Pleasant Holidays · Flights + hotel
Sheraton Puerto Rico Resort & Casino
4-starPuerto Rico, Caribbean · Old San Juan
From $1,457
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Hotel and resort deals
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Showing 181–210 of 255 hotels
Pleasant Holidays · Flights + hotel
El Silencio Lodge & Spa
4-starCosta Rica, Central America · Central Valley
Offer: $200 off
From $3,512
per person, 2 adults sharing
Stay Feb 5 – Feb 10, 2027
Pleasant Holidays · Flights + hotel
Hyatt Centric Waikiki Beach
4-starOahu, Hawaii
From $1,259
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays · Flights + hotel
Ilikai Hotel & Luxury Suites
4-starOahu, Hawaii
From $1,333
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays · Flights + hotel
The Fairmont Hotel Vancouver
4-starVancouver, Canada
From $1,341
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays · Flights + hotel
AC Hotel by Marriott Maui Wailea
4-starMaui, Hawaii
From $1,941
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays · Flights + hotel
The Kapalua Villas Maui
4-starMaui, Hawaii
From $2,178
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays · Flights + hotel
Sheraton Princess Kaiulani Waikiki Beach
3.5-starOahu, Hawaii
From $1,040
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays · Flights + hotel
Sunshine Suites Resort
3.5-starCayman Islands, Caribbean · Grand Cayman
From $1,838
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays · Flights + hotel
DoubleTree Resort by Hilton Fiji - Sonaisali Island
3.5-starViti Levu, Fiji · Sonaisali Island
From $1,523
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays · Flights + hotel
Amsterdam Manor Beach Resort
3.5-starAruba, Caribbean
From $2,915
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays · Flights + hotel
Ridley House - Key West Historic Inns
3.5-starFlorida Keys, United States · Key West, Florida
From $1,728
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays · Flights + hotel
Courtyard by Marriott Maui Kahului Airport
3-starMaui, Hawaii
From $1,618
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays · Flights + hotel
Aston Waikiki Sunset
3-starOahu, Hawaii
From $1,123
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays · Flights + hotel
Royal Kahana Maui by OUTRIGGER
2.5-starMaui, Hawaii
From $1,663
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays · Flights + hotel
Aston at Papakea Resort
2.5-starMaui, Hawaii · Kaanapali
From $1,454
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays · Flights + hotel
Espacio the Jewel of Waikiki
5-starOahu, Hawaii
From $9,588
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
All-inclusivePleasant Holidays · Flights + hotel
Secrets Tulum Resort and Beach Club
4.5-starCancun and Riviera Maya, Mexico · Tulum
From $1,814
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
All-inclusivePleasant Holidays · Flights + hotel
Palafitos Overwater Bungalows at El Dorado Maroma
4.5-starCancun and Riviera Maya, Mexico · Maroma
From $5,869
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays · Flights + hotel
Villa Marquis Member of Melia Collection
4-starFrance, Europe · The Champs-Elysees Avenue
From $2,060
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
All-inclusivePleasant Holidays · Flights + hotel
Secrets Papagayo Costa Rica
4-starCosta Rica, Central America · Guanacaste
From $5,192
per person, 2 adults sharing
Stay Jan 10 – Jan 15, 2027
Pleasant Holidays · Flights + hotel
InterContinental Bora Bora Le Moana Resort
4-starBora Bora, Tahiti
Offer: $200 off
From $2,350
per person, 2 adults sharing
Stay Jan 29 – Feb 3, 2027
Pleasant Holidays
Fairmont Orchid, Hawaii
5-starIsland of Hawaii, Hawaii · Kohala Coast, Hawaii
Request this hotel
Pleasant Holidays
Fairmont Sonoma Mission Inn & Spa
5-starNapa and Sonoma, United States
Request this hotel
Pleasant Holidays
InterContinental Bora Bora Resort & Thalasso Spa
5-starBora Bora, Tahiti
Request this hotel
Pleasant Holidays
Andaz Maui at Wailea Resort - a concept by Hyatt
5-starMaui, Hawaii
Request this hotel
Prices are for two adults sharing a room, taxes included.