All-inclusivePleasant Holidays · Flights + hotel
Couples Tower Isle
4.5-starJamaica, Caribbean
From $2,030
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Caribbean hotels and resorts
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Showing 1–30 of 34 hotels
All-inclusive
All-inclusivePleasant Holidays · Flights + hotel
Couples Negril
4.5-starJamaica, Caribbean
From $2,700
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
All-inclusivePleasant Holidays · Flights + hotel
Couples Swept Away
4.5-starJamaica, Caribbean
Offer: $200 off
From $1,907
per person, 2 adults sharing
Stay Feb 5 – Feb 10, 2027
All-inclusivePleasant Holidays · Flights + hotel
JOIA Rose Hall by Iberostar
4.5-starJamaica, Caribbean
From $2,521
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
All-inclusivePleasant Holidays · Flights + hotel
Couples Sans Souci
4.5-starJamaica, Caribbean
From $2,610
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
All-inclusivePleasant Holidays · Flights + hotel
Melia Punta Cana Beach, A Wellness Inclusive Resort - Adults Only
4.5-starDominican Republic, Caribbean · Dom. Republic, Punta Cana
From $1,693
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
All-inclusivePleasant Holidays · Flights + hotel
Secrets Baby Beach Aruba
4.5-starAruba, Caribbean
From $3,454
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
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
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
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
Royalton Hideaway Blue Waters, An Autograph Collection All-Inclusive Resort
4-starJamaica, Caribbean
Offer: $200 off
From $1,266
per person, 2 adults sharing
Stay Feb 5 – Feb 10, 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 · 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
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
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
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
Jade Mountain
5-starSaint Lucia, Caribbean · St. Lucia
From $5,775
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays · Flights + hotel
Ladera Resort
4.5-starSaint Lucia, Caribbean · St. Lucia
From $4,324
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
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Prices are for two adults sharing a room, taxes included.