Pleasant Holidays · Flights + hotel
Grand Cayman Marriott Beach Resort
4-starCayman Islands, Caribbean · Grand Cayman
From $3,914
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Hotel and resort deals
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Showing 121–150 of 242 hotels
Pleasant Holidays · Flights + hotel
Outrigger Fiji Beach Resort
4-starViti Levu, Fiji · Coral Coast Area
Offer: $200 off
From $724
per person, 2 adults sharing
Stay Jan 29 – Feb 3, 2027
Pleasant Holidays · Flights + hotel
Sheraton Fiji Golf & Beach Resort
4-starViti Levu, Fiji · Denarau Marina
Offer: $200 off
From $765
per person, 2 adults sharing
Stay Jan 29 – Feb 3, 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
Royalton Grenada, An Autograph Collection All-Inclusive Resort
4-starGrenada, Caribbean
From $1,411
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays · Flights + hotel
Casa Dorada Los Cabos Resort & Spa
4-starLos Cabos, Mexico · Cabo San Lucas
From $1,530
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays · Flights + hotel
Pacific Resort Rarotonga
4-starRarotonga, Cook Islands
Offer: $100 off, book by Nov 8, 2026
From $1,583
per person, 2 adults sharing
Stay Jan 29 – Feb 3, 2027
Pleasant Holidays · Flights + hotel
The Landings Resort and Spa
4-starSaint Lucia, Caribbean · St. Lucia
From $2,337
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
All-inclusivePleasant Holidays · Flights + hotel
Planet Hollywood Costa Rica by Royalton, An Autograph Collection All-Inc
4-starCosta Rica, Central America · Guanacaste
Offer: $200 off
From $2,664
per person, 2 adults sharing
Stay Feb 5 – Feb 10, 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
Pleasant Holidays · Flights + hotel
Aruba Marriott Resort & Stellaris Casino
4-starAruba, Caribbean
From $3,347
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
All-inclusivePleasant Holidays · Hotel only
Royalton Saint Lucia, An Autograph Collection All-Inclusive
4-starSaint Lucia, Caribbean · St. Lucia
From $1,249
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
All-inclusivePleasant Holidays · Flights + hotel
Royalton Negril, An Autograph Collection All-Inclusive Resort
4-starJamaica, Caribbean
From $1,878
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
All-inclusivePleasant Holidays · Flights + hotel
Majestic Mirage Costa Mujeres
4-starCancun and Riviera Maya, Mexico · Costa Mujeres
From $2,275
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
All-inclusivePleasant Holidays · Flights + hotel
Dreams Playa Bonita Panama
4-starPanama, Central America · Playa Bonita
Offer: $200 off
From $1,156
per person, 2 adults sharing
Stay Feb 5 – Feb 10, 2027
Pleasant Holidays · Flights + hotel
Fairmont El San Juan Hotel
4-starPuerto Rico, Caribbean · Carolina
From $2,024
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays · Flights + hotel
Wyndham Grand Rio Mar Rainforest Beach & Golf Resort
4-starPuerto Rico, Caribbean
From $2,211
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays · Flights + hotel
Villa del Palmar Beach Resort & Spa
3.5-starLos Cabos, Mexico · Cabo San Lucas
Offer: $200 off
From $623
per person, 2 adults sharing
Stay Feb 5 – Feb 10, 2027
All-inclusivePleasant Holidays · Flights + hotel
Cozumel Palace
3.5-starCozumel, Mexico
From $2,058
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays · Flights + hotel
Solmar Resort
3.5-starLos Cabos, Mexico · Pacific
From $870
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
All-inclusivePleasant Holidays · Flights + hotel
Sonesta Maho Beach Resort, Casino & Spa
3.5-starSint Maarten, Caribbean · Saint Maarten
From $1,454
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
All-inclusivePleasant Holidays · Flights + hotel
Velas Vallarta Puerto Vallarta
3.5-starPuerto Vallarta and Riviera Nayarit, Mexico · Marina Vallarta
Offer: $200 off
From $1,490
per person, 2 adults sharing
Stay Feb 5 – Feb 10, 2027
All-inclusivePleasant Holidays · Flights + hotel
Riu Ocho Rios
3.5-starJamaica, Caribbean
From $1,683
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
All-inclusivePleasant Holidays · Flights + hotel
Iberostar Selection Paraiso Lindo
3.5-starCancun and Riviera Maya, Mexico · Playa del Carmen
From $1,696
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
All-inclusivePleasant Holidays · Flights + hotel
Margaritaville Island Reserve, By Karisma Riviera Cancun
3.5-starCancun and Riviera Maya, Mexico · Puerto Morelos
From $1,730
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
All-inclusivePleasant Holidays · Flights + hotel
Iberostar Waves Rose Hall Beach
3.5-starJamaica, Caribbean
From $1,888
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
All-inclusivePleasant Holidays · Flights + hotel
Iberostar Selection Cancun
3.5-starCancun and Riviera Maya, Mexico
From $1,891
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
All-inclusivePleasant Holidays · Flights + hotel
Riu Playa Blanca
3.5-starPanama, Central America · Playa Blanca
Offer: $200 off
From $1,234
per person, 2 adults sharing
Stay Feb 5 – Feb 10, 2027
Pleasant Holidays · Flights + hotel
The Coral at Atlantis
3.5-starBahamas, Caribbean · Paradise Island
From $1,272
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
All-inclusivePleasant Holidays · Flights + hotel
Sunscape Curacao Resort, Spa & Casino
3.5-starCuracao, Caribbean
From $1,701
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Prices are for two adults sharing a room, taxes included.