A coastal town with colorful buildings, a rocky shoreline, and waves crashing against the rocks.

Puerto Rico Luxury Vacations

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Top Luxury vacation packages in Puerto Rico

Price found within the past 48 hours. Click for updated prices.
  • Jan 29 - Feb 3

    Ola Boutique Hotel + Flight

    Condado
    5 nights
    4.5 star property
    9.0/10 - Wonderful (1,047 reviews)
    Roundtrip • Toronto (YTO) - San Juan (SJU)
    YYZ - SJU • 1 stop SJU - YYZ • 1 stop
    CA $1,902
    CA $1,497
    per traveller
    found 22 hours ago
    Ola Boutique Hotel
  • Jan 27 - Feb 2

    Fairmont El San Juan Hotel + Flight

    Isla Verde
    6 nights
    5.0 star property
    8.6/10 - Excellent (2,234 reviews)
    Roundtrip • Toronto (YTO) - San Juan (SJU)
    YYZ - SJU • 1 stop SJU - YYZ • 1 stop
    Save 100% on your flight
    CA $3,767
    CA $2,657
    per traveller
    found 1 day ago
    Fairmont El San Juan Hotel
  • Jan 29 - Feb 3

    OLV Fifty Five - Adults Only + Flight

    Condado
    5 nights
    4.5 star property
    8.8/10 - Excellent (827 reviews)
    Roundtrip • Toronto (YTO) - San Juan (SJU)
    YYZ - SJU • 1 stop SJU - YYZ • 1 stop
    CA $2,764
    CA $2,058
    per traveller
    found 4 hours ago
    OLV Fifty Five - Adults Only
  • Jan 29 - Feb 3

    Condado Vanderbilt Hotel + Flight

    Condado
    5 nights
    5.0 star property
    9.4/10 - Exceptional (1,864 reviews)
    "Awesome"
    Reviewed November 7, 2026
    Roundtrip • Toronto (YTO) - San Juan (SJU)
    YYZ - SJU • 1 stop SJU - YYZ • 1 stop
    CA $2,840
    CA $2,205
    per traveller
    found 1 day ago
    Condado Vanderbilt Hotel
  • Jan 29 - Feb 3

    San Juan Marriott Resort and Stellaris Casino + Flight

    Condado
    5 nights
    4.5 star property
    9.0/10 - Wonderful (1,813 reviews)
    "We had a wonderful stay with ocean view. We loved overseeing the pool seeing the ocean and hearing the waves come in from our balcony. Everyone was friendly and helpful. The casino and live music was fun too."
    Reviewed November 7, 2026
    Roundtrip • Toronto (YTO) - San Juan (SJU)
    YYZ - SJU • 1 stop SJU - YYZ • 1 stop
    CA $2,757
    CA $2,146
    per traveller
    found 1 day ago
    San Juan Marriott Resort and Stellaris Casino

Discover the most popular places to visit in Puerto Rico

Top Luxury Puerto Rico Hotels

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.

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 $1,497, 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 21. 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.