Places to stay near San Sebastian Winery

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Top-rated holiday rentals near San Sebastian Winery

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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, 776 reviews

The St Augustine Tiny House -walk2 nites 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.
Flat in St. Augustine
4.97 out of 5 average rating, 773 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 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
4.95 out of 5 average rating, 106 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.

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
4.92 out of 5 average rating, 946 reviews

Moon Over the Courtyard in the Historic District

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

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, 232 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
An inviting exterior view of the home is presented, featuring a spacious front porch adorned with eight rocking chairs. Lush greenery and colorful plants frame the entrance, enhancing the charm of the property. A well-maintained pathway leads to the front steps, inviting guests inside.
Home in St. Augustine
4.98 out of 5 average rating, 163 reviews

Southern Comfort - Downtown|Hot Tub|Heated Pool

The Southern Comfort is a 4BR/3.5BA home located right in the heart of Downtown St. Augustine on the famous King Street. High-end, designer touches will be found in all features of the home with respect to the 110+ year old character preserved in the 2020 renovation. Centrally located with a blend of privacy, convenience and a modern luxury design. Private, sparkling heated pool and hot tub with lounges perfect for lazy days by the water. #1 Vacation Rental in 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, 219 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 sunlit courtyard is surrounded by cheerful yellow two-story buildings, featuring balconies and inviting entryways. Lush greenery and palm trees enhance the outdoor space, complemented by a manicured lawn and decorative plants. A wrought iron fence outlines the property.
Flat in St. Augustine
4.93 out of 5 average rating, 176 reviews

C4 Close to beaches, downtown, history, parking!

Relax in this cozy and comfortable Upstairs 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.

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, 100 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.
Flat in St. Augustine
5 out of 5 average rating, 137 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.
Flat in St. Augustine
4.98 out of 5 average rating, 150 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

Top guest favourite
The living area showcases a dark leather sofa adorned with colorful pillows, paired with a light wooden coffee table. A ceiling fan hangs above, and a large television is mounted on the wall. The space features original pine flooring and a decorative non-functioning fireplace.
Flat in St. Augustine
4.95 out of 5 average rating, 310 reviews

FREE BIKES Dog-friendly apt in the heart of St A

A beautiful, renovated, pet-friendly, first-floor apt in a historic house . A fully-stocked kitchen for cooking, beautiful bathroom, comfy bed. A shaded, shared backyard with picnic tables and charcoal bbq grills. A few minute walk to the Historic District , Francis Field and Flagler College, while still being in a quiet neighborhood. Free use of bicycles. One parking space. Pet fee is $40 per dog per stay (max of 2 dogs). No cats.

Popular amenities for holiday rentals near San Sebastian Winery