All-inclusivePleasant Holidays · Flights + hotel
Iberostar Waves Rose Hall Beach
3.5-starJamaica, Caribbean
From $1,888
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Caribbean hotels and resorts
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Showing 31–49 of 49 hotels
All-inclusive
All-inclusivePleasant Holidays · Flights + hotel
Sandals Royal Barbados
Barbados, Caribbean
From $4,602
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays · Flights + hotel
Kimpton Seafire Resort + Spa
5-starCayman Islands, Caribbean · Grand Cayman
From $4,716
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays · Flights + hotel
Sheraton Puerto Rico Resort & Casino
4-starPuerto Rico, Caribbean · Old San Juan
From $1,457
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays · Flights + hotel
Sunshine Suites Resort
3.5-starCayman Islands, Caribbean · Grand Cayman
From $1,838
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays · Flights + hotel
Amsterdam Manor Beach Resort
3.5-starAruba, Caribbean
From $2,915
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays
Sugar Beach, A Viceroy Resort
5-starSaint Lucia, Caribbean · St. Lucia
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Prices are for two adults sharing a room, taxes included.