Caribbean Islands Vacations

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Where to stay in Caribbean Islands

Find the best Caribbean Islands areas and neighborhoods for the activities you enjoy most. Learn more about Caribbean Islands
San Juan

Old San Juan

4.5/5(354 area reviews)

The fascinating museums and captivating waterfront views are top of the list for many visitors to Old San Juan. A stop by Port of San Juan or Castillo de San Cristobal might round out your trip.

Find hotels in Old San Juan

Find the Best Caribbean Islands Vacation Packages

Best time to go to Caribbean Islands

The best time to visit Caribbean Islands depends on your weather preferences. The hottest average temperature around Caribbean Islands is in September, when weather is mostly sunny and rainfall is light rain. The coolest average temperature around Caribbean Islands is in November when weather is mostly sunny and rainfall is light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudiness
January79.3°F (26.3°C)No RainMostly Sunny
February78.8°F (26.0°C)No RainMostly Sunny
March79.2°F (26.200000000000003°C)No RainMostly Sunny
April80.1°F (26.700000000000003°C)Light RainMostly Sunny
May80.4°F (26.9°C)Light RainMostly Sunny
June81.7°F (27.6°C)Light RainMostly Sunny
July82.2°F (27.9°C)Light RainMostly Sunny
August82.8°F (28.200000000000003°C)Light RainMostly Sunny
September82.9°F (28.3°C)Light RainMostly Sunny
October82.6°F (28.1°C)Light RainMostly Sunny
November78.3°F (25.700000000000003°C)Light RainMostly Sunny
December79.5°F (26.4°C)No RainMostly Sunny

Tips to save on your trip to Caribbean Islands

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • 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 Islands Hotel Deals

Grand Hyatt Baha Mar

Grand Hyatt Baha Mar

4.5 out of 5
One Baha Mar Boulevard Nassau New Providence
The price is ￥47,154 per night from Mar 22 to Mar 23
￥47,154
￥73,510 total
Mar 22 - Mar 23
includes taxes & fees
8.6/10 Excellent! (4,799 reviews)
Clean rooms, plenty of things to do, excellent food and excellent customer service.

Reviewed on Feb 26, 2026

Grand Hyatt Baha Mar
Serenade Punta Cana Beach & Spa Resort - All Inclusive

Serenade Punta Cana Beach & Spa Resort - All Inclusive

4.5 out of 5
Carretera Cabeza de Toro Punta Cana La Altagracia
8/10 Very Good! (6,665 reviews)
This was our second time at this resort the first time it was incredible AMAZING! That’s why we decided to come back but this time it was awful, buffet food was always the same, the burger truck in the beach had a really big line and unfortunately with kids we had to wait over 30 minutes instead ...

Reviewed on Feb 26, 2026

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Serenade Punta Cana Beach & Spa Resort - All Inclusive
Hotel Riu Republica - Adults only - All Inclusive

Hotel Riu Republica - Adults only - All Inclusive

4 out of 5
Playa Arena Gorda Punta Cana
7.2/10 Good! (5,480 reviews)
Beautiful places for Vacations Great service

Reviewed on Feb 26, 2026

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Hotel Riu Republica - Adults only - All Inclusive
See all 84,619 properties in Caribbean Islands
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.

Discover the most popular places to visit in Caribbean Islands

Eagle Beach which includes a sandy beach

Eagle Beach

Spot fish swimming in the crystal-clear waters, look for turtle nests on the shore and photograph Aruba’s famous windswept divi-divi trees.

Eagle Beach
Aerial view of the Punta Cana beach with white sand and turquoise water of the Caribbean Sea. Top places for summer vacations in all Inclusive resorts and hotels in Dominican Republic

Punta Cana Beach

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.

Punta Cana Beach
Luquillo Beach featuring a beach

Luquillo Beach

Sample local street food or doze under a palm tree on this picturesque stretch of coast.

Luquillo Beach

Frequently asked questions

Can I cancel my flight booking to Caribbean Islands due to COVID-19?
Head to our Customer Service Portal for important info about canceling or changing your flight because of COVID-19. Also, check the terms and conditions of your preferred carrier before booking your seat.
What's the best way to find cheap flights to Caribbean Islands that have flexible change policies?
We know that travel schedules can change from one day to the next, so booking a flexible ticket with Expedia is always a smart move. Just tick the "No change fee" box under the "Flexible change policies" filter. Your low-priced, flexible flight to Caribbean Islands is just a few clicks away.
What are some of the general tips for travelers to Caribbean Islands during the COVID-19 outbreak?
With new rules, restrictions and safety measures to follow, travel looks a bit different at present. Here's what you should know before you hop on that plane to Caribbean Islands:
  • Before booking anything, find out if any travel bans or restrictions apply — in both your destination and origin. Get the latest updates by checking government and travel websites.
  • Requirements state that you must wear a face mask throughout your travel experience, including at security checkpoints. Be ready to adjust your mask to verify your identity when asked by a TSA employee.
  • Rather than handing a TSA employee your boarding pass, position it straight on the reader yourself. Then, hold it up for inspection.
  • You can now take one container of hand sanitizer up to 12 oz (350 ml) in your carry-on luggage. This will need to be removed for screening.
  • Put any personal items (phone, wallet and keys) in your carry-on rather than a bin to minimize handling during the screening process.
  • Transport your food items in a clear plastic bag and also place them in a screening bin. Keeping your food separate from your carry-on means it's less likely a TSA employee will need to open your bag for inspection.

Which airlines fly to Caribbean Islands?
JetBlue is a widely known airline servicing Caribbean Islands. Search for airfares to Las Americas Intl. Airport (SDQ) and you'll have 503 JetBlue flights each month to choose from.
How can I find cheap tickets to Caribbean Islands?
One of the easiest ways to find cheap tickets to Caribbean Islands is to be flexible with your travel dates. Search for your flights, then click "flexible dates" at the top of your results. You'll see the cheapest prices for nearby days. The best price for a flight to Caribbean Islands in the last seven days was . Booking ahead of time will generally help you get an even bigger bargain.
How much is a flight to Caribbean Islands?
The cost of a round-trip airfare to Caribbean Islands in the last seven days varied between and . If you were traveling one way from (), you could have nabbed a low-cost fare from just .
What are the most popular airports to fly into in Caribbean Islands?
Caribbean Islands's primary airport is Las Americas Intl. Airport (SDQ). Get your next awesome adventure underway by booking a seat on one of the 1471 monthly flights to this destination.
When is the cheapest time to fly to Caribbean Islands?
Leave for Caribbean Islands earlier in the week and you'll usually be rewarded with lower-cost fares. Tuesday is typically the cheapest day to hop on a plane, followed closely by Monday. If you're eager to avoid the costliest flights, steer clear of Saturdays.
How much is a plane ticket to Caribbean Islands?
In the last seven days, airfares to Caribbean Islands fluctuated between and . Prices rise as your travel date nears, so snap up a good deal today.
Which airlines with flights to Caribbean Islands employ COVID-19 cleanliness policies?
As people start traveling once again, nearly all airlines have introduced physical distancing and other precautionary measures to reduce the spread of COVID-19. Here are just a few examples:
  • JetBlue - this airline is known for keeping the middle seat empty and capped capacity flights.
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • United Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.

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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.