Title: Caribbean Islands Vacation Packages & Trips 2026 from CA $1,265 | Expedia.ca [Caribbean Islands Travel Guide](https://expedia.ca/Caribbean-Islands.dx3000652683)[Hotels in Caribbean Islands](https://expedia.ca/Caribbean-Islands-Hotels.d3000652683.Travel-Guide-Hotels)[Vacation Rentals in Caribbean Islands](https://expedia.ca/Caribbean-Islands-Vacation-Rentals.d3000652683.Travel-Guide-VacationRentals)[Flights to Caribbean Islands](https://expedia.ca/Cheap-Flights-To-Caribbean-Islands.d3000652683.Travel-Guide-Flights)[Caribbean Islands Car Rentals](https://expedia.ca/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 Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 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.ca/Punta-Cana.d601906.Destination-Travel-Guides), one of the best cities here. When you're ready to stop dreaming and start travelling, Expedia will help turn your Caribbean Islands vacation into a reality. ## Top Caribbean Islands Vacation Deals Price found within the past 48 hours. Click for updated prices. ![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 CA $1,265 per person Apr 17 - Apr 23 found 22 hours ago Roundtrip non-stop flight included Hamilton (YHM) 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 ![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 CA $1,597 per person Apr 17 - Apr 23 found 22 hours ago Roundtrip non-stop flight included Hamilton (YHM) 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 ![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 CA $2,319 per person Apr 1 - Apr 6 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) 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 ![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 CA $1,373 per person Apr 17 - Apr 23 found 22 hours ago Roundtrip non-stop flight included Hamilton (YHM) 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 ![Oceans at Divi Little Bay](https://images.trvl-media.com/lodging/75000000/74270000/74267800/74267774/fee04e6c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Oceans at Divi Little Bay CA $2,561 per person Apr 3 - Apr 10 found 1 day ago Roundtrip flight included Hamilton (YHM) to Philipsburg (SXM) 8.4/10 Very Good! (266 reviews) For the money, one of the nicest surprises we have had traveling. Great location, fine room, mostly friendly staff, lots of interesting nooks and crannies to this resort. Will stay again soon. Reviewed on Feb 8, 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](https://expedia.ca/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(35 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.ca/go/package/search/FlightHotel/?FromAirport=Pretty%20Prairie,%20Kansas,%20United%20States%20of%20America&Destination=Old%20San%20Juan&DestID=553248633981709498&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Palm Beach which includes a 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.ca/go/package/search/FlightHotel/?FromAirport=Pretty%20Prairie,%20Kansas,%20United%20States%20of%20America&Destination=Palm%20Beach&DestID=9306&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Isla Verde Beach featuring a beach, sailing and boating](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(28 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.ca/go/package/search/FlightHotel/?FromAirport=Pretty%20Prairie,%20Kansas,%20United%20States%20of%20America&Destination=Isla%20Verde&DestID=6139938&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Grace Bay showing a house, a sandy beach and tropical scenes](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.ca/go/package/search/FlightHotel/?FromAirport=Pretty%20Prairie,%20Kansas,%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(20 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.ca/go/package/search/FlightHotel/?FromAirport=Pretty%20Prairie,%20Kansas,%20United%20States%20of%20America&Destination=Condado&DestID=506189&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ### Things to do in Caribbean Islands The Caribbean Islands are perfect for beach and culture-themed vacations, offering a variety of outdoor activities. Tourists can enjoy beach vacations, golf experiences, and beachfront relaxation, along with thrilling underwater sports like snorkeling. For those seeking adventure, the islands provide exciting island excursions. With a stunning natural backdrop, the Caribbean promises unforgettable experiences 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. | **![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. ## Ready to book your vacation to Caribbean Islands? Choose your dates ## 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 CA $469 CA $712 total Feb 24 - Feb 25 includes taxes & fees 8.6/10 Excellent! (4,756 reviews) Beautiful resort. Clean. Friendly staff. Reviewed on Feb 5, 2026 [](https://expedia.ca/Hotel-Search?startDate=24%2F02%2F2026&endDate=25%2F02%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 CA $495 CA $633 total Feb 23 - Feb 24 includes taxes & fees 7.8/10 Good! (6,642 reviews) Staff is very courteous; room comfortable and spacious Reviewed on Feb 5, 2026 [](https://expedia.ca/Hotel-Search?startDate=23%2F02%2F2026&endDate=24%2F02%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 CA $581 CA $743 total Mar 1 - Mar 2 includes taxes & fees 8.2/10 Very Good! (6,467 reviews) Very friendly staff, great facilities Reviewed on Feb 5, 2026 [](https://expedia.ca/Hotel-Search?startDate=01%2F03%2F2026&endDate=02%2F03%2F2026&selected=23535027&PinnedHotelID=23535027&HadPinnedHotel=true®ionId=3000652683) [See all 85,104 properties in Caribbean Islands](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=10%2F02%2F2026&endDate=11%2F02%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. ![](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.ca/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.ca/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) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](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.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ### Discover the most popular places to visit in Caribbean Islands ![Eagle Beach showing 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 4.5/5(85 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. [](https://expedia.ca/Eagle-Beach-Eagle-Beach.d6049225.Vacation-Attraction) ![Grace Bay Beach which includes a beach](https://images.trvl-media.com/place/6068053/0a810b30-58fd-44ad-933e-dafba721ecfc.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Grace Bay Beach 5/5(107 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. [](https://expedia.ca/Grace-Bay-Beach-Grace-Bay.d6068053.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 4.5/5(159 reviews) 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.ca/Punta-Cana-Beach-Punta-Cana.d6340523.Vacation-Attraction) ## Frequently asked questions ### Can I cancel my flight booking to Caribbean Islands due to COVID-19? ### What's the best way to find cheap flights to Caribbean Islands that have flexible change policies? ### What are some of the general tips for travelers to Caribbean Islands during the COVID-19 outbreak? > - 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? ### How can I find cheap tickets to Caribbean Islands? ### How much is a flight to Caribbean Islands? ### What are the most popular airports to fly into in Caribbean Islands? ### When is the cheapest time to fly to Caribbean Islands? ### How much is a plane ticket to Caribbean Islands? ### What months are the cheapest to book a flight to Caribbean Islands? ## 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. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points 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. 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