Anastasia Island Romantic Holidays

Book a Romantic Hotel + Flight or Car together to unlock savings

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    Save up to £335 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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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 Resort Hotel
Castillo Real Resort Hotel
3 out of 5
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 Wi-Fi, valet parking (surcharge) and a 24-hour front desk. Our guests praise the pool and the restaurant ...
8/10 Very Good! (1,203 reviews)
"I did not like that parking was valet parking only for $10 fee per day. I parked my own car and gave my key fob to valet person. Also, the hotel needs more than 2 clothing racks for guests to transport clothes from room to car. That was all I saw. Had to carry my own things to car because if that. ..."

Reviewed on 2 Jul 2025

Castillo Real Resort Hotel
Beautiful First Floor Ocean Gallery Condo 3 bedrooms/ 2 full bathrooms
Beautiful First Floor Ocean Gallery Condo 3 bedrooms/ 2 full bathrooms
Saint Augustine, FL
  • 19 min walk from St. Augustine Beach
Stay at this beach condo in St. Augustine. Enjoy free Wi-Fi, a water park and a fitness centre. Popular attractions St. Augustine Beach and Anastasia State Park ...
9.6/10 Exceptional! (108 reviews)
"Just felt that having to empty the water bucket from the portable air conditioner every 6 hrs was a total pain. Also can't understand why you would vent the hot air from it onto the screened in porch, the temp is already hot without the additional heat"

Reviewed on 17 Jun 2025

Beautiful First Floor Ocean Gallery Condo 3 bedrooms/ 2 full bathrooms
1ST STREET II BEACH HOUSE, UPDATED DOG FRIENDLY  FENCED IN YARD 1 BLOCK TO BEACH
1ST STREET II BEACH HOUSE, UPDATED DOG FRIENDLY FENCED IN YARD 1 BLOCK TO BEACH
St. Augustine, FL
  • 25 min walk from St. Augustine Beach
Stay at this holiday home in St. Augustine. Enjoy laundry facilities, patios and cable/satellite TV service. Popular attractions St. Augustine Beach and Anastasia ...
10/10 Exceptional! (84 reviews)
Sibling get together!
"Easy walk to beach and four restaurants. Park your car unload and enjoy. Everything was perfect! A1A Burritos was awesome but a very popular spot so plan to wait in line for a bit:)We woul return:)"

Reviewed on 5 May 2025

1ST STREET II BEACH HOUSE, UPDATED DOG FRIENDLY FENCED IN YARD 1 BLOCK TO BEACH
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.

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* 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.