***Check out and take advantage of our gap deals! October and November pricing marked down to fantastic special rates!***

The holidays are the best time of year in St. Augustine!! Enjoy a luxurious stay at Anchors Aweigh and experience the world famous Nights of Lights! Come see the magical sights in the Nation's Oldest City with over 3 million sparkling lights! National Geographic magazine named the display one of the 10 best locations in the world to see holiday lights! Nights of Lights begins November 22, 2026 to January 18, 2027. Anchors Aweigh is decorated and ready for all of our winter guests!

Your Voyage Awaits: Step into a world where the ocean is your backyard. The spacious master bedroom, a serene sanctuary with a king-sized bed, opens to a balcony offering breathtaking ocean views. In the guest room, twin bunk beds and a queen-sized bed promise restful nights after days filled with adventure. TVs equipped with cable are in each bedroom.

A Touch of Elegance: Both bathrooms have been fully remodeled, featuring granite and marble countertops, as well as modern finishes. Downstairs, the newly remodeled kitchen, with its exotic quartzite granite countertops, all white cabinets, and stainless steel appliances, is fully stocked and ready to use.

Seamless Living: The open-concept living area, merging kitchen, dining, and family rooms, is your space for making memories. Comfy seating, a large-screen TV, and views of palm trees and beach dunes create an ambiance of relaxed luxury. The back sliding glass doors open to a tile patio with outdoor seating and the lush grass yard. Only a few steps away from the boardwalk that takes you straight to the beach.

Ready for Anything: Enjoy the convenience of pulling into the first level garage to load and unload during your stay. Stocked with 2 beach cruisers, a charcoal grill, an ocean kayak, and beach chairs, there's also ample space for your sandy beach gear. Grab your family or friends for a game of frisbee, cornhole, or bocce ball! A full-sized washer and dryer mean you’re always ready for the next day.

St. Augustine – A Treasure Trove of Fun: As America’s oldest city, St. Augustine is not just a location; it's a journey through history. From the cobblestone streets to the historic forts, every corner tells a story. Family-friendly activities abound – whether it's exploring ancient ruins, enjoying local cuisine, or simply building sandcastles on the beach.

Neighborhood – This isn’t just St. Augustine. It’s laid-back Anastasia Island and St. Augustine Beach, where every day starts with a salty breeze and ends with a sunset stroll. Enjoy the 2 refreshing pools in Ponce Landing. One pool is heated when seasonally appropriate. Local cafes, taco joints, and surf shops are all nearby, and downtown’s rich history is just 5 miles away. It’s the kind of spot where you can do a lot or do absolutely nothing, and either one feels like the right move.

Our sister property right across the driveway, Portside, faces the pool and can be rented along with Anchors Aweigh to accommodate a total of 15 people. Portside has a vibe of its own. Brighter, vibrant, and a bit more funky. We know you'll love it too. If you have a larger group and want to rent 2 units to travel with family or a group of friends, book Portside and Anchors Aweigh together to give you a 4 bedroom, 4 bath combination with tons of room to spread out and have fun gatherings paired with privacy. Message Kim for more details or to book both properties together.

"Anchors Aweigh" isn't just a place to stay; it's a lifetime of memories. Every new day promises an exciting family adventure. Book now and set sail on an unforgettable voyage of relaxation and exploration in charming St. Augustine! Anchors Aweigh!