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
Caribbean hotels and resorts
Filters
Showing 31–60 of 67 hotels
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
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
Pleasant Holidays · Flights + hotel
Grand Cayman Marriott Beach Resort
4-starCayman Islands, Caribbean · Grand Cayman
From $3,914
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays · Flights + hotel
St. Kitts Marriott Resort & The Royal Beach Casino
4-starSt. Kitts and Nevis, Caribbean
Offer: $200 off
From $1,382
per person, 2 adults sharing
Stay Feb 5 – Feb 10, 2027
All-inclusivePleasant Holidays · Flights + hotel
Royalton Grenada, An Autograph Collection All-Inclusive Resort
4-starGrenada, Caribbean
From $1,411
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
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
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
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
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
Pleasant Holidays
Sugar Beach, A Viceroy Resort
5-starSaint Lucia, Caribbean · St. Lucia
Request this hotel
All-inclusivePrices are for two adults sharing a room, taxes included.