Holiday penthouses in Caribbean

View larger map

Price per night

£230 Average

Price per night

to

Bedrooms

Bathrooms

Location

Also consider

Villas St. Barts
3,541 properties
Villas Barbados
2,730 properties
Villas St. Maarten - Saint Martin
2,632 properties
Villas Dominican Republic
2,052 properties
Villas Jamaica
2,018 properties
Apartments Puerto Rico
1,242 properties
US Virgin Isles
760 properties
Villas Anguilla
757 properties
Villas Guadeloupe
671 properties
Villas Bahamas
668 properties
Villas Aruba
437 properties
Villas St. Lucia
425 properties
Houses St. Vincent and the Grenadines
424 properties
Villas British Virgin Isles
375 properties
Apartments Martinique
340 properties
Houses Antigua and Barbuda
312 properties
Holiday rentals Turks and Caicos Islands
301 properties
Houses Cayman Islands
261 properties
Villas Grenada
223 properties
Villas Curacao
209 properties
Payment Protection
To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

57 Holiday homes

Filters applied: Penthouse (57)

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

(6) Excellent 

1 / 44

Holiday penthouse with shared pool, golf nearby in Bavaro

Punta Cana / Bavaro

3 7 1 night min stay

Penthouse / 3 bedrooms / sleeps 7 / 1 night min stay

Add to shortlist

from £176 / night

£1375 / week

Book

from £176 / night

(6) Excellent 

1 / 21

Holiday penthouse with shared pool, golf nearby in Juan Dolio

San Pedro de Macoris Province / Juan Dolio

3 8 4 nights min stay

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

Add to shortlist

from £154 / night

£924 - £1154 / week

Book

from £154 / night

1 / 19

Santo Domingo City holiday penthouse rental

Santo Domingo / Santo Domingo City

3 8 4 nights min stay

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

Add to shortlist

from £173 / night

£1104 / week

Book

from £173 / night

Featured properties

1 / 14

Cabarete holiday penthouse rental

Puerto Plata Province / Cabarete

3 8 1 night min stay

Penthouse / 3 bedrooms / sleeps 8 / 1 night min stay

Add to shortlist

from £311 / night

£2069 / week

Book

from £311 / night

1 / 5

Penthouse accommodation in Simpson Bay with shared pool

Simpson Bay / Simpson Bay Beach

2 4 Min stay varies

Penthouse / 2 bedrooms / sleeps 4 / Min stay varies

Add to shortlist

from £207 / night

£1380 - £2069 / week

Book

from £207 / night

(4) Excellent 

1 / 16

Penthouse rental in Bavaro Beach with shared pool, golf nearby

Punta Cana / Bavaro Beach

4 6 2 nights min stay

Penthouse / 4 bedrooms / sleeps 6 / 2 nights min stay

Add to shortlist

from £276 / night

£1156 / week

Book

from £276 / night

1 / 23

Holiday penthouse with shared pool in Fajardo

Puerto Rico / Fajardo

3 6 5 nights min stay

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

Add to shortlist

from £180 / night

£1256 - £2221 / week

Book

from £180 / night

1 / 18

Holiday penthouse with shared pool in Sosua

Sosua / El Batey

3 7 Min stay varies

Penthouse / 3 bedrooms / sleeps 7 / Min stay varies

Add to shortlist

from £118 / night

£687 - £1000 / week

Book

from £118 / night

(1) Excellent 

1 / 24

Holiday penthouse in Rincon

Rincon / Barrio Puntas

3 7 Min stay varies

Penthouse / 3 bedrooms / sleeps 7 / Min stay varies

Add to shortlist

from £259 / night

£1449 - £2207 / week

Book

from £259 / night

1 / 14

Holiday penthouse rental

La Altagracia Province / Bayahibe

3 6 1 night min stay

Penthouse / 3 bedrooms / sleeps 6 / 1 night min stay

Add to shortlist

from £311 / night

£2138 / week

Book

from £311 / night

1 / 5

Penthouse rental in Fajardo with shared pool

Puerto Rico / Fajardo

3 13 2 nights min stay

Penthouse / 3 bedrooms / sleeps 13 / 2 nights min stay

Add to shortlist

from £207 / night

£966 / week

Book

from £207 / night

1 / 10

Holiday penthouse with shared pool in Las Terrenas

Samana Province / Las Terrenas

2 4 1 night min stay

Penthouse / 2 bedrooms / sleeps 4 / 1 night min stay

Add to shortlist

from £159 / night

£897 / week

Book

from £159 / night

1 / 13

Isabela holiday penthouse rental

Isabela / Barrio Bajuras

3 6 1 night min stay

Penthouse / 3 bedrooms / sleeps 6 / 1 night min stay

Add to shortlist

from £207 / night

£1449 / week

Book

from £207 / night

1 / 16

Holiday penthouse with shared pool, golf nearby in Humacao

Puerto Rico / Humacao

3 7 2 nights min stay

Penthouse / 3 bedrooms / sleeps 7 / 2 nights min stay

Add to shortlist

from £276 / night

£1932 - £2173 / week

Book

from £276 / night

1 / 13

Holiday penthouse rental

Isabela / Barrio Bajuras

3 6 1 night min stay

Penthouse / 3 bedrooms / sleeps 6 / 1 night min stay

Add to shortlist

from £207 / night

£1449 / week

Book

from £207 / night

1 / 12

Playa Cofresi holiday penthouse rental

Puerto Plata / Playa Cofresi

2 5 1 night min stay

Penthouse / 2 bedrooms / sleeps 5 / 1 night min stay

Add to shortlist

from £87 / night

£587 / week

Book

from £87 / night

1 / 13

Penthouse rental in Ocho Rios with shared pool, golf nearby

Saint Ann Parish / Ocho Rios

2 6 1 night min stay

Penthouse / 2 bedrooms / sleeps 6 / 1 night min stay

Add to shortlist

from £159 / night

£1087 / week

Book

from £159 / night

1 / 6

Holiday penthouse rental

Montego Bay / St James, Montego Bay

3 6 2 nights min stay

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

Add to shortlist

from £104 / night

£759 / week

Book

from £104 / night

1 / 13

Penthouse accommodation in Speightstown

Saint Peter Parish / Speightstown

3 6 Min stay varies

Penthouse / 3 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £150 / night

£1000 - £1750 / week

Book

from £150 / night

(1) Excellent 

1 / 56

Penthouse rental in San Juan

San Juan / Hato Rey

1 2 2 nights min stay

Penthouse / 1 bedroom / sleeps 2 / 2 nights min stay

Add to shortlist

from £66 / night

£380 / week

Book

from £66 / night

1 / 28

Bavaro Beach holiday penthouse rental

Punta Cana / Bavaro Beach

2 5 3 nights min stay

Penthouse / 2 bedrooms / sleeps 5 / 3 nights min stay

Add to shortlist

from £87 / night

£621 - £1173 / week

Book

from £87 / night

1 / 17

Holiday penthouse in Las Terrenas

Las Terrenas / El Portillo

2 6 Min stay varies

Penthouse / 2 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £138 / night

£242 - £1621 / week

Book

from £138 / night

1 / 8

Ocho Rios holiday penthouse rental

Saint Ann Parish / Ocho Rios

2 4 1 night min stay

Penthouse / 2 bedrooms / sleeps 4 / 1 night min stay

Add to shortlist

from £118 / night

£821 / week

Book

from £118 / night

1 / 28

Santo Domingo holiday penthouse rental

Santo Domingo Province / Santo Domingo

1 4 3 nights min stay

Penthouse / 1 bedroom / sleeps 4 / 3 nights min stay

Add to shortlist

from £48 / night

£311 / week

Book

from £48 / night

1 / 80

Boca Chica holiday penthouse rental

Santo Domingo Province / Boca Chica

3 10 4 nights min stay

Penthouse / 3 bedrooms / sleeps 10 / 4 nights min stay

Add to shortlist

from £190 / night

£1328 / week

Book

from £190 / night

1 / 9

Penthouse rental in Port-au-Prince

Ouest Department / Port-au-Prince

2 4 1 night min stay

Penthouse / 2 bedrooms / sleeps 4 / 1 night min stay

Add to shortlist

from £69 / night

£483 / week

Book

from £69 / night

1 / 15

Penthouse rental in Oyster Pond with shared pool

Saint-Martin / Oyster Pond

3 6 7 nights min stay

Penthouse / 3 bedrooms / sleeps 6 / 7 nights min stay

Add to shortlist

from £296 / night

£2066 / week

Book

from £296 / night

1 / 11

Holiday penthouse with shared pool, golf nearby in Bavaro Beach

Punta Cana / Bavaro Beach

1 4 Min stay varies

Penthouse / 1 bedroom / sleeps 4 / Min stay varies

Add to shortlist

from £104 / night

£518 - £690 / week

Book

from £104 / night

(2) Excellent 

1 / 8

Isabela holiday penthouse rental

Isabela / Barrio Bajuras

3 5 2 nights min stay

Penthouse / 3 bedrooms / sleeps 5 / 2 nights min stay

Add to shortlist

from £69 / night

£449 - £521 / week

Book

from £69 / night

1 / 11

Holiday penthouse in Paynes Bay

Saint James Parish / Paynes Bay

4 8 Min stay varies

Penthouse / 4 bedrooms / sleeps 8 / Min stay varies

Add to shortlist

from £1173 / night

£8207 / week

Book

from £1173 / night

1 / 31

Penthouse letting in Loiza with shared pool

Puerto Rico / Loiza

3 8 2 nights min stay

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

Add to shortlist

from £87 / night

£569 / week

Book

from £87 / night

1 / 39

Holiday penthouse with shared pool in Punta Cana

La Altagracia Province / Punta Cana

3 2 4 nights min stay

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

Add to shortlist

from £76 / night

£532 - £652 / week

Book

from £76 / night

(16) Very Good 

1 / 32

Holiday penthouse with golf nearby in Speightstown

Saint Peter Parish / Speightstown

2 4 Min stay varies

Penthouse / 2 bedrooms / sleeps 4 / Min stay varies

Add to shortlist

from £140 / night

£1600 / week

Book

from £140 / night

(1) Very Good 

1 / 21

Penthouse rental in Humacao with shared pool, golf nearby

Puerto Rico / Humacao

2 4 4 nights min stay

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

Add to shortlist

from £248 / night

£1474 / week

Book

from £248 / night

1 / 30

Penthouse accommodation in Loiza

Puerto Rico / Loiza

3 8 5 nights min stay

Penthouse / 3 bedrooms / sleeps 8 / 5 nights min stay

Add to shortlist

from £118 / night

£690 / week

Book

from £118 / night

1 / 5

Holiday penthouse with golf nearby in Puerto Plata

Puerto Plata Province / Puerto Plata

1 6 30 nights min stay

Penthouse / 1 bedroom / sleeps 6 / 30 nights min stay

Add to shortlist

from £23 / night

£161 / week

Book

from £23 / night

1 / 14

Penthouse rental in Loiza

Puerto Rico / Loiza

3 8 Min stay varies

Penthouse / 3 bedrooms / sleeps 8 / Min stay varies

Add to shortlist

from £128 / night

£663 - £725 / week

Book

from £128 / night

1 / 13

Holiday penthouse with shared pool in Bavaro

Punta Cana / Bavaro

2 3 4 nights min stay

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

Add to shortlist

from £63 / night

£745 / week

Book

from £63 / night

1 / 13

Holiday penthouse with golf nearby in Speightstown

Saint Peter Parish / Speightstown

3 6 Min stay varies

Penthouse / 3 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £140 / night

£840 - £1995 / week

Book

from £140 / night

1 / 40

Holiday penthouse in Santo Domingo

Santo Domingo Province / Santo Domingo

6 14 2 nights min stay

Penthouse / 6 bedrooms / sleeps 14 / 2 nights min stay

Add to shortlist

from £296 / night

£2069 - £2207 / week

Book

from £296 / night

1 / 10

Holiday penthouse in Sosua

Sosua / El Batey

2 5 1 night min stay

Penthouse / 2 bedrooms / sleeps 5 / 1 night min stay

Add to shortlist

from £114 / night

£638 - £742 / week

Book

from £114 / night

1 / 14

Holiday penthouse in Las Terrenas

Las Terrenas / Playa Bonita

3 6 3 nights min stay

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

Add to shortlist

from £311 / night

£2069 / week

Book

from £311 / night

1 / 24

Holiday penthouse with shared pool in Playa Cofresi

Puerto Plata / Playa Cofresi

2 7 3 nights min stay

Penthouse / 2 bedrooms / sleeps 7 / 3 nights min stay

Add to shortlist

from £114 / night

£759 / week

Book

from £114 / night

1 / 20

Holiday penthouse with shared pool in Mambo Beach

Willemstad / Mambo Beach

3 6 7 nights min stay

Penthouse / 3 bedrooms / sleeps 6 / 7 nights min stay

Add to shortlist

from £267 / night

£1649 - £2858 / week

Book

from £267 / night

(3) Excellent 

1 / 20

Holiday penthouse with shared pool in Mambo Beach

Willemstad / Mambo Beach

3 6 7 nights min stay

Penthouse / 3 bedrooms / sleeps 6 / 7 nights min stay

Add to shortlist

from £267 / night

£1649 - £2858 / week

Book

from £267 / night

(1) Excellent 

1 / 20

Holiday penthouse with shared pool in Playa Cofresi

Puerto Plata / Playa Cofresi

2 4 1 night min stay

Penthouse / 2 bedrooms / sleeps 4 / 1 night min stay

Add to shortlist

from £80 / night

£535 / week

Book

from £80 / night

(1) Poor 

1 / 16

Holiday penthouse with shared pool in Puerto Plata

Puerto Plata / Lifestyle Hacienda Resort

2 6 2 nights min stay

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

Add to shortlist

from £59 / night

£414 / week

Book

from £59 / night

1 / 14

Penthouse rental in Holetown with shared pool

Saint James Parish / Holetown

4 8 Min stay varies

Penthouse / 4 bedrooms / sleeps 8 / Min stay varies

Add to shortlist

from £966 / night

£6759 - £15449 / week

Enquire

from £966 / night

(13) Excellent 

1 / 24

Holiday penthouse with shared pool, golf nearby in Royal Westmoreland Golf Resort

Saint James Parish / Royal Westmoreland Golf Resort

2 4 Min stay varies

Penthouse / 2 bedrooms / sleeps 4 / Min stay varies

Add to shortlist

from £160 / night

£1120 - £1925 / week

Enquire

from £160 / night

1 / 14

Penthouse rental in Holetown with swimming pool

Saint James Parish / Holetown

4 8 Min stay varies

Penthouse / 4 bedrooms / sleeps 8 / Min stay varies

Add to shortlist

from £966 / night

£6759 - £9656 / week

Enquire

from £966 / night

Don’t let an old browser slow down your holiday

Your browser is out of date and might not work well with our website. Download the latest version to speed up your hunt for the perfect holiday home.

Just click on the icons to get to the download page