Pleasant Holidays · Flights + hotel
The Condado Plaza Hotel
4-starPuerto Rico, Caribbean · San Juan
From $1,011
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
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Showing 31–60 of 129 hotels
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
Caribe Hilton
4-starPuerto Rico, Caribbean · San Juan
From $1,305
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 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
Grand Palladium Palace Resort Spa & Casino
4-starDominican Republic, Caribbean · Dom. Republic, Punta Cana
Offer: $200 off
From $1,400
per person, 2 adults sharing
Stay Feb 5 – Feb 10, 2027
Pleasant Holidays · Flights + hotel
Margaritaville Beach Resort Nassau, Bahamas
4-starBahamas, Caribbean · Nassau
From $1,408
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
Pleasant Holidays · Flights + hotel
San Juan Marriott Resort & Stellaris Casino
4-starPuerto Rico, Caribbean · San Juan
From $1,629
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
Bahia Principe Escape Runaway Bay
4-starJamaica, Caribbean
From $1,748
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
All-inclusivePleasant Holidays · Flights + hotel
Riu Montego Bay
4-starJamaica, Caribbean
From $1,866
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
All-inclusivePleasant Holidays · Flights + hotel
Moon Palace Jamaica
4-starJamaica, Caribbean
From $2,167
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
All-inclusivePleasant Holidays · Flights + hotel
Iberostar Selection Rose Hall Suites
4-starJamaica, Caribbean
From $2,173
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
All-inclusivePleasant Holidays · Flights + hotel
Riu Palace Antillas
4-starAruba, Caribbean
From $2,249
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
All-inclusivePleasant Holidays · Flights + hotel
Riu Palace Jamaica
4-starJamaica, Caribbean
From $2,399
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
All-inclusivePleasant Holidays · Flights + hotel
Waves Hotel & Spa, An Autograph Collection Hotel
4-starBarbados, Caribbean
Offer: $200 off
From $2,674
per person, 2 adults sharing
Stay Feb 5 – Feb 10, 2027
Pleasant Holidays · Flights + hotel
Hilton Aruba Caribbean Resort & Casino
4-starAruba, Caribbean
From $2,981
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays · Flights + hotel
Renaissance Wind Creek Aruba Resort
4-starAruba, Caribbean
From $3,087
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
All-inclusivePleasant Holidays · Flights + hotel
Galley Bay Resort & Spa
4-starAntigua, Caribbean
From $5,448
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
All-inclusivePleasant Holidays · Flights + hotel
Princess Senses The Mangrove
4-starJamaica, Caribbean · Green Island
Offer: $200 off
From $7,087
per person, 2 adults sharing
Stay Feb 5 – Feb 10, 2027
Pleasant Holidays · Flights + hotel
The Royal at Atlantis
4-starBahamas, Caribbean
Offer: $200 off
From $1,220
per person, 2 adults sharing
Stay Feb 5 – Feb 10, 2027
All-inclusivePleasant Holidays · Flights + hotel
Riu Palace Aquarelle
4-starJamaica, Caribbean
Offer: $200 off
From $1,305
per person, 2 adults sharing
Stay Feb 5 – Feb 10, 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
Dreams Curacao Resort, Spa & Casino
4-starCuracao, Caribbean
Offer: $200 off
From $1,712
per person, 2 adults sharing
Stay Feb 5 – Feb 10, 2027
All-inclusivePleasant Holidays · Flights + hotel
Hyatt Vivid Punta Cana
4-starDominican Republic, Caribbean · Dom. Republic, Punta Cana
From $1,831
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
All-inclusivePleasant Holidays · Flights + hotel
Riu Reggae
4-starJamaica, Caribbean
From $1,971
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
All-inclusivePleasant Holidays · Flights + hotel
Riu Palace Tropical Bay
4-starJamaica, Caribbean
From $2,013
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 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 · Flights + hotel
The Verandah Antigua
4-starAntigua, Caribbean
From $2,510
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Prices are for two adults sharing a room, taxes included.