Anastasia Island Romantic Holidays
Book a Romantic Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to £750 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPackages with flights are ATOL protected
How to find a romantic Anastasia Island holiday
How can I find the best Anastasia Island vacation packages for couples?
Use our easy-to-use holiday search tools to plan your most-romantic getaway to Anastasia Island. Choose a hotel suite with an on-trend bathtub with a big view. Choose a stylish hire car with the top down to woo your heart. Choose candlelit cocktails on the shoreline, a horse ride by moonlight or a dolled-up night at the casino.
Can I book cheap Anastasia Island romantic holidays for two?
Get wallet-friendly away-from-it-all romantic accommodation at Expedia, so you have more kitty to spend on romantic activities. We have cheap romantic holidays to Anastasia Island that start from . Prices and availability are subject to change. Additional terms may apply.
What should I think about when booking a Anastasia Island romantic getaway?
The most romantic holidays are about building memories, about dancing and dining and keeping the spark alive. These are moments to level up the luxury – use the star filter to find the best of the best, maybe even tick the business-class flights filter to make the journey part of the adventure.
What should I look for in a luxury romantic holiday to Anastasia Island?
Spoil yourselves with a few luxuries on your romantic trip away. You can use our filters to add that extra touch of romance to your holiday: glamorous spas, divine private dining, exquisite room service.
Can I book a romantic hot-tub holiday in Anastasia Island?
What’s more romantic than a hot tub under the stars, together? Add a glass of fizz, a gorgeous view and Cupid’s arrow and you’re good. To find accommodation with bubbles, use our dedicated hot-tub filter.
How can I find romantic holidays for couples in Anastasia Island that are all inclusive?
Enjoying an all-inclusive holiday means you can really indulge your appetites together – with the promise of no awkward arguments about splitting the bill. Simply use our all-inclusive filter to see what romantic options are available.
Can I book a romantic trip to Anastasia Island with free cancellation and/or flexible dates?
Even the best laid plans fall through sometimes. Make sure you’re not caught out – using our filters to find free cancellation accommodation. Just make sure you check the all-important small print.
Why should I book my Anastasia Island romantic holiday with Expedia?
At Expedia, we know the not-so-secret ingredients to the perfect romantic holiday. Our handy filters help you search a huge range of options and book a holiday that gets your hearts racing.
Top Romantic Anastasia Island Hotels
Castillo Real St. Augustine Beach,Tapestry Collection Hilton
- 4 min drive from St. Augustine Beach
Beautiful First Floor 3 bedroom Ocean Gallery condo. Winter 28 day discounts.
- 18 min walk from St. Augustine Beach
"Absolutely love this property! The owners were great with communication and it was very reasonably price."
Reviewed on 17 Jul 2026
1ST STREET II BEACH HOUSE, UPDATED DOG FRIENDLY FENCED IN YARD 1 BLOCK TO BEACH
- 25 min walk from St. Augustine Beach
"My best friend flew from California to Savannah and together, we drove to St. Augustine for a week to stick our toes in the sand. Prior to booking the property, we knew it would provide more space and bedrooms than what we needed, but we couldn’t resist the house after reviewing several different ..."
Reviewed on 12 Aug 2026
Things to do
St.Augustine: Torture Museum, Ghost Hunt, & Tiny Art Tickets
St. Augustine Pirate and Treasure Museum Tickets
St. Augustine: St. Johns River Airboat Safari with a Guide
Top Romantic Holiday Destinations
- Romantic Holidays in Australia
- Romantic Holidays in Barcelona
- Romantic Holidays in Cornwall
- Romantic Holidays in Cyprus
- Romantic Holidays in France
- Romantic Holidays in Greece
- Romantic Holidays in Ibiza
- Romantic Holidays in Italy
- Romantic Holidays in Morocco
- Romantic Holidays in Paris
- Romantic Holidays in Portugal
- Romantic Holidays in Rome
- Romantic Holidays in Santorini
- Romantic Holidays in Scotland
- Romantic Holidays in Thailand
- Romantic Holidays in the Maldives
- Romantic Holidays in the United Kingdom
- Romantic Holidays in the USA
- Romantic Holidays in Turkey
- Romantic Holidays in Venice
* 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.
