Caribbean Islands Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$134 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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(1 area review)

The interesting museums and 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

Things to do in Caribbean Islands

The Caribbean Islands offer a perfect blend of beach relaxation and cultural experiences, ideal for outdoor enthusiasts. You can engage in thrilling underwater sports, embark on unforgettable adventures, and enjoy fun activities such as snorkelling days and scuba courses. Whether you seek an adrenaline rush or a serene day by the sea, the Caribbean promises an array of exciting options for every traveller.

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

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

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Caribbean Islands.
  • 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.

Top hotels in Caribbean Islands

Grand Hyatt Baha Mar

Grand Hyatt Baha Mar

4.5 out of 5
One Baha Mar Boulevard Nassau New Providence
Fully refundableReserve now, pay when you stay
The price is S$656 per night from 6 Mar to 7 Mar
S$656
6 Mar - 7 Mar
includes taxes & fees
8.6/10 Excellent! (4,753 reviews)
Amenities were unbelievable!

Reviewed on 5 Feb, 2026

Grand Hyatt Baha Mar
Lopesan Costa Bávaro Resort Spa & Casino - All Inclusive

Lopesan Costa Bávaro Resort Spa & Casino - All Inclusive

5 out of 5
Playas de Bavaro Punta Cana La Altagracia
The price is S$659 per night from 8 Mar to 9 Mar
S$659
8 Mar - 9 Mar
includes taxes & fees
8.2/10 Very Good! (6,459 reviews)
Lopesan exceeded our expectations in every way. The resort is beautiful, spacious, and extremely well maintained. Rooms are modern and spotless, the food is high quality with great variety, and the service is consistently professional and friendly. The pools and beach area are stunning and never ...

Reviewed on 31 Jan, 2026

Lopesan Costa Bávaro Resort Spa & Casino - All Inclusive
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
Fully refundableReserve now, pay when you stay
The price is S$561 per night from 25 Feb to 26 Feb
S$561
25 Feb - 26 Feb
includes taxes & fees
7.8/10 Good! (6,617 reviews)
A good hotel with very spacious rooms, modern furniture, and very good mattresses, pillows, and blankets. It was very comfortable to sleep there.

Reviewed on 1 Feb, 2026

Serenade Punta Cana Beach & Spa Resort - All Inclusive
See all 85,279 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.

Popular places to visit

El Yunque National Forest

El Yunque National Forest

This tropical rainforest offers many great hiking options, including stunning mountain views and beautiful waterfalls.

El Yunque National Forest
Mambo Beach At Willemstad In Netherlands Curacao. Idyllic Beach. Nature Landscape. Willemstad At Netherlands Curacao. Tourism Background. Island Seascape.

Mambo Beach

Nothing says holiday like spending a lazy day at Mambo Beach, a popular beach in Willemstad. Stroll along the seaside or visit the shops in this romantic area.

Mambo Beach
Condado Beach featuring kayaking or canoeing, tropical scenes and a beach

Condado Beach

This beach within the bustling city of San Juan is the perfect place to relax for a few hours.

Condado Beach

What to do in Caribbean Islands

Snorkeling with Sea Turtles

Snorkeling with Sea Turtles

S$84
per adult
96% of travellers recommend
Snorkeling with Sea Turtles
Saint Croix: Stand Up Paddleboard Rental

Saint Croix: Stand Up Paddleboard Rental

S$103
per adult
Saint Croix: Stand Up Paddleboard Rental
The Frederiksted St. Croix Sea Turtles Snorkeling Tour

The Frederiksted St. Croix Sea Turtles Snorkeling Tour

S$115
per adult
The Frederiksted St. Croix Sea Turtles Snorkeling Tour
See all activities in Caribbean Islands

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 cancelling 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 travellers 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 travelling 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 travelling 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.