Title: Roosevelt Roads Luxury Holidays 2026 | Expedia.co.uk ![](https://images.trvl-media.com/place/6360451/3441fe46-31f2-46bc-b307-613f9edf876d.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Roosevelt Roads Luxury Holidays ## Book a Luxury Hotel + Flight or Car together to unlock savings Photo by Shannon Willitts - ## Plan, book, travel with confidence - ### Better together Save up to £335 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 Packages with flights are ATOL protected ## Top flight + Luxury 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 £636 per person 6 Feb - 11 Feb found 1 day ago Return direct flight included London (LHR) 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 30 Dec 2025 ![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 Save 100% on your flight £1,090 per person 6 Feb - 11 Feb found 1 day ago Return direct flight included London (LHR) to San Juan (SJU) 9/10 Wonderful! (328 reviews) Great spot and staff Reviewed on 1 Jan 2026 ![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 Save 100% on your flight £1,092 per person 6 Feb - 11 Feb found 1 day ago Return direct flight included London (LHR) to San Juan (SJU) 8.6/10 Excellent! (577 reviews) This place is beautiful a must stay Reviewed on 25 Dec 2025 ![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 Save 100% on your flight £2,043 per person 9 Feb - 15 Feb found 7 hours ago Return direct flight included Manchester (MAN) to San Juan (SJU) 9.2/10 Wonderful! (126 reviews) Everyone was so helpful and it was a beautiful property that was well maintained. Reviewed on 28 Dec 2025 ![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 £916 per person 6 Feb - 11 Feb found 1 day ago Return direct flight included London (LHR) to San Juan (SJU) 9/10 Wonderful! (3,205 reviews) 1-Hot water to shower was impossible to achieve. 2-Room temp unable to regulate (always cold even when thermostat was off) fan always on cold 3-Every indoor area was freezing including restaurants. I became ill! 4-Navigation of property is difficult. 5-Television hotel guide should indicate restaurants menus along with daily activities. 6-Corporate managements guess relations are a failure. (hotel staff do care) Many more issues are noticeable. This property could be the GEM of Puerto Rico if managed correctly. Reviewed on 31 Dec 2025 Don't see what you're looking for? See all available trips from London to Roosevelt Roads [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-02-02/2026-02-09/?FromAirport=LHR&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Luxury holidays in Roosevelt Roads 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 £1,309 per person 6 Feb - 11 Feb found 1 day ago Return direct flight included London (LHR) to San Juan (SJU) 8.6/10 Excellent! (2,206 reviews) We were extremely pleased with the hotel and staff with the exception of one employee. Reviewed on 1 Jan 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 £2,085 per person 9 Feb - 15 Feb found 7 hours ago Return direct flight included Manchester (MAN) to San Juan (SJU) 9.2/10 Wonderful! (1,616 reviews) Beautiful hotel, great staff, lives up to its reputation. Reviewed on 29 Dec 2025 Don't see what you're looking for? See all available trips from London to Roosevelt Roads [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-02-02/2026-02-09/?FromAirport=LHR&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## All you need to know about luxury holidays in Roosevelt Roads #### What can I expect from a luxury Roosevelt Roads holiday? Luxury on holiday is all about relaxing and feeling good. Whether you choose a sumptuous spa, Michelin-starred restaurant or super-king bed is your call. Use our amenities filters to find the things that tick all your boxes. #### How can I find all-inclusive luxury holidays in Roosevelt Roads? Tick the all-inclusive and 5-star filters to find the crème de la crème of Roosevelt Roads holidays. With everything included in the package price, you can drink and dine to your heart’s content, without worrying about that bill at the end. #### Can I book a cheap luxury holiday to Roosevelt Roads? A luxury holiday doesn’t have to break the bank. Travel out of peak season, choose a hotel or resort a little way out or go for a last-minute getaway and you’ll find some cracking deals. Sort by price to find luxury holidays to Roosevelt Roads starting at £636\. Prices and availability are subject to change. Additional terms may apply. #### Are there luxury spa holidays in Roosevelt Roads? For sunset massages on the shoreline and view-filled saunas, use our spa filter to find your ideal Roosevelt Roads spa hotel. Book a whole weekend soaking away your stresses, or hop into the spa after the beach, some golf or a local advent-ahhhh. #### What should I look for when booking a luxury family holiday in Roosevelt Roads? Luxury isn’t just for adults. Those little touches designed for little people make a family holiday genuinely stress free … which is the greatest luxury of all. Look for spacious suites, pools toddlers can splash in, and breakfast buffets with waffles, pancakes and Nutella galore. #### Can I book luxury last-minute holidays to Roosevelt Roads? You can wangle a top-notch luxury holiday in Roosevelt Roads for a fraction of the normal price by booking last minute. Just enter your dates and see what’s available – if you’re flexible ... even better! #### Can I book a luxury holiday in Roosevelt Roads with free cancellation and/or flexible dates? If you’re splashing out on a luxury holiday, make sure your money is safe by booking with free cancellation. Just use the fully refundable filter and make sure you read all the terms and conditions. #### Why should I book my luxury travel to Roosevelt Roads with Expedia? Nobody does luxury quite like Expedia. With so many gorgeous properties in Roosevelt Roads to choose from, as well as access to first-class flight deals and hire cars with horsepower, there’s no better place to book. ## More holidays 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 Holidays [](https://expedia.co.uk/lp/theme-holidays/all-inclusive-holidays?rfrr=editorial.All_Inclusive%20Holidays.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 Holidays [](https://expedia.co.uk/lp/theme-holidays/beach-holidays?rfrr=editorial.Beach_Holidays.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 Friendly Holidays [](https://expedia.co.uk/lp/theme-holidays/kid-friendly-holidays?rfrr=editorial.Family_Friendly%20Holidays.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 Holidays [](https://expedia.co.uk/lp/theme-holidays/golf-holidays?rfrr=editorial.Golf_Holidays.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 Holidays [](https://expedia.co.uk/lp/theme-holidays/luxury-holidays?rfrr=editorial.Luxury_Holidays.click) ![gay friendly holiday packages](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) LGBTQ+ Holidays [](https://expedia.co.uk/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ+_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Holidays [](https://expedia.co.uk/lp/theme-holidays/romantic-holidays?rfrr=editorial.Romantic_Holidays.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 Holidays [](https://expedia.co.uk/lp/theme-holidays/ski-holidays?rfrr=editorial.Ski_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/22/hero-image-pet-friendly_copy.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Pet Friendly Holidays [](https://expedia.co.uk/lp/theme-holidays/pet-friendly-holidays?rfrr=editorial.Pet_Friendly%20Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Where to go when [](https://expedia.co.uk/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click) ### Top Luxury Holiday Destinations > - 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Savings not available on all packages. Flight-inclusive packages are ATOL protected. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels when you book in 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