Pleasant Holidays · Flights + hotel
The Royal Hawaiian, a Luxury Collection Resort, Waikiki
5-starOahu, Hawaii
From $2,109
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Hotel and resort deals
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Showing 1–30 of 242 hotels
All-inclusivePleasant Holidays · Flights + hotel
Hotel Xcaret Mexico
5-starCancun and Riviera Maya, Mexico · Xcaret
Offer: $200 off
From $2,990
per person, 2 adults sharing
Stay Feb 5 – Feb 10, 2027
All-inclusivePleasant Holidays · Flights + hotel
Grand Velas Riviera Nayarit
5-starPuerto Vallarta and Riviera Nayarit, Mexico · Nuevo Vallarta
From $3,612
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays · Flights + hotel
Waldorf Astoria Costa Rica Punta Cacique
5-starCosta Rica, Central America · Guanacaste
Offer: $200 off
From $5,346
per person, 2 adults sharing
Stay Feb 5 – Feb 10, 2027
Pleasant Holidays · Flights + hotel
InterContinental Fiji Golf Resort & Spa
5-starViti Levu, Fiji · Natadola
Offer: $200 off
From $759
per person, 2 adults sharing
Stay Jan 29 – Feb 3, 2027
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
Pleasant Holidays · Flights + hotel
Hyatt Regency Maui Resort & Spa
5-starMaui, Hawaii · Kaanapali
From $2,310
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays · Hotel only
Vomo Island Fiji
5-starMamanuca Islands, Fiji · Vomo Island
Offer: $200 off
From $2,767
per person, 2 adults sharing
Stay Jan 29 – Feb 3, 2027
Pleasant Holidays · Flights + hotel
The Ritz-Carlton Maui, Kapalua
5-starMaui, Hawaii
From $3,231
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays · Flights + hotel
One&Only Palmilla
5-starLos Cabos, Mexico · Corridor
From $4,152
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
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
All-inclusivePleasant Holidays · Flights + hotel
Grand Velas Riviera Maya
5-starCancun and Riviera Maya, Mexico · Playa del Carmen
From $4,196
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays · Flights + hotel
The St. Regis Bora Bora Resort
5-starBora Bora, Tahiti
Offer: $200 off
From $4,282
per person, 2 adults sharing
Stay Jan 29 – Feb 3, 2027
Pleasant Holidays · Flights + hotel
Four Seasons Resort Bora Bora
5-starBora Bora, Tahiti
Offer: $200 off
From $4,417
per person, 2 adults sharing
Stay Jan 29 – Feb 3, 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
Pleasant Holidays · Flights + hotel
Conrad Punta de Mita
5-starPuerto Vallarta and Riviera Nayarit, Mexico · Punta Mita
From $1,610
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays · Flights + hotel
Four Seasons Resort The Nam Hai, Hoi An
5-starVietnam, Asia
Offer: $150 off
From $2,093
per person, 2 adults sharing
Stay Feb 12 – Feb 17, 2027
Pleasant Holidays · Flights + hotel
Alila Mayakoba
5-starCancun and Riviera Maya, Mexico · Mayakoba
From $2,277
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays · Flights + hotel
The Ritz-Carlton, Amelia Island
5-starJacksonville, United States · Amelia Island
From $2,531
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays · Flights + hotel
Fairmont Mayakoba
5-starCancun and Riviera Maya, Mexico · Mayakoba
From $2,839
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
Aulani, Disney Vacation Club Villas
5-starOahu, Hawaii
From $2,429
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
All-inclusivePleasant Holidays · Flights + hotel
JW Marriott Costa Elena Resort & Spa, All-Inclusive
5-starCosta Rica, Central America · Guanacaste
Offer: $200 off
From $2,488
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
Conrad Bora Bora Nui
5-starBora Bora, Tahiti
Offer: $200 off
From $2,812
per person, 2 adults sharing
Stay Jan 29 – Feb 3, 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
All-inclusivePleasant Holidays · Flights + hotel
Grand Velas Los Cabos
5-starLos Cabos, Mexico · Corridor
From $4,499
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays · Flights + hotel
The Ritz-Carlton, Naples
5-starNaples and Marco Island, United States · Vanderbilt Beach
From $9,027
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
Pleasant Holidays · Flights + hotel
Hotel del Coronado, Curio Collection by Hilton
4.5-starSan Diego, United States · Coronado, California
From $1,842
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Prices are for two adults sharing a room, taxes included.