Caribbean Islands Holidays from £2,048

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Your Caribbean Islands Holiday

Leave the planning up to us with a Caribbean Islands holiday package. With everything arranged before you jet off, the only thing you'll need to do is sit back, relax and enjoy this destination's countless delights. Begin your trip to Caribbean Islands by spending a few nights in Punta Cana, one of the best cities here. When you're ready to stop dreaming and start travelling, Expedia will help turn your Caribbean Islands holiday into a reality.

Top Caribbean Islands Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

Oyster Pond
£2,048
per person
27 Oct - 2 Nov
found 1 day ago
Return flight included
Birmingham (BHX) to Philipsburg (SXM)
9.2/10 Wonderful! (1,003 reviews)
This property is nice.. it almost felt deserted as we didn’t see anyone at night. It was very clean, comfortable and we had everything needed. My only complaint was the room needed more light. I’d stay here again .

Reviewed on 8 Aug 2026

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

Pelican Key
£2,139
per person
27 Oct - 2 Nov
found 1 day ago
Return flight included
Birmingham (BHX) to Philipsburg (SXM)
9.2/10 Wonderful! (1,484 reviews)
Seul bémol pour moi est le bruit occasionné le soir par les Bar aux alentour de la baie. il ne vaut pas être un couche tôt. La vue est belle face aux bateaux amarrés, Bon choix de resto aux alentours. Juste à coté du casino pour ceux et celles qui aiment bien alle dépenser un petit 20 le soir.

Reviewed on 13 Aug 2026

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

Pelican Key
£2,102
per person
27 Oct - 2 Nov
found 1 day ago
Return flight included
Birmingham (BHX) to Philipsburg (SXM)
9/10 Wonderful! (1,922 reviews)
Sonesta Ocean Point All Inclusive, Adults Only Resort

Sonesta Ocean Point All Inclusive, Adults Only Resort

£2,777
per person
27 Oct - 2 Nov
found 1 day ago
Return flight included
Birmingham (BHX) to Philipsburg (SXM)
8.8/10 Excellent! (1,003 reviews)
Best trip every clean hotel great staff and location was amazing definitely recommend this hotel to anybody

Reviewed on 13 Aug 2026

Sonesta Maho Beach All Inclusive Resort Casino & Spa

Sonesta Maho Beach All Inclusive Resort Casino & Spa

£2,593
per person
27 Oct - 2 Nov
found 1 day ago
Return flight included
Birmingham (BHX) to Philipsburg (SXM)
8/10 Very good! (3,112 reviews)
It was a pleasant stay!

Reviewed on 13 Aug 2026

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
A beach with clear turquoise water, palm trees, and a hotel in the background.

Palm Beach

Enjoy yourself at this white-sand Caribbean beach that combines incredible underwater sights and tangerine sunsets with a youthful nightlife.

Find hotels in Palm Beach
A beach with a boat, palm trees, and a city skyline in the background.

Isla Verde

White-sands, beautifully clear water and excellent water sports make this beach one of the most popular in Puerto Rico.

Find hotels in Isla Verde
A densely packed urban area with colorful buildings and a clear sky.

Old San Juan

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
A sandy beach with palm trees, a rocky breakwater, and calm ocean waves.

Condado

Experience San Juan at its most modern in a chic neighborhood packed with high-end fashion shops, elegant casinos and popular restaurants.

Find hotels in Condado
A beach with clear turquoise water, white sand, and a few footprints. There are houses and palm trees in the background.

Grace Bay

This picturesque stretch of white sand and warm, turquoise water is home to luxury resorts, restaurants and one of the world’s largest barrier reefs.

Find hotels in Grace Bay

Things to do in Caribbean Islands

The Caribbean Islands offer a splendid mix of beach relaxation and cultural experiences, perfect for outdoor enthusiasts. Visitors can engage in thrilling activities like snorkelling, scuba diving, and various adventure sports. Unforgettable adventures await, from leisurely snorkel days to exciting Caribbean escapades, ensuring a memorable holiday filled with fun activities.

*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

  • 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.

Top hotels in Caribbean Islands

Grand Hyatt Baha Mar

Grand Hyatt Baha Mar

One Baha Mar Boulevard Nassau New Providence
Fully refundableReserve now, pay when you stay
£265
26 Aug - 27 Aug
includes taxes & fees
Grand Hyatt Baha Mar
Hyatt Regency Grand Reserve Puerto Rico

Hyatt Regency Grand Reserve Puerto Rico

200 Coco Beach Blvd. Highway 955-I Río Grande
Fully refundableReserve now, pay when you stay
£251
10 Sept - 11 Sept
includes taxes & fees
Hyatt Regency Grand Reserve Puerto Rico
Lopesan Costa Bávaro Resort Spa & Casino - All Inclusive

Lopesan Costa Bávaro Resort Spa & Casino - All Inclusive

Playas de Bavaro Punta Cana La Altagracia
Fully refundableReserve now, pay when you stay
£252
13 Sept - 14 Sept
includes taxes & fees
8.4/10 Very good! (7,336 reviews)
"Loved it 10/10."

Reviewed on 13 Aug 2026

Lopesan Costa Bávaro Resort Spa & Casino - All Inclusive
See all 86,636 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.
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Stay near popular Caribbean Islands 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.
See properties
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.
See properties
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 galleries.
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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 holiday 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.
See properties

Frequently asked questions

Why should I book my Caribbean Islands holiday with Expedia?
With exceptional-value flights, car hire and accommodation options all in one place, Expedia makes planning your Caribbean Islands adventure a piece of cake. Moreover, we can help you bundle your bookings into a package holiday so you can save even more. Choose from amazing escapes, add flights and/or a hire car (and maybe also some exciting activities!) and get incredible prices. Need to change plans? Expedia has a flexible cancellation policy for many bookings. To learn more, make your way to our Customer Service Portal link.
When is the best time of year to holiday in Caribbean Islands?
If you love the buzz of peak season, travel to Caribbean Islands in February, March and April. Travelling during the quieter months of September, November and December will help you avoid the crowds. Organise your trip to Caribbean Islands according to what kind of adventure you want. January is the coolest month, when average daytime temperatures are 24ºC. In June, the warmest period, you'll experience averages of 27ºC during the day.
What are the top hotels for my holiday in Caribbean Islands?
Look up Christopher Hotel and Tropical Hotel St Barth. They're top picks for many travellers headed to St. Barthelemy. If San Juan is the next stop on your itinerary, ESJ Towers Hotel and Sheraton Puerto Rico Resort & Casino are great options.
How do I get a cheap holiday to Caribbean Islands?
Browse and lock in everything in the one place with our Caribbean Islands holidays. You'll discover deals on flights, hotels and more that'll keep your bank account happy and your adventurous spirit alive. And, with more than 400 air carriers and 321,000 hotels globally to choose from, you have countless opportunities to mix and match your own way. Learn more about how you can save money on your holiday when you bundle your flight and hotel bookings with Expedia.
What should I do on my Caribbean Islands holiday?
There are so many things to put on your travel itinerary during your holiday in Caribbean Islands. Dunns River Falls, Dickenson Bay Beach, Marigot Bay and The Baths are some of the leading attractions.
What are the best cities to stay in when on holiday in Caribbean Islands?
You can't go past Gros Islet, with fantastic attractions including Pigeon Island National Park and Reduit Beach to explore. Or, if sights like Anse Chastanet Beach and Sulphur Springs are more your scene, Soufrière is the place for you.
Do I need a visa for my Caribbean Islands holiday?
Official government websites have all the information you need on visa requirements, application procedures and any necessary documentation. Your nationality and the purpose of your visit, whether it be for holidays or work, will determine if you'll need a visa for Caribbean Islands. Also make sure your passport is up to date and has a minimum of six months validity remaining after your planned date of return. Do all your travel planning well ahead of time to avoid any nasty last-minute surprises.
What should I wear on my Caribbean Islands holiday?
First, consider the sorts of activities you have planned during your Caribbean Islands holiday and take versatile pieces that you can easily mix and match. For fashion inspiration or even information on dress codes, look up style blogs or relevant social media accounts. In Caribbean Islands, daytime average temperatures reach 27ºC during June, making it the warmest month. January is the coolest time of the year here, with the mercury averaging 24ºC in the day. Pack with confidence by checking the forecast for each place on your itinerary.
What does an Expedia Caribbean Islands holiday include?
Expedia has all you need to lock in your Caribbean Islands trip, but what goes into your package is up to you. Pick from a combination of flights, hire cars and hotels. Searching for some tours or experiences to keep you entertained? Once you've made your booking, you can add them too. No matter your budget or style, there's a deal to meet your needs. Explore a variety of styles on Expedia and find the perfect fit for you and your crew. From the most popular property types, like villas and apartments, to many other options, you'll find plenty of holiday escapes in Caribbean Islands to choose from so you can plan your stay exactly how you like it.
Does Expedia offer Book Now, Pay Later Caribbean Islands holidays?
Yes. Expedia has partnered with online lender Klarna to help you conveniently pay for your holiday in instalments. Simply pick the payment plan that suits best during checkout and take the stress out of budgeting for your trip. Make sure you bundle your flights, accommodation and activities with Expedia to get the biggest bang for your holiday buck. Consider these flexible payment options below:
  • Pay monthly holidays: If paying small amounts each month works for you, Klarna offers just that! Paying in several transactions will make your holiday dreams come true.
  • No-deposit holidays: When you see an incredible deal but don't have the full amount yet, Klarna's no-deposit holiday plan will allow you to Book Now, Pay Later to lock it in.
Can I choose my airline with a Caribbean Islands Expedia holiday?
Yes — and it's simple too. Expedia has access to more than 400 partner airlines throughout the world. Our packages give you the flexibility to take your pick of available flights, hotels and activities that suit you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.