Title: Roosevelt Roads Cheap 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 Cheap Holidays ## Book a Cheap 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 + Cheap hotel deals in Roosevelt Roads Price found within the past 48 hours. Click for updated prices. ![Wyndham Palmas Beach and Golf Boutique Resort](https://images.trvl-media.com/lodging/31000000/30080000/30079000/30078988/42731778_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Wyndham Palmas Beach and Golf Boutique Resort £584 per person 16 Mar - 21 Mar found 17 hours ago Return flight included New York (NYC) to San Juan (SJU) 8.4/10 Very Good! (651 reviews) There were several pools. One with a swim up bar, infinity pool, lounging area and hot tub. Shaded areas in the pool were an amazing feature. The second pool area has a beach like entrance and was geared towards families. Very inpressed. Reviewed on 22 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 £918 per person 16 Mar - 21 Mar found 17 hours ago Return flight included New York (NYC) to San Juan (SJU) 8.6/10 Excellent! (577 reviews) The staff was great, the area was great and property was great Reviewed on 28 Jan 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 Save 100% on your flight £1,608 per person 3 Mar - 10 Mar just found Return direct flight included London (LHR) to San Juan (SJU) 9/10 Wonderful! (328 reviews) Great location, nice accommodations. Reviewed on 28 Jan 2026 ![Don Rafa Boutique Hotel & Residences](https://images.trvl-media.com/lodging/85000000/84360000/84351100/84351100/fa3a024b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Don Rafa Boutique Hotel & Residences Santurce £774 per person 16 Mar - 21 Mar found 17 hours ago Return flight included New York (NYC) to San Juan (SJU) 9.4/10 Exceptional! (334 reviews) The staff was very kind and helpful, the room was clean and spacious for us. Reviewed on 29 Jan 2026 ![Alma San Juan ](https://images.trvl-media.com/lodging/103000000/102040000/102037600/102037501/6fd8d30c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Alma San Juan Old San Juan £763 per person 16 Mar - 21 Mar found 17 hours ago Return flight included New York (NYC) to San Juan (SJU) 9/10 Wonderful! (298 reviews) The location was terrific, and the staff was outstanding! Reviewed on 28 Jan 2026 Don't see what you're looking for? See all available trips from New York to Roosevelt Roads [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-02-28/2026-03-07/?FromAirport=NYC&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Cheap 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 £1,898 per person 23 Mar - 30 Mar found 5 hours ago Return direct flight included London (LON) to San Juan (SJU) 8.6/10 Excellent! (2,206 reviews) Clean rooms, wonderful amenities. We loved it! Reviewed on 27 Jan 2026 ![Fairmont El San Juan Villa Experience](https://images.trvl-media.com/lodging/65000000/64580000/64577200/64577147/f326ce2d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Fairmont El San Juan Villa Experience Isla Verde Save 100% on your flight £2,464 per person 3 Mar - 10 Mar just found Return direct flight included London (LHR) to San Juan (SJU) 7.6/10 Good! (128 reviews) One of the best hotels in PR Reviewed on 2 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 £1,901 per person 3 Mar - 10 Mar just found Return direct flight included London (LHR) to San Juan (SJU) 9.2/10 Wonderful! (1,616 reviews) The resort was beautiful, and even at full capacity, it never felt crowded or overwhelming. The atmosphere was relaxing, and the layout made it easy to enjoy the amenities without feeling rushed. The staff was consistently friendly and helpful, which made the stay even more enjoyable. Reviewed on 30 Jan 2026 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/2026-02-28/2026-03-07/?FromAirport=LON&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 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) ## More Holiday Ideas [Flights to Roosevelt Roads ](https://expedia.co.uk/Cheap-Flights-To-Roosevelt-Roads.d6360451.Travel-Guide-Flights)[ Roosevelt Roads Hotels ](https://expedia.co.uk/Roosevelt-Roads-Hotels.d6360451.Travel-Guide-Hotels)[ Roosevelt Roads Holiday Rentals ](https://expedia.co.uk/Roosevelt-Roads-Holiday-Rentals.d6360451.Travel-Guide-HolidayRentals)[ Roosevelt Roads Car Hire ](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Roosevelt-Roads.d6360451.Car-Hire-Guide)[ Roosevelt Roads Holidays ](https://expedia.co.uk/Roosevelt-Roads.d6360451.Holidays-City-Breaks) \* Savings based on package bookings compared to the price of the same components booked separately. 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