Pleasant Holidays · Flights + hotel
Secret Bay
5-starDominica, Caribbean
From $4,182
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Caribbean hotels and resorts
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Showing 1–30 of 42 hotels
Pleasant Holidays · Flights + hotel
Park Hyatt St. Kitts
5-starSt. Kitts and Nevis, Caribbean
From $3,167
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
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
Pleasant Holidays · Flights + hotel
The Westin Grand Cayman Seven Mile Beach Resort & Spa
4.5-starCayman Islands, Caribbean · Grand Cayman
From $3,122
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays · Flights + hotel
Hyatt Regency Aruba Resort Spa and Casino
4.5-starAruba, Caribbean
From $3,715
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
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
Dreams Playa Esmeralda Resort & Spa
4.5-starDominican Republic, Caribbean · Miches
From $1,587
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 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
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
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
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
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
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
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
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
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
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
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
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
Prices are for two adults sharing a room, taxes included.