Title: San Juan Vacation Packages & Trips 2026 from CA $1,339 | Expedia.ca [Hotels in San Juan](https://expedia.ca/San-Juan-Hotels.d6337909.Travel-Guide-Hotels)[Vacation Rentals in San Juan](https://expedia.ca/San-Juan-Vacation-Rentals.d6337909.Travel-Guide-VacationRentals)[San Juan Car Rentals](https://expedia.ca/Car-Rentals-In-San-Juan.d6337909.Car-Rental-Guide) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # San Juan 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 San Juan Vacation With everything planned before you go away, our San Juan vacation packages mean you can focus more on having fun. No matter if you're based in the neighborhood of Downtown Port of Spain, which is great for culture, or somewhere else, this city promises an array of discoveries. If your trip to San Juan includes a little sightseeing, check out popular attractions like [Queens Park Savanah](https://www.expedia.ca/Queens-Park-Savanah-Downtown-Port-of-Spain.d6119456.Vacation-Attraction), [Ariapita Avenue](https://www.expedia.ca/Ariapita-Avenue-Port-of-Spain.d553248635970007325.Vacation-Attraction) and [Movietowne](https://www.expedia.ca/Movietowne-Port-of-Spain.d6184699.Vacation-Attraction). Your San Juan vacation is clicks away. Explore hotels, flights and more on Expedia for a getaway that's tailored to suit your travel style. ## Top San Juan Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Woodbrook on the Avenue](https://images.trvl-media.com/lodging/20000000/19770000/19770000/19769980/37fd8822_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Woodbrook on the Avenue Woodbrook CA $1,339 per person May 15 - May 18 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to Port of Spain (POS) 9/10 Wonderful! (80 reviews) The room was clean and well prepared for us. Reviewed on Feb 1, 2026 ![Hyatt Regency Trinidad](https://images.trvl-media.com/lodging/2000000/1800000/1793200/1793103/238cf6ef_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyatt Regency Trinidad Downtown Port of Spain CA $1,675 per person May 15 - May 18 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to Port of Spain (POS) 9.2/10 Wonderful! (1,016 reviews) Clean rooms, comfy beds, very friendly staff Reviewed on Mar 29, 2026 ![The Chancellor Hotel](https://images.trvl-media.com/lodging/7000000/6670000/6660600/6660557/fbc91ba7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Chancellor Hotel CA $1,457 per person May 15 - May 18 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to Port of Spain (POS) 7.2/10 Good! (34 reviews) This is a nice central place to stay for Carnival. The staff was friendly, our place was cleaned well everyday, check in and check out was easy. Reviewed on Mar 10, 2026 ![Chaquacabana Resort & Beach Club](https://images.trvl-media.com/lodging/96000000/95330000/95328900/95328885/w828h826x0y0-92ef4abf_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Chaquacabana Resort & Beach Club CA $1,473 per person May 15 - May 18 found 23 hours ago Roundtrip non-stop flight included Montreal (YMQ) to Port of Spain (POS) 6/10 (95 reviews) The view into the Oean and down the islands is magical. The outdoor settings is nice however, this hotel needs some upgrades. The outdoor especially for night time need some proper lightings and caution tapes are not reflective. It's a easy fall. Food was tasty, menu/drinks a little on the pricey side. The rooms settings are cozy. I like the sitting area then into the bedroon however, the sofa was dirty and smelly and our room was full of mosquitoes. As advertised there were no tea/coffee,cups or basic utilisels in the room. One suggestion, as a first timer the room numbering should be placed on the front of every building instead of a person having to walk to every single door to identify. Generally love the outdoor environment but there is need for improvement and upgrades. Reviewed on Mar 26, 2026 ![The Royal Hotel](https://images.trvl-media.com/lodging/106000000/105980000/105974100/105974080/03e5a2e4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Royal Hotel CA $1,587 per person May 15 - May 18 found 23 hours ago Roundtrip non-stop flight included Montreal (YMQ) to Port of Spain (POS) 7.8/10 Good! (48 reviews) Had a small ant infestation and the rooms need to be updated, but it was clean. Staff was very friendly and helpful. Reviewed on Mar 4, 2026 ## Ready to book your vacation to San Juan? Choose your dates ## San Juan Hotel Deals ![SherNest Guest House](https://images.trvl-media.com/lodging/102000000/101290000/101289000/101288928/222f0684_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### SherNest Guest House 25 GORBIN #1 San Juan San Juan-Laventille Regional Corporation CA $115 CA $138 total May 2 - May 3 includes taxes & fees 8.8/10 Excellent! (3 reviews) The space is great it needs updating though. I saw from last year other guests suggested a few things that would make a guest’s stay much more enjoyable but those things one year later has not been done. We stayed for carnival and the distance to events held in the Savannah was amazing. Message to ... Reviewed on Feb 27, 2026 [](https://expedia.ca/Hotel-Search?startDate=02%2F05%2F2026&endDate=03%2F05%2F2026&selected=101288928&PinnedHotelID=101288928&HadPinnedHotel=true®ionId=6337909) ![The Bey](https://images.trvl-media.com/lodging/77000000/76940000/76939500/76939477/1c72db91_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Bey 43 Jogie Rd San Juan San Juan-Laventille Regional Corporation 10/10 Exceptional! (1 review) The owner was very nice and accommodating. I felt comfortable and at home. Would definitely recommend to anyone. Reviewed on Jul 30, 2022 [Get rates](https://expedia.ca/Hotel-Search?startDate=15%2F04%2F2026&endDate=16%2F04%2F2026&selected=76939477&PinnedHotelID=76939477&HadPinnedHotel=true®ionId=6337909) [](https://expedia.ca/Hotel-Search?startDate=15%2F04%2F2026&endDate=16%2F04%2F2026&selected=76939477&PinnedHotelID=76939477&HadPinnedHotel=true®ionId=6337909) ![Cozy Bed & Breakfast Private Room](https://images.trvl-media.com/lodging/108000000/107230000/107228300/107228261/bcfa6ba9_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Cozy Bed & Breakfast Private Room Santa Cruz San Juan CA $125 CA $153 total Apr 7 - Apr 8 includes taxes & fees 10/10 Exceptional! (1 review) Pleasantly Suprised This was our first visit to Trinidad and didnt know what to expect. Upon arrival we were happy to see that this was a beautifully secluded neighborhood. Our host Wendy was amazing and communicated with us throughout our stay. I recommended this Cozy bed and breakfast. You won't regret it!! ... Reviewed on Jan 14, 2025 [](https://expedia.ca/Hotel-Search?startDate=07%2F04%2F2026&endDate=08%2F04%2F2026&selected=107228261&PinnedHotelID=107228261&HadPinnedHotel=true®ionId=6337909) [See all 415 properties in San Juan](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=02%2F04%2F2026&endDate=03%2F04%2F2026®ionId=6337909) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. 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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. Scan the QR code with your device camera and download our app