Title: Luxury Vacations in Puerto Rico 2026 | Expedia.ca ![](https://images.trvl-media.com/place/3179/47a0ef66-6e92-4553-afb1-7846ef2214a1.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Puerto Rico Luxury Vacations ## 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 ## Flight and Luxury hotel deals in Puerto Rico Price found within the past 48 hours. Click for updated prices. ![The Condado Plaza Hotel](https://images.trvl-media.com/lodging/1000000/10000/7200/7143/e18049f2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Condado Plaza Hotel Condado CA $1,629 per person Mar 24 - Mar 29 found 2 hours ago Roundtrip non-stop flight included Montreal (YUL) to San Juan (SJU) 8/10 Very Good! (1,814 reviews) very nice hotel- not as modern as I thought, but it was a nice hotel - Great location. Reviewed on Jan 21, 2026 ![Olive Boutique Hotel, A Small Luxury Hotel of the World (Adults Only)](https://images.trvl-media.com/lodging/6000000/5200000/5196300/5196263/66510c0c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Olive Boutique Hotel, A Small Luxury Hotel of the World (Adults Only) Condado CA $1,706 per person Mar 24 - Mar 29 found 2 hours ago Roundtrip non-stop flight included Montreal (YUL) to San Juan (SJU) 9/10 Wonderful! (645 reviews) We had a great stay at O:live boutique hotel. I’m sorry we didn’t have more time to explore the restaurant, pool, etc but this was a one night stay pre-cruise and we already had dinner reservations off-property. Check in was quick and efficient, the front desk staff was very pleasant. The lobby is cozy and intimate - as is the whole hotel. Our room 203 was a nice surprise - it had a big private courtyard with lounge seating, cafe table and chairs, and a really cool outdoor tub/shower. The bedding was very comfortable, the bathroom clean and modern. I would definitely stay here again and I would set aside some time to experience the pool, restaurant, etc. Reviewed on Jan 10, 2026 ![El Conquistador Resort](https://images.trvl-media.com/lodging/1000000/450000/447600/447559/926a31f3_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### El Conquistador Resort Cabezas CA $2,013 per person Mar 29 - Apr 4 found 1 day ago Roundtrip non-stop flight included Ottawa (YOW) to San Juan (SJU) 9/10 Wonderful! (3,205 reviews) Great facilities, warm staff, overall wonderful visit. Will def try and return - truly excellent experience. Reviewed on Jan 20, 2026 ![Caribe Hilton](https://images.trvl-media.com/lodging/1000000/10000/9300/9228/9307be9a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Caribe Hilton San Juan Antiguo CA $1,958 per person Mar 24 - Mar 29 found 2 hours ago Roundtrip non-stop flight included Montreal (YUL) to San Juan (SJU) 8.6/10 Excellent! (2,396 reviews) Everything was perfect from check-in to Check-out.. Had a nice getaway with my wife.. with out kids or Dogs. Enjoyed San Sebastian Festival.. Reviewed on Jan 19, 2026 ![Condado Vanderbilt Hotel](https://images.trvl-media.com/lodging/10000000/9110000/9105300/9105241/2628fada_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Condado Vanderbilt Hotel Condado CA $2,196 per person Mar 24 - Mar 29 found 2 hours ago Roundtrip non-stop flight included Montreal (YUL) to San Juan (SJU) 9.2/10 Wonderful! (1,616 reviews) Room was large, quiet and comfortable, the hotel is beautiful and restored to a very modern level, every staff member was so nice, attentive and made our stay perfect. Would definitely recommend to anyone looking for a perfect Puerto Rican vacation Reviewed on Jan 18, 2026 Don't see what you're looking for? See all available trips from Columbus to Puerto Rico [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-02-22/2026-03-01/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=PRI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Luxury holidays in Puerto Rico Price found within the past 48 hours. Click for updated prices. ![Wyndham Grand Rio Mar Rainforest Beach and Golf Resort](https://images.trvl-media.com/lodging/1000000/50000/41700/41642/0558d37f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Wyndham Grand Rio Mar Rainforest Beach and Golf Resort Mameyes II CA $2,129 per person Feb 21 - Feb 25 found 3 hours ago Roundtrip non-stop flight included Toronto (YYZ) to San Juan (SJU) 8.6/10 Excellent! (2,206 reviews) Had an excellent time and gorgeous Reviewed on Jan 19, 2026 ![Condado Vanderbilt Hotel](https://images.trvl-media.com/lodging/10000000/9110000/9105300/9105241/2628fada_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Condado Vanderbilt Hotel Condado CA $2,196 per person Mar 24 - Mar 29 found 2 hours ago Roundtrip non-stop flight included Montreal (YUL) to San Juan (SJU) 9.2/10 Wonderful! (1,616 reviews) Room was large, quiet and comfortable, the hotel is beautiful and restored to a very modern level, every staff member was so nice, attentive and made our stay perfect. Would definitely recommend to anyone looking for a perfect Puerto Rican vacation Reviewed on Jan 18, 2026 ![The St. Regis Bahia Beach Resort, Puerto Rico](https://images.trvl-media.com/lodging/4000000/3810000/3800200/3800119/f088cdb4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The St. Regis Bahia Beach Resort, Puerto Rico Herreras CA $7,555 per person Mar 29 - Apr 4 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to San Juan (SJU) 9.4/10 Exceptional! (450 reviews) Don't see what you're looking for? See all available trips from Columbus to Puerto Rico [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-02-22/2026-03-01/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=PRI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Luxury holidays in Puerto Rico Price found within the past 48 hours. Click for updated prices. ![The Condado Plaza Hotel](https://images.trvl-media.com/lodging/1000000/10000/7200/7143/e18049f2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Condado Plaza Hotel Condado CA $1,588 per person Feb 26 - Mar 1 found 1 day ago Roundtrip flight included Montreal (YMQ) to San Juan (SJU) 8/10 Very Good! (1,814 reviews) very nice hotel- not as modern as I thought, but it was a nice hotel - Great location. Reviewed on Jan 21, 2026 ![El Conquistador Resort](https://images.trvl-media.com/lodging/1000000/450000/447600/447559/926a31f3_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### El Conquistador Resort Cabezas CA $1,629 per person Apr 2 - Apr 5 found 9 hours ago Roundtrip non-stop flight included Toronto (YYZ) to San Juan (SJU) 9/10 Wonderful! (3,205 reviews) Great facilities, warm staff, overall wonderful visit. Will def try and return - truly excellent experience. Reviewed on Jan 20, 2026 ![Hyatt Regency Grand Reserve Puerto Rico](https://images.trvl-media.com/lodging/1000000/980000/979700/979694/08d6d09c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyatt Regency Grand Reserve Puerto Rico Zarzal CA $1,781 per person Feb 26 - Mar 1 just found Roundtrip non-stop flight included Montreal (YMQ) to San Juan (SJU) 9/10 Wonderful! (2,764 reviews) We stayed at the Hyatt Regency Grand Reserve for our honeymoon and we cannot say enough positive things about it!! We had an Oceanside room. It was spotless clean. The staff was SO friendly — especially the bellboys who drive you around the resort. Food was fantastic. We would absolutely stay here again!! Reviewed on Jan 21, 2026 Don't see what you're looking for? See all available trips from Columbus to Puerto Rico [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-02-22/2026-03-01/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=PRI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Luxury holidays in Puerto Rico Price found within the past 48 hours. Click for updated prices. ![Olive Boutique Hotel, A Small Luxury Hotel of the World (Adults Only)](https://images.trvl-media.com/lodging/6000000/5200000/5196300/5196263/66510c0c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Olive Boutique Hotel, A Small Luxury Hotel of the World (Adults Only) Condado CA $1,615 per person Apr 1 - Apr 5 found 15 hours ago Roundtrip non-stop flight included Detroit (DTW) to San Juan (SJU) 9/10 Wonderful! (645 reviews) We had a great stay at O:live boutique hotel. I’m sorry we didn’t have more time to explore the restaurant, pool, etc but this was a one night stay pre-cruise and we already had dinner reservations off-property. Check in was quick and efficient, the front desk staff was very pleasant. The lobby is cozy and intimate - as is the whole hotel. Our room 203 was a nice surprise - it had a big private courtyard with lounge seating, cafe table and chairs, and a really cool outdoor tub/shower. The bedding was very comfortable, the bathroom clean and modern. I would definitely stay here again and I would set aside some time to experience the pool, restaurant, etc. Reviewed on Jan 10, 2026 ![El Conquistador Resort](https://images.trvl-media.com/lodging/1000000/450000/447600/447559/926a31f3_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### El Conquistador Resort Cabezas CA $1,631 per person Apr 1 - Apr 5 found 15 hours ago Roundtrip non-stop flight included Detroit (DTW) to San Juan (SJU) 9/10 Wonderful! (3,205 reviews) Great facilities, warm staff, overall wonderful visit. Will def try and return - truly excellent experience. Reviewed on Jan 20, 2026 ![Caribe Hilton](https://images.trvl-media.com/lodging/1000000/10000/9300/9228/9307be9a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Caribe Hilton San Juan Antiguo CA $2,320 per person Mar 25 - Mar 29 found 1 day ago Roundtrip non-stop flight included Calgary (YYC) to San Juan (SJU) 8.6/10 Excellent! (2,396 reviews) Everything was perfect from check-in to Check-out.. Had a nice getaway with my wife.. with out kids or Dogs. Enjoyed San Sebastian Festival.. Reviewed on Jan 19, 2026 Don't see what you're looking for? See all available trips from Columbus to Puerto Rico [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-02-22/2026-03-01/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=PRI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Plan the perfect luxury Puerto Rico vacation with Expedia #### What are some benefits when booking luxury Puerto Rico vacations? When you book a luxury Puerto Rico vacation, you get to enjoy some of the best amenities and special features available. Luxury vacation options often feature spa facilities right in your accommodation, along with room service and an on-site restaurant. The quality of the bedding and even the water pressure tends to be better, so it's the perfect solution for travellers looking to put their feet up and relax. #### How can I find all-inclusive luxury vacations in Puerto Rico? If you're looking for something luxurious in Puerto Rico, all you have to do is take advantage of our search filters. You can implement a filter to only show 5-star accommodations as well as some amenities you may be interested in, like spa facilities and hot tubs. When you opt for an all-inclusive package, you can enjoy luxury alongside a potential discount for booking your accommodation and flight together. #### Can I book a cheap luxury vacation? While luxury vacations tend to be on the more costly end of the spectrum, ranging from CA $1,588, there are a few methods you can try to lower the price as much as possible. When booking a flight and accommodation together, you can enjoy savings of up to 24\. After implementing filters for luxury features, you can also sort by price to list the cheapest luxury packages first. #### Are there luxury spa vacations? Yes, luxury spa vacations are available and quite popular in Puerto Rico. When you book one of these experiences, it's easier than ever to relax, unwind and recharge in between excursions. Either way, you can easily find spa vacations by implementing the spa filter in your search. #### What should I look for in a luxury family vacation in Puerto Rico? When booking something for the whole family, it's important to consider exactly what kind of experience your family will want.Luxury packages make it easy to keep everyone happy with creature comforts. Kids especially enjoy features like pools, a delicious breakfast and plenty of space. Suites tend to offer your family members a bit more privacy and comfort compared to simple rooms throughout Puerto Rico. #### Can I book last-minute luxury vacations? Yes, last-minute bookings are often available in Puerto Rico. All you have to do is enter your travel dates to see what's available. Sometimes, you'll even find additional discounts for booking last-minute, as accommodations are desperate to fill their last remaining spaces. #### What can help me find the best luxury vacation deals in Puerto Rico? You can use a few strategies to find the best deals on luxury vacation packages. Consider travelling during the off-season to take advantage of the typically lower overall prices. Additionally, staying in the less popular parts of Puerto Rico or travelling to more obscure destinations altogether can often lead to lower prices. #### Can I book a luxury vacation that is fully refundable? Yes, fully refundable reservations are sometimes available on luxury vacation packages in Puerto Rico. You can implement a filter for it specifically or check out the policy section on any one of your search results. It should clearly state what's necessary to qualify for a fully refundable booking. #### Why should I book my luxury vacation with Expedia? When you book with Expedia, you can enjoy a one-stop shop for all your travel planning needs. We offer accommodations as well as flights, and you may even be able to enjoy discounts by booking them together. Of course, Expedia Rewards members will find even more discounts and earn points that can be put toward discounts on future bookings. ## Luxury Hotels in Puerto Rico ![Condado Vanderbilt Hotel](https://images.trvl-media.com/lodging/10000000/9110000/9105300/9105241/2628fada_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Condado Vanderbilt Hotel 1055 Ashford Avenue San Juan - 6 min drive from Port of San Juan CA $692 CA $922 total Feb 10 - Feb 11 includes taxes & fees Book a stay at this luxury hotel in San Juan. Enjoy free WiFi, 4 outdoor pools, and a full-service spa. Our guests praise the helpful staff and the clean rooms ... 9.2/10 Wonderful! (1,678 reviews) This hotel was great overall! The staff is so friendly and have great hospitality. We got a room upgrade upon arrival which was nice. There’s multiple restaurants in the hotel, we tried a few and they were great. The spa is also amazing. Lots of places to explore around the area. There’s a liquor ... Reviewed on Jan 17, 2026 [](https://expedia.ca/San-Juan-Hotels-Condado-Vanderbilt-Hotel.h9105241.Hotel-Information) ![Hotel El Convento](https://images.trvl-media.com/lodging/1000000/30000/23200/23106/e387c3ae_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hotel El Convento 100 Cristo St San Juan - 7 min walk from Port of San Juan CA $449 CA $588 total Jan 26 - Jan 27 includes taxes & fees Book a stay at this luxury hotel in San Juan. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms ... 9/10 Wonderful! (1,006 reviews) Room was a little small. Reviewed on Jan 14, 2026 [](https://expedia.ca/San-Juan-Hotels-Hotel-El-Convento.h23106.Hotel-Information) ![The St. Regis Bahia Beach Resort, Puerto Rico](https://images.trvl-media.com/lodging/4000000/3810000/3800200/3800119/f088cdb4_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The St. Regis Bahia Beach Resort, Puerto Rico State Road 187 Kilometer 4.2 Río Grande - 45 min drive from Port of San Juan CA $2,559 CA $2,939 total Jan 23 - Jan 24 includes taxes & fees Book a stay at this luxury resort in Río Grande. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the helpful staff in our reviews. ... 9.2/10 Wonderful! (451 reviews) The greatest Reviewed on Nov 22, 2025 [](https://expedia.ca/San-Juan-Hotels-Four-Seasons-Resort-And-Residence-Puerto-Rico.h3800119.Hotel-Information) [See all 8,323 properties in Puerto Rico](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package®ionId=148) 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