Penthouses in Caribbean

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North America Holidays
172843 properties
Caribbean Holidays
24144 properties
Villas Dominican Republic
3,355 properties
Villas St. Barts
3,303 properties
Villas Barbados
2,530 properties
Villas St. Maarten - Saint Martin
2,446 properties
Villas Jamaica
2,412 properties
Apartments Puerto Rico
1,793 properties
Villas Guadeloupe
988 properties
Villas Bahamas
858 properties
US Virgin Isles
711 properties
Villas Aruba
572 properties
Villas St. Lucia
540 properties
Villas Antigua and Barbuda
533 properties
Apartments Martinique
531 properties
Villas St. Vincent and the Grenadines
434 properties
Holiday rentals Turks and Caicos Islands
399 properties
Villas Anguilla
397 properties
Villas Curacao
374 properties
Villas British Virgin Isles
321 properties
Villas Grenada
258 properties
Houses Trinidad and Tobago
250 properties

Caribbean

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70 Holiday homes

Filters applied: Penthouse

(4) Excellent 

13

Penthouse accommodation in Caribbean

Saint Peter Parish / Speightstown

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary

from £150 / night

£1050 - £1750 / week

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Responds fast!
avg. 3 hours 9 minutes

from £150 / night

(3) Excellent 

20

Holiday penthouse with shared pool in Caribbean

Willemstad / Mambo Beach

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool
“THE Place to stay in Curacao!!!” We just got back from a week in Curacao with our three daughters. I had a hard time deciding where to stay and kept going back and forth between wanting to stay in the Jan Thiel area and the Ocean Resort ( Sea Aquarium
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from £297 / night

£2079 - £3188 / week

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from £297 / night

(18) Very Good 

32

Holiday penthouse with golf nearby in Barbados

Saint Peter Parish / Speightstown

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Suitable for children age 5+
“Caribbean Dreamin'” My girlfriend and I enjoyed the absolute BEST week we could have hoped for at this apartment. Both Trisha and her housekeeper, Marva, could not have been more helpful and accommodating. And the apartment was a perfect base to en
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from £150 / night

£1000 - £1600 / week

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from £150 / night

(1) Excellent 

17

Holiday penthouse in Caribbean

Las Terrenas / El Portillo

2 6 2 nights min

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

from £193 / night

£1154 - £1385 / week

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from £193 / night

20

Holiday penthouse with shared pool in Caribbean

Willemstad / Mambo Beach

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool

from £297 / night

£2079 - £3188 / week

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from £297 / night

24

Penthouse letting in Caribbean with shared pool, golf nearby

Saint James Parish / Holetown

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £400 / night

£2800 - £5089 / week

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from £400 / night

(37) Excellent 

89

Holiday penthouse rental

Bequia / Richmond

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 0.75 km
  • Swimming pool
  • Car not necessary
“An ideal holiday” Tropical Hideaway was utterly delightful in every respect. The brand-new property is beautiful, offering several accommodations, each differently imaginative and carefully equipped with quality furnishings, nestled in a lovely growin
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from £280 / night

£1777 - £2539 / week

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from £280 / night

24

Penthouse rental in Barbados with shared pool

Saint James Parish / Holetown

4 8 Min stay varies

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

from £1385 / night

£9693 - £26924 / week

Enquire View

from £1385 / night

16

Holiday penthouse in Caribbean

Puerto Plata Province / Cabarete

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Child friendly

from £46 / night

£318 / week

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Responds fast!
avg. 59 minutes

from £46 / night

13

Caribbean holiday penthouse rental

Isabela / Barrio Bajuras

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min
  • Air conditioning

from £135 / night

£943 / week

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Responds fast!
avg. 3 hours 23 minutes

from £135 / night

(11) Excellent 

Certificate of Excellence

21

Holiday penthouse with shared pool, golf nearby in Caribbean

San Pedro de Macoris Province / Juan Dolio

3 8 4 nights min

  • 3 bedrooms
  • Sleeps 8
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool
“This location is awesome but a but remote” I really enjoyed my stay. Rosemary is a great lady to deal with. The domestics staff made all the difference. The only issue is distance to the beach. If you like golf though this place is amazing
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Certificate of Excellence

from £173 / night

£1035 / week

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from £173 / night

74

Holiday penthouse in Caribbean

Punta Cana / Bavaro

3 12 4 nights min

  • 3 bedrooms
  • Sleeps 12
  • 4 nights min
  • Child friendly
  • Pet friendly

from £108 / night

£754 / week

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Responds fast!
avg. 21 minutes

from £108 / night

13

Penthouse rental in Caribbean with shared pool, golf nearby

Saint Ann Parish / Ocho Rios

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Air conditioning

from £177 / night

£1212 / week

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from £177 / night

(23) Excellent 

50

Holiday penthouse with shared pool, golf nearby in Caribbean

Saint James Parish / Royal Westmoreland Golf Resort

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+
“Amazing Apartment, Great Location and Facilities” We stayed here for one week and had an absolutely amazing time. The apartment is fantastic value for money with a great sea view and has everything you could wish for. It's ideal that it's located at R
…see more

from £170 / night

£1190 - £1925 / week

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from £170 / night

(2) Excellent 

25

Penthouse rental in Barbados with swimming pool

Saint James Parish / Holetown

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Wonderful Property” We had the most amazing time at Smugglers Cove. Our condo was so beautiful, the decor was fab and we loved having the plunge pool on the terrace it was superb. Our cook prepared breakfast daily, we dined out mostly for lunch and so
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from £1077 / night

£7539 - £17231 / week

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from £1077 / night

(1) Excellent 

24

Penthouse rental in Caribbean with shared pool

Saint James Parish / Holetown

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Swimming pool
“Wow Amazing” The villa was incredible. We were blown away the minute we arrived. Everything was perfect we cannot say one bad things about this place, the beach, the people, the food all of it was amazing.
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from £1308 / night

£9154 - £21539 / week

Enquire View

from £1308 / night

42

Holiday penthouse in Caribbean

Las Terrenas / Playa Bonita

3 6 3 nights min

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

from £347 / night

£2308 / week

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from £347 / night

14

Holiday penthouse with shared pool in St. Lucia

Castries Quarter / Marigot Bay

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning

from £210 / night

£1470 / week

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from £210 / night

52

Holiday penthouse in St. Barthelemy

St. Barts / Gustavia

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 3 km
  • Child friendly
  • Car not necessary

from £815 / night

£5703 - £14115 / week

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from £815 / night

17

Penthouse rental in Caribbean

Puerto Plata Province / Cabarete

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Child friendly

from £100 / night

£695 / week

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from £100 / night

(1) Excellent 

24

Holiday penthouse with shared pool in Caribbean

Sosua / El Batey

3 7 1 night min

  • 3 bedrooms
  • Sleeps 7
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Swimming pool

from £137 / night

£804 / week

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from £137 / night

11

Holiday penthouse rental

Puerto Plata Province / Cabarete

3 6 3 nights min

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

from £227 / night

£993 / week

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from £227 / night

15

Penthouse rental in Caribbean with shared pool

Sint Maarten / Oyster Pond

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £330 / night

£2304 / week

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from £330 / night

20

Penthouse rental in Turks and Caicos

Providenciales / Turtle Cove

3 4 Min stay varies

  • 3 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool

from £231 / night

£1616 / week

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from £231 / night

(1) Excellent 

46

Holiday penthouse in Caribbean

Santo Domingo Province / Santo Domingo

6 14 2 nights min

  • 6 bedrooms
  • Sleeps 14
  • 2 nights min
  • Nearest beach 25 km
  • Child friendly
  • Air conditioning

from £307 / night

£2149 / week

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from £307 / night

(1) Excellent 

34

Holiday penthouse in Dominican Republic

Puerto Plata Province / Puerto Plata

2 6 3 nights min

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

from £120 / night

£693 / week

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Responds fast!
avg. 3 hours 42 minutes

from £120 / night

(5) Excellent 

18

Puerto Rico holiday penthouse rental

Puerto Rico / Rincon

3 8 2 nights min

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

from £154 / night

£962 - £1070 / week

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from £154 / night

(1) Excellent 

30

Dominican Republic holiday penthouse rental

Santo Domingo Province / Santo Domingo

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

from £54 / night

£347 / week

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from £54 / night

16

Holiday penthouse with shared pool, golf nearby in Caribbean

Puerto Rico / Humacao

3 7 2 nights min

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

from £250 / night

£2154 / week

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Responds fast!
avg. 3 hours 39 minutes

from £250 / night

(1) Excellent 

19

Caribbean holiday penthouse rental

Santo Domingo / Santo Domingo City

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Air conditioning

from £139 / night

£924 - £1193 / week

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from £139 / night

(1) Very Good 

49

Penthouse letting in Caribbean with shared pool

Puerto Rico / Loiza

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Swimming pool

from £97 / night

£635 / week

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Responds fast!
avg. 1 hour 0 minutes

from £97 / night

(2) Excellent 

25

Penthouse rental in Caribbean

Kingston Parish / Kingston

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Child friendly
  • Air conditioning

from £74 / night

£512 / week

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Responds fast!
avg. 2 hours 54 minutes

from £74 / night

(2) Excellent 

11

Penthouse rental in Puerto Rico with shared pool

Puerto Rico / Fajardo

3 12 2 nights min

  • 3 bedrooms
  • Sleeps 12
  • 2 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“The best place to stay in Fajardo” This is a two-story penthouse apartment. It is located in a gated community, and we felt very safe during our entire stay. It has assigned parking spaces and is accessible by stairs and elevator. The first floor c
…see more

from £231 / night

£1077 / week

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from £231 / night

36

Turks and Caicos holiday penthouse rental

Providenciales / Turtle Cove

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Nearest beach 0.5 km
  • Swimming pool
  • Child friendly

from £250 / night

£1750 / week

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from £250 / night

(8) Excellent 

95

Holiday penthouse with shared pool, golf nearby in Caribbean

La Altagracia Province / Punta Cana

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Swimming pool

from £230 / night

£1534 / week

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Responds fast!
avg. 1 hour 42 minutes

from £230 / night

4

Holiday penthouse in Dominican Republic

Puerto Plata Province / Imbert

2 6 3 nights min

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

from £69 / night

£478 / week

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from £69 / night

5

Holiday penthouse with golf nearby in Caribbean

Puerto Plata Province / Puerto Plata

1 6 30 nights min

  • 1 bedroom
  • Sleeps 6
  • 30 nights min
  • Child friendly
  • Air conditioning

from £26 / night

£180 / week

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from £26 / night

8

Dominican Republic holiday penthouse rental

Punta Cana / Bavaro

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

from £193 / night

£1539 / week

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from £193 / night

10

Holiday penthouse with shared pool in Caribbean

La Altagracia Province / Punta Cana

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly

from £193 / night

£1347 - £4508 / week

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from £193 / night

(1) Excellent 

80

Dominican Republic holiday penthouse rental

Santo Domingo Province / Boca Chica

3 10 3 nights min

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

from £227 / night

£1589 / week

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from £227 / night

1