The Best Boutique Hotels in St Augustine, Florida

At the St George Inn, wake up every morning to views of the Castillo de San Marcos and the Old City Gate. Sitting at the entrance of the historic district, this intimate hotel invites you to spend hours in its courtyard sampling glass after glass of wine from the on-site wine bar, Bin 39. Don’t worry about calling a cab when your cheeks get a little rosy; the St George Inn is on the pedestrian-only St George Street, allowing you to safely stumble the half-mile down to Pizzalley’s for a different kind of red or white sauce.

Mark Twain, Sinclair Lewis and Abraham Lincoln have all laid their heads down in the centuries-old building that now houses the Collector Luxury Inn, just south of the historic district. You can learn plenty more about the rich history of this site on a private tour of the property, though the best local lore is traded in the Well Bar over strong pours of Legends of the Fall cocktails. Meanwhile, the romantic art, architecture and ambience adorning the inn and gardens make it an adults-only oasis.

No, you haven’t had too many house-made sangrias during Bayfront Marin House’s happy hour – you really did see a pirate ship cruising across Matanzas Bay. It’s one of the many vessels you’ll catch in your spyglass when relaxing on your private deck. Walk a few paces north, and the hearties of the Black Raven will invite ye aboard for a night full of sea shanties and rum punch. But, don’t worry – you’ll make it back to Bayfront Marin House in time for its famous french toast in the morning.

Only the Bridge of Lions stands between your waterfront suite at the Edgewater Inn and the historic district. You won’t mind the short walk or the riverside tranquility as you lounge in the outdoor pool. Give the east side of the city a fair shake, exploring sights such as the St Augustine Alligator Farm Zoological Park and the St Augustine Lighthouse and Maritime Museum. The cash-only O’Steen’s Restaurant is one of the most popular places in town to grab fantastic fried shrimp.

When staying at the Agustin Inn, you might start to feel a little spoiled, with two-course gourmet breakfasts, weekend champagne socials and the whirlpool tub in your room. Just a few feet from the best boutiques on St George Street, it’s only natural that you’d want to stroll the strip bouncing in and out of the clothing, jewelry and chocolate shops. Feeling the need to ground yourself? End the night at the White Lion around the corner from your room and sip pints of cheap beer on the patio with the Castillo de San Marcos as your drinking buddy.

St Augustine is so much more than its storied past, and the Flagler Inn is one of the best bases for uncommon exploration. The Vilano Beach Nature Boardwalk and Fort Mose Historic State Park offer serene walks along the Tolomato River. The Royal St Augustine Golf and Country Club and the St Augustine Aquarium are a short drive away. Whenever you’re done hanging around the hotel’s pool or fitness center, you can rent a free bicycle or hop on a trolley or train tour that’ll take you into the center of the historic district.

The grand yet relaxed approachability of the Casa Monica Resort and Spa will wow you. Royal massages and body treatments at the Poseidon Spa will pamper you with luxury, while the effortlessly smooth bartenders in the Cobalt Lounge will mix a masterful cocktail while making you feel like you’re a regular at your local watering hole. With ornate decor, fine art galleries, collegiate neighbors and a Starbucks on-site, you’ll love how Casa Monica brilliantly weaves casual comfort together with unparalleled opulence.

Ponce de Leon’s Fountain of Youth is within walking distance of the Ponce St Augustine Hotel. However, there are several other spas in the area if you desire a little revitalization, too. A good night’s rest in the Ponce’s king suite and a few hours in the outdoor hot tub could probably do the trick just as well.