Title: Roosevelt Roads Ski Holidays 2025/2026 | 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 Ski Holidays ## Book a Ski 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 + Ski 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 £865 per person 1 Feb - 8 Feb found 4 hours ago Return direct flight included London (LON) to San Juan (SJU) 9/10 Wonderful! (100 reviews) I did not have hot water for 6 days. Property did not disclose they would be without water beforehand. Also, no microwave or utensils. Sub par but good for price. Reviewed on 30 Oct 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2026-02-01/2026-02-08/?FromAirport=LON&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=104571256&paandie=true&HotelClass=40&dealMarker=mGzB9ZsE-1kk29sSPTJpxyerDuwO8Ezmt0R_fJrMmFHTlYZKKK19fIvR-4VS5tbI) ![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 Save 100% on your flight £1,519 per person 1 Jan - 8 Jan found 1 day ago Return direct flight included London (LHR) to San Juan (SJU) 9.2/10 Wonderful! (542 reviews) Muy buen ambiente, su personal atento y dispuesto en todo momento para lo q necesitáramos. La habitación y baños buena limpieza y todo en orden con las utilidades. En un area céntrica para moverse tanto en San Juan como el Condado. Recomendado al 100%. Reviewed on 9 Nov 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2026-01-01/2026-01-08/?FromAirport=LHR&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=104217135&paandie=true&HotelClass=40&dealMarker=ieRjR772kOxtYmwC_ajy1WYGLudVIuHd6xg4uyZxD0Zif0TtDPBHZcQXhqotdTs2) ![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 £1,354 per person 1 Feb - 8 Feb found 4 hours ago Return direct flight included London (LON) to San Juan (SJU) 9/10 Wonderful! (290 reviews) Everything great. The only bad thing was the housekeeping knocking the door very early in the morning. Reviewed on 10 Nov 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2026-02-01/2026-02-08/?FromAirport=LON&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=527599&paandie=true&HotelClass=40&dealMarker=J0Y-jfEAGoCdHFgpHa5HlEYZo6Lo8n0zWefKa7eY9R1oVYPPAU91zFma1PJzJC0e) ![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 £2,599 per person 27 Dec - 3 Jan found 16 hours ago Return direct flight included London (LON) to San Juan (SJU) 8.6/10 Excellent! (563 reviews) Amazing location , helpful attentive kind staff , unique vibes definitely would recommend Reviewed on 30 Oct 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2025-12-27/2026-01-03/?FromAirport=LON&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=23155605&paandie=true&HotelClass=40&dealMarker=J0Y-jfEAGoCdHFgpHa5HlDVbIdY5OEmfneQXYHyV0NKPsOdQELYgjGp74wt5j8ze) ![DoubleTree by Hilton San Juan](https://images.trvl-media.com/lodging/1000000/30000/20200/20198/54ba0f8d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### DoubleTree by Hilton San Juan Santurce £1,034 per person 1 Feb - 8 Feb found 4 hours ago Return direct flight included London (LON) to San Juan (SJU) 9/10 Wonderful! (1,014 reviews) The breakfast isn’t free Reviewed on 20 Oct 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2026-02-01/2026-02-08/?FromAirport=LON&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20198&paandie=true&HotelClass=40&dealMarker=P2oJBHaqqcX9SJa466RX5LjyR_9Od35eovUJa1m6BCOZ5kDIdHGy-bq_6JI30mcN) 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/2025-12-10/2025-12-17/?FromAirport=LON&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Ski 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 £1,722 per person 1 Feb - 8 Feb found 4 hours ago Return direct flight included London (LON) to San Juan (SJU) 9.2/10 Wonderful! (1,602 reviews) We had such a great experience at the Condado Vanderbilt Hotel. The property is beautiful — elegant, clean, and perfectly located with gorgeous ocean views. The staff were attentive and friendly, always making sure we were comfortable and well taken care of. The pools were relaxing with plenty of lounge areas, and the food at the on-site restaurants was excellent. We also loved how easy it was to walk to nearby restaurants and shops — everything you need is right around the corner. Our room was spacious and well-maintained, and the overall atmosphere of the hotel felt luxurious yet welcoming. We truly enjoyed our time here and would definitely stay again on our next trip to Puerto Rico. Reviewed on 2 Nov 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2026-02-01/2026-02-08/?FromAirport=LON&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=9105241&paandie=true&HotelClass=50&dealMarker=EzaReZ9EoJWRRmgYDfCFNh9IzBHw0q8ThjY5bmhE6R5sUV1T0jqjLalPiWTgpmuG) ![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 £4,282 per person 27 Dec - 3 Jan found 16 hours ago Return direct flight included London (LON) to San Juan (SJU) 7.6/10 Good! (127 reviews) Bianca and Melanie at the front desk were both very helpful and accommodating. Reviewed on 28 Sept 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2025-12-27/2026-01-03/?FromAirport=LON&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=64577147&paandie=true&HotelClass=50&dealMarker=J0Y-jfEAGoCdHFgpHa5HlIGjK8rB2VafuBoAEiD-COyOcViYsfWBbI-h-prE1dW6) ![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 £3,086 per person 27 Dec - 3 Jan found 16 hours ago Return direct flight included London (LON) to San Juan (SJU) 8.4/10 Very Good! (2,018 reviews) It was a great trip and staff was amazing Reviewed on 6 Nov 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2025-12-27/2026-01-03/?FromAirport=LON&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1592&paandie=true&HotelClass=50&dealMarker=EzaReZ9EoJWRRmgYDfCFNgsnUjUwcKB5MaT6RTcqip5gOgJmbFRkAX5as45s5eAQ) 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/2025-12-10/2025-12-17/?FromAirport=LON&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Planning your Roosevelt Roads ski holiday #### How can I book the best ski holiday to Roosevelt Roads in 2025/2026? Search through alpine adventures on Expedia to plan your perfect snowy ski holiday in Roosevelt Roads. Just choose your dates and see what’s available. You might prefer a hotel with a heated outdoor pool, or a private chalet for après ski parties; either way, use the property filters to your ideal match. If ski-in-ski-out is important, use the map view to find those idyllic slopeside properties. #### How can I find cheap Roosevelt Roads ski holidays? Boot hire, lift passes, lessons: ski holidays can get pricey, quickly. To make your ski trip more affordable, book Roosevelt Roads accommodation a little further from the lifts and go self-catering to cut back on eating out. Sort your search results by price to find options from £865. Prices and availability are subject to change. Additional terms may apply. #### Can I book last-minute ski holidays to Roosevelt Roads? Use our handy last-minute deals page to look for ski holidays to Roosevelt Roads at a steal. If your dates are fixed, simply input the details and see what specials are available. #### What should I consider when booking family ski holidays in Roosevelt Roads? Roosevelt Roads is well set up for kids. For the teeniest ski-woks, day care in the snow is a blast. As they get older, they love whizzing around on the hill in ski school. Choose a hotel near the lifts and nursery slopes to save a whole lot of ski-carrying hassle in the mornings. With all that extra time and energy, you can take your sweet time to find a family-favourite bolthole on the mountain for hot chocolate with marshmallows ski breaks. #### Can I book all-inclusive ski holidays to Roosevelt Roads? All-inclusive ski holidays are fairly rare, but you can use our filter to see if there are any available in Roosevelt Roads. If not, consider booking your flights and accommodation together to save money that way instead. #### When's the best time of year to plan a ski trip to Roosevelt Roads? Ski season in Roosevelt Roads generally starts around December and slopes off around April. Keep an eye on the snow forecasts though, as you can often find some brilliant deals at the start or end of the season, when it’s also much quieter. #### How can I find the best deals on Roosevelt Roads ski holiday packages? If you can be flexible with your ski holiday dates, avoid school holidays and instead buckle up your boots at the start or end of season. Sort your search results by price and look out for self-catered accommodation to save on notoriously expensive ski-resort drinking and dining. #### Can I book a Roosevelt Roads ski trip with free cancellation and/or flexible dates? If you’re not 100% sure on plans or just want peace of mind, choose a ski holiday with free cancellation. You can use our free cancellation filter to find properties in Roosevelt Roads that offer it. #### Why should I book a ski holiday package in Roosevelt Roads with Expedia? Schuss your way to the slopes with Expedia’s smooth booking process. From flights to hotels and even car hire, you’ll find everything you need to plan the ultimate winter wonderland ski holiday. ## 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 Ski 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 ![QR code to download the app](data:image/png;base64,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)