Title: Caribbean Islands Vacation Packages 2026 from $807 | Expedia.com [Caribbean Islands Travel Guide](https://expedia.com/Caribbean-Islands.dx3000652683)[Hotels in Caribbean Islands](https://expedia.com/Caribbean-Islands-Hotels.d3000652683.Travel-Guide-Hotels)[Vacation Rentals in Caribbean Islands](https://expedia.com/Caribbean-Islands-Vacation-Rentals.d3000652683.Travel-Guide-VacationRentals)[Flights to Caribbean Islands](https://expedia.com/Cheap-Flights-To-Caribbean-Islands.d3000652683.Travel-Guide-Flights)[Car Rentals in Caribbean Islands](https://expedia.com/Car-Rentals-In-Caribbean-Islands.d3000652683.Car-Rental-Guide) ![](https://images.trvl-media.com/place/3000652683/0f906013-1c42-421c-97bc-ef4a41f0db0e.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Caribbean Islands Vacations from $807 ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 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 ### Your Caribbean Islands Vacation Leave the planning up to us with a Caribbean Islands vacation 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](https://www.expedia.com/Punta-Cana.d601906.Destination-Travel-Guides), one of the best cities here. When you're ready to stop dreaming and start traveling, Expedia will help turn your Caribbean Islands vacation into a reality. ## The Latest Caribbean Islands vacation packages Price found within the past 48 hours. Click for updated prices. ![Holland House Beach Hotel](https://images.trvl-media.com/lodging/2000000/1170000/1160500/1160500/ef6e99b8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Holland House Beach Hotel Downtown Philipsburg Save 100% on your flight $807 per person May 6 - May 11 found 2 days ago Roundtrip non-stop flight included Boston (BOS) to Philipsburg (SXM) 9.2/10 Wonderful! (1,002 reviews) Wonderful staff, great location on the boardwalk Reviewed on Feb 22, 2026 ![Simpson Bay Resort, Marina & Spa](https://images.trvl-media.com/lodging/2000000/1260000/1256900/1256868/30f27be9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Simpson Bay Resort, Marina & Spa Pelican Key $1,148 per person Apr 13 - Apr 20 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Philipsburg (SXM) 9/10 Wonderful! (1,463 reviews) Friendly staff, all inclusive resort, decent restaurants, beach and ocean swimming. Reviewed on Feb 20, 2026 ![The Villas at Simpson Bay Resort](https://images.trvl-media.com/lodging/5000000/4560000/4553800/4553784/7e74429d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Villas at Simpson Bay Resort Pelican Key $1,621 per person Mar 28 - Apr 2 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Philipsburg (SXM) 9.2/10 Wonderful! (1,309 reviews) \*Modern clean rooms. \*Having a few dishes, microwave, mini-fridge turned out to be handy. \*Staff was very friendly. \*Breakfast buffet was excellent. \*Onsite restaurants and many nearby was nice. \*Broad selection at the Replay Restaurant & Bar. It was the only one we ate at twice. Reviewed on Feb 21, 2026 ![Princess Heights Luxury Boutique Condo Hotel](https://images.trvl-media.com/lodging/1000000/570000/561400/561365/3eb207bd_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Princess Heights Luxury Boutique Condo Hotel Oyster Pond $1,252 per person Mar 28 - Apr 2 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Philipsburg (SXM) 9.2/10 Wonderful! (973 reviews) Room was quite clean and commodious. Staff was accessible and friendly. Reviewed on Feb 21, 2026 ![Panorama Residences at Monte Vista](https://images.trvl-media.com/lodging/121000000/120450000/120440200/120440175/89140f9f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Panorama Residences at Monte Vista Point Blanche Save 100% on your flight $847 per person Apr 30 - May 3 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Philipsburg (SXM) 10/10 Exceptional! (1 review) Great stay room was perfect peaceful clean perfect view Reviewed on Feb 17, 2026 Don't see what you're looking for? See all available trips from Des Moines to Caribbean Islands [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-23/2026-03-30/?FromAirport=Des%20Moines,%20Iowa,%20United%20States%20of%20America&Destination=SXM&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=PKG_SPRING_PROMO_3000652683) ## 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](https://expedia.com/Caribbean-Islands.dx3000652683) ![San Juan](https://images.trvl-media.com/place/553248633981709498/285d265c-4268-4cc4-9dc2-9fb6e2e1f6af.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### 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 hotel + flight trips in Old San Juan](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Des%20Moines,%20Iowa,%20United%20States%20of%20America&Destination=Old%20San%20Juan&DestID=553248633981709498&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Palm Beach featuring a sandy beach](https://images.trvl-media.com/place/6070840/380ee14d-39b1-4cb9-9da9-5ef8cbc7f03c.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Palm Beach Enjoy yourself at this white-sand Caribbean beach that combines incredible underwater sights and tangerine sunsets with a youthful nightlife. [Find hotel + flight trips in Palm Beach](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Des%20Moines,%20Iowa,%20United%20States%20of%20America&Destination=Palm%20Beach&DestID=9306&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Isla Verde Beach featuring boating, sailing and a beach](https://images.trvl-media.com/place/6139938/233b223a-97e9-4ba1-901f-12d14e70222e.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Isla Verde 4/5(687 area reviews) White-sands, beautifully clear water and excellent water sports make this beach one of the most popular in Puerto Rico. [Find hotel + flight trips in Isla Verde](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Des%20Moines,%20Iowa,%20United%20States%20of%20America&Destination=Isla%20Verde&DestID=6139938&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Condado](https://images.trvl-media.com/place/506189/30f3a227-250d-400a-ad63-ee532120010a.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Condado 4.5/5(760 area reviews) Oceanfront and upscale, Condado boasts picturesque beaches alongside hotels, nightclubs, casinos, and shops. Stroll through La Ventana al Mar park, and enjoy easy access to public transport via T21 and D53 bus routes. [Find hotel + flight trips in Condado](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Des%20Moines,%20Iowa,%20United%20States%20of%20America&Destination=Condado&DestID=506189&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Bávaro](https://images.trvl-media.com/place/601946/e00b52e5-0d2d-47e8-96f9-d3bd243f8130.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Bávaro Where the Atlantic meets the Caribbean is a buzzing resort home to palm-lined beaches, great nightlife, chic retail, and sporting adventures in and out of the water. [Find hotel + flight trips in Bávaro](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Des%20Moines,%20Iowa,%20United%20States%20of%20America&Destination=B%C3%A1varo&DestID=601946&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ### Discover the most popular places to visit in Caribbean Islands ![Eagle Beach which includes a sandy beach](https://images.trvl-media.com/place/6049225/34f38398-b430-441e-8ae2-fd610a8bd4f1.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### 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. [](https://expedia.com/Eagle-Beach-Eagle-Beach.d6049225.Vacation-Attraction) ![San Juan Cruise Port, Puerto Rico](https://images.trvl-media.com/place/6227475/39a3ae76-4944-4651-9195-2a2fd4be46bc.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Port of San Juan 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. [](https://expedia.com/Port-Of-San-Juan-San-Juan-Antiguo.d6227475.Vacation-Attraction) ![Bavaro beach, Punta Cana, Dominican republic](https://images.trvl-media.com/place/6094797/85b6590f-fc1b-40a5-bf56-11b835f3802c.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Bavaro Beach Nothing says vacation like spending a lazy day at Bavaro Beach, a popular beach in Punta Cana. Discover the lively bars and entertainment choices in this relaxing area. [](https://expedia.com/Bavaro-Beach-Bavaro.d6094797.Vacation-Attraction) ## Caribbean Islands Hotel Deals ![Grand Hyatt Baha Mar](https://images.trvl-media.com/lodging/8000000/7780000/7779300/7779293/8fc5fb82_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Grand Hyatt Baha Mar One Baha Mar Boulevard Nassau New Providence Fully refundableReserve now, pay when you stay $424 nightly $465 total Mar 22 - Mar 23 Total with taxes and fees 8.6/10 Excellent! (4,788 reviews) Friendly staff, clean room, resort had more than enough options for everyone. Reviewed on Feb 19, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F22%2F2026&endDate=3%2F23%2F2026&selected=7779293&PinnedHotelID=7779293&HadPinnedHotel=true®ionId=3000652683) ![Serenade Punta Cana Beach & Spa Resort - All Inclusive](https://images.trvl-media.com/lodging/45000000/44450000/44442700/44442694/0df8ab30_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Serenade Punta Cana Beach & Spa Resort - All Inclusive Carretera Cabeza de Toro Punta Cana La Altagracia Fully refundableReserve now, pay when you stay $327 nightly $419 total Mar 24 - Mar 25 Total with taxes and fees 7.8/10 Good! (6,657 reviews) Yes Reviewed on Feb 16, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F24%2F2026&endDate=3%2F25%2F2026&selected=44442694&PinnedHotelID=44442694&HadPinnedHotel=true®ionId=3000652683) ![Hotel Riu Republica - Adults only - All Inclusive](https://images.trvl-media.com/lodging/13000000/12850000/12848900/12848883/1639414b_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hotel Riu Republica - Adults only - All Inclusive Playa Arena Gorda Punta Cana 7.2/10 Good! (5,500 reviews) Staff was good, Mostly clean. Music sometimes too loud. Spring breakers mostly pleasant but loud and frightening late at night. Reviewed on Feb 22, 2026 [Get rates](https://expedia.com/Hotel-Search?startDate=3%2F9%2F2026&endDate=3%2F10%2F2026&selected=12848883&PinnedHotelID=12848883&HadPinnedHotel=true®ionId=3000652683) [](https://expedia.com/Hotel-Search?startDate=3%2F9%2F2026&endDate=3%2F10%2F2026&selected=12848883&PinnedHotelID=12848883&HadPinnedHotel=true®ionId=3000652683) [See all 84,619 properties in Caribbean Islands](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F24%2F2026&endDate=2%2F25%2F2026®ionId=3000652683) 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. ## Find the Best Caribbean Islands Vacation Packages ### Things to do in Caribbean Islands The Caribbean Islands offer a perfect blend of beach relaxation and cultural exploration. Visitors can enjoy a variety of activities, including underwater sports like scuba diving with provided gear, and adventure activities that include exploring pirate coves. Golf enthusiasts will find excellent courses, while the surrounding recreational areas provide ample opportunities for outdoor fun. A trip to the Caribbean promises unforgettable experiences for every type of traveler. \*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. | **![calendar](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | | ---------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------------------- | | January | 79.3°F (26.3°C) | No Rain | Mostly Sunny | | February | 78.8°F (26.0°C) | No Rain | Mostly Sunny | | March | 79.2°F (26.200000000000003°C) | No Rain | Mostly Sunny | | April | 80.1°F (26.700000000000003°C) | Light Rain | Mostly Sunny | | May | 80.4°F (26.9°C) | Light Rain | Mostly Sunny | | June | 81.7°F (27.6°C) | Light Rain | Mostly Sunny | | July | 82.2°F (27.9°C) | Light Rain | Mostly Sunny | | August | 82.8°F (28.200000000000003°C) | Light Rain | Mostly Sunny | | September | 82.9°F (28.3°C) | Light Rain | Mostly Sunny | | October | 82.6°F (28.1°C) | Light Rain | Mostly Sunny | | November | 78.3°F (25.700000000000003°C) | Light Rain | Mostly Sunny | | December | 79.5°F (26.4°C) | No Rain | Mostly 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. ## More vacations you might like ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.com/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.com/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Kid Friendly Vacations 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![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.com/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ![Gay Friendly Vacations](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) LGBTQ Friendly Vacations [](https://expedia.com/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ_Friendly%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2017/07/05/170615_Adventure_1320_2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adventure Vacations [](https://expedia.com/lp/theme-vacations/adventure-vacations?rfrr=editorial.Adventure_Vacations.click) ![Vacations in Month](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Where to go when 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![](https://forever.travel-assets.com/flex/flexmanager/images/2019/05/16/Hyatt%20Zilara%20Cancun%20-%20All%20Inclusive%20-%20Adults%20Only.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adults Only Vacations [](https://expedia.com/lp/theme-vacations/adults-only-vacations?rfrr=editorial.Adults_Only%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/waterpark-vacations.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Waterpark Vacations [](https://expedia.com/lp/theme-vacations/waterpark-vacations?rfrr=editorial.Waterpark_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/Caribean_scuba_diving.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Scuba Diving Vacations [](https://expedia.com/lp/theme-vacations/scuba-diving-vacations?rfrr=editorial.Scuba_Diving%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/aruba_yoga.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Yoga Vacations [](https://expedia.com/lp/theme-vacations/yoga-vacations?rfrr=editorial.Yoga_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2023/04/04/EPS-RBC-SummerBeachVacations-AdobeStock_206356322.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Cheap Vacations [](https://expedia.com/lp/theme-vacations/cheap-vacations?rfrr=editorial.Cheap_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/06/26/1175883311.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Solo Vacations [](https://expedia.com/lp/b/vacations/solo-vacations?rfrr=editorial.Solo_Vacations.click) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save even more - get up to 20% on select hotels when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app