Romantic Holidays in Anastasia Island 2026

Plan, book, travel with confidence
Better together
Save up to €900 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

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 business-friendly hotel in St. Augustine. Enjoy free Wi-Fi, breakfast (surcharge) and a fitness centre. Our guests praise the pool and the restaurant ...

8.6/10 Excellent! (145 reviews)

Couples like: bar, Hot tub

Travellers say...

"been there 17 times - can walk to the beach and breakfast is the best!"

Reviewed on 24 Sept 2026

Beautiful First Floor 2 bedroom plus 1 lanai bedroom Ocean Gallery condo.

Saint Augustine FL

18 min walk from St. Augustine Beach

Stay at this beach condo in St. Augustine. Enjoy free Wi-Fi, a fitness centre and a garden. Popular attractions St. Augustine Beach and Anastasia State Park ...

9.6/10 Exceptional! (130 reviews)

"I actually think that this was the cleanest vrbo place that I have rented. I rent from vrbo and other places probably 6 or more times a years. This was the cleanest, easiest place to rent. Will definitely keep it in mind for next time."

Reviewed on 10 Sept 2026

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 ...

See all 3,467 properties in Anastasia Island

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.