Caribbean apartment or villa with a heated pool | Holiday Lettings

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793 Holiday homes

Filters applied: Heated pool (793)

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

(4) Excellent 

1 / 19

Holiday beach hut rental

Puerto Rico / Naguabo

4 bedroomsSleeps 107 nights min stay

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min stay

from $301 / night

$2101 / week

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from $301 / night

(6) Excellent 

1 / 28

Christiansted holiday apartment rental

St. Croix / Christiansted

2 bedroomsSleeps 47 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay

from $158 / night

$1101 - $1806 / week

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from $158 / night

1 / 13

Holiday villa in Negril

Negril / Negril Beach

3 bedroomsSleeps 61 night min stay

  • 3 bedrooms
  • Sleeps 6
  • 1 night min stay

from $400 / night

$2800 / week

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from $400 / night

Featured properties

(2) Excellent 

1 / 24

Holiday condo in East End

St. Thomas / East End

3 bedroomsSleeps 7Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies

from $300 / night

$2000 - $3799 / week

Book Book View

from $300 / night

(3) Good 

1 / 17

Holiday condo in Freeport

Grand Bahama Island / Freeport

2 bedroomsSleeps 67 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay

from $176 / night

$1226 - $1376 / week

Book Book View

from $176 / night

(4) Excellent 

1 / 9

Holiday apartment rental

Aruba / Oranjestad

2 bedroomsSleeps 61 night min stay

  • 2 bedrooms
  • Sleeps 6
  • 1 night min stay

from $181 / night

$1261 - $2171 / week

Book Book View

from $181 / night

(1) Excellent 

1 / 20

Ocho Rios holiday hotel apartment rental

Saint Ann Parish / Ocho Rios

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies

from $102 / night

$653 - $2016 / week

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from $102 / night

(17) Very Good 

1 / 80

Holiday apartment with shared pool in Turtle Cove

Providenciales / Turtle Cove

Sleeps 23 nights min stay

  • Sleeps 2
  • 3 nights min stay

from $181 / night

$1960 / week

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from $181 / night

1 / 20

Holiday apartment in Isla Verde

Carolina / Isla Verde

2 bedroomsSleeps 74 nights min stay

  • 2 bedrooms
  • Sleeps 7
  • 4 nights min stay

from $255 / night

$0 / week

Book Book View

from $255 / night

(1) Excellent 

1 / 38

Holiday villa rental

Saint Ann Parish / St. Ann's Bay

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies

from $107 / night

$0 / week

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from $107 / night

(4) Excellent 

1 / 29

Holiday villa in Runaway Bay

Saint Ann Parish / Runaway Bay

2 bedroomsSleeps 5Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies

from $210 / night

$4047 / week

Book Book View

from $210 / night

(1) Excellent 

1 / 17

Condo rental in Turtle Cove with indoor pool, golf nearby

Providenciales / Turtle Cove

1 bedroomSleeps 42 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 2 nights min stay

from $301 / night

$2000 / week

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from $301 / night

(9) Excellent 

1 / 23

Apartment rental in Speightstown

Speightstown / Port St Charles

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies

from $415 / night

$2900 - $7613 / week

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from $415 / night

1 / 17

Holiday villa in Charlotte Amalie

St. Thomas / Charlotte Amalie

2 bedroomsSleeps 8Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies

from $150 / night

$1051 - $7351 / week

Book Book View

from $150 / night

(16) Very Good 

1 / 63

Holiday apartment in Christiansted

St. Croix / Christiansted

1 bedroomSleeps 44 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 4 nights min stay

from $135 / night

$945 / week

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from $135 / night

(6) Excellent 

1 / 28

Apartment rental in Paradise Island with golf nearby

New Providence Island / Paradise Island

3 bedroomsSleeps 83 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min stay

from $376 / night

$2501 - $5901 / week

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from $376 / night

(4) Excellent 

1 / 31

Holiday villa with golf nearby in Puerto Plata

Puerto Plata Province / Puerto Plata

5 bedroomsSleeps 12Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies

from $321 / night

$2000 - $5001 / week

Book Book View

from $321 / night

(2) Very Good 

1 / 23

Holiday condo in Freeport

Grand Bahama Island / Freeport

2 bedroomsSleeps 41 night min stay

  • 2 bedrooms
  • Sleeps 4
  • 1 night min stay

from $219 / night

$750 / week

Book Book View

from $219 / night

(1) Terrible 

1 / 24

Freeport holiday condo rental

Freeport / Lucaya

2 bedroomsSleeps 87 nights min stay

  • 2 bedrooms
  • Sleeps 8
  • 7 nights min stay

from $225 / night

$1576 / week

Book Book View

from $225 / night

(10) Very Good 

1 / 28

Holiday apartment with shared pool, golf nearby in Noord

Aruba / Noord

1 bedroomSleeps 2Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies

from $75 / night

$800 - $1287 / week

Book Book View

from $75 / night

(2) Excellent 

1 / 33

Holiday villa in Ocho Rios

Saint Ann Parish / Ocho Rios

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies

from $116 / night

$1015 - $1320 / week

Book Book View

from $116 / night

(8) Excellent 

1 / 16

Trois-Ilets holiday condo rental

Arrondissement of Le Marin / Trois-Ilets

3 bedroomsSleeps 67 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay

from $135 / night

$1001 / week

Book Book View

from $135 / night

(3) Excellent 

1 / 20

Holiday apartment in Bavaro

Punta Cana / Bavaro

3 bedroomsSleeps 7Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies

from $182 / night

$1269 - $1812 / week

Book Book View

from $182 / night

(11) Excellent 

1 / 63

St. Ann's Bay holiday home rental

Saint Ann Parish / St. Ann's Bay

2 bedroomsSleeps 43 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min stay

from $98 / night

$681 / week

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from $98 / night

(3) Good 

1 / 18

Holiday condo in Ocho Rios

Saint Ann Parish / Ocho Rios

1 bedroomSleeps 43 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 3 nights min stay

from $80 / night

$561 - $701 / week

Book Book View

from $80 / night

(7) Excellent 

1 / 22

Runaway Bay holiday bungalow rental

Saint Ann Parish / Runaway Bay

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies

from $126 / night

$875 / week

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from $126 / night

1 / 23

Villa letting in Fajardo with shared pool

Puerto Rico / Fajardo

3 bedroomsSleeps 10Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies

from $416 / night

$2751 - $3500 / week

Book Book View

from $416 / night

(3) Excellent 

1 / 6

Home rental in Montego Bay

Saint James Parish / Montego Bay

3 bedroomsSleeps 63 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min stay

from $400 / night

$2800 / week

Book Book View

from $400 / night

(1) Very Good 

1 / 5

Holiday condo in Charlotte Amalie

St. Thomas / Charlotte Amalie

2 bedroomsSleeps 87 nights min stay

  • 2 bedrooms
  • Sleeps 8
  • 7 nights min stay

from $286 / night

$2000 / week

Book Book View

from $286 / night

(3) Excellent 

1 / 22

Holiday condo in St James, Montego Bay

Montego Bay / St James, Montego Bay

1 bedroomSleeps 33 nights min stay

  • 1 bedroom
  • Sleeps 3
  • 3 nights min stay

from $101 / night

$651 - $826 / week

Book Book View

from $101 / night

(1) Excellent 

1 / 26

Holiday apartment rental

Sint Maarten / Cupecoy Bay

1 bedroomSleeps 4Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies

from $226 / night

$1600 / week

Book Book View

from $226 / night

(10) Excellent 

1 / 12

Apartment letting in Christiansted

St. Croix / Christiansted

1 bedroomSleeps 22 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 2 nights min stay

from $86 / night

$596 / week

Book Book View

from $86 / night

(7) Very Good 

1 / 16

Villa rental in Le Diamant

Arrondissement of Le Marin / Le Diamant

3 bedroomsSleeps 8Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies

from $237 / night

$1653 - $2833 / week

Book Book View

from $237 / night

(5) Excellent 

1 / 24

Condo rental in Sosua

Sosua / El Batey

2 bedroomsSleeps 5Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies

from $101 / night

$600 - $750 / week

Book Book View

from $101 / night

(12) Excellent 

1 / 20

Holiday apartment rental

Turks and Caicos Islands / Providenciales

Sleeps 23 nights min stay

  • Sleeps 2
  • 3 nights min stay

from $200 / night

$1301 / week

Book Book View

from $200 / night

1 / 12

Saint Phillip Parish holiday villa rental

Antigua / Saint Phillip Parish

1 bedroomSleeps 23 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 3 nights min stay

from $116 / night

$812 / week

Book Book View

from $116 / night

(1) Excellent 

1 / 24

Holiday villa rental

Saint Ann Parish / Ocho Rios

3 bedroomsSleeps 83 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min stay

from $150 / night

$1015 - $1855 / week

Book Book View

from $150 / night

(15) Very Good 

1 / 14

Holiday apartment rental

St. Thomas / East End

1 bedroomSleeps 44 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 4 nights min stay

from $89 / night

$0 / week

Book Book View

from $89 / night

(26) Very Good 

1 / 45

Holiday studio with swimming pool, tennis court in San Juan

Puerto Rico / San Juan

1 bedroomSleeps 44 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 4 nights min stay

from $145 / night

$1015 / week

Book Book View

from $145 / night

(1) Excellent 

1 / 22

Holiday apartment in Isla Verde

Carolina / Isla Verde

1 bedroomSleeps 43 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 3 nights min stay

from $161 / night

$1101 / week

Book Book View

from $161 / night

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