Anastasia Island Luxury Vacations

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

  • Plan, book, travel with confidence

  • payments icon

    Better together

    Save up to ¥45,448 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Top Luxury Anastasia Island Hotels

Ocean Breeze Inn

Ocean Breeze Inn

2 out of 5
311 A1A Beach Boulevard, St. Augustine, FL
  • 5 min drive from St. Augustine Beach
Ocean Breeze Inn awaits for a deluxe vacation. Popular amenities include 3 beach bars and an outdoor pool.
7.8/10 Good! (1,044 reviews)
"The OBI was perfect location and price for my friend and I who had come to see the Sierra Ferrell concert at the St. Augustine Amphitheater. The room had everything we needed, a comfortable bed, and check in/out was easy. We Ubered to the show for only $10, and walked back after through the adjacent ..."

Reviewed on Sep 14, 2025

Ocean Breeze Inn
Quality Inn & Suites St Augustine Beach Area

Quality Inn & Suites St Augustine Beach Area

2.5 out of 5
901 A1A Beach Blvd, St. Augustine, FL
  • 9 min walk from St. Augustine Beach
Pamper yourself with a luxury stay at Quality Inn & Suites St Augustine Beach Area, where you can enjoy amenities like hydromassage showers, HDTVs, and ...
7/10 Good! (1,013 reviews)
"We love to stay here! Right by the beach amd affordable"

Reviewed on Sep 23, 2025

Quality Inn & Suites St Augustine Beach Area
Castillo Real St. Augustine Beach,Tapestry Collection Hilton

Castillo Real St. Augustine Beach,Tapestry Collection Hilton

3 out of 5
530 A1a Beach Blvd, St. Augustine, FL
  • 4 min drive from St. Augustine Beach
Be treated to luxurious accommodations at Castillo Real St. Augustine Beach,Tapestry Collection Hilton, where you can enjoy amenities like pillowtop beds, premium ...
8.8/10 Excellent! (30 reviews)
"Loved this place- will definitely return there"

Reviewed on Sep 22, 2025

Castillo Real St. Augustine Beach,Tapestry Collection Hilton
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.