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
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Showing 61–76 of 76 hotels
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-inclusive
All-inclusive
All-inclusive
All-inclusive
All-inclusive
All-inclusive
All-inclusivePrices are for two adults sharing a room, taxes included.