Places to stay near San Sebastian Winery

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Top-rated holiday rentals near San Sebastian Winery

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Top Guest favourite
A charming view of the Italian restaurant Pizzalley's, featuring a decorative balcony adorned with hanging plants. The building’s colorful facade complements the vibrant street lined with trees and vintage-style street lamps, creating a lively atmosphere in the historic district.
Apartment in St. Augustine
4.97 out of 5 average rating, 797 reviews

Balcony apt on USA’s oldest Street (St. George St)

"The Heart of St. Augustine" Voted #1 Airbnb in St Augustine by Trip 101, # 5 Top 10 Airbnb's in St. Augustine" by Territory Supply and in the "Top 15 Best Airbnb's in Florida" by Road Affair. Live music, scrumptious food, craft drinks, and the hustle and bustle of people walking the historic St. George St, all surround you. Relax and people watch from your balcony. Sightseeing, restaurants, trolley stop and nightlife are steps away. This apt is in the center of it all. NYE is a 3 night min

Top Guest favourite
Home in St. Augustine
4.94 out of 5 average rating, 120 reviews

Lux Coastal Cottage in Historic District

Inviting remodeled cottage boasts luxury finishes on the interior while maintaining the appeal of historic downtown Saint Augustine. Come & enjoy the authentic experience of nestling in one of the few ‘shotgun cottages’ still standing in historic Lincolnville. Offering 2 King bedrooms where you’ll relish luxury linens, memory foam mattresses, ceiling fans, large closets & custom art. Enjoy a spa-like restroom with cascading waterfall tile & pebble laid shower floor offering endless hot water.

Top Guest favourite
A charming two-story cottage is seen behind an ornate wrought-iron gate, framed by vibrant green grass and well-maintained landscaping. Large windows allow natural light to fill the exterior, and a cheerful yellow door adds a welcoming touch.
Cottage in St. Augustine
5 out of 5 average rating, 253 reviews

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

Top Guest favourite
Home in St. Augustine
4.94 out of 5 average rating, 212 reviews

Downtown HistoricLuxury • Designer Kitchen & Baths

Off Street Parking for 2 vehicles 2 Min. walk to St George St 5 Min drive to Anastasia State Park Beach 6 Min drive to Fitness Club/Pool High Speed Starlink Internet Luxury Retreat in Historic Downtown. Indulge in a charming vacation rental featuring a spacious living room, gourmet kitchen, and luxury baths. Immerse yourself in the rich history and vibrant culture, with its charming streets and local attractions. Whether seeking adventure or relaxation, this retreat offers the perfect base.

Guest favourite
Guesthouse in St. Augustine
4.95 out of 5 average rating, 137 reviews

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.

Guest favourite
A stone fountain stands at the center of a lush courtyard, surrounded by vibrant green ferns and tropical plants. A wooden bench is positioned nearby, offering a tranquil space for relaxation amid the serene sounds of cascading water.
Place to stay in St. Augustine
4.91 out of 5 average rating, 984 reviews

Moon Over the Courtyard in the Historic District

You have found your cozy oasis tucked under an ancient Oak tree in a lush Tropical Courtyard in the Historic District of St Augustine. Sit by the fountain, feed the roaming tortoises by day or enjoy the fire and the 1000's of tiny lights on the tree canopy by night. This small space studio exemplifies the appeal of tiny living: compact, clean, and efficient. The Courtyard is a short walk from all of the Historic Districts Shops, Restaurants and Attractions. However we need your phone #

Top Guest favourite
Condo in St. Augustine
4.97 out of 5 average rating, 144 reviews

Middle of Historic District + Quiet at Night

Cordova Gold is located near the infamous Casa Monica hotel, behind the Lightner Museum & Flagler College. Walk to everything historic St. Augustine has to offer but enjoy the peaceful local neighborhood after your activities. Our condo building was built between 1885 - 1893 by Henry Flagler to serve as the servants' quarters for his Ponce de Leon Hotel, now known as Flagler College. We have 1 dedicated parking spot in our lot along with 1 off-street parking space which is very rare.

Top Guest favourite
Apartment in St. Augustine
4.97 out of 5 average rating, 164 reviews

C8 Perfect location in city, balcony, free parking

Relax in this cozy and comfortable upstairs apartment with balcony. Don't worry about the struggle of downtown parking, PARKING IS FREE on site (2 designated spots 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 offer Roku TV. We have a drip coffee maker, coffee, decaf, creamers, and sugar.

Guest favourite
Apartment in St. Augustine
4.93 out of 5 average rating, 306 reviews

Studio Apartment, king bed, Downtown St Augustine

High ceilings greet you at this second floor studio located in Historic Downtown St. Augustine. Originally built in 1910 and completely updated in 2023, this carriage house apartment is just two blocks from St. George St, walking distance to Flagler and all of downtown St Augustine. This studio has a full kitchen, king size bed and private patio. Free off street parking, so you are able to park, walk around and enjoy everything downtown has to offer.

Top Guest favourite
Apartment in St. Augustine
4.97 out of 5 average rating, 177 reviews

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

Top Guest favourite
A contemporary living space features a white daybed adorned with yellow pillows and a gray sofa with matching cushions. Light-colored wooden flooring complements a wooden coffee table at the center. Two sets of double doors lead to a bright outdoor area, enhancing the airy feel.
Apartment in St. Augustine
5 out of 5 average rating, 148 reviews

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, ...

Top Guest favourite
A bright bedroom features a four-poster bed dressed in white linens. Two bedside lamps offer gentle illumination, while large windows allow natural light to fill the space. The light-colored walls and flooring create a serene atmosphere.
Apartment in St. Augustine
4.95 out of 5 average rating, 248 reviews

Lemon Street Studio (Very Walkable + Free Parking)

Located just a few blocks from all that downtown has to offer, the Lemon Street Studio is the perfect way to enjoy your trip to St Augustine. Less than a 10 minute walk to St George Street, the Castillo de San Marcos, the Bayfront, and Flagler College. The one bedroom apartment welcomes you with free off-street parking, a private entrance, and a stylish space to relax after hitting the town.

Popular amenities for holiday rentals near San Sebastian Winery