Title: Golf Vacations in Roosevelt Roads 2026 | Expedia.ca ![](https://images.trvl-media.com/place/6360451/3441fe46-31f2-46bc-b307-613f9edf876d.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Roosevelt Roads Golf Vacations ## Book a Hotel + Flight or Car together to unlock savings Photo by Shannon Willitts - ## 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 Golf hotel deals in Roosevelt Roads Price found within the past 48 hours. Click for updated prices. ![Romeo Gay Hotel](https://images.trvl-media.com/lodging/105000000/104580000/104571300/104571256/c3574a90_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Romeo Gay Hotel San Juan Antiguo CA $1,415 per person Mar 13 - Mar 20 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to San Juan (SJU) 9/10 Wonderful! (121 reviews) Parking was good, hotel and room was clean, front desk was really nice and the location was good. Reviewed on Dec 30, 2025 ![Ola Boutique Hotel](https://images.trvl-media.com/lodging/105000000/104220000/104217200/104217135/7963308f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Ola Boutique Hotel Condado CA $1,438 per person Apr 2 - Apr 9 found 12 hours ago Roundtrip non-stop flight included Edmonton (YEG) to San Juan (SJU) 9.2/10 Wonderful! (589 reviews) Staff was awesome, room was clean. Breakfast was the same every day, omelette, sausage/hot dogs, yogurt, strong coffee, and juice. Outside of the building didn’t match photos on website or Expedia. There were no amenities, rooftop was closed, no spa, no hot tub. Great access to everything in San Juan. No restaurant on site, no laundry, not in a nature reserve it’s in the middle of San Juan. No sauna, no banquet hall, elevator was questionable. For the price it was a great stay, but if you need a hot tub or spa you’ll have to drive. Check in wasn’t on time, but we got a similar room after waiting a few hours. No golf course nearby! We really enjoyed our stay water pressure and temperature was awesome! Reviewed on Jan 3, 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 $2,557 per person Mar 18 - Mar 24 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 9/10 Wonderful! (645 reviews) Tatiana was a great host who helped us out tremendously. Reviewed on Nov 30, 2025 ![OLV Fifty Five - Adults Only](https://images.trvl-media.com/lodging/24000000/23160000/23155700/23155605/29ce7de9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### OLV Fifty Five - Adults Only Condado CA $1,974 per person Mar 1 - Mar 7 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 8.6/10 Excellent! (577 reviews) It was a great Stay, very nice and great customer service from the staff. Jessica, front desk worker was amazing. Kelvin Reviewed on Jan 9, 2026 ![Aire de O:live](https://images.trvl-media.com/lodging/1000000/530000/527600/527599/8d4c39ed_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Aire de O:live Isla Verde CA $2,991 per person Mar 5 - Mar 12 found 1 day ago Roundtrip flight included Edmonton (YEG) to San Juan (SJU) 9/10 Wonderful! (328 reviews) Entire stay was 10/10\. Highly recommend! Reviewed on Jan 8, 2026 Don't see what you're looking for? See all available trips from Columbus to Roosevelt Roads [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-02-10/2026-02-17/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Golf holidays in Roosevelt Roads Price found within the past 48 hours. Click for updated prices. ![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 $3,097 per person Mar 13 - Mar 20 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to San Juan (SJU) 9.2/10 Wonderful! (1,616 reviews) We stay here all the time. Best place ever! 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 $7,224 per person Mar 18 - Mar 24 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 9.4/10 Exceptional! (450 reviews) Beautiful resort. We loved every minute. Reviewed on Oct 25, 2025 ![Fairmont El San Juan Hotel](https://images.trvl-media.com/lodging/1000000/10000/1600/1592/99d8d575_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Fairmont El San Juan Hotel Isla Verde CA $4,059 per person Mar 13 - Mar 20 found 12 hours ago Roundtrip flight included Edmonton (YEG) to San Juan (SJU) 8.4/10 Very Good! (2,051 reviews) We had a great stay at Fairmont El San Juan Hotel and really enjoyed our four-night stay. The staff was friendly, professional, and welcoming, and the hotel has a beautiful atmosphere with well-maintained spaces. Our room was comfortable and clean, and overall service was excellent. One small suggestion: it would be very helpful if, at check-in, the hotel clearly explained what is included in the resort fee. We later found out it covered several amenities that we were not aware of and unfortunately did not get to use. Overall, a wonderful experience and we would definitely stay here again. Reviewed on Jan 7, 2026 Don't see what you're looking for? See all available trips from Columbus to Roosevelt Roads [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-02-10/2026-02-17/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Golf holidays in Roosevelt Roads 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 $1,646 per person Mar 13 - Mar 16 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) 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 ![Aire de O:live](https://images.trvl-media.com/lodging/1000000/530000/527600/527599/8d4c39ed_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Aire de O:live Isla Verde CA $1,934 per person Mar 13 - Mar 16 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to San Juan (SJU) 9/10 Wonderful! (328 reviews) Entire stay was 10/10\. Highly recommend! Reviewed on Jan 8, 2026 ![Ola Boutique Hotel](https://images.trvl-media.com/lodging/105000000/104220000/104217200/104217135/7963308f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Ola Boutique Hotel Condado CA $1,669 per person Mar 5 - Mar 8 found 18 hours ago Roundtrip flight included Toronto (YTO) to San Juan (SJU) 9.2/10 Wonderful! (589 reviews) Staff was awesome, room was clean. Breakfast was the same every day, omelette, sausage/hot dogs, yogurt, strong coffee, and juice. Outside of the building didn’t match photos on website or Expedia. There were no amenities, rooftop was closed, no spa, no hot tub. Great access to everything in San Juan. No restaurant on site, no laundry, not in a nature reserve it’s in the middle of San Juan. No sauna, no banquet hall, elevator was questionable. For the price it was a great stay, but if you need a hot tub or spa you’ll have to drive. Check in wasn’t on time, but we got a similar room after waiting a few hours. No golf course nearby! We really enjoyed our stay water pressure and temperature was awesome! Reviewed on Jan 3, 2026 Don't see what you're looking for? See all available trips from Columbus to Roosevelt Roads [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-02-10/2026-02-17/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Golf holidays in Roosevelt Roads Price found within the past 48 hours. Click for updated prices. ![Isla Verde Beachfront Retreat With Parking](https://images.trvl-media.com/lodging/121000000/120580000/120573300/120573221/f6cf00c9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Isla Verde Beachfront Retreat With Parking Isla Verde CA $1,533 per person Apr 3 - Apr 7 found 18 hours ago Roundtrip non-stop flight included Toronto (YYZ) to San Juan (SJU) No reviews ![Las Casitas Village at El Conquistador](https://images.trvl-media.com/lodging/92000000/91570000/91562100/91562080/7e550371_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Las Casitas Village at El Conquistador Cabezas CA $3,080 per person Mar 13 - Mar 17 found 22 hours ago Roundtrip non-stop flight included Toronto (YYZ) to San Juan (SJU) 9.2/10 Wonderful! (126 reviews) The staff was great. Housekeeping was great. Angel made great omelettes. Valeria the manager at Las Casitas was very attentive. Reviewed on Jan 9, 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 $1,733 per person Mar 12 - Mar 16 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) 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 Roosevelt Roads [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-02-10/2026-02-17/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Discover the ultimate golf vacation from Roosevelt Roads with Expedia #### 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 $1,415, 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 36, 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. ## 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 Golf Vacation Destinations > - [Golf vacations in Mexico ](https://www.expedia.ca/lp/theme-vacations/golf-vacations/117/Mexico) > - [Golf vacations Myrtle Beach ](https://www.expedia.ca/lp/theme-vacations/golf-vacations/601685/Myrtle-Beach) > - [Golf vacations in Portugal ](https://www.expedia.ca/lp/theme-vacations/golf-vacations/147/Portugal) > - [Golf vacations in Thailand ](https://www.expedia.ca/lp/theme-vacations/golf-vacations/178/Thailand) > - [Golf vacations in Belek ](https://www.expedia.ca/lp/theme-vacations/golf-vacations/6034717/Belek) > - [Golf vacations in Las Vegas ](https://www.expedia.ca/lp/theme-vacations/golf-vacations/178276/Las-Vegas) > - [Golf vacations in Scotland ](https://www.expedia.ca/lp/theme-vacations/golf-vacations/11219/Scotland) > - [Golf vacations in Tenerife ](https://www.expedia.ca/lp/theme-vacations/golf-vacations/6047194/Tenerife) > - [Golf vacations in the Caribbean ](https://www.expedia.ca/lp/theme-vacations/golf-vacations/6022969/Caribbean) > - [Golf vacations in Lanzarote ](https://www.expedia.ca/lp/theme-vacations/golf-vacations/282/Lanzarote) > - [Golf vacations in Italy ](https://www.expedia.ca/lp/theme-vacations/golf-vacations/86/Italy) > - [Golf vacations in Turkey ](https://www.expedia.ca/lp/theme-vacations/golf-vacations/183/Turkey) > - [Golf vacations in Vilamoura ](https://www.expedia.ca/lp/theme-vacations/golf-vacations/11395/Vilamoura) > - [Golf vacations in Ireland ](https://www.expedia.ca/lp/theme-vacations/golf-vacations/84/Ireland) > - [Golf vacations in the Dominican Republic ](https://www.expedia.ca/lp/theme-vacations/golf-vacations/50/Dominican-Republic) > - [Golf vacations in the United Kingdom ](https://www.expedia.ca/lp/theme-vacations/golf-vacations/190/United-Kingdom) > - [Golf vacations in Hawaii ](https://www.expedia.ca/lp/theme-vacations/golf-vacations/213/Hawaii) > - [Golf vacations in Algarve ](https://www.expedia.ca/lp/theme-vacations/golf-vacations/182215/Algarve) > - [Golf vacations in Cyprus ](https://www.expedia.ca/lp/theme-vacations/golf-vacations/45/Cyprus) ## More Vacations Ideas [Flights to Roosevelt Roads ](https://expedia.ca/Cheap-Flights-To-Roosevelt-Roads.d6360451.Travel-Guide-Flights)[ Roosevelt Roads Hotels ](https://expedia.ca/Roosevelt-Roads-Hotels.d6360451.Travel-Guide-Hotels)[ Roosevelt Roads Vacation Rentals ](https://expedia.ca/Roosevelt-Roads-Vacation-Rentals.d6360451.Travel-Guide-VacationRentals)[ Roosevelt Roads Car Rentals ](https://expedia.ca/Car-Rentals-In-Roosevelt-Roads.d6360451.Car-Rental-Guide)[ Roosevelt Roads Vacations ](https://expedia.ca/Roosevelt-Roads.d6360451.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