Pleasant Holidays · Flights + hotel
Royal Sonesta San Juan
4-starPuerto Rico, Caribbean · San Juan
From $1,509
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Caribbean hotels and resorts
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Showing 61–90 of 109 hotels
All-inclusivePleasant Holidays · Flights + hotel
Riu Palace Paradise Island
4-starBahamas, Caribbean · Paradise Island
From $1,558
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays · Flights + hotel
The Landings Resort and Spa
4-starSaint Lucia, Caribbean · St. Lucia
From $2,337
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays · Flights + hotel
Divi Aruba Phoenix Beach Resort
4-starAruba, Caribbean
From $2,911
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays · Flights + hotel
Aruba Marriott Resort & Stellaris Casino
4-starAruba, Caribbean
From $3,347
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 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
Royalton Negril, An Autograph Collection All-Inclusive Resort
4-starJamaica, Caribbean
From $1,878
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
All-inclusivePleasant Holidays · Flights + hotel
Sonesta Ocean Point Resort & Spa
4-starSint Maarten, Caribbean · Saint Maarten
From $1,934
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays · Flights + hotel
Fairmont El San Juan Hotel
4-starPuerto Rico, Caribbean · Carolina
From $2,024
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays · Flights + hotel
Wyndham Grand Rio Mar Rainforest Beach & Golf Resort
4-starPuerto Rico, Caribbean
From $2,211
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
All-inclusivePleasant Holidays · Flights + hotel
Sonesta Maho Beach Resort, Casino & Spa
3.5-starSint Maarten, Caribbean · Saint Maarten
From $1,454
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-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
Pleasant Holidays · Flights + hotel
The Coral at Atlantis
3.5-starBahamas, Caribbean · Paradise Island
From $1,272
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
All-inclusivePleasant Holidays · Flights + hotel
Sunscape Curacao Resort, Spa & Casino
3.5-starCuracao, Caribbean
From $1,701
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays · Flights + hotel
Divi Village Golf & Beach Resort
3.5-starAruba, Caribbean
From $2,154
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
All-inclusivePleasant Holidays · Flights + hotel
The Club Barbados Resort & Spa
3.5-starBarbados, Caribbean
From $2,358
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
All-inclusivePleasant Holidays · Flights + hotel
Pineapple Beach Club Antigua
3-starAntigua, Caribbean
From $2,853
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays · Flights + hotel
Holiday Inn Resort Aruba-Beach Resort & Casino
3-starAruba, Caribbean
From $2,303
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
All-inclusivePleasant Holidays · Flights + hotel
Sandals Royal Barbados
Barbados, Caribbean
From $4,602
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
All-inclusivePleasant Holidays · Flights + hotel
Sandals Ochi Beach Resort
Jamaica, Caribbean
From $2,392
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
All-inclusivePleasant Holidays · Flights + hotel
Sandals St. Lucia Grand Bay
Saint Lucia, Caribbean · St. Lucia
From $2,956
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
All-inclusivePleasant Holidays · Flights + hotel
Sandals Royal Bahamian Spa Resort & Offshore Island
Bahamas, Caribbean
From $3,044
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
All-inclusivePleasant Holidays · Flights + hotel
Beaches Turks and Caicos
Turks and Caicos, Caribbean · Turks & Caicos
Offer: $200 off
From $4,569
per person, 2 adults sharing
Stay Feb 5 – Feb 10, 2027
All-inclusivePleasant Holidays · Flights + hotel
Sandals St. Lucia Halcyon Beach
Saint Lucia, Caribbean · St. Lucia
From $2,620
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays · Flights + hotel
The St. Regis Bermuda Resort
5-starBermuda, Caribbean
Offer: $200 off
From $1,959
per person, 2 adults sharing
Stay Feb 5 – Feb 10, 2027
Pleasant Holidays · Flights + hotel
The Ritz-Carlton, Turks & Caicos
5-starTurks and Caicos, Caribbean · Turks & Caicos
Offer: $200 off
From $4,485
per person, 2 adults sharing
Stay Feb 5 – Feb 10, 2027
Pleasant Holidays · Flights + hotel
La Concha Resort, Puerto Rico, Autograph Collection
4-starPuerto Rico, Caribbean · San Juan
From $1,598
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
All-inclusive
Pleasant Holidays · Flights + hotel
Wyndham Alltra Punta Cana All Inclusive Resort
4-starDominican Republic, Caribbean · Dom. Republic, Punta Cana
From $1,482
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays
The Ritz-Carlton, Grand Cayman
5-starCayman Islands, Caribbean · Grand Cayman
Request this hotel
Prices are for two adults sharing a room, taxes included.