Title: Caribbean Islands Vacation Packages & Trips 2026 from CA $1,600 | 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. ![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 $1,600 per person Apr 1 - Apr 8 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to Philipsburg (SXM) 9/10 Wonderful! (1,463 reviews) Staff was great; location was very convenient, easy access to beaches, restaurant, night life. Room was spacious and clean. Reviewed on Jan 28, 2026 ![Baker's Suites](https://images.trvl-media.com/lodging/8000000/7750000/7741800/7741757/7b7d5aaa_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Baker's Suites CA $1,616 per person Mar 21 - Mar 28 found 1 day ago Roundtrip flight included Montreal (YMQ) to Philipsburg (SXM) 9.2/10 Wonderful! (679 reviews) Great location and wonderful, helpful staff. Two good restaurants within a minute's walk, easy beach access to lovely, clean Simpson Bay. Bus route to town (tickets $1.50-2.00) and around island just a 5 minute walk. Couldn't have been better. Reviewed on Jan 25, 2026 ![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 CA $4,469 per person Mar 15 - Mar 21 found 1 day ago Roundtrip flight included Hamilton (YHM) to Philipsburg (SXM) 9.2/10 Wonderful! (1,002 reviews) Great hotel, very good service. The breakfast is amazing! Great atmosphere at night Reviewed on Jan 28, 2026 ![The Morgan Resort Spa Village](https://images.trvl-media.com/lodging/18000000/17530000/17525000/17524915/bf19cc27_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Morgan Resort Spa Village CA $4,776 per person Mar 15 - Mar 21 found 1 day ago Roundtrip flight included Hamilton (YHM) to Philipsburg (SXM) 9/10 Wonderful! (1,866 reviews) Excellent resort!! Beautiful views and amazing staff! The pool is beautiful and relaxing. If you are looking to go to the beach, check out Mullet bay in walking distance. Will be back! Reviewed on Jan 28, 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 $1,641 per person Apr 17 - Apr 23 found 24 hours ago Roundtrip non-stop flight included Hamilton (YHM) to Philipsburg (SXM) 9.2/10 Wonderful! (1,309 reviews) Excellent location and amenities Reviewed on Jan 26, 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=Boydton,%20Virginia,%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=Boydton,%20Virginia,%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=Boydton,%20Virginia,%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=Boydton,%20Virginia,%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=Boydton,%20Virginia,%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 Fully refundableReserve now, pay when you stay CA $461 CA $701 total Feb 22 - Feb 23 includes taxes & fees 8.6/10 Excellent! (4,749 reviews) Room was clean, contemporary and nice. It was cold in the room. Reviewed on Jan 25, 2026 [](https://expedia.ca/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=7779293&PinnedHotelID=7779293&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 $593 CA $758 total Feb 23 - Feb 24 includes taxes & fees 8.2/10 Very Good! (6,446 reviews) The whole resort was spotless and very well kept. The staff were fantastic. The food was excellent. And the drinks were the absolute best. Great entertainment, but the best I think were the activity people. They kept us busy and laughing. Great time for young and old. Reviewed on Jan 24, 2026 [](https://expedia.ca/Hotel-Search?startDate=23%2F02%2F2026&endDate=24%2F02%2F2026&selected=23535027&PinnedHotelID=23535027&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 $445 CA $569 total Feb 23 - Feb 24 includes taxes & fees 7.8/10 Good! (6,637 reviews) Food was great Reviewed on Jan 26, 2026 [](https://expedia.ca/Hotel-Search?startDate=23%2F02%2F2026&endDate=24%2F02%2F2026&selected=44442694&PinnedHotelID=44442694&HadPinnedHotel=true®ionId=3000652683) [See all 85,115 properties in Caribbean Islands](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=29%2F01%2F2026&endDate=30%2F01%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 relaxing 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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