Romantic St. Augustine’s streets are lined with beautiful buildings from the 19th century — or earlier. Many of those historic structures are now elegant bed-and-breakfasts with free morning meals, nightly happy hours, and plenty of Old World charm.

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1

Bayfront Marin House Historic Inn

St. Augustine, Florida, United States

Originally built in the 1790s, this stately, two-story home has gone through a number of iterations before becoming a 15-room bed-and-breakfast. Guest rooms are named after local figures or places and individually decorated: some have four-poster wood beds and French armoires, while others go lighter on the antique furniture. Many rooms have lovely views of the bay, and swings on their piece of the wraparound porch. A full homemade Southern breakfast is served for free in a sun-filled room. There are bikes, beach chairs, and umbrellas on loan for day trips, and a daily happy hour in the lobby with homemade hors d’oeuvres and sangria. 

2

Bayfront Westcott House Bed & Breakfast

St. Augustine, Florida, United States

This 1880s bed-and-breakfast is one of a handful of historic properties in St. Augustine's Old City. Interiors are traditionally decorated, with colorful flower arrangements, gorgeous antiques, and period details like crystal doorknobs. The home's long porches overlook the Mantanzas River, and there are views of the St. Augustine Lighthouse. A full gourmet breakfast is part of the room rate and includes an entree, such as eggs Benedict, as well as pastries and fruit. Breakfast can be served in the dining room, on a veranda overlooking the river, or in the inn’s courtyard. In-room breakfasts are also available for an additional hefty fee. There’s a free evening social hour with hors d’oeuvres and drinks, and storytellers recount the city’s history on select nights. Free coffee, tea, bottled water, and soda are also available throughout the day. 

3

The Kenwood Inn

St. Augustine, Florida, United States

The Kenwood Inn is a Queen Anne-style bed-and-breakfast on the edge of the Old City. Its 13 rooms are individually decorated; some have features like whirlpool tubs, fireplaces, and access to the wraparound porch. An excellent homemade breakfast is included with the room rate (the breakfast room has lovely views down Bridge and Marine Streets through its leaded glass windows), as is a daily happy hour. 

4

Carriage Way Inn Bed & Breakfast

St. Augustine, Florida, United States

With its plantation-style wood-slatted facade fronted by a two-tier veranda, this Victorian property is awash in Old Southern charm. The hotel has 13 rooms, each named after a jewel or a precious metal and styled accordingly -- meaning most of the rooms have sparkling touches alongside their antique-style furnishings, exposed brick, and wood floors. Amenities include free Wi-Fi, air-conditioning, and flat-screen TVs, though the most popular feature just might be the free cream sherry. An extensive and excellent breakfast of hot and cold dishes is served in the hotel's elegant dining room, and free drinks and snacks, including wine and homemade cookies, are offered throughout the day.

5

Old City House Inn and Restaurant

St. Augustine, Florida, United States

Standing in the heart of the historic district, this 1873 stone-and-stucco property is lauded in town as a fine-dining spot, and the daily homemade breakfast, included in the room rate, is both varied and fresh. There are a few loaner bikes, a daily happy hour with wine and snacks, and a backyard patio, where guests can have a meal, or simply relax in the shade of the surrounding riot of foliage. The seven rooms are somewhat small and perhaps a bit overstuffed, but all have private entrances, flat-screen TVs, and free Wi-Fi; some have mini-fridges and jetted tubs.