Golf Vacations in Roosevelt Roads 2026

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Flight and Golf hotel deals in Roosevelt Roads

Price found within the past 48 hours. Click for updated prices.

Hotel Puerto Valdes

Puerta de Tierra

CA $1,111

per person

Oct 6 - Oct 11

found 12 hours ago

Roundtrip non-stop flight included

Montreal (YMQ) to San Juan (SJU)

8.8/10 Excellent! (713 reviews)

Walking distance to old SJ; small and cozy hotel

Reviewed on Aug 15, 2026

OLV Fifty Five - Adults Only

Condado

CA $1,245

per person

Nov 9 - Nov 13

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to San Juan (SJU)

8.8/10 Excellent! (727 reviews)

Aire de O:live

Isla Verde

CA $1,661

per person

Oct 18 - Oct 24

found 9 hours ago

Roundtrip flight included

Montreal (YMQ) to San Juan (SJU)

9.2/10 Wonderful! (736 reviews)

Would not recommend this O:live whatsoever, from the initial check in to the check out. Was left waiting over 3+ hours for check in, further someone kicked my luggage at the front desk and reception/staff said nor did absolutely anything. Further, my review of the food at the hotel, is that it’s quite lackluster. The hotel attempts to portray luxury but reality its anything but it. I travel quite extensively, and have stayed at real 5+ ⭐️, and plenty of real 4 star hotels. This is 2 star hotel(similar to a holiday inn or Hampton inn) pretending to be a “luxury boutique hotel”. This was my first time in PR, and I was hoping to try a smaller brand hotel instead of going to rio grande for the four season or dorado for the ritz, but I’ve now learned to trust my instinct. If you’re looking for a trashy, near the beach fake luxury hotel, then go ahead and book. If you aren’t, I’d recommend you don’t stay here. For those looking at some of the “better reviews”, I’m unsure if they’re real or if they are likely from less seasoned traveler. Cherry on top: I asked for late check out so I wouldn’t have to wait as long at the airport, and in consideration of my bad experience, they scoffed and said do what you have to, hence where I am now. (That’s my review of the customer service, instead of assuaging a peeved occupant, they challenge me).

Reviewed on Aug 15, 2026

Ola Boutique Hotel

Condado

CA $1,281

per person

Sep 27 - Oct 4

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to San Juan (SJU)

9/10 Wonderful! (925 reviews)

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5* Golf holidays in Roosevelt Roads

Price found within the past 48 hours. Click for updated prices.

Fairmont El San Juan Hotel

Isla Verde

CA $1,225

per person

Oct 6 - Oct 11

found 12 hours ago

Roundtrip non-stop flight included

Montreal (YMQ) to San Juan (SJU)

8.6/10 Excellent! (2,152 reviews)

Rooms were excellent in the villa. Restaurants had great food. Wonderful pool and beach staff. Night manager was extremely helpful at check in after our flights were canceled and arriving a day late.

Reviewed on Aug 15, 2026

Signature Collection at Rio Mar

Mameyes II

CA $3,548

per person

Oct 2 - Oct 6

found 10 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to San Juan (SJU)

No reviews

Everything is 10 times more expensive compare to any other place I visites

Reviewed on Aug 8, 2026

Fairmont El San Juan Villa Experience

Isla Verde

CA $2,699

per person

Sep 27 - Oct 4

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to San Juan (SJU)

7.6/10 Good! (150 reviews)

Exceeded our expectations in cleanliness, staff was courteous went out of their way to make sure our stay was memorable.

Reviewed on Aug 14, 2026

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3 Night Golf holidays in Roosevelt Roads

Price found within the past 48 hours. Click for updated prices.

Hotel Puerto Valdes

Puerta de Tierra

CA $706

per person

Sep 26 - Sep 29

found 19 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to San Juan (SJU)

8.8/10 Excellent! (713 reviews)

Walking distance to old SJ; small and cozy hotel

Reviewed on Aug 15, 2026

OLV Fifty Five - Adults Only

Condado

CA $979

per person

Sep 26 - Sep 29

found 19 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to San Juan (SJU)

8.8/10 Excellent! (727 reviews)

Fairmont El San Juan Hotel

Isla Verde

CA $1,380

per person

Nov 11 - Nov 14

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to San Juan (SJU)

8.6/10 Excellent! (2,152 reviews)

Rooms were excellent in the villa. Restaurants had great food. Wonderful pool and beach staff. Night manager was extremely helpful at check in after our flights were canceled and arriving a day late.

Reviewed on Aug 15, 2026

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4 Night Golf holidays in Roosevelt Roads

Price found within the past 48 hours. Click for updated prices.

Villas De Playa 2

Higuillar

CA $758

per person

Oct 2 - Oct 6

found 12 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to San Juan (SJU)

9/10 Wonderful! (4 reviews)

It was overall a good experience.

Reviewed on Jun 18, 2026

Isla Verde Beachfront Retreat With Parking

Isla Verde

CA $981

per person

Oct 2 - Oct 6

found 12 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to San Juan (SJU)

10/10 Exceptional! (2 reviews)

Hotel Puerto Valdes

Puerta de Tierra

CA $835

per person

Nov 9 - Nov 13

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to San Juan (SJU)

8.8/10 Excellent! (713 reviews)

Walking distance to old SJ; small and cozy hotel

Reviewed on Aug 15, 2026

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What are some benefits when booking golf vacations from Roosevelt Roads?

Booking a golf vacation means putting golf at the centre of your entire experience. Not only will you be able to enjoy easy access to the greens, but you'll often have access to all the equipment you need as well. Plus, golf stays tend to be on the more luxurious end of the spectrum, so you're likely to have some other high-end amenities as well.

How can I find the best golf vacations in Roosevelt Roads?

The best way to find golf vacations in Roosevelt Roads is to take advantage of numerous search filters. You can look for golf stays specifically, with additional filters available for certain courses in some destinations. Plus, if you travel during the off-season in , you may even be able to get high-end stays at a discount.

Are there cheap golf packages available?

Yes, you'll find prices as low as CA $706, but the overall price depends on several factors. The time of year you travel to Roosevelt Roads and the amenities you opt for can play a role in the cost of your package. Some package deals offer discounts of up to 39, but that's just a general trend rather than a guarantee.

Can I book golf and spa vacation packages?

Golf is often considered a luxury activity, so it's only natural that it be paired with other high-end experiences. You can implement the spa filter to sort for properties that have spa facilities, which can be especially useful for resting and rejuvenating in between games.

How can I find luxury golf vacations in Roosevelt Roads?

A lot of golf vacations are already luxurious given the nature of the game, but there are a few things you can do to push it as far as it can go. Use search filters to highlight only 5-star properties to ensure you're getting the best of the best. Business-class flights are available as well in most cases.

Can I book an all-inclusive golf vacation in Roosevelt Roads?

In many cases, yes. There's even a search filter for all-inclusivity, so you can sort for all-inclusive stays specifically. Even when an all-inclusive experience that matches your needs isn't available, you may be able to find some half-board options. This is also one of the best ways to find luxury golf vacations.

Why should I book golf packages including flights?

When you book your flight and your accommodations together, you can enjoy some serious savings compared to what you'd find booking separately. We're your one-stop shop for all your travel needs, and convenience is just the beginning when booking golf vacations from Roosevelt Roads with us.

Should I book a last-minute golf vacation?

Booking last-minute to Roosevelt Roads shouldn't be your first choice, but if you like to travel spontaneously, there are a few benefits to enjoy. Occasionally, you may be able to save money by booking last-minute, as accommodations are interested in filling their last few vacancies as fast as they can. The deals aren't guaranteed, however, so keep that in mind when planning. Sometimes, accommodations will simply be sold out.

Can I book a golf vacation that is fully refundable?

Yes, you'll find several options that are fully refundable among our packages in Roosevelt Roads. You can even filter for fully refundable stays specifically. Just remember to check out each accommodation's policy specifically to make sure your booking qualifies.

Why should I book my golf trip with Expedia?

When you book with Expedia, you can enjoy a one-stop shop for all your travel needs. You can search through a massive collection of packages and potentially unlock discounts by booking your flight and accommodations together. Even more discounts may be available for Expedia Rewards members, such as special deals and the ability to earn points to put toward discounts on future bookings.