3 bedrooms / sleeps 8 / Min stay varies

Add to shortlist

from £156 / night

£1087 - £2825 / week

Book

from £156 / night

1 / 18

Villa rental in Eagle Beach with swimming pool, golf nearby

Aruba / Eagle Beach

5 12 7 nights min stay

Villa / 5 bedrooms / sleeps 12 / 7 nights min stay

Add to shortlist

from £247 / night

£1725 / week

Book

from £247 / night

(14) Very Good 

1 / 25

Holiday villa in Cap Estate Town

Cap Estate / Cap Estate Town

8 18 1 night min stay

Villa / 8 bedrooms / sleeps 18 / 1 night min stay

Add to shortlist

from £194 / night

£1352 - £12166 / week

Book

from £194 / night

(1) Excellent 

1 / 46

Holiday villa with indoor pool in Philipsburg

Sint Maarten / Philipsburg

3 6 Min stay varies

Villa / 3 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £242 / night

£1656 - £4483 / week

Book

from £242 / night

(2) Excellent 

1 / 63

Apartment rental in Bavaro with shared pool, golf nearby

Punta Cana / Bavaro

3 6 Min stay varies

Apartment / 3 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £207 / night

£1380 - £1794 / week

Book

from £207 / night

(1) Excellent 

1 / 19

Willikies holiday villa rental

Willikies / The Peninsula

3 8 7 nights min stay

Villa / 3 bedrooms / sleeps 8 / 7 nights min stay

Add to shortlist

from £358 / night

£2500 / week

Book

from £358 / night

(3) Excellent 

1 / 27

Negril holiday villa rental

Westmoreland Parish / Negril

4 8 Min stay varies

Villa / 4 bedrooms / sleeps 8 / Min stay varies

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from £360 / night

£2500 / week

Book

from £360 / night

(3) Excellent 

1 / 31

Holiday villa with golf nearby in Puerto Plata

Puerto Plata Province / Puerto Plata

5 12 Min stay varies

Villa / 5 bedrooms / sleeps 12 / Min stay varies

Add to shortlist

from £221 / night

£1380 - £3449 / week

Book

from £221 / night

(3) Excellent 

1 / 31

Holiday home with shared pool in Gros Islet

Gros Islet Quarter / Gros Islet

3 8 3 nights min stay

House / 3 bedrooms / sleeps 8 / 3 nights min stay

Add to shortlist

from £173 / night

£1328 - £2849 / week

Book

from £173 / night

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