CRUISES

HOTELS & RESORTS

VACATIONS

Pleasant Holidays

Pleasant Holidays is a wholesaler offering vacation packages to destinations worldwide including Caribbean, Hawaii, Mexico, Tahiti, Europe, Asia and more.

Vacations & Packages by Pleasant Holidays

Offer
Departure
Cruise Line
Price
3-Nights Montego Bay, Royalton White Sands Resort
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $336
5-Nights Cabo San Lucas, One&Only Palmilla
DATES 9/10/2020 - 12/14/2021
Pleasant Holidays
from $3350
3-Nights Montego Bay, Hyatt Zilara Rose Hall
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $643
5-Nights The Island of Hawaii, The Fairmont Orchid, Hawaii
DATES 5/7/2020 - 12/15/2021
Pleasant Holidays
from $1096
3-Nights Cabo San Lucas, Cabo Azul Resort
DATES 8/13/2020 - 9/30/2020
Pleasant Holidays
from $561
3-Nights Cancun, Beach Palace
DATES 8/7/2020 - 9/30/2020
Pleasant Holidays
from $484
5-Nights Providenciales, The Shore Club
DATES 2/20/2020 - 12/15/2020
Pleasant Holidays
from $2064
3-Nights Punta Cana, Excellence Punta Cana
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $441
3-Nights Punta Cana, Punta Cana Princess All Suites Resort, Spa & Casino
DATES 8/12/2020 - 9/30/2020
Pleasant Holidays
from $368
3-Nights St. Thomas, The Ritz-Carlton, St. Thomas
DATES 8/14/2020 - 9/30/2020
Pleasant Holidays
from $674
3-Nights Montego Bay, Half Moon
DATES 8/11/2020 - 9/30/2020
Pleasant Holidays
from $1183
3-Nights Punta Cana, Hard Rock Hotel & Casino Punta Cana
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $494
3-Nights Providenciales, The Shore Club
DATES 8/11/2020 - 9/30/2020
Pleasant Holidays
from $951
3-Nights St. John's, Antigua, Royalton Antigua
DATES 6/24/2020 - 9/30/2020
Pleasant Holidays
from $609
3-Nights Aruba, Manchebo Beach Resort & Spa
DATES 6/25/2020 - 9/30/2020
Pleasant Holidays
from $508
3-Nights Riviera Nayarit, Grand Velas Riviera Nayarit
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $990
3-Nights Punta Cana, Secrets Royal Beach Punta Cana
DATES 8/3/2020 - 9/30/2020
Pleasant Holidays
from $384
3-Nights Punta Cana, Now Larimar Punta Cana
DATES 8/12/2020 - 9/30/2020
Pleasant Holidays
from $642
3-Nights Oranjestad, Aruba, Hyatt Place Aruba Airport
DATES 6/25/2020 - 9/30/2020
Pleasant Holidays
from $236
3-Nights Punta Cana, Grand Palladium Palace Resort, Spa & Casino
DATES 8/5/2020 - 9/30/2020
Pleasant Holidays
from $290
3-Nights Punta Cana, Riu Palace Bavaro
DATES 8/12/2020 - 9/30/2020
Pleasant Holidays
from $270
3-Nights Cancun, Fiesta Americana Condesa Cancun
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $358
3-Nights Riviera Maya, Iberostar Paraiso del Mar
DATES 8/7/2020 - 9/30/2020
Pleasant Holidays
from $283
3-Nights Rio Grande, P.R., Rio Mar Beach Resort and Spa, A Wyndham Grand Resort
DATES 8/14/2020 - 9/30/2020
Pleasant Holidays
from $358
3-Nights Cancun, Grand Park Royal Luxury Resort Cancun
DATES 8/7/2020 - 9/30/2020
Pleasant Holidays
from $604
3-Nights Montego Bay, Grand Palladium Jamaica Resort & Spa
DATES 8/10/2020 - 9/30/2020
Pleasant Holidays
from $324
3-Nights Puerto Vallarta, Velas Vallarta
DATES 8/13/2020 - 9/30/2020
Pleasant Holidays
from $534
3-Nights Cozumel, Cozumel Palace
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $459
3-Nights Soufriere (St. Lucia), Anse Chastanet
DATES 8/14/2020 - 9/30/2020
Pleasant Holidays
from $524
3-Nights Riviera Maya, Valentin Imperial, Riviera Maya
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $422
3-Nights Puerto Vallarta, Casa Velas Hotel Boutique
DATES 8/13/2020 - 9/30/2020
Pleasant Holidays
from $696
3-Nights Puerto Vallarta, Playa Los Arcos Beach Resort
DATES 8/6/2020 - 9/30/2020
Pleasant Holidays
from $196
3-Nights Cancun, Riu Palace Peninsula
DATES 8/7/2020 - 9/30/2020
Pleasant Holidays
from $328
3-Nights Riviera Maya, Viceroy Riviera Maya
DATES 8/7/2020 - 9/30/2020
Pleasant Holidays
from $587
3-Nights Riviera Maya, Secrets Maroma Beach Riviera Cancun
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $616
3-Nights Palm Beach, Aruba, Aruba Marriott Resort & Stellaris Casino
DATES 6/24/2020 - 9/30/2020
Pleasant Holidays
from $578
3-Nights Puerto Vallarta, Villa Premiere Boutique Hotel & Romantic Getaway
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $319
5-Nights Oahu, Outrigger Waikiki Beach Resort
DATES 2/20/2020 - 12/15/2020
Pleasant Holidays
from $1016
5-Nights Willemstad, Curacao , Sunscape Curacao Resort, Spa & Casino
DATES 3/4/2020 - 12/15/2020
Pleasant Holidays
from $792
3-Nights Cancun, Dreams Vista Cancun Resort & Spa
DATES 8/3/2020 - 9/30/2020
Pleasant Holidays
from $396
3-Nights Riviera Maya, Dreams Riviera Cancun Resort & Spa
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $420
3-Nights Riviera Nayarit, Riu Palace Pacifico
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $316
3-Nights Riviera Maya, Barcelo Maya Colonial/ Tropical
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $472
3-Nights Ochos Rios, Sandals Ochi
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $657
3-Nights Puerto Vallarta, Sunscape Puerto Vallarta Resort & Spa
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $242
3-Nights Riviera Maya, UNICO 20°87°
DATES 6/25/2020 - 9/30/2020
Pleasant Holidays
from $772
3-Nights Cancun, The Grand at Moon Palace Cancun
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $790
3-Nights Cabo San Lucas, Waldorf Astoria Los Cabos Pedregal
DATES 8/6/2020 - 9/30/2020
Pleasant Holidays
from $1347
3-Nights St. Lucia, Royalton Saint Lucia Resort & Spa
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $533
3-Nights Grand Cayman, Sunshine Suites Resort
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $364
3-Nights Puerto Vallarta, NH Krystal Puerto Vallarta
DATES 8/13/2020 - 9/30/2020
Pleasant Holidays
from $131
5-Nights The Island of Hawaii, Sheraton Kona Resort and Spa at Keauhou Bay
DATES 2/5/2020 - 1/2/2021
Pleasant Holidays
from $1064
3-Nights Riviera Maya, Secrets Akumal Riviera Maya
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $570
3-Nights Paradise Island, The Ocean Club, A Four Seasons Resort
DATES 8/11/2020 - 9/30/2020
Pleasant Holidays
from $1505
3-Nights Cabo San Lucas, Pueblo Bonito Rose
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $465
3-Nights Cancun, Riu Caribe
DATES 8/7/2020 - 9/30/2020
Pleasant Holidays
from $250
5-Nights Curacao, Santa Barbara Beach & Golf Resort
DATES 3/4/2020 - 12/15/2020
Pleasant Holidays
from $534
5-Nights Tetiaroa, The Brando
DATES 10/23/2019 - 10/31/2020
Pleasant Holidays
from $12704
3-Nights Punta Cana, Dreams Macao Beach Punta Cana
DATES 8/12/2020 - 9/30/2020
Pleasant Holidays
from $376
3-Nights San Juan, El San Juan Resort & Casino
DATES 8/14/2020 - 9/30/2020
Pleasant Holidays
from $610
3-Nights Oranjestad, Aruba, Divi Aruba
DATES 6/24/2020 - 9/30/2020
Pleasant Holidays
from $870
3-Nights Riviera Maya, Grand Velas Riviera Maya
DATES 7/6/2020 - 9/30/2020
Pleasant Holidays
from $1309
3-Nights Cancun, Dreams Natura Resort & Spa
DATES 8/7/2020 - 9/30/2020
Pleasant Holidays
from $420
5-Nights Playa del Carmen, Grand Hyatt Playa del Carmen Resort
DATES 2/20/2020 - 12/15/2020
Pleasant Holidays
from $1033
3-Nights Cabo San Lucas, ME Cabo
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $397
3-Nights Ocho Rios, Jamaica, Couples San Souci
DATES 8/11/2020 - 9/30/2020
Pleasant Holidays
from $532
3-Nights Riviera Maya, IBEROSTAR Selection Paraiso Maya
DATES 8/5/2020 - 9/30/2020
Pleasant Holidays
from $360
3-Nights St. Michael, Barbados, Hilton Barbados
DATES 6/25/2020 - 9/30/2020
Pleasant Holidays
from $286
3-Nights Cabo San Lucas, Villa La Estancia Beach Resort & Spa - Cabo
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $384
3-Nights Playa Mujeres, TRS Coral Hotel
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $562
3-Nights Riviera Maya, Riu Palace Riviera Maya
DATES 8/7/2020 - 9/30/2020
Pleasant Holidays
from $324
3-Nights Palm Beach, Aruba, Riu Palace Aruba
DATES 6/24/2020 - 9/30/2020
Pleasant Holidays
from $752
3-Nights Puerto Vallarta, Secrets Vallarta Bay Puerto Vallarta
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $462
3-Nights Cancun, JW Marriott Cancun Resort & Spa
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $230
3-Nights Cabo San Lucas, Playa Grande Resort & Spa
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $296
3-Nights Grand Cayman, Kimpton Seafire Resort + Spa
DATES 8/6/2020 - 9/30/2020
Pleasant Holidays
from $796
3-Nights Cabo San Lucas, Esperanza, an Auberge Resort
DATES 8/6/2020 - 9/30/2020
Pleasant Holidays
from $1407
3-Nights Cabo San Lucas, Grand Velas Los Cabos
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $1791
3-Nights Akumal, Grand Palladium Colonial Resort & Spa
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $317
3-Nights Riviera Maya, Sandos Playacar Beach Resort
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $246
3-Nights Cancun, Hyatt Ziva Puerto Vallarta
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $394
3-Nights Providenciales, Amanyara
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $3071
3-Nights Cancun, Live Aqua Cancun
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $500
3-Nights Cancun, Sun Palace
DATES 8/3/2020 - 9/30/2020
Pleasant Holidays
from $493
3-Nights Montego Bay, Holiday Inn Resort, Montego Bay - All-Inclusive
DATES 8/11/2020 - 9/30/2020
Pleasant Holidays
from $631
3-Nights Punta Cana, Melia Caribe Tropical Resort
DATES 8/12/2020 - 9/30/2020
Pleasant Holidays
from $296
3-Nights Jolly Harbour, Cocos Hotel Antigua
DATES 6/25/2020 - 9/30/2020
Pleasant Holidays
from $726
3-Nights Negril, Hideaway at Royalton Negril Resort and Spa
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $588
3-Nights Cancun, Hideaway at Royalton Riviera Cancun
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $462
3-Nights Cancun, NIZUC Resort & Spa
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $584
3-Nights Punta Cana, The Reserve at Paradisus Punta Cana
DATES 8/13/2020 - 9/30/2020
Pleasant Holidays
from $396
5-Nights Grand Cayman, The Ritz-Carlton Grand Cayman
DATES 2/20/2020 - 12/15/2020
Pleasant Holidays
from $874
3-Nights San Juan, InterContinental Resort & Casino San Juan
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $354
3-Nights Montego Bay, Iberostar Rose Hall Beach
DATES 8/11/2020 - 9/30/2020
Pleasant Holidays
from $336
3-Nights Riviera Maya, Grand Palladium Kantenah Resort & Spa
DATES 8/7/2020 - 9/30/2020
Pleasant Holidays
from $317
3-Nights Punta Cana, CHIC Punta Cana
DATES 8/6/2020 - 9/30/2020
Pleasant Holidays
from $330
3-Nights Providenciales, The Palms Turks and Caicos
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $932
3-Nights Cabo San Lucas, Hard Rock Hotel Los Cabos
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $512
3-Nights Cancun, Excellence Riviera Cancun
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $468
5-Nights San Jose del Cabo, Marquis Los Cabos All Inclusive Resort & Spa
DATES 9/10/2020 - 12/14/2021
Pleasant Holidays
from $928
3-Nights Cancun, Ocean Riviera Paradise
DATES 8/10/2020 - 9/30/2020
Pleasant Holidays
from $272
3-Nights Oistins, Barbados, Sandals Royal Barbados
DATES 6/26/2020 - 9/30/2020
Pleasant Holidays
from $1187
3-Nights Montego Bay, Sandals Montego Bay
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $1190
3-Nights Punta Cana, Hideaway at Royalton Punta Cana
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $336
3-Nights Puerto Vallarta, The St. Regis Punta Mita Resort
DATES 8/13/2020 - 9/30/2020
Pleasant Holidays
from $944
5-Nights Grand Cayman, Margaritaville Beach Resort Grand Cayman
DATES 12/17/2019 - 12/10/2020
Pleasant Holidays
from $1207
5-Nights Atlantis, The Cove at Atlantis
DATES 5/7/2020 - 12/15/2021
Pleasant Holidays
from $1975
3-Nights St. James, Barbados, The Fairmont Royal Pavilion
DATES 6/25/2020 - 9/30/2020
Pleasant Holidays
from $778
3-Nights Grand Cayman (George Town), The Westin Grand Cayman Seven Mile Beach Resort & Spa
DATES 8/10/2020 - 9/30/2020
Pleasant Holidays
from $630
5-Nights Grand Cayman, The Westin Grand Cayman Seven Mile Beach Resort & Spa
DATES 12/12/2019 - 12/10/2020
Pleasant Holidays
from $1330
3-Nights Providenciales, The Alexandra Resort
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $2100
3-Nights Cancun, Secrets The Vine Cancun
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $598
3-Nights Montego Bay, Round Hill Hotel & Villas
DATES 8/10/2020 - 9/30/2020
Pleasant Holidays
from $550
3-Nights Cabo San Lucas, Hyatt Ziva Los Cabos
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $438
3-Nights Riviera Maya, Fairmont Mayakoba
DATES 7/6/2020 - 9/30/2020
Pleasant Holidays
from $305
3-Nights Curacao, Avila Hotel
DATES 8/10/2020 - 9/30/2020
Pleasant Holidays
from $302
3-Nights Cabo San Lucas, Breathless Cabo San Lucas Resort & Spa
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $622
3-Nights Punta Cana, Riu Palace Punta Cana
DATES 8/12/2020 - 9/30/2020
Pleasant Holidays
from $270
3-Nights Negril, Grand Lido Negril Resort and Spa
DATES 8/3/2020 - 9/30/2020
Pleasant Holidays
from $576
3-Nights Riviera Maya, Barcelo Maya Riviera - Adults Only
DATES 8/7/2020 - 9/30/2020
Pleasant Holidays
from $502
5-Nights Maui, Sheraton Maui Resort & Spa
DATES 2/5/2020 - 1/2/2021
Pleasant Holidays
from $1789
3-Nights Riviera Maya, El Dorado Royale, A Spa Resort by Karisma
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $505
3-Nights Cozumel, Secrets Aura Cozumel
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $321
3-Nights Palm Beach, Aruba, Riu Palace Aruba
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $752
3-Nights Gros Islet, Hideaway at Royalton Saint Lucia
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $546
3-Nights Cabo San Lucas, Nobu Hotel Los Cabos
DATES 8/14/2020 - 9/30/2020
Pleasant Holidays
from $645
5-Nights Bora Bora, InterContinental Bora Bora Resort & Thalasso Spa
DATES 12/16/2019 - 12/31/2020
Pleasant Holidays
from $2966
3-Nights Puerto Aventuras, Dreams Puerto Aventuras Resort & Spa
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $290
3-Nights Montego Bay, Royalton Blue Waters
DATES 8/10/2020 - 9/30/2020
Pleasant Holidays
from $638
3-Nights Cancun, Hyatt Ziva Cancun
DATES 6/25/2020 - 9/30/2020
Pleasant Holidays
from $517
3-Nights Puerto Vallarta, Riu Jalisco
DATES 8/13/2020 - 9/30/2020
Pleasant Holidays
from $256
3-Nights Bridgetown, Barbados, The Crane Resort and Residences
DATES 6/25/2020 - 9/30/2020
Pleasant Holidays
from $406
3-Nights Playa del Carmen, Catalonia Playa Maroma
DATES 8/7/2020 - 9/30/2020
Pleasant Holidays
from $258
3-Nights Cancun, Grand Palladium Costa Mujeres Resort & Spa
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $428
3-Nights Cancun, Iberostar Selection Cancun
DATES 8/7/2020 - 9/30/2020
Pleasant Holidays
from $441
5-Nights Oahu, Aston Waikiki Beach Hotel
DATES 2/20/2020 - 12/15/2020
Pleasant Holidays
from $685
3-Nights Kralendijk, Bonaire, Courtyard by Marriott Bonaire Dive Resort
DATES 6/26/2020 - 9/30/2020
Pleasant Holidays
from $368
3-Nights Palm Beach, Aruba, The Ritz-Carlton, Aruba
DATES 6/24/2020 - 9/30/2020
Pleasant Holidays
from $716
3-Nights Noord, RIU Palace Antillas
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $673
3-Nights Punta Cana, Grand Palladium Bavaro Resort & Spa
DATES 8/3/2020 - 9/30/2020
Pleasant Holidays
from $326
3-Nights Punta Cana, Riu Bambu
DATES 8/12/2020 - 9/30/2020
Pleasant Holidays
from $207
5-Nights Taha'a, Le Taha'a Private Island Resort & Spa
DATES 2/20/2020 - 12/15/2020
Pleasant Holidays
from $2164
3-Nights Kralendijk, Caribbean Antilles, Divi Flamingo Beach Resort & Casino
DATES 6/25/2020 - 9/30/2020
Pleasant Holidays
from $326
3-Nights Riviera Maya, Hotel Marina El Cid Cancun, Riviera Maya
DATES 8/7/2020 - 9/30/2020
Pleasant Holidays
from $268
3-Nights Nuevo Vallarta, Marival Distinct Luxury Residences
DATES 7/6/2020 - 9/30/2020
Pleasant Holidays
from $500
3-Nights Punta Cana, The Grand Reserve at Paradisus Palma Real
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $634
5-Nights Willemstad, Curacao, Dreams Curacao Resort, Spa & Casino
DATES 3/4/2020 - 12/15/2020
Pleasant Holidays
from $904
3-Nights Montego Bay, Hilton Rose Hall Resort & Spa
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $406
3-Nights Puerto Vallarta, Hotel Mousai Puerto Vallarta
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $536
5-Nights Riviera Maya, Banyan Tree Mayakoba
DATES 6/9/2020 - 12/14/2021
Pleasant Holidays
from $3047
3-Nights Cancun, Grand Fiesta Americana Coral Beach Cancun
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $1126
3-Nights Riviera Maya, El Dorado Seaside Suites, a Gourmet Inclusive® Resort, by Karisma
DATES 8/6/2020 - 9/30/2020
Pleasant Holidays
from $453
5-Nights Cabo San Lucas, Montage Los Cabos
DATES 9/10/2020 - 12/14/2021
Pleasant Holidays
from $2752
3-Nights Cabo San Lucas, Pueblo Bonito Sunset Beach
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $565
3-Nights Montego Bay, Iberostar Grand Rose Hall
DATES 8/10/2020 - 9/30/2020
Pleasant Holidays
from $596
3-Nights Cancun, Dreams Sands Cancun Resort & Spa
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $368
3-Nights Grand Cayman, The Ritz-Carlton Grand Cayman
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $754
3-Nights San Juan, Condado Vanderbilt Hotel
DATES 8/14/2020 - 9/30/2020
Pleasant Holidays
from $530
3-Nights Cabo San Lucas, Garza Blanca Resort & Spa Los Cabos
DATES 8/13/2020 - 9/30/2020
Pleasant Holidays
from $514
3-Nights Riviera Maya, Riu Playacar
DATES 8/7/2020 - 9/30/2020
Pleasant Holidays
from $254
5-Nights Curacao, Avila Hotel
DATES 3/4/2020 - 12/15/2020
Pleasant Holidays
from $504
3-Nights Negril, Beaches Negril
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $1112
3-Nights Palm Beach, Aruba, Hyatt Regency Aruba Resort, Spa & Casino
DATES 6/24/2020 - 9/30/2020
Pleasant Holidays
from $854
3-Nights Punta Cana, TRS Turquesa Hotel
DATES 8/12/2020 - 9/30/2020
Pleasant Holidays
from $422
3-Nights Cancun, The Grand at Moon Palace Cancun
DATES 6/25/2020 - 9/30/2020
Pleasant Holidays
from $790
3-Nights St. John's, Antigua, Sandals Grand Antigua Resort & Spa
DATES 6/24/2020 - 9/30/2020
Pleasant Holidays
from $1020
3-Nights San Jose del Cabo, Secrets Puerto Los Cabos Golf & Spa Resort
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $372
3-Nights Christ Church, Sandals Barbados
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $1068
3-Nights San Jose del Cabo, Le Blanc Spa Resort Los Cabos
DATES 8/5/2020 - 9/30/2020
Pleasant Holidays
from $904
3-Nights Cabo San Lucas, Riu Santa Fe
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $273
3-Nights Cabo San Lucas, Royal Solaris Los Cabos Resort
DATES 8/6/2020 - 9/30/2020
Pleasant Holidays
from $240
3-Nights Montego Bay, Sandals Royal Caribbean
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $1095
3-Nights Puerto Vallarta, Melia Puerto Vallarta
DATES 8/13/2020 - 9/30/2020
Pleasant Holidays
from $374
3-Nights Cancun, The Ritz-Carlton, Cancun
DATES 8/10/2020 - 9/30/2020
Pleasant Holidays
from $372
3-Nights Punta Cana, IBEROSTAR Grand Hotel Bavaro
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $638
3-Nights Providenciales, Beach Enclave
DATES 8/12/2020 - 9/30/2020
Pleasant Holidays
from $8718
3-Nights Paradise Island, The Cove at Atlantis
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $914
3-Nights Nassau, British Colonial Hilton Nassau
DATES 8/11/2020 - 9/30/2020
Pleasant Holidays
from $297
3-Nights Puerto Morelos, Breathless Riviera Cancun Resort & Spa
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $466
3-Nights Palm Beach, Aruba, The Ritz-Carlton, Aruba
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $716
5-Nights Kauai, Kauai Marriott Resort
DATES 2/5/2020 - 1/2/2021
Pleasant Holidays
from $993
3-Nights Punta Cana, Excellence El Carmen
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $488
5-Nights Montego Bay, Hyatt Ziva Rose Hall
DATES 5/7/2020 - 12/15/2021
Pleasant Holidays
from $1244
3-Nights Christ Church, Barbados, Sandals Barbados
DATES 6/25/2020 - 9/30/2020
Pleasant Holidays
from $1068
3-Nights Playa Mujeres, Finest Playa Mujeres
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $482
3-Nights Riviera Maya, Playacar Palace
DATES 8/7/2020 - 9/30/2020
Pleasant Holidays
from $548
3-Nights , Sandals Regency La Toc Golf Resort & Spa in St. Lucia
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $879
3-Nights Puerto Vallarta, Villa del Palmar Flamingos Beach Resort & Spa
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $190
3-Nights Cabo San Lucas, Grand Solmar Land's End Resort and Spa
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $698
3-Nights Soufriere, St. Lucia, Sugar Beach, A Viceroy Resort
DATES 8/5/2020 - 9/30/2020
Pleasant Holidays
from $846
3-Nights Oranjestad, Aruba, Amsterdam Manor
DATES 6/25/2020 - 9/30/2020
Pleasant Holidays
from $456
3-Nights Cabo San Lucas, Dreams Los Cabos Suites Golf Resort & Spa
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $390
3-Nights Cabo San Lucas, The Cape, a Thompson Hotel
DATES 8/6/2020 - 9/30/2020
Pleasant Holidays
from $625
3-Nights Runaway Bay, Jamaica, Grand Bahia Principe Jamaica
DATES 8/6/2020 - 9/30/2020
Pleasant Holidays
from $267
3-Nights Riviera Maya, Secrets Maroma Beach Riviera Cancun
DATES 6/25/2020 - 9/30/2020
Pleasant Holidays
from $616
3-Nights San Juan, Caribe Hilton San Juan
DATES 8/14/2020 - 9/30/2020
Pleasant Holidays
from $324
3-Nights Riviera Maya, Iberostar Quetzal
DATES 8/7/2020 - 9/30/2020
Pleasant Holidays
from $292
3-Nights Riviera Maya, El Dorado Maroma, A Spa Resort by Karisma
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $662
3-Nights San Jose del Cabo, Marquis Los Cabos All Inclusive Resort & Spa
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $588
3-Nights Soufriere (St. Lucia), Ladera Resort
DATES 8/14/2020 - 9/30/2020
Pleasant Holidays
from $1316
3-Nights Negril, Jamaica, Couples Swept Away Negril
DATES 8/10/2020 - 9/30/2020
Pleasant Holidays
from $658
3-Nights Puerto Vallarta, Garza Blanca Preserve Beach Resort & Spa
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $274
3-Nights Puerto Vallarta, Dreams Villamagna Nuevo Vallarta
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $337
3-Nights Cancun, Riu Cancun
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $253
3-Nights Cabo San Lucas, Villa del Arco Beach Resort & Grand Spa
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $444
3-Nights Negril , Couples Negril
DATES 8/3/2020 - 9/30/2020
Pleasant Holidays
from $628
3-Nights Negril, Jamaica, Grand Pineapple Beach Negril
DATES 8/11/2020 - 9/30/2020
Pleasant Holidays
from $238
3-Nights St. John , The Westin St. John Resort & Villas
DATES 8/14/2020 - 9/30/2020
Pleasant Holidays
from $484
3-Nights San Jose del Cabo, Barcelo Grand Faro Los Cabos
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $572
3-Nights Punta Cana, The Westin Puntacana Resort & Club
DATES 8/13/2020 - 9/30/2020
Pleasant Holidays
from $336
3-Nights Riviera Maya, Iberostar Paraiso Lindo
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $326
3-Nights Nassau, The Coral at Atlantis
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $430
5-Nights Grand Cayman, Sunshine Suites Resort
DATES 12/12/2019 - 12/10/2020
Pleasant Holidays
from $753
3-Nights Negril, Riu Palace Tropical Bay
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $341
3-Nights Cabo San Lucas, The Westin Resort & Spa, Los Cabos
DATES 8/13/2020 - 9/30/2020
Pleasant Holidays
from $370
3-Nights Punta de Mita, Mexico, W Punta de Mita
DATES 8/6/2020 - 9/30/2020
Pleasant Holidays
from $588
3-Nights Cabo San Lucas, Grand Fiesta Americana Los Cabos All Inclusive Golf & Spa
DATES 8/13/2020 - 9/30/2020
Pleasant Holidays
from $500
3-Nights Cancun, Excellence Playa Mujeres
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $640
3-Nights Aruba, Holiday Inn Resort Aruba
DATES 6/24/2020 - 9/30/2020
Pleasant Holidays
from $306
3-Nights Cancun, Riu Palace Las Americas
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $324
3-Nights Punta Cana, Royalton Bavaro Resort & Spa
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $315
3-Nights Montego Bay, Excellence Oyster Bay
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $664
3-Nights San Juan, Sheraton Puerto Rico Hotel & Casino
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $423
3-Nights Cancun, Reflect Cancun Resort & Spa
DATES 8/7/2020 - 9/30/2020
Pleasant Holidays
from $325
3-Nights San Jose del Cabo, Reflect Krystal Grand Los Cabos
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $264
3-Nights Riviera Maya, Catalonia Royal Tulum
DATES 8/6/2020 - 9/30/2020
Pleasant Holidays
from $301
6-Nights Vanua Levu, Jean-Michel Cousteau Resort, Fiji
DATES 10/23/2019 - 10/31/2020
Pleasant Holidays
from $2756
3-Nights Playa del Carmen, Hotel Xcaret Mexico
DATES 6/25/2020 - 9/30/2020
Pleasant Holidays
from $725
3-Nights Cancun, Temptation Resort & Spa Cancun
DATES 8/10/2020 - 9/30/2020
Pleasant Holidays
from $394
3-Nights Playa del Carmen, Grand Hyatt Playa del Carmen Resort
DATES 8/3/2020 - 9/30/2020
Pleasant Holidays
from $466
3-Nights Punta Cana, Dreams Punta Cana Resort & Spa
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $278
3-Nights Punta Cana, Barcelo Bavaro Palace Deluxe
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $313
5-Nights Grand Cayman, Grand Cayman Marriott Beach Resort
DATES 12/12/2019 - 12/10/2020
Pleasant Holidays
from $1043
3-Nights Punta Cana, Grand Palladium Punta Cana
DATES 8/12/2020 - 9/30/2020
Pleasant Holidays
from $290
3-Nights Cancun, Coral Level at Iberostar Selection Cancun
DATES 8/7/2020 - 9/30/2020
Pleasant Holidays
from $521
3-Nights Braco, Jamaica, Melia Braco Village
DATES 8/11/2020 - 9/30/2020
Pleasant Holidays
from $382
3-Nights Negril, Azul Beach Resort Negril by Karisma
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $414
3-Nights Cozumel, Presidente InterContinental Cozumel
DATES 8/5/2020 - 9/30/2020
Pleasant Holidays
from $400
3-Nights Cancun, Hard Rock Hotel Cancun
DATES 8/7/2020 - 9/30/2020
Pleasant Holidays
from $504
3-Nights Punta Cana, Nickelodeon™ Hotels & Resorts Punta Cana
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $533
3-Nights Cabo San Lucas, JW Marriott Los Cabos Beach Resort & Spa
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $444
5-Nights San Jose del Cabo, Marquis Los Cabos All Inclusive Resort & Spa
DATES 2/20/2020 - 12/15/2020
Pleasant Holidays
from $979
3-Nights Punta Cana, Hyatt Ziva Cap Cana
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $544
3-Nights Puerto Vallarta, Grand Fiesta Americana Puerto Vallarta
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $361
3-Nights Cabo San Lucas, Riu Palace Cabo San Lucas
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $362
5-Nights Oahu, Moana Surfrider, A Westin Resort & Spa
DATES 6/9/2020 - 12/14/2021
Pleasant Holidays
from $1109
3-Nights Riviera Maya, Barcelo Maya Palace
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $576
3-Nights Puerto Morelos, Now Sapphire Riviera Cancun
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $348
3-Nights Cabo San Lucas, Hilton Los Cabos Beach & Golf Resort
DATES 8/6/2020 - 9/30/2020
Pleasant Holidays
from $360
3-Nights Puerto Vallarta, Hilton Puerto Vallarta
DATES 8/13/2020 - 9/30/2020
Pleasant Holidays
from $265
5-Nights Maui, Grand Wailea, A Waldorf Astoria Resort
DATES 5/7/2020 - 12/15/2021
Pleasant Holidays
from $2214
3-Nights Puerto Vallarta, Hard Rock Hotel Vallarta
DATES 8/6/2020 - 9/30/2020
Pleasant Holidays
from $512
3-Nights Montego Bay, Secrets Wild Orchid Montego Bay
DATES 8/10/2020 - 9/30/2020
Pleasant Holidays
from $594
3-Nights Cancun, Hyatt Zilara Cancun
DATES 6/26/2020 - 9/30/2020
Pleasant Holidays
from $514
3-Nights Cabo San Lucas, Solmar Resorts
DATES 8/3/2020 - 9/30/2020
Pleasant Holidays
from $177
3-Nights Negril, Jamaica, Sunset At The Palms Resort & Spa
DATES 8/10/2020 - 9/30/2020
Pleasant Holidays
from $496
3-Nights San Juan, The Condado Plaza Hilton
DATES 8/14/2020 - 9/30/2020
Pleasant Holidays
from $664
3-Nights Playa del Carmen, Hilton Playa del Carmen, an All-Inclusive Adult Only Resort
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $478
3-Nights Oranjestad, Aruba, Renaissance Aruba Resort & Casino
DATES 6/24/2020 - 9/30/2020
Pleasant Holidays
from $348
3-Nights Cancun, Ocean Riviera Paradise
DATES 7/6/2020 - 9/30/2020
Pleasant Holidays
from $208
3-Nights Punta Cana, Luxury Bahia Principe Ambar
DATES 8/5/2020 - 9/30/2020
Pleasant Holidays
from $252
3-Nights Cancun, Excellence Playa Mujeres
DATES 6/25/2020 - 9/30/2020
Pleasant Holidays
from $640
3-Nights Riviera Maya, Andaz Mayakoba Resort Riviera Maya
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $332
3-Nights Ocho Rios, Riu Ocho Rios
DATES 8/3/2020 - 9/30/2020
Pleasant Holidays
from $293
3-Nights Cancun, NH Krystal Cancun
DATES 8/6/2020 - 9/30/2020
Pleasant Holidays
from $180
3-Nights Riviera Maya, Iberostar Tucan
DATES 8/7/2020 - 9/30/2020
Pleasant Holidays
from $292
3-Nights Cozumel, Sunscape Sabor Cozumel
DATES 8/10/2020 - 9/30/2020
Pleasant Holidays
from $214
3-Nights Providenciales, Beaches Turks & Caicos Resort & Spa
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $1110
3-Nights Cabo San Lucas, Villa del Palmar Beach Resort & Spa, Los Cabos
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $182
3-Nights Grand Cayman, Grand Cayman Marriott Beach Resort
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $374
5-Nights Cabo San Lucas, Grand Velas Los Cabos
DATES 9/10/2020 - 12/14/2021
Pleasant Holidays
from $3419
5-Nights Scottsdale, Hyatt Regency Scottsdale Resort & Spa At Gainey Ranch
DATES 6/9/2020 - 12/14/2021
Pleasant Holidays
from $1465
3-Nights Oistins, Sandals Royal Barbados
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $1187
3-Nights Punta Cana, Now Onyx Punta Cana
DATES 8/6/2020 - 9/30/2020
Pleasant Holidays
from $366
3-Nights Nassau, The Royal at Atlantis
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $520
3-Nights Castries, Cap Maison Resort & Spa
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $662
3-Nights Riviera Maya, Riu Palace Mexico
DATES 8/7/2020 - 9/30/2020
Pleasant Holidays
from $324
3-Nights Punta de Mita, Four Seasons Resort Punta Mita
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $1500
3-Nights Punta Cana, Secrets Cap Cana Resort & Spa
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $531
3-Nights Puerto Vallarta, Riu Vallarta Hotel
DATES 8/13/2020 - 9/30/2020
Pleasant Holidays
from $254
3-Nights Nuevo Vallarta, Reflect Krystal Grand Nuevo Vallarta
DATES 8/6/2020 - 9/30/2020
Pleasant Holidays
from $262
3-Nights Ocho Rios, Jamaica, Goldeneye
DATES 8/11/2020 - 9/30/2020
Pleasant Holidays
from $868
3-Nights Negril, The Caves
DATES 8/5/2020 - 9/30/2020
Pleasant Holidays
from $884
3-Nights St. James, Barbados, The House by Elegant Hotels
DATES 6/25/2020 - 9/30/2020
Pleasant Holidays
from $608
3-Nights Cancun, Generations Riviera Maya, a Gourmet Inclusive® Resort, by Karisma
DATES 8/7/2020 - 9/30/2020
Pleasant Holidays
from $581
3-Nights St. James, Barbados, Waves Hotel & Spa by Elegant Hotels
DATES 6/26/2020 - 9/30/2020
Pleasant Holidays
from $580
3-Nights St. Philip, Antigua, Hammock Cove Antigua
DATES 6/25/2020 - 9/30/2020
Pleasant Holidays
from $1048
3-Nights Puerto Vallarta, Now Amber Puerto Vallarta
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $428
3-Nights Playa Mujeres, Secrets Playa Mujeres Golf & Spa Resort
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $478
3-Nights Dorado, Dorado Beach, a Ritz-Carlton Reserve
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $1755
3-Nights Curacao, Renaissance Curacao Resort & Casino
DATES 8/10/2020 - 9/30/2020
Pleasant Holidays
from $276
3-Nights Riviera Maya, Ocean Coral & Turquesa Resort
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $188
3-Nights San Jose del Cabo, Solaz, a Luxury Collection Resort, Los Cabos
DATES 8/14/2020 - 9/30/2020
Pleasant Holidays
from $671
3-Nights Ocho Rios, Jamaica, Couples Tower Isle
DATES 8/10/2020 - 9/30/2020
Pleasant Holidays
from $532
3-Nights Isla Mujeres, Mexico, Riu Dunamar
DATES 8/7/2020 - 9/30/2020
Pleasant Holidays
from $256
5-Nights Moorea, Hilton Moorea Lagoon Resort & Spa
DATES 12/16/2019 - 12/31/2021
Pleasant Holidays
from $1266
3-Nights Negril, Sandals Negril Beach Resort & Spa
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $762
3-Nights Providenciales, Blue Haven Resort
DATES 8/12/2020 - 9/30/2020
Pleasant Holidays
from $2250
3-Nights Soufriere (St. Lucia), Jade Mountain
DATES 8/14/2020 - 9/30/2020
Pleasant Holidays
from $2216
3-Nights Montego Bay, Royalton Negril Resort & Spa
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $388
3-Nights Paradise Island, Riu Palace Paradise Island
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $495
3-Nights Punta Cana, Eden Roc at Cap Cana
DATES 8/12/2020 - 9/30/2020
Pleasant Holidays
from $1104
3-Nights Antigua, Jumby Bay, A Rosewood Resort
DATES 6/24/2020 - 9/30/2020
Pleasant Holidays
from $2418
3-Nights Providenciales, Grace Bay Club
DATES 8/5/2020 - 9/30/2020
Pleasant Holidays
from $1342
3-Nights Cancun, Omni Cancun Hotel & Villas
DATES 8/7/2020 - 9/30/2020
Pleasant Holidays
from $272
3-Nights Riviera Maya, Hard Rock Hotel Riviera Maya
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $512
3-Nights Cancun, Le Blanc Spa Resort
DATES 8/6/2020 - 9/30/2020
Pleasant Holidays
from $1434
3-Nights Aruba, Barcelo Aruba
DATES 6/24/2020 - 9/30/2020
Pleasant Holidays
from $730
3-Nights Palm Beach, Aruba, Hilton Aruba Caribbean Resort & Casino
DATES 6/24/2020 - 9/30/2020
Pleasant Holidays
from $398
3-Nights Cancun, Dreams Playa Mujeres Golf & Spa Resort
DATES 6/25/2020 - 9/30/2020
Pleasant Holidays
from $428
3-Nights Providenciales, Point Grace Hotel
DATES 8/12/2020 - 9/30/2020
Pleasant Holidays
from $1013
3-Nights Riviera Maya, Now Jade Riviera Cancun
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $313
3-Nights Puerto Vallarta, Crown Paradise Club Puerto Vallarta
DATES 8/13/2020 - 9/30/2020
Pleasant Holidays
from $259
3-Nights Gros Islet (St. Lucia), Calabash Cove Resort & Spa
DATES 8/14/2020 - 9/30/2020
Pleasant Holidays
from $628
3-Nights Riviera Maya, Riu Yucatan
DATES 8/7/2020 - 9/30/2020
Pleasant Holidays
from $260
3-Nights Providenciales, The West Bay Club
DATES 8/11/2020 - 9/30/2020
Pleasant Holidays
from $558
3-Nights San Jose del Cabo, Sandos Finisterra Los Cabos Resort
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $328
3-Nights San Juan, La Concha, A Renaissance Resort
DATES 8/14/2020 - 9/30/2020
Pleasant Holidays
from $448
3-Nights Playa Mujeres, Atelier Playa Mujeres
DATES 8/3/2020 - 9/30/2020
Pleasant Holidays
from $456
3-Nights Punta Cana, Royalton Punta Cana Resort & Casino
DATES 8/12/2020 - 9/30/2020
Pleasant Holidays
from $315
5-Nights The Island of Hawaii, Mauna Kea Beach Hotel
DATES 9/18/2019 - 12/20/2020
Pleasant Holidays
from $2212
3-Nights Playa del Carmen, Hotel Xcaret Mexico
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $725
3-Nights Palm Beach, Aruba, RIU Palace Antillas
DATES 6/24/2020 - 9/30/2020
Pleasant Holidays
from $673
3-Nights Aruba, Tamarijn Aruba
DATES 6/24/2020 - 9/30/2020
Pleasant Holidays
from $810
3-Nights Cancun, Crown Paradise Club Cancun
DATES 8/7/2020 - 9/30/2020
Pleasant Holidays
from $281
3-Nights Castries, St. Lucia, Windjammer Landing Villa Beach Resort
DATES 8/5/2020 - 9/30/2020
Pleasant Holidays
from $274
3-Nights Cabo San Lucas, Tesoro Los Cabos
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $220
3-Nights Playa del Carmen, The Fives Beach Hotel & Residences
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $1068
3-Nights St. John's, Antigua, Pineapple Beach Club Antigua
DATES 6/24/2020 - 9/30/2020
Pleasant Holidays
from $624
3-Nights Cabo San Lucas, Las Ventanas al Paraiso, A Rosewood Resort
DATES 8/6/2020 - 9/30/2020
Pleasant Holidays
from $1428
3-Nights Playa del Carmen, Paradisus Playa del Carmen La Esmeralda
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $456
3-Nights Punta Cana, Zoetry Agua Punta Cana
DATES 8/12/2020 - 9/30/2020
Pleasant Holidays
from $703
3-Nights Riviera Maya, Dreams Tulum Resort & Spa
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $384
3-Nights Riviera Maya, Secrets Capri Riviera Cancun
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $418
3-Nights Cabo San Lucas, Pueblo Bonito Pacifica Resort & Spa
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $472
3-Nights Puerto Vallarta, Canto Del Sol Plaza Vallarta
DATES 8/13/2020 - 9/30/2020
Pleasant Holidays
from $308
3-Nights St. Lucia, Sandals Grande St. Lucian Spa & Beach Resort
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $1138
3-Nights Cabo San Lucas, Chileno Bay Resort & Residences
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $1759
3-Nights Nassau, Harborside Resort at Atlantis
DATES 8/11/2020 - 9/30/2020
Pleasant Holidays
from $589
3-Nights Cancun, Royalton Rivera Cancun Resort & Spa
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $378
3-Nights Cabo San Lucas, Montage Los Cabos
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $1068
3-Nights Cabo San Lucas, Casa Dorada Los Cabos Resort & Spa
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $460
3-Nights Cancun, Grand Palladium White Sand
DATES 8/3/2020 - 9/30/2020
Pleasant Holidays
from $348
3-Nights Punta Cana, Paradisus Palma Real Resort
DATES 8/6/2020 - 9/30/2020
Pleasant Holidays
from $454
3-Nights Montego Bay, Grand Palladium Lady Hamilton
DATES 8/11/2020 - 9/30/2020
Pleasant Holidays
from $430
3-Nights Kingston, Jamaica, Strawberry Hill
DATES 8/11/2020 - 9/30/2020
Pleasant Holidays
from $389
3-Nights Puerto Vallarta, Sheraton Buganvilias Resort
DATES 8/13/2020 - 9/30/2020
Pleasant Holidays
from $154
3-Nights Marigot Bay (St. Lucia), Capella Marigot Bay Resort & Marina
DATES 8/14/2020 - 9/30/2020
Pleasant Holidays
from $531
3-Nights Puerto Vallarta, Villa del Palmar Beach Resort & Spa
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $120
3-Nights La Romana, Dreams Dominicus La Romana
DATES 8/12/2020 - 9/30/2020
Pleasant Holidays
from $290
5-Nights Curacao, Renaissance Curacao Resort & Casino
DATES 3/4/2020 - 12/15/2020
Pleasant Holidays
from $612
3-Nights San Jose del Cabo, Paradisus Los Cabos
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $500
3-Nights Puerto Morelos, Mexico, Desire Resort & Spa
DATES 8/7/2020 - 9/30/2020
Pleasant Holidays
from $776
3-Nights Punta Cana, Iberostar Dominicana
DATES 8/12/2020 - 9/30/2020
Pleasant Holidays
from $274
5-Nights Grand Cayman, Kimpton Seafire Resort + Spa
DATES 12/12/2019 - 12/10/2020
Pleasant Holidays
from $1863
3-Nights Noord, Aruba, Boardwalk Boutique Hotel Aruba
DATES 6/25/2020 - 9/30/2020
Pleasant Holidays
from $558
3-Nights Bridgetown, Barbados, Courtyard by Marriott Bridgetown, Barbados
DATES 6/26/2020 - 9/30/2020
Pleasant Holidays
from $351
3-Nights Montego Bay, Riu Reggae
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $312
3-Nights Cancun, Now Emerald Cancun
DATES 8/7/2020 - 9/30/2020
Pleasant Holidays
from $306
3-Nights Riviera Maya, El Dorado Casitas Royale, by Karisma
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $781
3-Nights Cozumel, Grand Park Royal Cozumel
DATES 8/10/2020 - 9/30/2020
Pleasant Holidays
from $576
5-Nights Bora Bora, The St. Regis Bora Bora Resort
DATES 2/20/2020 - 12/15/2020
Pleasant Holidays
from $3384
3-Nights Providenciales, Seven Stars Resort
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $1049
3-Nights Puerto Vallarta, Paradise Village Beach & Spa
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $346
3-Nights Punta de Mita, Marival Armony Luxury Resort & Suites
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $442
3-Nights Cancun, Azul Beach Resort Riviera Cancun by Karisma
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $356
5-Nights San Jose del Cabo, Paradisus Los Cabos
DATES 9/10/2021 - 12/14/2021
Pleasant Holidays
from $1267
5-Nights Providenciales, The Shore Club
DATES 6/9/2020 - 12/14/2021
Pleasant Holidays
from $3054
3-Nights San Juan, Sheraton Old San Juan Hotel & Casino
DATES 8/6/2020 - 9/30/2020
Pleasant Holidays
from $315
3-Nights Cancun, Excellence Riviera Cancun
DATES 6/25/2020 - 9/30/2020
Pleasant Holidays
from $468
3-Nights Riviera Maya, Ocean Coral & Turquesa Resort
DATES 8/10/2020 - 9/30/2020
Pleasant Holidays
from $200
3-Nights Montego Bay, Hyatt Ziva Rose Hall
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $726
3-Nights Ocho Rios, Jamaica, Jamaica Inn
DATES 8/11/2020 - 9/30/2020
Pleasant Holidays
from $668
3-Nights La Romana, Casa de Campo
DATES 8/12/2020 - 9/30/2020
Pleasant Holidays
from $595
3-Nights Puerto Vallarta, Fiesta Americana Puerto Vallarta
DATES 8/13/2020 - 9/30/2020
Pleasant Holidays
from $295
3-Nights San Juan, San Juan Marriot Resort and Stellaris Casino
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $314
3-Nights Providenciales, The Sands at Grace Bay
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $429
5-Nights Oahu, Moana Surfrider, A Westin Resort & Spa
DATES 2/5/2020 - 1/2/2021
Pleasant Holidays
from $1317
3-Nights Cozumel, El Cid La Ceiba Beach Hotel
DATES 8/10/2020 - 9/30/2020
Pleasant Holidays
from $178
5-Nights Grand Cayman, The Ritz-Carlton Grand Cayman
DATES 12/12/2019 - 12/10/2020
Pleasant Holidays
from $2922
3-Nights Willemstad, Curacao , Sunscape Curacao Resort, Spa & Casino
DATES 8/10/2020 - 9/30/2020
Pleasant Holidays
from $382
3-Nights Playa del Carmen, Occidental Grand Xcaret
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $268
3-Nights Punta Cana, IBEROSTAR Punta Cana
DATES 8/12/2020 - 9/30/2020
Pleasant Holidays
from $255
3-Nights Ochos Rios, Moon Palace Jamaica
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $525
3-Nights Riviera Maya, Banyan Tree Mayakoba
DATES 8/7/2020 - 9/30/2020
Pleasant Holidays
from $1118
3-Nights Punta Cana, Dreams Palm Beach Punta Cana
DATES 7/6/2020 - 9/30/2020
Pleasant Holidays
from $341
3-Nights Cabo San Lucas, One&Only Palmilla
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $1812
3-Nights Riviera Maya, Riu Tequila
DATES 8/7/2020 - 9/30/2020
Pleasant Holidays
from $254
3-Nights Cancun, Villa del Palmar Cancun
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $208
3-Nights Cancun, Dreams Playa Mujeres Golf & Spa Resort
DATES 7/1/2020 - 9/30/2020
Pleasant Holidays
from $428
3-Nights Providenciales, Wymara Resort and Villas Turks + Caicos
DATES 8/6/2020 - 9/30/2020
Pleasant Holidays
from $1191
3-Nights Punta Cana, The Reserve at Paradisus Palma Real
DATES 8/12/2020 - 9/30/2020
Pleasant Holidays
from $608