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Vacations Under $500

(49 offers included)
Dates: Jun 03, 2026 through Dec 19, 2026
Location(s):
Kona, Hawaii
Guaranteed room upgrade + $100 food & beverage credit at The Fairmont Orchid
Dates: Jun 04, 2026 through Dec 23, 2026
Location(s):
St. Martin
Up to $150 in instant savings + Resort coupons at Sonesta Ocean Point Resort
Kenya Wildlife Safari 2027 - Land Only Classic Collection, Locally Hosted Small Group
Nights: 8
Dates: May 04, 2026 through Dec 31, 2027
Location(s):
Nairobi, Nairobi / Samburu, Samburu National Reserve, Samburu National Reserve / Lake Nakuru, Lake Nakuru / Masai Mara, Masai Mara National Reserve, Masai Mara National Reserve / Nairobi / Depart
No Image Available
Nights: 9
Dates: Aug 01, 2023 through Dec 31, 2026
Location(s):
Zagreb, Zagreb, Opatija, Opatija, Opatija, Zadar, Zadar, Split, Split, Split, Dubrovnik, Dubrovnik
Discover contrasting landscapes within one fascinating destination. Your private guide will show you cultural sites, breathtaking lakes and waterfalls, and the idyllic, seaside cities and towns along the Adriatic Coast. This wonderfully personalized vacation was created for those that want to experience the highlights and must-sees of all that Croatia offers with a private driving guide sharing their own personal experiences and insight as well as informing you about the historic and contempo...
Departing on Nov 26, 2026 on the MSC Sinfonia
Nights: 7
Dates: Nov 26, 2026 through Dec 03, 2026
Ship: MSC Sinfonia
Itinerary:
Civitavecchia (Rome) Italy, Valencia Spain, Barcelona, Spain, Marseille (Provence) France, Genoa (Portofino) Italy, Livorno (Florence) Italy, Civitavecchia (Rome) Italy
from
$536.21
(USD)
Per Person
Inside
$536.21
Cat: IM1
$76.60/Night
Outside
$652.21
Cat: OO
$93.17/Night
Balcony
$1,007.21
Cat: BM1
$143.89/Night
Suite
$1,247.21
Cat: SR1
$178.17/Night
No Image Available
Nights: 1
Dates: Oct 01, 2023 through Dec 31, 2026
Location(s):
Chichicastenango
Home to one of the largest open-air markets in Central America, you'll find everything from textiles, colorful woolen blankets and masks to fresh fruit and flowers for sale.
Dates: Jun 03, 2026 through Sep 30, 2026
Location(s):
Riviera Maya
$100 in instant savings at Moon Palace Cancun
Departing on Oct 16, 2026 on the Ovation of the Seas
Nights: 3
Dates: Oct 16, 2026 through Oct 19, 2026
Itinerary:
Los Angeles, California, Ensenada, Mexico, Cruising, Los Angeles, California
from
$451.17
(USD)
Per Person
Inside
$451.17
Cat: 2W
$150.39/Night
Outside
$749.17
Cat: 2N
$249.72/Night
Balcony
$624.17
Cat: 2F
$208.06/Night
Suite
$1,414.17
Cat: J4
$471.39/Night
The Connoisseur's Collection Tailor-Made Safari
Nights: 12
Dates: May 01, 2026 through Dec 31, 2026
Location(s):
Arrive Cape Town, South Africa, Cape Town, Cape Town / Kruger Private Reserve, Kruger Private Reserve, Kruger Private Reserve / Livingstone, Zambia, Livingstone, Livingstone / Okavango Delta, Botswana, Okavango Delta, Okavango Delta / Johannesburg / Depart
Departing on Oct 09, 2026 on the Ovation of the Seas
Nights: 3
Dates: Oct 09, 2026 through Oct 12, 2026
Itinerary:
Los Angeles, California, Cruising, Ensenada, Mexico, Los Angeles, California
from
$462.18
(USD)
Per Person
Inside
$462.18
Cat: 2W
$154.06/Night
Outside
$728.18
Cat: 2N
$242.73/Night
Balcony
$813.18
Cat: 2E
$271.06/Night
Suite
$1,953.18
Cat: J4
$651.06/Night
Dates: Jun 04, 2026 through Oct 31, 2026
Location(s):
Cancun
Guaranteed room upgrade at Iberostar Selection Cancun
Dates: Jul 03, 2026 through Jan 08, 2027
Location(s):
Scottsdale
Guaranteed room upgrade + Waived resort fee + Early check-in & late checkout at Hilton Scottsdale Resort & Villas
No Image Available
Nights: 6
Dates: Oct 31, 2023 through Dec 31, 2026
Location(s):
Cardiff, Cardiff, Brecon, Brecon
Discover the all charms this fascinating country has to offer, while sampling traditional Welsh cuisine along with a myriad of activities. Spend a day exploring the magnificent Brecon Beacon National Park, take a ride on the Brecon Mountain Railway, plus visits to a distillery, a winery, and a cheese tasting. An itinerary for both the serious and casual food lovers; you'll journey through some of their historic cities and countryside, replete with extraordinary landscapes and astounding cast...
Departing on Feb 18, 2027 on the Serenade of the Seas
Nights: 3
Dates: Feb 18, 2027 through Feb 21, 2027
Itinerary:
San Diego, California, Ensenada, Mexico, Cruising, San Diego, California
from
$493.13
(USD)
Per Person
Inside
$493.13
Cat: 2W
$164.38/Night
Outside
$688.13
Cat: 4N
$229.38/Night
Balcony
$939.13
Cat: 4D
$313.04/Night
Suite
$1,386.13
Cat: J3
$462.04/Night
Dates: Mar 04, 2026 through Dec 22, 2026
Location(s):
Riviera Maya
Kids & teens stay & eat free + ALL-FUN INCLUSIVE® amenities at Hotel Xcaret Mexico
Departing on Mar 23, 2027 on the MSC Bellissima
Nights: 4
Dates: Mar 23, 2027 through Mar 27, 2027
Itinerary:
Shanghai China, Kagoshima Japan, Tokyo Japan
from
$329.00
(USD)
Per Person
Inside
$329.00
Cat: IR1
$82.25/Night
Outside
$359.00
Cat: OO
$89.75/Night
Balcony
$519.00
Cat: BP
$129.75/Night
Suite
$929.00
Cat: SL1
$232.25/Night
Nights: 6
Dates: Jul 07, 2025 through Dec 31, 2028
Location(s):
Dublin Arrival, Private Driver Services Begin, Ben Bulben Forest Walk & Glencar Waterfall, Achill Island Day Trip, Connemara Sightseeing & Kylemore Abbey, Galway Walking Tour & Remainder of Day at Leisure, Dublin Departure
Experience Ireland your way with our most personalized style of travel for up to 9 guests.  Enjoy your own private car with a driver who knows the local history and has plenty of insider stories to share. Perfect for heritage seekers, multi-generational families, and milestone celebrations.
Nights: 10
Dates: Jul 07, 2025 through Dec 31, 2028
Location(s):
Catania Arrival, Taormina, Mount Etna, Taormina - Tropea, Tropea - Puglia, Alberobello, Lecce - Ostuni, Puglia - Minori, Amalfi Coast, Naples Departure
Experience Italy your way with our most personalized style of travel for up to 9 guests.  Enjoy your own private car with a driver who knows the local history and has plenty of insider stories to share. Perfect for heritage seekers, multi-generational families, and milestone celebrations.
Departing on Mar 05, 2028 on the MSC Grandiosa
Nights: 4
Dates: Mar 05, 2028 through Mar 09, 2028
Itinerary:
Port Canaveral (Orlando) Florida, Ocean Cay Msc Marine Reserve Bahamas, Nassau Bahamas, Port Canaveral (Orlando) Florida
from
$490.90
(USD)
Per Person
Inside
$490.90
Cat: IR1
$122.73/Night
Outside
$552.90
Cat: OO
$138.23/Night
Balcony
$612.90
Cat: BP
$153.23/Night
Suite
$1,019.90
Cat: SL1
$254.98/Night
No Image Available
Nights: 8
Dates: Aug 01, 2023 through Dec 31, 2026
Location(s):
Madrid, Madrid, Córdoba, Córdoba, Seville, Seville, Seville, Granada, Granada
Combine the vibrant capital city of Madrid with southern Spain. Ride the Spanish rails through scenic terrain to experience spectacular Moorish monuments, traditional Flamenco music and dance, and mountainous countryside that will enchant and inspire.
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Nights: 9
Dates: Oct 01, 2023 through Dec 31, 2026
Location(s):
Placencia, Placencia, Cayo District, Cayo District, Cayo District, Ambergris Caye, Ambergris Caye
The ultimate Belizean vacation with beaches, Mayan ruins and adventure! Visit two of Belize's most popular beach destinations; Placencia, where you will enjoy the rich Garifuna culture and the mainland's best beaches, and Ambergris Caye, the world's second-largest barrier reef. In between, go inland to the Cayo District and explore Mayan ruins as well as dazzling cave systems.
Nights: 7
Dates: Jul 07, 2025 through Dec 31, 2028
Location(s):
Florence Arrival, Siena - Chianti Classico - San Gimignano, Florence Cradle of Renaissance Tour, Pisa - Lucca, Cinque Terre - Italian Riviera, Portofino - Santa Margherita, Santa Margherita - Milan - Stresa, Stresa - Lake Maggiore, Milan Departure
Experience Italy your way with our most personalized style of travel for up to 9 guests.  Enjoy your own private car with a driver who knows the local history and has plenty of insider stories to share. Perfect for heritage seekers, multi-generational families, and milestone celebrations.
Customized Private Driver Vacations for Travelers with Special Needs For those who need a little more time to get around.
Dates: Jan 01, 2024 through Dec 31, 2026
Location(s):
Ireland, England, Scotland, Italy, Iceland
Experience Ireland, Britain, Iceland, or Italy your way with our most personalized style of travel for up to 9 guests.  Enjoy your own private car with a driver who knows the local history and has plenty of insider stories to share.  Perfect for heritage seekers, multi-generational families, and milestone celebrations.  The only limit is your imagination - let us design a custom tour for you or choose from one of the suggested itineraries below.
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Dates: Apr 02, 2026 through Dec 31, 2028
Itinerary:
Antarctica, South America
With our Explorer's Choice offer, you customize your experience.
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Dates: Jun 01, 2026 through Dec 31, 2026
Itinerary:
Mediterranean, Northern Europe, Arctic
For a limited time, enjoy Air Credit Savings of up to $3,000 per suite-plus bonus savings of up to 40% savings on select Mediterranean, Northern Europe, and Arctic expeditions.
Departing on Mar 15, 2027 on the MSC Musica
Nights: 4
Dates: Mar 15, 2027 through Mar 19, 2027
Ship: MSC Musica
Itinerary:
Santos (Sao Paulo) Brazil, Buzios Brazil, Ilha Grande Brasilien, Santos (Sao Paulo) Brazil
from
$485.29
(USD)
Per Person
Inside
$525.29
Cat: IR1
$131.32/Night
Outside
$605.29
Cat: OO
$151.32/Night
Balcony
$755.29
Cat: BR1
$188.82/Night
Splendors Of Southern Africa 2026 Concierge Collection, Locally-Hosted Small Group
Nights: 10
Dates: Jun 15, 2026 through Dec 31, 2027
Location(s):
Arrive Cape Town, South Africa, Cape Town, Cape Town / Kruger Private Reserve, Kruger Private Reserve, Kruger Private Reserve / Victoria Falls, Zimbabwe, Victoria Falls, Victoria Falls / Depart
Dates: Jun 15, 2026 through Dec 15, 2026
Location(s):
Maui Island
Free room upgrade at Grand Wailea Maui, A Waldorf Astoria Resort
Departing on Aug 31, 2026 on the MSC Seaside
Nights: 4
Dates: Aug 31, 2026 through Sep 04, 2026
Ship: MSC Seaside
Itinerary:
Miami Florida, Nassau Bahamas, Ocean Cay Msc Marine Reserve Bahamas, Miami Florida
from
$208.80
(USD)
Per Person
Inside
$228.80
Cat: IR1
$57.20/Night
Outside
$298.80
Cat: OR1
$74.70/Night
Balcony
$348.80
Cat: BR1
$87.20/Night
Suite
$588.80
Cat: BGA
$147.20/Night
No Image Available
Dates: Jun 03, 2026 through Dec 31, 2029
Itinerary:
Europe, Australia, East and Southeast Asia
Special offers on all-inclusive ocean voyages.
No Image Available
Nights: 7
Dates: Oct 31, 2023 through Dec 31, 2026
Location(s):
Cardiff, Cardiff, Saundersfoot, Saundersfoot, Saundersfoot, Cardigan, Cardigan
Delve into this fascinating country that has retained a distinct cultural identity, while sampling traditional Welsh cuisine along with a myriad of activities. Spend a day foraging on their rugged coastline, take a Wildlife Boat excursion, all interspersedwith visits to a micro-brewery, a winery, and a cheese tasting. An itinerary for both the serious and the not-so serious foodies; you'll journey through some of their historic cities and countryside, replete with extraordinary landscapes an...
Departing on Oct 29, 2026 on the MSC Sinfonia
Nights: 3
Dates: Oct 29, 2026 through Nov 01, 2026
Ship: MSC Sinfonia
Itinerary:
Civitavecchia (Rome) Italy, Valencia Spain, Tarragona Spain
from
$264.35
(USD)
Per Person
Inside
$264.35
Cat: IM1
$88.12/Night
Outside
$329.35
Cat: OO
$109.78/Night
Balcony
$509.35
Cat: BM1
$169.78/Night
Suite
$608.35
Cat: SR1
$202.78/Night
No Image Available
Nights: 4
Dates: Oct 01, 2023 through Dec 31, 2026
Location(s):
Rio Negro
You'll explore some of the most remote rainforest in all of the Amazon basin, for an up-close look at exotic rarities in their natural habitat. You will be cruising on the classic M/Y Tucano; it is a comfortable river boat, designed to be able to access the small tributaries and hidden channels where larger vessels cannot go.
Departing on May 04, 2028 on the MSC Grandiosa
Nights: 3
Dates: May 04, 2028 through May 07, 2028
Itinerary:
Port Canaveral (Orlando) Florida, Nassau Bahamas, Ocean Cay Msc Marine Reserve Bahamas, Port Canaveral (Orlando) Florida
from
$359.00
(USD)
Per Person
Inside
$359.00
Cat: IR1
$119.67/Night
Outside
$419.00
Cat: OO
$139.67/Night
Balcony
$459.00
Cat: BP
$153.00/Night
Suite
$789.00
Cat: SL1
$263.00/Night
No Image Available
Nights: 2
Dates: Oct 31, 2023 through Dec 31, 2026
Location(s):
Windermere, Grasmere
Take a whirlwind trip through Cumbria, home to the English Lake district and considered one of the most beautiful regions of the UK. You'll visit Hill Top, Beatrix Potter's house Spend a night in Grasmere, Cumbria's most popular village and Windermere, the charming village nestled on the lake. Experience all the activities on a working Lake District farm, board the Ullswater Steamer for a scenic cruise, plus stroll through the recently renovated Lowther castle and gardens.
Departing on Sep 15, 2028 on the MSC Seaside
Nights: 3
Dates: Sep 15, 2028 through Sep 18, 2028
Ship: MSC Seaside
Itinerary:
Miami Florida, Ocean Cay Msc Marine Reserve Bahamas, Nassau Bahamas, Miami Florida
from
$229.00
(USD)
Per Person
Inside
$259.00
Cat: IR1
$86.33/Night
Outside
$319.00
Cat: OR1
$106.33/Night
Balcony
$379.00
Cat: BR1
$126.33/Night
Suite
$569.00
Cat: BGA
$189.67/Night
No Image Available
Nights: 6
Dates: Oct 01, 2023 through Dec 31, 2026
Location(s):
Rio Negro
You'll explore some of the most remote rainforest in all of the Amazon basin, for an up-close look at exotic rarities in their natural habitat. You will be cruising on the classic M/Y Tucano; it is a comfortable river boat, designed to be able to access the small tributaries and hidden channels where larger vessels cannot go.
Departing on Oct 26, 2026 on the MSC Seaside
Nights: 7
Dates: Oct 26, 2026 through Nov 02, 2026
Ship: MSC Seaside
Itinerary:
Miami Florida, Nassau Bahamas, Ocean Cay Msc Marine Reserve Bahamas, Miami Florida, Nassau Bahamas, Ocean Cay Msc Marine Reserve Bahamas, Miami Florida
from
$437.57
(USD)
Per Person
Inside
$437.57
Cat: IR2
$62.51/Night
Outside
$527.57
Cat: OR1
$75.37/Night
Suite
$3,100.57
Cat: YC1
$442.94/Night
Departing on Apr 23, 2027 on the MSC Divina
Nights: 3
Dates: Apr 23, 2027 through Apr 26, 2027
Ship: MSC Divina
Itinerary:
Civitavecchia (Rome) Italy, Mykonos Greece, Marmaris Turkey
from
$349.00
(USD)
Per Person
Inside
$349.00
Cat: IM2
$116.33/Night
Outside
$429.00
Cat: OM2
$143.00/Night
Balcony
$499.00
Cat: BP
$166.33/Night
Suite
$779.00
Cat: SRS
$259.67/Night
Departing on Mar 31, 2027 on the MSC Virtuosa
Nights: 3
Dates: Mar 31, 2027 through Apr 03, 2027
Ship: MSC Virtuosa
Itinerary:
Maceio Brazil, Santos (Sao Paulo) Brazil
from
$420.00
(USD)
Per Person
Inside
$420.00
Cat: IR2
$140.00/Night
Outside
$489.00
Cat: OO
$163.00/Night
Balcony
$569.00
Cat: BP
$189.67/Night
Suite
$949.00
Cat: SL1
$316.33/Night
No Image Available
Nights: 10
Dates: Oct 01, 2023 through Dec 31, 2026
Location(s):
Quito, Quito, Galapagos Islands, Galapagos Islands, Guayaquil, Cuenca
Experience magical Ecuador - its culture, history, landscapes and biodiversity. Begin in Quito, situated at 9300 feet in the heart of the Andes, just south of the Equatorial Line. The country's colonial history is reflected in Quito's Historic Centre and the lovely city of Cuenca, both UNESCO World Heritage sites. Get In touch with indigenous culture at the famous handicrafts market at Otavalo, and the surrounding villages. Visit Ecuador's other major city, Guayaquil, before flying to the Gal...
No Image Available
Nights: 4
Dates: Oct 01, 2023 through Dec 31, 2026
Location(s):
Arrive Vientiane, Vientiane, Vientiane to Luang Prabang, Luang Prabang, Depart Luang Prabang
Blessed with immense natural beauty and a fascinating history, Laos has much to offer. This introduction showcases the cultural highlights of its laid-back capital, Vientiane, and charming Luang Prabang, with its stunning scenery, lush forest and beautiful waterfalls.
No Image Available
Dates: Jun 08, 2026 through Dec 31, 2027
Location(s):
Kenya, Tanzania, South Africa, Rwanda
Feel the ground shake as the Great Migration thunders across the Serengeti, track the Big Five in a private Kruger reserve, and soar above Victoria Falls by helicopter. Whether your African story calls for the sweeping plains of Tanzania, the elegance and “Out of Africa" appeal of Kenya, the diversity of South Africa, or the magical allure of gorilla trekking in Rwanda, it's now closer than ever.
Dates: May 01, 2026 through Dec 23, 2026
Location(s):
Liberia
Kids stay & eat free at Riu Guanacaste
No Image Available
Nights: 3
Dates: May 01, 2023 through Dec 31, 2026
Location(s):
Manaus
The Manatee Amazon Explorer riverboat was specially built for cruises in the Ecuadorian rainforest on the Rio Napo. During the cruise you will enjoy delicious cuisine, and your excursions will be led by multilingual naturalist guides. Some of the highlights of your Amazon experience will be a visit to Yasuni National Park and Biosphere Reserve, and Monkey Island.
Departing on Oct 30, 2026 on the MSC Divina
Nights: 3
Dates: Oct 30, 2026 through Nov 02, 2026
Ship: MSC Divina
Itinerary:
Civitavecchia (Rome) Italy, Genoa (Portofino) Italy, Tarragona Spain
from
$340.00
(USD)
Per Person
Inside
$380.00
Cat: IM2
$126.67/Night
Outside
$470.00
Cat: OM2
$156.67/Night
Balcony
$498.00
Cat: BP
$166.00/Night
Suite
$804.00
Cat: SRS
$268.00/Night
No Image Available
Nights: 6
Dates: Oct 01, 2023 through Dec 31, 2026
Location(s):
Santiago, Santiago, Wine Country, Wine Country, Wine Country, Valparaiso, Valparaiso, Santiago
Santiago, the capital of Chile, is the gateway to the world-renowned wine region of the Central Valley. Drive south through the most notable wine regions between the Andes and the lower coastal range. Spend 2 nights in the Colchagua area, and visit wineries during the day. Savor the wine and food of the area before continuing your drive to the vibrant and charming port city of Valparaiso, with more winery visits along the way.
Departing on Sep 22, 2026 on the Quantum of the Seas
Nights: 4
Dates: Sep 22, 2026 through Sep 26, 2026
Itinerary:
Los Angeles, California, Cruising, Ensenada, Mexico, Cruising, Los Angeles, California
from
$486.85
(USD)
Per Person
Inside
$486.85
Cat: 2W
$121.71/Night
Outside
$718.85
Cat: 4M
$179.71/Night
Balcony
$693.85
Cat: 2D
$173.46/Night
Suite
$1,873.85
Cat: J3
$468.46/Night
Departing on Oct 18, 2026 on the Queen Mary 2
Nights: 2
Dates: Oct 18, 2026 through Oct 20, 2026
Ship: Queen Mary 2
Itinerary:
London (Southampton), England, Hamburg, Germany
A charming 2-night break from Southampton to the lovely German city of Hamburg.
from
$369.00
(USD)
Per Person
Inside
$369.00
Cat: IC
$184.50/Night
Balcony
$429.00
Cat: DB
$214.50/Night
Suite
$829.00
Cat: P1
$414.50/Night