Title: Caribbean Islands Vacation Packages & Trips 2026/2026 from CA $1,696 | 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. ![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 $1,696 per person Jan 23 - Jan 30 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Philipsburg (SXM) 9.2/10 Wonderful! (973 reviews) The stay at Princess Heights was wonderful as usual, staff was friendly and courteous as always. The room was clean, bed was comfortable and the continental breakfast was fantastic. We asked for a room directly off the parking lot and they delivered. I would highly recommend Princess Heights. Reviewed on Nov 29, 2025 ![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 CA $3,042 per person Jan 23 - Jan 30 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Philipsburg (SXM) 9.2/10 Wonderful! (1,309 reviews) Great location with lots to do within walking distance. Our room was perfect, very clean and modern. Staff members were welcoming and helpful. The beaches surrounding this resort are far better than the others we checked out in other areas. I'd 100% come back here! Reviewed on Dec 8, 2025 ![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 $2,414 per person Jan 23 - Jan 30 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Philipsburg (SXM) 9/10 Wonderful! (1,463 reviews) top end room, towels, bed and kitchen. Reviewed on Dec 8, 2025 ![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 $3,052 per person Jan 23 - Jan 30 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Philipsburg (SXM) 8.4/10 Very Good! (266 reviews) The staff is great. Uncomfortable and small queen size bed but overall good. Reviewed on Dec 8, 2025 ![Divi Little Bay Beach Resort](https://images.trvl-media.com/lodging/1000000/480000/470900/470827/e8112429_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Divi Little Bay Beach Resort CA $3,312 per person Jan 23 - Jan 30 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Philipsburg (SXM) 8.4/10 Very Good! (1,002 reviews) Beautiful property, fantastic beach resort was extremely clean.Staff were very kind and helpful. The food at both gizmo's beach bar and the mix rooftop restaurant was exceptional. I would highly recommend visiting mix on barbecue night. Reviewed on Dec 7, 2025 ## 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://a.travel-assets.com/findyours-php/viewfinder/images/res70/243000/243650-Old-San-Juan.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 Pier 4 might round out your trip. [Find hotel + flight trips in Old San Juan](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Oskaloosa,%20Iowa,%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://a.travel-assets.com/findyours-php/viewfinder/images/res70/109000/109499-Palm-Beach.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=Oskaloosa,%20Iowa,%20United%20States%20of%20America&Destination=Palm%20Beach&DestID=9306&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Default Image](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/553000/553995-arena-gorda-beach.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Bávaro The stunning beaches and fantastic nightlife are just a few highlights of Bávaro. Make a stop by Bavaro Beach or Cocotal Golf and Country Club while you're exploring the area. [Find hotel + flight trips in Bávaro](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Oskaloosa,%20Iowa,%20United%20States%20of%20America&Destination=B%C3%A1varo&DestID=601946&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Condado](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/243000/243546-Condado.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=Oskaloosa,%20Iowa,%20United%20States%20of%20America&Destination=Condado&DestID=506189&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Grace Bay showing a house, a sandy beach and tropical scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/62000/62206-Grace-Bay.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=Oskaloosa,%20Iowa,%20United%20States%20of%20America&Destination=Grace%20Bay&DestID=55041&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ### Things to do in Caribbean Islands The Caribbean Islands offer a perfect blend of culture-themed adventures and stunning beach getaways. Visitors can indulge in beach vacations, enjoy golf at scenic courses, and explore beachfront experiences. For the adventurous, there are thrilling underwater sports and excellent snorkeling spots, as well as exciting island adventures waiting to be discovered. Get ready to immerse yourself in the vibrant atmosphere and natural beauty of the Caribbean. \*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 - Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Caribbean Islands. - 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 $419 CA $653 total Dec 14 - Dec 15 includes taxes & fees 8.6/10 Excellent! (4,639 reviews) The hotel was amazing & the staff was extremely accommodating, polite & professional. The only issue was with housekeeping, as each day we had to call multiple times to get our room clean. When you come back from the pool & have zero clean towels, it is frustrating. The hotel scored 100% on every ... Reviewed on Dec 6, 2025 [](https://expedia.ca/Hotel-Search?startDate=14%2F12%2F2025&endDate=15%2F12%2F2025&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 Fully refundableReserve now, pay when you stay CA $602 CA $771 total Jan 6 - Jan 7, 2026 includes taxes & fees 8.2/10 Very Good! (6,281 reviews) Excellent service Reviewed on Dec 4, 2025 [](https://expedia.ca/Hotel-Search?startDate=06%2F01%2F2026&endDate=07%2F01%2F2026&selected=23535027&PinnedHotelID=23535027&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! (5,254 reviews) Gracias deberían de tener en cuenta pal de cosas como el olor en el elevador el agua caliente y el otro elevado no sirve pero de lo demás 10/10 gracias Reviewed on Dec 6, 2025 [Get rates](https://expedia.ca/Hotel-Search?startDate=22%2F12%2F2025&endDate=23%2F12%2F2025&selected=12848883&PinnedHotelID=12848883&HadPinnedHotel=true®ionId=3000652683) [](https://expedia.ca/Hotel-Search?startDate=22%2F12%2F2025&endDate=23%2F12%2F2025&selected=12848883&PinnedHotelID=12848883&HadPinnedHotel=true®ionId=3000652683) [See all 85,087 properties in Caribbean Islands](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=09%2F12%2F2025&endDate=10%2F12%2F2025®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://a.travel-assets.com/findyours-php/viewfinder/images/res70/116000/116373-Eagle-Beach.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://a.travel-assets.com/findyours-php/viewfinder/images/res70/62000/62218-Sibonne-Beach.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) ![Punta Cana Beach](https://mediaim.expedia.com/destination/1/3e4e01dc5bcf1fae1ef86872da8fcc0b.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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