Pleasant Holidays · Flights + hotel
SLS Baha Mar
5-starBahamas, Caribbean · Baha Mar
From $1,571
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Caribbean hotels and resorts
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Showing 1–30 of 76 hotels
Pleasant Holidays · Flights + hotel
The Ritz-Carlton, St. Thomas
5-starU.S. Virgin Islands, Caribbean · St. Thomas, USVI
Offer: $200 off
From $4,191
per person, 2 adults sharing
Stay Feb 5 – Feb 10, 2027
Pleasant Holidays · Flights + hotel
The Ocean Club, A Four Seasons Resort, Bahamas
5-starBahamas, Caribbean · Paradise Island
From $7,508
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
All-inclusivePleasant Holidays · Flights + hotel
Zoetry Marigot Bay St. Lucia
5-starSaint Lucia, Caribbean · St. Lucia
Offer: $200 off
From $1,795
per person, 2 adults sharing
Stay Feb 5 – Feb 10, 2027
Pleasant Holidays · Flights + hotel
The Ritz-Carlton, Aruba
5-starAruba, Caribbean
From $4,153
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
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
Dorado Beach, a Ritz-Carlton Reserve
5-starPuerto Rico, Caribbean · Carolina
From $9,468
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
All-inclusivePleasant Holidays · Flights + hotel
Zemi Miches Punta Cana, All-Inclusive Resort, Curio Collection by Hilton
4.5-starDominican Republic, Caribbean · Miches
Offer: $200 off
From $1,844
per person, 2 adults sharing
Stay Feb 5 – Feb 10, 2027
All-inclusivePleasant Holidays · Flights + hotel
Majestic Mirage Punta Cana
4.5-starDominican Republic, Caribbean · Dom. Republic, Punta Cana
Offer: $200 off
From $1,491
per person, 2 adults sharing
Stay Feb 5 – Feb 10, 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 Reef Atlantis
4.5-starBahamas, Caribbean · Paradise Island
From $1,650
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
All-inclusivePleasant Holidays · Flights + hotel
Hyatt Ziva Cap Cana
4.5-starDominican Republic, Caribbean · Dom. Republic, Punta Cana
Offer: $200 off
From $2,307
per person, 2 adults sharing
Stay Feb 5 – Feb 10, 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
Pleasant Holidays · Flights + hotel
The Cove Atlantis
4.5-starBahamas, Caribbean · Paradise Island
From $2,161
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
Pleasant Holidays · Flights + hotel
Fairmont Royal Pavilion
4.5-starBarbados, Caribbean
From $6,066
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 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
Pleasant Holidays · Flights + hotel
The Condado Plaza Hotel
4-starPuerto Rico, Caribbean · San Juan
From $1,011
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
Caribe Hilton
4-starPuerto Rico, Caribbean · San Juan
From $1,305
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 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
Grand Palladium Palace Resort Spa & Casino
4-starDominican Republic, Caribbean · Dom. Republic, Punta Cana
Offer: $200 off
From $1,400
per person, 2 adults sharing
Stay Feb 5 – Feb 10, 2027
Pleasant Holidays · Flights + hotel
Margaritaville Beach Resort Nassau, Bahamas
4-starBahamas, Caribbean · Nassau
From $1,408
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
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
Iberostar Selection Rose Hall Suites
4-starJamaica, Caribbean
From $2,173
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
Waves Hotel & Spa, An Autograph Collection Hotel
4-starBarbados, Caribbean
Offer: $200 off
From $2,674
per person, 2 adults sharing
Stay Feb 5 – Feb 10, 2027
Prices are for two adults sharing a room, taxes included.