Places to stay near San Sebastian Winery

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Top-rated holiday rentals near San Sebastian Winery

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Guest favourite
The exterior of the turquoise tiny house is presented, featuring a welcoming front porch with wooden railings. Lush greenery and palm trees surround the home, creating a serene atmosphere. The entrance is highlighted by a small set of steps leading to the porch.
Tiny home in St. Augustine
4.8 out of 5 average rating, 788 reviews

The St Augustine Tiny House - nights of lights!

Charming 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. Unforgettable charm awaits! Hammocks ready

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, 784 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, 578 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, 417 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 spacious waterfront deck offers lounge seating with blue cushions, set against a vibrant sunset sky filled with pink and orange hues. A hammock is positioned nearby, with palm trees framing the stunning view of the water and docks in the background.
Home in St. Augustine
5 out of 5 average rating, 139 reviews

Waterfront - Lion’s Bridge & Old Town View

Walk across the Bridge of Lions to downtown St. Augustine with amazing restaurants and attractions. Half a mile to historic downtown! Less than 1 mile to the Castillo de San Marcos fort. Anastasia State Park Beach, the world famous Alligator Farm and Zipline, and the lighthouse are less than two miles away. Several restaurants and bars only a few blocks away. Whether going to the old fort, lighthouse or Flagler College, our home provides a great base for exploring an amazing part of Florida!

Top Guest favourite
A classic 43-foot Gulf Star yacht is moored in calm waters, exhibiting a spacious deck with a covered seating area. The hull is painted in a crisp white, reflecting sunlight, while nearby masts and boats frame the picturesque marina scene.
Boat in St. Augustine
4.96 out of 5 average rating, 114 reviews

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.

Top Guest favourite
The exterior of a two-story cottage showcases wooden shingle siding and a welcoming front porch. Lush greenery and colorful plants surround the house, with potted flowers placed in the foreground. Sunlight highlights the charming architectural details against a clear blue sky.
Cottage in St. Augustine
4.98 out of 5 average rating, 236 reviews

Charming 2/2 Cottage ~ Walk to Historic Downtown

This St. Augustine home is right in the heart of quaint & historic downtown! The lovely two level cottage has an upstairs full bath and two private bedrooms each with a queen bed. Downstairs is a second full bath, as well as a living room and full kitchen. The space is perfect for 1-4 guests. A short 8-10 minute walk allows visitors to explore the many downtown historic sites, museums & restaurants. One parking spot is available on our lot. Free street parking for additional cars.

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 and LaNuvelle * 10 minute walk to central downtown St Augustine

Top Guest favourite
The exterior of the house features a wrap-around porch with white railings, complemented by shaded areas and lush landscaping. A brick pathway leads up to the entrance, framed by palm trees and greenery, showcasing a welcoming facade against a clear blue sky.
Home in St. Augustine
4.99 out of 5 average rating, 228 reviews

Downtown • Historic Luxury • DesignerKitchen&Baths

Off Street Parking 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 3-BR Retreat in Historic Downtown. Indulge in a charming vacation rental featuring a spacious living room, gourmet kitchen, and luxury bath. 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.

Top Guest favourite
A serene outdoor space is surrounded by lush green palm trees and various potted plants. Soft gravel covers the ground, with pathways leading to a green door, enhancing the natural ambiance of the area.
Home in St. Augustine
4.96 out of 5 average rating, 108 reviews

Luxe Lemon Lower in Historic Downtown St Aug.

Stay in the heart of Historic Downtown St Augustine in this 100yr old 2BR/1B completely renovated in 2023! Only a 7 min walk to Downtown a 12 min drive to the beach, you'll love this charming home! Guests should be adults or older children. 1 parking space available. Note: The loft atop this unit is also rentable, w/ connected or disconnected private entrance, & sleeps 2. Ask us or search "AirBNB Lemon LOFT" or "AirBNB Lemon WHOLE" to rent loft or the whole house.

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
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, 102 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.

Popular amenities for holiday rentals near San Sebastian Winery