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 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, 242 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 * Fenced yard, 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 St Augustine

Guest favourite
A bright loft space features a cozy sitting area with a stylish rattan chair and a small bistro table. The kitchenette showcases deep blue cabinets and essential appliances, while warm wood flooring complements the ceiling's light tones. A large smart TV is mounted on the wall.
Guest suite in St. Augustine
4.9 out of 5 average rating, 146 reviews

Luxe Lemon Loft in Historic Downtown St Aug

Stay in the heart of charming Historic Downtown St. Augustine! Renovated private loft w/ private entrance. Comfy king bed & posh sitting area. Enjoy coffee/wine at kitchenette bistro table. Freshen up in the separate shower room & toilet room. Brand new AC keeps you cool after a short stroll through historic downtown, or the 10 min to the beach or lighthouse. One parking space available. Self check-in w/ lock box. Note: The downstairs is for rent too. Search AirBNB or ask us about "LemonLower".

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, 787 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
A three-tiered fountain is situated in a lush tropical garden, surrounded by various palm and fern plants. Water flows gently from the top tier and cascades down to the basin below, creating a peaceful ambiance in this serene outdoor space.
Treehouse in St. Augustine
4.93 out of 5 average rating, 581 reviews

courtyardtreehouseinthehistoricdistrict

You have found your cozy oasis tucked in a (Real) Treehouse lodged in Ancient Oak. Set in a lush tropical garden in the historic district. It’s a minimalist’s dream, exemplifying the appeal of tiny living: compact, clean, efficient and 2 1/2 blocks to the historic districts shopping and restaurants. Relax on the Sun Deck, Rain Deck or in the Courtyard’s Tropical Garden The day time peaceful beauty is only eclipsed by the the nighttime display of laser lights projected onto the oaks canopy.

Top Guest favourite
The exterior of the casita features a gabled roof with large glass windows, allowing natural light to enter. Two double doors provide access, surrounded by lush green plants and palms. A covered entryway leads to the main entrance, enhancing the inviting appearance.
Guesthouse in St. Augustine
4.95 out of 5 average rating, 419 reviews

The Garden Casita in St. Augustine Florida

Secluded garden casita tucked away three tenths of a mile from the city gates. Take the private garden pathway to serenity's doorstep, and gain access to WIFI, free parking, and a kitchenette equipped with the basic necessities. The zen garden serves as a wonderful resting space to relax and unwind from your day. The casita features a queen size bed with luxury linens, desk nook and a full bathroom. Come find your peace at the Garden Casita on the grounds of a 100 year old private home.

Top Guest favourite
A sunny courtyard is framed by two yellow apartment buildings, surrounded by well-maintained landscaping. Palm trees and shrubs add greenery, while a pathway leads through the center, enhancing the inviting outdoor space.
Apartment in St. Augustine
4.97 out of 5 average rating, 208 reviews

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.

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, 147 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
An open living space is highlighted by a ceiling fan and includes a cozy sofa, a television on a stand, and a small dining table with a chair. Sunlight fills the adjacent sunroom, featuring large windows and a view of greenery.
Apartment in St. Augustine
4.98 out of 5 average rating, 167 reviews

1 BR Apt with Sunroom-Walk to Historic Hub

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 upper level apt. has an open concept kitchen and living room area which flows into a sunroom that is the perfect place to enjoy your morning coffee. This apt. is a one bedroom (queen) with master bath and is perfect for 2 guests. ** Off street parking for one car; free street parking for additional cars

Guest favourite
A cozy living area features a comfortable sofa paired with a light-colored armchair and a round coffee table. Natural light flows through multiple windows, illuminating the space. The full kitchen is visible, showcasing modern appliances and blue cabinetry, complemented by woven wall decor.
Apartment in St. Augustine
4.95 out of 5 average rating, 221 reviews

Charming 1 Bedroom apt, Historic St Augustine

You will love this newly remodeled one bedroom apartment in Historic St. Augustine. Originally built in 1910 and completely updated in 2023. Just two blocks from St. George St, walking distance to Flagler and all of downtown St Augustine. This apartment offers one bedroom with king size bed, full kitchen and private patio. Free off street parking, so you are able to park, walk around and enjoy everything downtown has to offer.

Guest favourite
The two-story exterior of the home is highlighted by wooden details and an inviting green door. A spacious balcony is visible on the upper level, adorned with seating, while lush palm trees and a landscaped area add a touch of greenery to the property.
Apartment in St. Augustine
4.89 out of 5 average rating, 597 reviews

Experience Downtown / 2 Balconies / LUX BATH

Experience downtown St. Augustine! Just 3 blocks from St. George St, this upper level apartment is walking distance to all downtown and uptown attractions. The space has a large kitchen, private and large bedroom with a huge balcony overlooking the street (great for the parades and festivals). The lux bathroom, on site laundry, and private rear (and front) balconies create a comfortable setting for families or groups.

Top Guest favourite
The bungalow's exterior is framed by a lush garden filled with colorful plants and flowers. There are structured seating areas visible on the front porch, surrounded by decorative elements. The house features traditional architectural details, with a blend of dark and light colors under a clear blue sky.
Place to stay in St. Augustine
4.96 out of 5 average rating, 103 reviews

St. George Historic Bungalow

Come stay at this St. George Historic 1915 Bungalow featured in the well known book, The Houses of St. Augustine. Enjoy being in one of the city’s most pleasant and distinctive neighborhoods. Be reminded of the history that surrounds you as horse carriages stroll by while you enjoy your coffee or wine on the large front porch. The house borders on the lovely Maria Sanchez Lake that inhabits many birds year round.

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, 239 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