Title: Caribbean Islands Vacation Packages 2026 from $716 | 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 $716 ## 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. ![Sapphire Beach Club Resort](https://images.trvl-media.com/lodging/1000000/870000/861000/860944/46903e22_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sapphire Beach Club Resort Maho $716 per person Mar 18 - Mar 24 found 1 day ago Roundtrip flight included Boston (BOS) to Philipsburg (SXM) 7/10 Good! (691 reviews) Unbelievable vacation! Saphire was the perfect hotel for us! Reviewed on Feb 7, 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 $1,051 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) Loved the resort, room was perfect. The AC worked great.staff were amazing. Free shuttle to the grocery store at the bottom of the hill when you didn’t feel like hiking down or call them from the grocery store for a lift back was great Reviewed on Feb 8, 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 $889 per person May 2 - May 9 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Philipsburg (SXM) 9.2/10 Wonderful! (973 reviews) This is a difficult review. A snowstorm hit my area which caused my flight to be canceled. I called the hotel who refused any refund bc my room was unrefundable. Eventually the manager agreed to extend my reservation for two day. I was able to find a flight out two days later. The staff itself were incredibly nice and helpful. The room was clean. Housekeeping was nice as well. The view from my room was incredible but our balcony was shared with the others rooms. Meaning others could actually possibly look straight into my room. So at night I would have to close my blinds. The TV didn’t work at all and the AC didn’t work the last night of my stay (in fairness I didn’t report the TV). You really need a rental car to get anywhere. There is a beach within walking distance which was very nice. Hotel did have free parking but some nights it was difficult to find an open space. Reviewed on Feb 7, 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 Save 100% on your flight $1,321 per person May 2 - May 9 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Philipsburg (SXM) 9.2/10 Wonderful! (1,309 reviews) It was our 2nd time there. It was great. We love being able to walk to restaurants and live music. Staff is always friendly and funny! Reviewed on Feb 6, 2026 ![Oyster Bay Beach Resort](https://images.trvl-media.com/lodging/2000000/1100000/1095400/1095348/00eb22aa_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Oyster Bay Beach Resort Oyster Pond Save 100% on your flight $742 per person May 2 - May 9 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Philipsburg (SXM) 8.6/10 Excellent! (952 reviews) The room, the views, the accommodations… it was all super great! Reviewed on Feb 7, 2026 Don't see what you're looking for? See all available trips from Columbus to Caribbean Islands [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-09/2026-03-16/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=SXM&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 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=Downtown%20Columbus,%20Columbus,%20Ohio,%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=Downtown%20Columbus,%20Columbus,%20Ohio,%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=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Isla%20Verde&DestID=6139938&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Grace Bay which includes a sandy beach, tropical scenes and a house](https://images.trvl-media.com/place/55041/188ee024-741b-4ba1-9481-68e0d53a406c.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### 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 hotel + flight trips in Grace Bay](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Grace%20Bay&DestID=55041&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=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Condado&DestID=506189&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) ![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](https://images.trvl-media.com/place/6340523/e49022b0-93bf-47c5-a7a0-5c1dda57a240.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### 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. [](https://expedia.com/Punta-Cana-Beach-Punta-Cana.d6340523.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 $475 nightly $520 total Feb 24 - Feb 25 Total with taxes and fees 8.6/10 Excellent! (4,749 reviews) Good but a bit crowded Reviewed on Feb 3, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F24%2F2026&endDate=2%2F25%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 $362 nightly $463 total Feb 23 - Feb 24 Total with taxes and fees 7.8/10 Good! (6,641 reviews) Nice room, staff at the adults only section of the resort were very helpful Reviewed on Feb 5, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F23%2F2026&endDate=2%2F24%2F2026&selected=44442694&PinnedHotelID=44442694&HadPinnedHotel=true®ionId=3000652683) ![Lopesan Costa Bávaro Resort Spa & Casino - All Inclusive](https://images.trvl-media.com/lodging/24000000/23540000/23535100/23535027/54f6b2a6_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Lopesan Costa Bávaro Resort Spa & Casino - All Inclusive Playas de Bavaro Punta Cana La Altagracia $425 nightly $543 total Mar 1 - Mar 2 Total with taxes and fees 8.2/10 Very Good! (6,465 reviews) Everything was spectacular. Simply loved it Reviewed on Feb 4, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F1%2F2026&endDate=3%2F2%2F2026&selected=23535027&PinnedHotelID=23535027&HadPinnedHotel=true®ionId=3000652683) [See all 84,783 properties in Caribbean Islands](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F10%2F2026&endDate=2%2F11%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