Anastasia Island Romantic Holidays 2026

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Top Romantic Anastasia Island Hotels

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! (147 reviews)

"This is our second home. My kids are growing up here. Kid friendly pool . Staff is amazing. Foor is excellent."

Reviewed on 6 Oct 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 3,466 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.