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. ![ Ciqala Suites Hotel](https://images.trvl-media.com/lodging/5000000/4540000/4538800/4538751/c9106895_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Ciqala Suites Hotel Santurce CA $729 per person Mar 15 - Mar 19 found 8 hours ago Roundtrip flight included Boston (BOS) to San Juan (SJU) 7.8/10 Good! (1,003 reviews) The property was clean with good housekeeping every day. The staff is very friendly, professional and knowledgeable. The area was pretty safe as well as accessible to nearby dining spots and beaches by walk. Liked how the guests can spend some time at the rooftop even if we weren’t dining. The only complaint was with the breakfast. Day 1 we had to skip breakfast in the room because it wasn’t delivered even after the 1 hour slot passed. The juices were just average. Pancakes were burnt one day. Reviewed on Jan 6, 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 $2,171 per person Mar 14 - Mar 19 found 3 hours ago Roundtrip non-stop flight included Ottawa (YOW) 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 ![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 $1,633 per person Mar 15 - Mar 19 found 8 hours ago Roundtrip flight included Boston (BOS) to San Juan (SJU) 9/10 Wonderful! (2,764 reviews) Everything is outstanding from check in to check out. Staff was hands down the best. Reviewed on Jan 11, 2026 ![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 $1,902 per person Mar 14 - Mar 19 found 4 hours ago Roundtrip non-stop flight included Ottawa (YOW) to San Juan (SJU) 8/10 Very Good! (1,814 reviews) There are occasional items that reveal a slightly thread-bare tendency. A dab of paint here, a washed or painted wall, or other minor stuff that could spruce up the place just a tiny bit and make it completely feel like a 4-star establishment. For example our safe was either broken or needed a battery. Not a big deal but letting the small stuff go can lead to bigger issues later Reviewed on Jan 8, 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 $6,335 per person Mar 15 - Mar 20 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to San Juan (SJU) 9.4/10 Exceptional! (450 reviews) Beautiful resort. We loved every minute. Reviewed on Oct 25, 2025 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/2026-02-12/2026-02-19/?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 $2,366 per person Mar 20 - Mar 24 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to San Juan (SJU) 8.6/10 Excellent! (2,206 reviews) Very nice stay. Great staff. Quite expensive. Reviewed on Jan 12, 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 $6,335 per person Mar 15 - Mar 20 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to San Juan (SJU) 9.4/10 Exceptional! (450 reviews) Beautiful resort. We loved every minute. Reviewed on Oct 25, 2025 ![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 $2,558 per person Mar 14 - Mar 19 found 4 hours ago Roundtrip non-stop flight included Ottawa (YOW) to San Juan (SJU) 9.2/10 Wonderful! (1,616 reviews) Everything the staff clean rooms amenities this will continue to be the hotel I will continue to stay when I all in Puerto Rico ! Reviewed on Jan 11, 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/2026-02-12/2026-02-19/?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. ![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 $1,390 per person Mar 22 - Mar 24 found 1 day ago Roundtrip flight included Vancouver (YVR) 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 ![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 $1,798 per person Mar 11 - Mar 14 found 5 hours ago Roundtrip non-stop flight included Toronto (YYZ) to San Juan (SJU) 9.2/10 Wonderful! (1,616 reviews) Everything the staff clean rooms amenities this will continue to be the hotel I will continue to stay when I all in Puerto Rico ! Reviewed on Jan 11, 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 $2,790 per person Feb 13 - Feb 16 found 1 day ago Roundtrip flight included Calgary (YYC) to San Juan (SJU) 8.6/10 Excellent! (2,396 reviews) The pool was very cold! One of our rooms did not have a balcony. We overlooked the fort on the backside of the building. Reviewed on Jan 11, 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/2026-02-12/2026-02-19/?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. ![ESJ Beach Hotel](https://images.trvl-media.com/lodging/1000000/610000/603200/603169/49d76820_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### ESJ Beach Hotel Isla Verde CA $802 per person Mar 15 - Mar 19 found 8 hours ago Roundtrip flight included Boston (BOS) to San Juan (SJU) 6.8/10 (4,221 reviews) The hotel was very nice the mint bar and the cute little cafe where great I do wish the pool was open or maybe being better compensated for not having a pool Reviewed on Jan 11, 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 $1,293 per person Mar 15 - Mar 19 found 1 hour ago Roundtrip flight included Boston (BOS) 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 ![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 $981 per person Mar 15 - Mar 19 found 8 hours ago Roundtrip flight included Boston (BOS) to San Juan (SJU) 8/10 Very Good! (1,814 reviews) There are occasional items that reveal a slightly thread-bare tendency. A dab of paint here, a washed or painted wall, or other minor stuff that could spruce up the place just a tiny bit and make it completely feel like a 4-star establishment. For example our safe was either broken or needed a battery. Not a big deal but letting the small stuff go can lead to bigger issues later Reviewed on Jan 8, 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/2026-02-12/2026-02-19/?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 $729, 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 23\. 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 $736 CA $980 total Jan 25 - Jan 26 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! (1,669 reviews) Outdoor pool area us nice Reviewed on Jan 5, 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 $378 CA $495 total Jan 14 - Jan 15 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! (1,005 reviews) Loved staying in this historic site. Beautiful property, great location to restaurants, shopping, and El Moro. It can be difficult to find parking if arriving later in the day, some of the parking decks nearby were full when we checked. Reviewed on Jan 3, 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 $2,574 CA $2,956 total Jan 13 - Jan 14 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-The-St-Regis-Bahia-Beach-Resort.h3800119.Hotel-Information) [See all 8,279 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. Additional terms may apply. ## More vacations you might like ![](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) ### Top Luxury Vacation Destinations > - [Luxury vacations in India ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/80/India) > - [Luxury vacations in France ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/59/France) > - [Luxury vacations in Switzerland ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/174/Switzerland) > - [Luxury vacations in Canada ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/31/Canada) > - [Luxury vacations in Jamaica ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/88/Jamaica) > - [Luxury vacations in Italy ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/86/Italy) > - [Luxury vacations in New Zealand ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/133/New-Zealand) > - [Luxury vacations in the Maldives ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/109/Maldives) > - [Luxury vacations in Costa Rica ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/42/Costa-Rica) > - [Luxury vacations in Florida Keys ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/6023765/Florida-Keys) > - [Luxury vacations in Mexico ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/117/Mexico) > - [Luxury vacations in the Caribbean ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/6022969/Caribbean) > - [Luxury vacations in Zanzibar ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/4186/Zanzibar) > - [Luxury vacations in Cancun ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/179995/Cancun) > - [Luxury vacations in Kerala ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/602187/Kerala) > - [Luxury vacations in Australia ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/10/Australia) > - [Luxury vacations in Puglia ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/6048562/Puglia) > - [Luxury vacations in Cuba ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/44/Cuba) > - [Luxury vacations in Cyprus ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/45/Cyprus) ## More Vacations Ideas [Puerto Rico Flights ](https://expedia.ca/Destinations-In-Puerto-Rico.d148.Flight-Destinations)[ Puerto Rico Hotels ](https://expedia.ca/Destinations-In-Puerto-Rico.d148.Hotel-Destinations)[ Puerto Rico Vacation Rentals ](https://expedia.ca/Destinations-In-Puerto-Rico.d148.Vacation-Rental-Destinations)[ Puerto Rico Car Rentals ](https://expedia.ca/Destinations-In-Puerto-Rico.d148.Car-Rental-Destinations)[ Puerto Rico Vacations ](https://expedia.ca/Puerto-Rico.d148.Destination-Travel-Guides) \* 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. Scan the QR code with your device camera and download our app