Pleasant Holidays · Flights + hotel
Hilton Santa Barbara Beachfront Resort
4-starSanta Barbara, United States · Waterfront
From $1,839
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Hotel and resort deals
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Showing 151–180 of 334 hotels
All-inclusivePleasant Holidays · Flights + hotel
Hard Rock Hotel Riviera Maya
4-starCancun and Riviera Maya, Mexico · Puerto Aventuras
Offer: $200 off
From $1,864
per person, 2 adults sharing
Stay Feb 5 – Feb 10, 2027
All-inclusivePleasant Holidays · Flights + hotel
Riu Montego Bay
4-starJamaica, Caribbean
From $1,866
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
All-inclusivePleasant Holidays · Flights + hotel
Iberostar Selection Paraiso Maya Suites
4-starCancun and Riviera Maya, Mexico · Playa del Carmen
From $1,902
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
All-inclusivePleasant Holidays · Flights + hotel
El Dorado Seaside Palms
4-starCancun and Riviera Maya, Mexico · Akumal
From $1,915
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
All-inclusivePleasant Holidays · Flights + hotel
Hilton Cancun Mar Caribe All-Inclusive Resort
4-starCancun and Riviera Maya, Mexico
From $1,942
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
All-inclusivePleasant Holidays · Flights + hotel
Hacienda del Mar Los Cabos, An Autograph Collection All Inclusive Resort
4-starLos Cabos, Mexico · Corridor
From $1,950
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays · Flights + hotel
Matangi Private Island Resort
4-starTaveuni, Fiji · Matangi Island
Offer: $200 off
From $2,027
per person, 2 adults sharing
Stay Jan 29 – Feb 3, 2027
All-inclusivePleasant Holidays · Flights + hotel
Iberostar Selection Coral Cancun
4-starCancun and Riviera Maya, Mexico
From $2,115
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays · Flights + hotel
Sheraton Maui Resort & Spa
4-starMaui, Hawaii · Kaanapali
From $2,136
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
Hard Rock Hotel Cancun
4-starCancun and Riviera Maya, Mexico
From $2,186
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
Playacar Palace
4-starCancun and Riviera Maya, Mexico · Playa del Carmen
From $2,316
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
All-inclusivePleasant Holidays · Flights + hotel
Hilton Tulum Riviera Maya All-Inclusive Resort
4-starCancun and Riviera Maya, Mexico · Tulum
From $2,390
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
All-inclusivePleasant Holidays · Flights + hotel
Riu Palace Jamaica
4-starJamaica, Caribbean
From $2,399
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
Marriott Cancun, An All-Inclusive Resort
4-starCancun and Riviera Maya, Mexico
From $2,499
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
All-inclusivePleasant Holidays · Flights + hotel
Nickelodeon Hotels & Resorts Riviera Maya
4-starCancun and Riviera Maya, Mexico · Playa del Carmen
From $2,570
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
All-inclusivePleasant Holidays · Flights + hotel
Almare, Luxury Collection Adult All-Inclusive, Isla Mujeres
4-starCancun and Riviera Maya, Mexico · Isla Mujeres
From $2,678
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
All-inclusivePleasant Holidays · Flights + hotel
JOIA Paraiso by Iberostar
4-starCancun and Riviera Maya, Mexico · Playa del Carmen
From $2,854
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
Renaissance Wind Creek Aruba Resort
4-starAruba, Caribbean
From $3,087
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
All-inclusivePleasant Holidays · Flights + hotel
Princess Senses The Mangrove
4-starJamaica, Caribbean · Green Island
Offer: $200 off
From $7,087
per person, 2 adults sharing
Stay Feb 5 – Feb 10, 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
All-inclusivePleasant Holidays · Flights + hotel
Riu Palace Aquarelle
4-starJamaica, Caribbean
Offer: $200 off
From $1,305
per person, 2 adults sharing
Stay Feb 5 – Feb 10, 2027
Pleasant Holidays · Flights + hotel
Sunset Resort
4-starRarotonga, Cook Islands
Offer: $100 off, book by Nov 8, 2026
From $1,331
per person, 2 adults sharing
Stay Jan 29 – Feb 3, 2027
Pleasant Holidays · Hotel only
Alaia Belize, Autograph Collection
4-starBelize, Central America · Ambergris Caye
Offer: $200 off
From $1,336
per person, 2 adults sharing
Stay Feb 5 – Feb 10, 2027
Prices are for two adults sharing a room, taxes included.