Places to stay near San Sebastian Winery

The St Augustine Tiny House - park/walk to town!

The original TINY HOUSE in the heart of St Augustine! Discover downtown’s most unique stay, steps from downtown attractions. Easily walk to shops and dining, with 3 onsite parking spots. Relax in a private fenced yard. This is a true Tiny House (400 sq ft) features 1 bedroom, 1 bath, cozy living space, and a kitchen. Enjoy Cable TV, WiFi, and a quaint patio with table for outdoor moments. Near Ice Plant Restaurant & St Aug Fish Camp. Pet-friendly with fee. Enjoy your time away! Hammocks ready!!

Walk Historic Downtown! “Blue Heaven”

Stunningly renovated cottage combines modern amenities with vintage charm... * 2 master suites with queen beds * Quiet neighborhood walking distance to explore The Nation's Oldest City * Clawfoot tubs inside and out (along with showers, of course!) * Big screened-in porch with hanging daybed * Off-street paved parking * Fully fenced backyard, Weber grill, gas fire pit * Fast Wi-Fi and Smart TV * 2 blocks to Fish Camp, Ice Plant, LaNuvelle, trolley stop * 10 minute walk to central downtown

Historic Downtown Studio

Experience the charm and elegance of historic St. Augustine, Fl in our quaint carriage house. Located with in walking distance of many iconic landmarks, such as Flagler College, and the San Sebastián winery. Immerse yourself in the city culture, unique shops and dining scene. Whether you're seeking a romantic getaway or a cozy solo retreat, our carriage house offers a blend of comfort and convenience. Book your stay with us and experience the charm of this historic destination like a local.

Funshine - Vacation on a 43' Gulfstar Yacht

A unique, memorable place, anything but ordinary. Try living the boating lifestyle on a classic and quaint vintage 43 foot Gulf Star yacht. Only 1.2 miles to the historical St. Augustine Bayfront and less than 10 miles to many of our gorgeous beaches. This 2-bedroom 1.5 bath beauty allows you to experience a life on a live-a-board. You will vacation within a reasonable walking distance to many of the attractions in St Augustine, a winery, distillery, several museums, many restaurants.

Downtown • Parking for 2 + Wraparound Porch

Historic Whitney House • Newly renovated 1,700 sq ft designer home Private driveway parking for 2 • Steps to trolley & St. George Street Gourmet kitchen, 2 en-suite bedrooms, 3 luxury baths, Starlink WiFi, wrap-around porch + sunny deck. Fitness club & pool passes included. Modern luxury in the heart of historic downtown St. Augustine. Perfect for couples or small groups seeking modern luxury, easy parking, and a walkable base right in the heart of historic downtown St. Augustine.

C5 Perfect location in city center, patio, beaches

Relax in this cozy and comfortable downstairs apartment with patio. Don't worry about the struggle of downtown parking, PARKING IS FREE on site (1 designated spot for your apartment). So many nearby attractions just steps (or a trolley ride) from the door including shopping on St. George St, restaurants and sandy beaches where you can rent paddle boards, kayaks, small sailboats and more. We have a drip coffee maker, coffee, decaf, creamers, and sugar. We offer Roku TV.

~Romantic Historic 1888 Cottage~Walk to Downtown

Come live in history! This cottage traces its roots back to humble beginnings and it still stands today as one of Lincolnville's original historic treasures. Nestled in the heart of America's oldest city, this endearing circa 1888 cottage offers an intimate, refined escape with a boutique ambiance. This is the ideal retreat for travelers seeking a romantic getaway or guests who wish to be transported to a more graceful time. Modest in scale but grand in experience.

The Shire on 1 acre marshfront with dock and Spa

One of a kind 1930s historic home, newly renovated and transformed into a beautiful secluded getaway. new luxury finishes, while holding its traditional charm. No Events allowed. Rooftop deck, sunrise views of the Atlantic ocean, Downtown, and sunsets over the river. The new dock with covered roof hosts a national geographic like eco system. It’s short walk to the beach and 3 miles to downtown St George street. Follow along @carcabaroad for weekly content of the home.

Cute & Compact 1BR-Walk to town

This St. Augustine apt. is an 5-7 minute walk to St. Augustine's downtown hub and a 15 min. drive to the beach. This centrally located lower level apt. has an open concept kitchen and living room area. There is a small porch that allows guests to sit outside to enjoy their morning coffee. This apt. is a one BR (queen) with master bath and is perfect for 2 guests. ** One parking space provided on site and Free street parking for additional cars

DOWNTOWN COTTAGECORE, 7 min walk to historic ctr.

The cottage/apt is in downtown St Augustine. You are 3 blocks or about a 7 min. walk away from the historic center (St George Street, Bayfront, the fort,..) It takes +- 10 min. to drive to Vilano Beach or St. Aug. Beach. The interior of the cottage, part of the house that was built by Henry Flagler in 1896, has been completely renovated into a contemporary charming living space. The kitchen corner has fridge, microwave, small cooktop, ...

Designer Cottage•Gourmet Kitchen•Lux Baths•FirePit

4 min Drive to Historic Downtown 15min Drive to the Beach Looking to get away from the hustle and bustle of the city? This designer cottage is nestled in a lush natural setting, which is the perfect place to recharge. Downtown and the scenic beaches in Anastasia State Park Beach is just a short drive away. With spacious living and modern amenities, the cottage offers maximum comfort and convenience. Learn more below!

Historic Lincolnville Retreat!

Step back in time to the enchanting 1920s in our beautifully preserved historic home, nestled in the heart of Lincolnville. This charming residence combines the elegance of a bygone era with modern comforts. Located in a tranquil area just steps away from the iconic Old Town Trolley tour stop, you’ll have easy access to the Lincolnville Historical Museum and other local attractions in walking distance.