Caribbean Beach Vacations

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Flight and Beach hotel deals in Caribbean

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Palace Paradise Island - Adults Only - All Inclusive
Excellence Punta Cana - Adults Only All Inclusive
Majestic Mirage Punta Cana, All Suite Resort - All Inclusive
Bahia Principe Escape Ambar - Hyatt Inclusive Collection - Adults Only - All Inclusive
Hotel Riu Palace Antillas - Adults Only - All Inclusive
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See all available trips from Chicago to Caribbean
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5* Beach holidays in Caribbean

Price found within the past 48 hours. Click for updated prices.
Majestic Mirage Punta Cana, All Suite Resort - All Inclusive
Excellence Punta Cana - Adults Only All Inclusive
Condado Vanderbilt Hotel
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See all available trips from Chicago to Caribbean
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3 Night Beach holidays in Caribbean

Price found within the past 48 hours. Click for updated prices.
Excellence Punta Cana - Adults Only All Inclusive
Hotel Riu Palace Paradise Island - Adults Only - All Inclusive
Bahia Principe Escape Ambar - Hyatt Inclusive Collection - Adults Only - All Inclusive
Don't see what you're looking for?
See all available trips from Chicago to Caribbean
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4 Night Beach holidays in Caribbean

Price found within the past 48 hours. Click for updated prices.
Majestic Mirage Punta Cana, All Suite Resort - All Inclusive
Hotel Riu Palace Paradise Island - Adults Only - All Inclusive
Excellence Punta Cana - Adults Only All Inclusive
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See all available trips from Chicago to Caribbean
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Find the best beach vacations in Caribbean

What are some benefits when booking beach vacations in Caribbean?

When you travel to the beach in Caribbean, soft sands and inviting waters, warm sun and gentle breezes will help you relax. This applies to the whole family, as kids and adults can find something fun to do, so family beach vacations are the quintessential family trip.


How can I book the best beach vacations in Caribbean?

To find the best beach vacation, you'll need to book the right accommodations for your family. What the best is depends on what you want from your Caribbean trip. Fortunately, you can use various filters combined with the beach filter to sort for what you want. Additionally, you'll need to consider the time of year you visit.

Can I book cheap beach vacations in Caribbean?

There are quite a few things you can do to get cheap beach vacations in Caribbean. Prices range from CA $1,300, and if you want to keep yours on the lower side, you may want to consider just how close to the beach you are. If you don't mind a bit of a walk, further away is typically cheaper. Additionally booking something with a kitchen can help you save by avoiding dining out.

Can I book beach packages?

Yes, and you'll find quite a few beach packages available in Caribbean. These package deals let you save by booking your accommodation and your flight together with savings of up to 46.

Why should I book family beach vacations?

When you're travelling with the family to Caribbean, booking your vacation by the beach is one of the best ways to keep everyone happy. There's a reason why some of the most memorable family trips for kids are family beach vacations. You'll be just steps away from the water, and you can often enjoy stunning views of the shore from your room.

How can I find a beachfront vacation in Caribbean?

It's easy to find a beachfront vacation accommodation in Caribbean using the search filter. You can filter for waterfront properties specifically that will only show you results that have beautiful views of the shoreline.

How can I book last-minute beach vacations?

Travelling at the last minute doesn't mean you're out of luck to have a dream beach vacation. Last-minute beach vacations may even offer a nice discount as the owners of hotels or other accommodations try to fill their remaining vacancies. All you have to do is input your travel dates and Caribbean as your destination and see what's available.

Can I find all-inclusive beach vacations ?

Yes, all you have to do to find all-inclusive beach vacations in Caribbean is to use the search filter. It will automatically restrict your results to all-inclusive deals that allow you to plan the entire trip in advance.

Can I book a beach trip that's fully refundable?

Any fully refundable booking can bring peace of mind, and we're happy to offer this feature in several packages and locations throughout . All you have to do to find them is check the policies section on each accommodation page. Of course, you can filter for fully-refundable results specifically, too.

Why should I book beach vacations with Expedia?

When you book with Expedia, you'll find a one-stop shop for all your planning needs. You can book your flight and accommodation at the same place and potentially get a discount for booking these together. You can also take advantage of the Expedia Rewards program. Becoming a member is free, and when you do, you'll earn points with every booking will add discounts on subsequent trips.

Beach Hotels in Caribbean

Hyatt Vacation Club at Hacienda del Mar, Dorado

Hyatt Vacation Club at Hacienda del Mar, Dorado

3.5 out of 5
301 Hwy 693 Vega Alta
The price is CA $243 per night from Aug 17 to Aug 18
CA $243
CA $327 total
Aug 17 - Aug 18
includes taxes & fees
Book a stay at this beach resort in Vega Alta. Enjoy free WiFi, a beach locale, and a fitness center. Our guests praise the pool and the restaurant in our reviews. ...
9.4/10 Exceptional! (3,817 reviews)
"We had a great stay at the resort and were pleasantly surprised that we were able to check in a little earlier than expected, which gave us extra time to settle in and start enjoying our vacation. The view from our balcony was beautiful and provided the perfect spot to relax with a morning coffee ..."

Reviewed on Jul 17, 2026

Hyatt Vacation Club at Hacienda del Mar, Dorado
Ocean Blue & Sand Beach Resort - All Inclusive

Ocean Blue & Sand Beach Resort - All Inclusive

4.5 out of 5
Car. Arena Gorda Punta Cana La Altagracia
The price is CA $475 per night from Jul 21 to Jul 22
CA $475
CA $475 total
Jul 21 - Jul 22
includes taxes & fees
Book a stay at this luxury property in Punta Cana. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the restaurant in our reviews. ...
8.6/10 Excellent! (5,640 reviews)
"Staff not attentive at all."

Reviewed on Jul 16, 2026

Ocean Blue & Sand Beach Resort - All Inclusive
Margaritaville Beach Resort - Nassau

Margaritaville Beach Resort - Nassau

4 out of 5
2 Bay Street Nassau New Providence
The price is CA $305 per night from Aug 12 to Aug 13
CA $305
CA $489 total
Aug 12 - Aug 13
includes taxes & fees
Book a stay at this beach hotel in Nassau. Enjoy free WiFi, 4 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
Margaritaville Beach Resort - Nassau
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.