Title: Romantic Vacations in Anastasia Island 2025/2026 | Expedia.ca ![](https://images.trvl-media.com/place/6068741/a85942d5-34fb-464d-a5f1-43fcd53bc31c.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Anastasia Island Romantic Vacations ## Book a Hotel + Flight or Car together to unlock savings Stay added Flight added Car - Economy - Premium economy - Business class - First class Leaving from Going to Dates Travellers ## Room 1 Adults ChildrenAges 2 to 17 InfantsYounger than 2 I only need accommodation for part of my trip - ## 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 ## 4 Night Romantic holidays in Anastasia Island Price found within the past 48 hours. Click for updated prices. ![Holiday Inn Express St. Augustine Dtwn - Historic by IHG](https://images.trvl-media.com/lodging/1000000/490000/484600/484510/133e5f29_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Holiday Inn Express St. Augustine Dtwn - Historic by IHG Davis Shores CA $1,195 per person Dec 25 - Dec 29 found 1 day ago Roundtrip non-stop flight included Calgary (YYC) to Orlando (MCO) 8/10 Very Good! (1,006 reviews) Very quaint little property. Quiet, but close to beach and downtown St. Augustine. Would stay again. Newer property, but bathroom and shower very slippery. Breakfast was hit and miss. Reviewed on Oct 21, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-25/2025-12-29/?FromAirport=YYC&Destination=MCO&NumRoom=1&NumAdult=2&NumChild=0&hotelId=484510&paandie=true&dealMarker=VQOyAN7p_xUUaMfVEk5jcxdCgGW2LgwrBPmHqiZxmgp_5ZD3mg7WZXeloRjxkN5_) ![Guy Harvey Resort on St Augustine Beach](https://images.trvl-media.com/lodging/1000000/10000/6500/6477/ae448125_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Guy Harvey Resort on St Augustine Beach CA $1,267 per person Dec 25 - Dec 29 found 1 day ago Roundtrip non-stop flight included Calgary (YYC) to Orlando (MCO) 8.8/10 Excellent! (2,722 reviews) The room had everything we needed . Fridge , microwave and Keurig . Bathroom tub area was dated but everything is kept clean. Staff is wonderful . Great pool area, beach and laundry room . Reviewed on Oct 22, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-25/2025-12-29/?FromAirport=YYC&Destination=MCO&NumRoom=1&NumAdult=2&NumChild=0&hotelId=6477&paandie=true&dealMarker=zsdb7AqbqTyQd7e-XzjFS6pTzu21PAefSMC-pnq0fi8cJ0xttSZCWdrIbqozQPz9) ![Hilton Garden Inn St. Augustine Beach](https://images.trvl-media.com/lodging/1000000/290000/281600/281535/ff24d454_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Garden Inn St. Augustine Beach CA $1,249 per person Dec 25 - Dec 29 found 1 day ago Roundtrip non-stop flight included Calgary (YYC) to Orlando (MCO) 8/10 Very Good! (1,011 reviews) Good place to stay. The only downside is the daily parking fee. Reviewed on Oct 12, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-25/2025-12-29/?FromAirport=YYC&Destination=MCO&NumRoom=1&NumAdult=2&NumChild=0&hotelId=281535&paandie=true&dealMarker=zsdb7AqbqTyQd7e-XzjFS6pTzu21PAefSMC-pnq0fi9O9H8oRJTbP4i7gt-eyskV) Don't see what you're looking for? See all available trips from Columbus to Anastasia Island [View all trips](https://expedia.ca/go/package/search/FlightHotel/2025-11-22/2025-11-29/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=DAB&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Plan unforgettable romantic Anastasia Island vacations #### What are some of the benefits of booking a romantic Anastasia Island vacation? When booking a romantic Anastasia Island vacation, you'll find quite a few options to make the experience with your partner absolutely unforgettable. Luxury amenities like hot tubs and spa facilities are prominent, but a lot of romantic vacation getaways also make it easy to explore some of the best spots in St. Augustine. #### How can I find the best vacation packages for couples? If you're looking for a romantic vacation getaway, all you have to do is implement the romantic search filter. That will automatically remove any property that isn't suitable for couples. Just put in your travel dates and the Anastasia Island destination, and you'll be met with an array of options for you and your partner to enjoy. #### Can I find cheap romantic vacations for 2 in Anastasia Island? Yes, there are several options for booking cheap romantic vacations that don't break the bank. You'll find prices as low as CA $1,195 and can enjoy savings of up to 21 when you book your hotel and flight together. Budget and luxury options are both available along with everything in between. Sorting your results by price will allow you to view the cheapest options first. #### What do I need to consider when booking a romantic getaway in Anastasia Island? Romantic vacation getaways succeed based on catering to what you and your partner specifically want to do. Think about what your partner enjoys and what you want to do as a couple, then opt for something that is especially geared toward fulfilling your ideal romantic vacation getaway experience. Search filters for amenities and proximity to certain attractions throughout Anastasia Island certainly come in handy here. #### What amenities should I look for in a luxury romantic vacation? If you and your partner are interested in luxury, you won't have to look far for a romantic vacation getaway that fits. In luxury accommodations, you can enjoy amenities like room service and a hot tub. Some accommodations may even have their own spa facilities complete with massage services that will add an extra touch of romance to your excursion to Anastasia Island. #### Can I book a romantic Anastasia Island vacation with a hot tub? Yes, and it's easy when you take advantage of available search filters. All you have to do is implement the hot tub filter from the amenities section into your search. This will automatically remove any stays from your search results that do not have hot tubs in them. #### How can I find romantic vacation getaways that are all-inclusive? An all-inclusive trip allows you to plan out your romantic vacation getaway in advance, letting you get a solid number on cost and a full itinerary before you set out. To start this kind of planning, simply apply the filter for all-inclusive trips in your Anastasia Island search. #### Can I book a romantic trip to Anastasia Island that is fully refundable? Several romantic Anastasia Island vacations come with fully refundable reservations. You can filter for this specifically, but every accommodation will list its policy for cancellation in their policy section, which is visible after clicking on a search result. Always make sure to check their policy to determine the requirements. #### Why should I book a romantic vacation with Expedia? Booking your trip with Expedia makes the entire planning process that much easier, as we're your convenient, all-in-one stop for all your travel needs. You can book your stay and your flight, with special discounts potentially available for booking together. Additionally, you can enjoy more discounts by becoming an Expedia Rewards member and getting points to put toward your next booking. Becoming a member is free, so don't hesitate to take advantage. ## Romantic Hotels in Anastasia Island ![Castillo Real St. Augustine Beach,Tapestry Collection Hilton](https://images.trvl-media.com/lodging/2000000/1190000/1189600/1189517/e32cc7eb_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Castillo Real St. Augustine Beach,Tapestry Collection Hilton 530 A1a Beach Blvd, St. Augustine, FL - 4 min drive from St. Augustine Beach Stay at this 3-star hotel in St. Augustine. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Our guests praise the pool and the restaurant in ... 8.8/10 Excellent! (33 reviews) Very nice remodel and beautiful! We only ate breakfast in the restaurant but I highly recommend eating there. We look forward to getting to stay here again. Reviewed on Oct 10, 2025 [](https://expedia.ca/St-Augustine-Hotels-Castillo-Real.h1189517.Hotel-Information) ![Beautiful First Floor Ocean Gallery Condo 3 bedrooms/ 2 full bathrooms](https://images.trvl-media.com/lodging/19000000/18970000/18967900/18967857/8dd2d2e4_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Beautiful First Floor Ocean Gallery Condo 3 bedrooms/ 2 full bathrooms Saint Augustine - 18 min walk from St. Augustine Beach Book a stay at this beach condo in St. Augustine. Enjoy free WiFi, a fitness center, and a garden. Popular attractions St. Augustine Beach and Butler Beach are ... 9.6/10 Exceptional! (109 reviews) Great vacation! Really clean and well equipped. Owners obviously stay here frequently. We Will be back! Reviewed on Jul 7, 2025 [](https://expedia.ca/St-Augustine-Hotels-Discounted-First-Floor-Ocean-Gallery-Condo-Winter-Months-48-50.h18967857.Hotel-Information) ![1ST STREET II BEACH HOUSE, UPDATED DOG FRIENDLY FENCED IN YARD 1 BLOCK TO BEACH](https://images.trvl-media.com/lodging/20000000/19390000/19383700/19383653/25547d5b_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### 1ST STREET II BEACH HOUSE, UPDATED DOG FRIENDLY FENCED IN YARD 1 BLOCK TO BEACH St. Augustine - 25 min walk from St. Augustine Beach Stay at this vacation home in St. Augustine. Enjoy laundry facilities, patios, and cable/satellite TV service. Popular attractions St. Augustine Beach and St. ... 10/10 Exceptional! (84 reviews) The house was perfect for pets. Fenced in backyard for our dog to run around in. You can see the water from the balcony. Exactly one block from the beach. It is perfectly located on the strip. We would definitely recommend this house to anyone. Reviewed on Oct 11, 2025 [](https://expedia.ca/St-Augustine-Hotels-1ST-STREET-II-BEACH-HOUSE.h19383653.Hotel-Information) [See all 3,397 properties in Anastasia Island](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package®ionId=553248635083907403) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. ## 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 Romantic Vacation Destinations > - 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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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)