Pleasant Holidays · Flights + hotel
Grand Hyatt Baha Mar
4.5-starBahamas, Caribbean · Baha Mar
From $1,636
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Caribbean hotels and resorts
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14 hotels
All-inclusivePleasant Holidays · Flights + hotel
Hard Rock Hotel Punta Cana
4.5-starDominican Republic, Caribbean · Dom. Republic, Punta Cana
Offer: $200 off
From $1,480
per person, 2 adults sharing
Stay Feb 5 – Feb 10, 2027
All-inclusivePleasant Holidays · Flights + hotel
Riu Palace Bavaro
4-starDominican Republic, Caribbean · Dom. Republic, Punta Cana
Offer: $200 off
From $1,142
per person, 2 adults sharing
Stay Feb 5 – Feb 10, 2027
Pleasant Holidays · Flights + hotel
Hyatt Regency Grand Reserve Puerto Rico
4-starPuerto Rico, Caribbean
From $1,332
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
All-inclusivePleasant Holidays · Flights + hotel
Ocean Coral Spring
4-starJamaica, Caribbean
From $1,602
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
All-inclusivePleasant Holidays · Flights + hotel
Riu Negril
4-starJamaica, Caribbean
From $1,726
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
All-inclusivePleasant Holidays · Flights + hotel
St. James's Club and Villas
4-starAntigua, Caribbean
From $2,400
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays · Hotel only
Windjammer Landing Resort and Residences
4-starSaint Lucia, Caribbean · St. Lucia
Offer: $200 off
From $1,669
per person, 2 adults sharing
Stay Feb 5 – Feb 10, 2027
All-inclusivePleasant Holidays · Flights + hotel
Riu Palace Aruba
4-starAruba, Caribbean
Offer: $200 off
From $2,250
per person, 2 adults sharing
Stay Feb 5 – Feb 10, 2027
All-inclusivePleasant Holidays · Hotel only
Royalton Saint Lucia, An Autograph Collection All-Inclusive
4-starSaint Lucia, Caribbean · St. Lucia
From $1,249
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
All-inclusivePleasant Holidays · Flights + hotel
Riu Ocho Rios
3.5-starJamaica, Caribbean
From $1,683
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
All-inclusive
All-inclusive
All-inclusivePrices are for two adults sharing a room, taxes included.