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 47 hotels
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
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
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
Couples Tower Isle
4.5-starJamaica, Caribbean
From $2,030
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
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
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
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
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
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
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
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
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
St. James's Club and Villas
4-starAntigua, Caribbean
From $2,400
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays · Flights + hotel
Hilton Aruba Caribbean Resort & Casino
4-starAruba, Caribbean
From $2,981
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays · Flights + hotel
The Royal at Atlantis
4-starBahamas, Caribbean
Offer: $200 off
From $1,220
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
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
Riu Palace Aruba
4-starAruba, Caribbean
Offer: $200 off
From $2,250
per person, 2 adults sharing
Stay Feb 5 – Feb 10, 2027
Pleasant Holidays · Flights + hotel
St. Kitts Marriott Resort & The Royal Beach Casino
4-starSt. Kitts and Nevis, Caribbean
Offer: $200 off
From $1,382
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
Pleasant Holidays · Flights + hotel
Divi Aruba Phoenix Beach Resort
4-starAruba, Caribbean
From $2,911
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Prices are for two adults sharing a room, taxes included.