Caribbean Vacations & Trips from ￥171,275

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Top destinations in Caribbean

A marina with a white boat named 'Achina' docked, surrounded by palm trees and a building with a green roof.

Punta Cana

Punta Cana
A beach with clear turquoise water, white sand, and green foliage in the foreground.

St. Thomas

St. Thomas
A tropical beach with turquoise waters, green hills, and a clear sky.

St. John

St. John
A pier with kayaks and a sailboat.

Montego Bay

Montego Bay
A cruise ship docked at a port with a clear blue sea and a small island in the background.

Nassau

Nassau
Turquoise waters, green islands, and lush vegetation.

Providenciales

Providenciales
A beach with clear turquoise water, a person sunbathing, and palm trees in the background.

Oranjestad

Oranjestad

The Latest Caribbean Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Bahia Principe Escape Bouganville - Hyatt Inclusive Collection - Adults Only - All Inclusive

Bahia Principe Escape Bouganville - Hyatt Inclusive Collection - Adults Only - All Inclusive

￥171,275
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
León (BJX) to Santo Domingo (SDQ)
8.8/10 Excellent! (2,669 reviews)
Service was good. Regarding the food, plenty of but there’s an opportunity for improvement

Reviewed on Aug 7, 2026

310Guest-House LaVida

310Guest-House LaVida

Old San Juan
￥415,026
per person
Oct 12 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to San Juan (SJU)
9.2/10 Wonderful! (55 reviews)
My stay was perfect! . Check in process was seamless. Entered the code into the lock box as the instructions stated. I had no issues receiving the keys. Upon the walk in , the apt was spotless. Location was perfect. I was on the strip with a grocery store one block down. Tons of restaurants and bars within a 3 block radius . The balcony was beautiful! There was a tray filled with snacks for me to keep. A bottle the of water was in the refrigerator complimentary. The communication with the owner was great. They made sure to check on me day 1 and see if I needed anything or if there was anything they can do to make my stay more comfortable. I appreciated that.

Reviewed on Aug 3, 2026

DUNA by DW

DUNA by DW

Santurce
￥441,452
per person
Oct 12 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to San Juan (SJU)
9.4/10 Exceptional! (90 reviews)
Numero Uno Beach House

Numero Uno Beach House

Santurce
￥430,144
per person
Oct 12 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to San Juan (SJU)
9.4/10 Exceptional! (491 reviews)
Ocean Breeze Villa

Ocean Breeze Villa

Puerta de Tierra
￥430,917
per person
Oct 12 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to San Juan (SJU)
9.2/10 Wonderful! (27 reviews)
Excellent! Thank you! Great location, safe location, very friendly and helpful staff, close to nice places to eat. The studio was beautiful with a very nice view from the balcony. My husband and I already started recommending this place. Puerto Rico is beautiful, we enjoyed Old San Juan, enjoyed history, eat the delicious mofongo, arroz mamposteao, the pastelitos, the views, the ocean and mountains. We will come back for sure.

Reviewed on Aug 2, 2026

Things to do in Caribbean

Shopping

Experience the vibrant shopping scene in the Caribbean at Renaissance Shopping Mall, which offers a mix of business, entertainment, and family-friendly vibes. Visit the Straw Market for a unique local atmosphere and souvenirs. For everyday needs, Mega Mart provides a convenient shopping option.

Recreation

Experience the natural beauty of Scape Park, where you can indulge in wellness activities amidst lush landscapes and serene vibes. At Coco Beach Golf and Country Club, enjoy luxury amenities and a round of golf, while Arecibo Observatory offers engaging family entertainment in a unique astronomical setting.

Adventure

Mystic Mountain offers thrilling activities like zip-lining and bobsledding through lush landscapes. Aquaventure features exhilarating water slides and lazy rivers, perfect for family fun. The Skyride to Paradise Point provides breathtaking views as you ascend, making it a delightful outdoor adventure for all ages.

Nightlife

Experience the vibrant nightlife of the Caribbean at Coco Bongo Punta Cana, where romance meets electrifying entertainment. Visit Floyd's Pelican Bar for a laid-back atmosphere and refreshing drinks. Don't miss Casa de la Musica de Centro, where city vibes and live music create an unforgettable night out.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in Caribbean

The Caribbean offers a diverse array of attractions for every traveler, featuring beautiful beaches, serene bays, and historic churches. Explore vibrant cultures and enjoy outdoor experiences while discovering popular Caribbean destinations. To enhance your trip, consider looking into Caribbean vacation packages that provide unforgettable experiences tailored to your interests.

  • Eagle Beach: Experience the stunning beauty of Eagle Beach, known for its powdery white sand and turquoise waters. This beach offers a serene atmosphere perfect for relaxation, sunbathing, and swimming. The vibrant beach vibes create an inviting environment for both families and solo travelers.
  • El Yunque National Forest: Explore El Yunque, a lush rainforest teeming with diverse wildlife and breathtaking scenery. Enjoy eco-friendly adventures with hiking trails that lead to stunning waterfalls and panoramic views. It's a paradise for outdoor enthusiasts and nature lovers.
  • Magens Bay Beach: Discover Magens Bay Beach, famous for its tranquil waters and picturesque surroundings. Ideal for swimming and sunbathing, this bay offers a scenic backdrop for a perfect day outdoors. It’s a favorite spot for both relaxation and recreation.

Best time to go to Caribbean

The best time to visit Caribbean is dependent on what kind of holiday you are seeking. September is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. November is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January79.3°F (26.3°C)No RainMostly SunnySlightly HighAverage
February78.8°F (26.0°C)No RainMostly SunnyAverageSlightly High
March79.2°F (26.200000000000003°C)No RainMostly SunnyAverageSlightly High
April80.1°F (26.700000000000003°C)Light RainMostly SunnyAverageAverage
May80.4°F (26.9°C)Light RainMostly SunnySlightly LowAverage
June81.7°F (27.6°C)Light RainMostly SunnyAverageAverage
July82.2°F (27.9°C)Light RainMostly SunnySlightly HighAverage
August82.8°F (28.200000000000003°C)Light RainMostly SunnyAverageAverage
September82.9°F (28.3°C)Light RainMostly SunnySlightly HighSlightly Low
October82.6°F (28.1°C)Light RainMostly SunnySlightly LowSlightly Low
November78.3°F (25.700000000000003°C)Light RainMostly SunnySlightly LowSlightly Low
December79.5°F (26.4°C)No RainMostly SunnyAverageSlightly High

Tips to save on your trip to Caribbean

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Caribbean.
  • Consider traveling to Caribbean during the low season (September to November) for more affordable options.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Caribbean Hotel Deals

Hotel El Convento

Hotel El Convento

100 Cristo St San Juan
Fully refundableReserve now, pay when you stay
￥27,925
￥36,525 total
Sep 1 - Sep 2
includes taxes & fees
9.2/10 Wonderful! (1,017 reviews)
"Stunningly beautiful and impeccably maintained, historic property (375 years old), with excellent service from a top-notch staff, in the best location in San Juan. Wonderful rooms and unheralded amenities for old town including a fitness center, as well as a rooftop pool, hot tub, and sun deck with ..."

Reviewed on Aug 7, 2026

Hotel El Convento
British Colonial - Nassau

British Colonial - Nassau

Number One Bay St Nassau
Fully refundableReserve now, pay when you stay
￥27,621
￥42,646 total
Sep 7 - Sep 8
includes taxes & fees
British Colonial - Nassau
Hotel Rumbao, a Tribute Portfolio Hotel

Hotel Rumbao, a Tribute Portfolio Hotel

100 Brumbaugh Street San Juan Puerto Rico
Fully refundableReserve now, pay when you stay
￥26,134
￥35,108 total
Aug 31 - Sep 1
includes taxes & fees
9/10 Wonderful! (1,840 reviews)
"The stay was amazing from the day we arrived to the day we left! Staff were so friendly and helpful. Hotel was clean. Bottled water available any time. Hotel location is walkable to El Moro, restaurants and shopping."

Reviewed on Aug 6, 2026

Hotel Rumbao, a Tribute Portfolio Hotel
See all 88,662 properties in Caribbean
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Can I travel to Caribbean right now?
For all the up-to-date facts about visiting Caribbean, take a look at our Covid-19 Travel Advisor. From quarantine policies to travel restrictions and more, Expedia will help make your trip planning as stress-free as possible.
If I'm not able to travel, can I cancel my Caribbean vacation package?
Your situation can change suddenly, so yes, you can. You may be able to change or cancel your Caribbean vacation package for free if you've booked in the last 24 hours. For bookings made more than 24 hours ago, you can still cancel and rebook, but your car rental company, hotel or airline may charge a fee. Looking for more information? Look up our Customer Service Portal. We'll help make sure your trip goes off without a hitch.
When is the best time of year to visit Caribbean?
There's a real advantage to taking your Caribbean vacation in . You can usually pick up the best deals at this time. , on the other hand, is the most expensive time to visit. If you like the buzz of peak season, head to Caribbean in . The calmer months of will help you avoid the crowds.
How far in advance should I book my Caribbean vacation?
It all depends on the air carrier, but you can usually look up international airfares on Expedia up to a year in advance. While it's advisable to book ahead of time, lucky travelers will occasionally find a cheaper ticket only weeks before the date of departure.
What should I know before booking a Caribbean travel package?
So many places to go, so many things to see and do. With a travel package, you'll be able to afford more of them. Bundle your hotels, rental cars and flights and make big savings.

Stay near popular Caribbean attractions

An old church with a tiled roof, stone walls, and two bell towers.

Altos de Chavon Village

A replica 16th-century Mediterranean village perched on a rocky outcrop above the River Chavón.
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A beach scene with a flag, beach chairs, umbrellas, and a vendor cart.

Eagle Beach

9.4/10 (6,014 reviews)
Spot fish swimming in the crystal-clear waters, look for turtle nests on the shore and photograph Aruba’s famous windswept divi-divi trees.
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A cruise ship docked near a coastal city with buildings and palm trees.

Port of San Juan

9.0/10 (16,423 reviews)
Explore the waterfront in San Juan with a trip to Port of San Juan. Discover the area's top-notch restaurants and its acclaimed art scene.
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A beach with people walking, clear blue water, and green vegetation in the foreground.

Grace Bay Beach

9.8/10 (5,552 reviews)
Stretch out on fine white sands and marvel at the intense turquoise blue of the Caribbean waters on this pristine and photogenic stretch of shore.
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A coastal resort area with a beach, clear turquoise waters, and a clear sky.

Punta Cana Beach

8.8/10 (30,329 reviews)
Nothing says vacation like spending a lazy day at Punta Cana Beach, a popular beach in Punta Cana. Amble around this romantic area's seaside and enjoy its lively bars.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.