Pleasant Holidays · Flights + hotel
Kimpton Seafire Resort + Spa
5-starCayman Islands, Caribbean · Grand Cayman
From $4,716
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Caribbean hotels and resorts
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Showing 91–120 of 129 hotels
Pleasant Holidays · Flights + hotel
InterContinental Dominica Cabrits Resort & Spa
4.5-starDominica, Caribbean · Portsmouth
From $1,721
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
Pleasant Holidays · Flights + hotel
Zoetry Curacao Resort & Spa
4.5-starCuracao, Caribbean
From $2,178
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays · Flights + hotel
Cap Maison Resort & Spa
4.5-starSaint Lucia, Caribbean · St. Lucia
From $4,578
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays · Flights + hotel
Embassy Suites by Hilton Aruba Resort
4-starAruba, Caribbean
From $2,362
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays · Flights + hotel
Sheraton Puerto Rico Resort & Casino
4-starPuerto Rico, Caribbean · Old San Juan
From $1,457
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays · Flights + hotel
Radisson Blu Aruba
4-starAruba, Caribbean
From $2,941
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays · Flights + hotel
Rosalie Bay Resort
3.5-starDominica, Caribbean
From $912
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays · Flights + hotel
Sunshine Suites Resort
3.5-starCayman Islands, Caribbean · Grand Cayman
From $1,838
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays · Flights + hotel
Courtyard Aruba Resort
3.5-starAruba, Caribbean
From $2,327
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays · Flights + hotel
Amsterdam Manor Beach Resort
3.5-starAruba, Caribbean
From $2,915
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
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Pleasant Holidays
Sugar Beach, A Viceroy Resort
5-starSaint Lucia, Caribbean · St. Lucia
Request this hotel
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All-inclusivePrices are for two adults sharing a room, taxes included.