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! (132 reviews)

"Very friendly staff, clean, beautiful You are paying mostly for bells and whistles Low water pressure in shower, ice machine on a different floor. There was no breakfast mentioned only a bar and restaurant. Couldn't see but a small spot of ocean so definitely NoT an ocean view You pay for parking ..."

Reviewed on 31 Aug 2026

Beautiful First Floor 3 bedroom Ocean Gallery condo. Winter 28 day discounts.

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! (127 reviews)

"Absolutely love this property! The owners were great with communication and it was very reasonably price."

Reviewed on 17 July 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 3,486 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.