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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 Lincolnville

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!!

4.8 out of 5 average rating, 846 reviews
Top Guest favourite
The property's exterior is illuminated by soft lighting, highlighting the unique architecture. A decorative fountain is situated in the foreground, surrounded by manicured grass. The building features multiple windows with shutters, and an American flag is displayed near the entrance.
Apartment in St. Augustine

La Posada:Downtown Historic District. Pet Friendly

Originally built in 1887 as an Inn called La Posada, then renovated into an Airbnb in 2021, you'll be staying in this 3 bedroom, 1 bath apt. Located within walking distance to the Fort, Distillery, pubs, museums, Flagler College, churches, bayfront, bike/scooter rentals, and trolley stop. Enjoy cooking in a full kitchen. Private parking for guests only. Easy access in and out from US1 avoiding the downtown traffic. Only steps away from the famous Nights of Lights starting Nov 21- Jan 16,2027

4.9 out of 5 average rating, 210 reviews
Top Guest favourite
The living area features soft turquoise walls and light hardwood flooring. A spacious white sofa is complemented by green accent pillows. A wall-mounted television and decorative surfboards add character to the space. Natural light fills the room through the window, creating a bright atmosphere.
Bungalow in Lincolnville

The Hideaway ~ half mile from downtown

Welcome to "The Hideaway." Enjoy this 2bd/1ba coastal inspired bungalow, stocked and furnished with your comfort and convenience in mind. Enter through a screened porch, and unwind as you step into the main living area - spacious enough for up to six guests, yet exceedingly cozy for a romantic stay for two. Located in Historic Lincolnville - A half mile walk from downtown St. Augustine, and a 10 minute scenic drive to St. Augustine or Vilano Beach. Truly a perfect location and hidden gem.

4.9 out of 5 average rating, 693 reviews
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

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

4.97 out of 5 average rating, 836 reviews
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 Lincolnville

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

5.0 out of 5 average rating, 278 reviews
Guest favourite
A spacious king-sized bed is dressed in a soft comforter, accented by decorative pillows. Natural light streams in through two windows, revealing a glimpse of the greenery outside. Nightstands with lamps flank the bed, and an air conditioning unit is mounted on the wall.
Guesthouse in St. Augustine

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.

4.95 out of 5 average rating, 175 reviews
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

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.

4.98 out of 5 average rating, 319 reviews
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

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.

4.96 out of 5 average rating, 139 reviews
Guest favourite
Apartment in St. Augustine

Carriage Hse in the trees, Historic St. Augustine

You have found your cozy oasis tucked under tall shade trees in a private, lush tropical courtyard in the historic district. This relaxing space is walking distance to everything. It's adorned with 2 covered porches, the Courtyard porch and breakfast porch. Enjoy and relax in the courtyard lit by hundreds of tiny laser lights at night. You will likely see our tortoises roaming the completely fenced property. In warm weather enjoy the shared pool. *Guests must be quiet ish after 9:30

4.9 out of 5 average rating, 235 reviews
Top Guest favourite
Home in St. Augustine

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.

4.94 out of 5 average rating, 233 reviews
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

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.

4.97 out of 5 average rating, 234 reviews
Top Guest favourite
The living room features a light-colored sofa adorned with blue pillows, accompanied by two armchairs. A round mirror hangs on the wall, and natural light floods the space through multiple windows. A decorative plant stands near the entrance, and a minimalist coffee table is centered in the room.
Home in St. Augustine

Charming Home in historic downtown, walk to it all

Our home, Casita Uva de Playa, is the perfect centrally-located home in the Historic Region of Downtown St Augustine. You can walk less than 1/2 mile into the city for a perfect breakfast biscuit, taste amazing cuban food, take in all the history, or enjoy a martini. You can also take a short 10 minute car ride to the beach. Or just relax in our quiet cottage. Your comfort and relaxation while on vacation is our priority. Come stay with us!

4.99 out of 5 average rating, 118 reviews

Popular amenities for holiday rentals near San Sebastian Winery

KitchenWifiPoolFree parking on premisesAir conditioning

Other top sights near San Sebastian Winery

Castillo de San Marcos National Monument

1,143 locals recommend

Lightner Museum

358 locals recommend

Flagler College

279 locals recommend

Ripleys Believe It Or Not Museum

307 locals recommend

San Sebastian Winery

303 locals recommend

St. Augustine Distillery

276 locals recommend

Condo rentals with Wi-Fi

Top Guest favourite
A brightly lit living area features a comfortable brown sofa and two accent chairs with blue cushions. A coffee table is positioned centrally, complementing the light rug beneath. The dining area is visible, showcasing a dark table set for six, with wall art enhancing the space.
Condo in Lincolnville

Middle of Historic District + Quiet at Night

4.98 out of 5 average rating, 164 reviews
Guest favourite
Condo in St. Augustine

Marina View|Camachee Harbor Waterfront Escape

4.89 out of 5 average rating, 168 reviews
Guest favourite
A modern living room features a comfortable gray sofa, a hammock chair, and a flat-screen TV mounted on a wooden media console. Natural light enters through sliding glass doors adorned with patterned curtains, while a neutral area rug covers the floor.
Condo in St. Augustine

Island Suite l Walk to Downtown!

4.9 out of 5 average rating, 470 reviews
Top Guest favourite
A spacious living area features wood-paneled walls and large glass doors, offering views of the ocean. A chandelier hangs from the ceiling. The seating area includes a comfortable couch and a dark coffee table, while a television with vibrant display adds a touch of modernity.
Condo in St. Augustine

Treehouse Artist Haven Direct Oceanfront 2br

4.92 out of 5 average rating, 118 reviews
Guest favourite
A spacious living area features a light-colored sectional sofa adorned with decorative pillows. A wooden coffee table is placed centrally, accompanied by a woven basket and a lamp. A wall clock and a fish wall art add subtle decor, while natural light brightens the room.
Condo in St. Augustine

The Turtle Sanctuary

4.91 out of 5 average rating, 110 reviews
Guest favourite
Condo in St. Augustine

Walk to town, short drive to the beach.

4.87 out of 5 average rating, 172 reviews
Top Guest favourite
A balcony table is set for two, featuring white plates and cups, with expansive ocean views. Lush greenery and sandy beach can be seen in the distance under a clear blue sky, creating a serene and inviting outdoor space.
Condo in St. Augustine Beach

Ocean Front Gem: Top Floor Corner Unit

4.98 out of 5 average rating, 262 reviews
Top Guest favourite
The living area features comfortable seating, including a soft blue sofa and an armchair, arranged around a white coffee table. Light-colored décor and subtle greenery create a relaxed ambiance. The space is illuminated by a contemporary chandelier, with a view of the kitchen and dining area in the background.
Condo in St. Augustine Beach

Newly renovated! Steps to BEACH & POOL!

4.96 out of 5 average rating, 200 reviews

Family-friendly house rentals

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 Lincolnville

Southern Comfort - Downtown|Hot Tub|Heated Pool

4.97 out of 5 average rating, 192 reviews
Top Guest favourite
Home in St. Augustine

HtdPool w/Arcade, Fire, GolfCart Access, 1.2 mi DT

4.99 out of 5 average rating, 146 reviews
Top Guest favourite
A charming exterior view of a historic house is presented, featuring light green siding and a welcoming front porch. A white picket fence borders the property, and soft lighting illuminates the entrance, surrounded by lush greenery and colorful flowers.
Home in St. Augustine

Leonardi Downtown Craftsman

4.97 out of 5 average rating, 132 reviews
Guest favourite
A spacious hot tub is centrally positioned in a private outdoor area, surrounded by a wooden privacy fence. Red Adirondack-style chairs are arranged nearby, providing a relaxed seating area. Lush greenery and palm trees enhance the serene atmosphere of the garden space.
Home in St. Augustine

Stay in A Castle In St. Augustine, Hot Tub, Firepl

4.93 out of 5 average rating, 131 reviews
Top Guest favourite
Home in St. Augustine

1 Mile to Downtown • 3BR/2BA/7 Beds

4.97 out of 5 average rating, 193 reviews
Top Guest favourite
A comfortable living area features a large sectional sofa adorned with yellow and grey cushions. A flat-screen television hangs above a decorative fireplace. A coffee table with a small plant is centered on a textured area rug, and natural light filters through the nearby windows.
Home in St. Augustine

SaraCasa - First Floor House 2Br/1.5Bath

4.9 out of 5 average rating, 334 reviews
Top Guest favourite
A spacious bedroom is highlighted by a modern black canopy bed with crisp white bedding. A vibrant flamingo artwork adorns the wall, complemented by an arrangement of framed prints. A flat-screen TV is mounted above a stylish dresser, adding functionality to the inviting space.
Home in St. Augustine

Designer Cottage•Gourmet Kitchen•Lux Baths•FirePit

4.96 out of 5 average rating, 102 reviews
Guest favourite
The exterior of a modern two-story home is displayed, featuring a mix of light and dark gray materials. A welcoming entrance is accessed by a set of stairs, with landscaped areas visible on both sides, including palm trees and shrubs.
Home in Lincolnville

192 Riberia Downtown Luxury Home

4.94 out of 5 average rating, 113 reviews

Apartment rentals with air conditioning

Guest favourite
A cozy bedroom is highlighted by a double bed adorned with floral bedding and decorative cushions. Soft, warm light is emitted from two bedside lamps on wooden nightstands. Artwork and photographs decorate the walls, and delicate curtains frame the window, allowing natural light to fill the space.
Apartment in St. Augustine

Victorian Era-5-10 Min Walk Downtown Attractions

4.9 out of 5 average rating, 547 reviews
Top Guest favourite
A spacious bedroom features a large bed with white bedding. Natural light enters through multiple windows, complemented by white shutters. A comfortable armchair is situated near the window, enhancing the cozy atmosphere of the room.
Apartment in St. Augustine

Updated Victorian apt in heart of downtown +VIEWS!

4.96 out of 5 average rating, 415 reviews
Guest favourite
A serene sleeping area features a spacious bed covered with a patterned blanket showcasing sea life themes. Two soft pillows rest against the headboard. A ceiling fan provides gentle airflow, while artwork inspired by the beach decorates the walls.
Apartment in St. Augustine

Beach Charm in Downtown St. Augustine.

4.91 out of 5 average rating, 408 reviews
Guest favourite
Apartment in St. Augustine

Cozy Garden - Sleeps 4- hottub/outdoor shower!

4.92 out of 5 average rating, 156 reviews
Guest favourite
The exterior of a two-story building showcases a contemporary design with a vibrant turquoise front door and matching chairs on the balcony. White wooden siding contrasts with dark railings, while lush greenery and landscaping enhance the entrance.
Apartment in St. Augustine

*2BR* Luxe Loft Close to Everything | Balcony

4.98 out of 5 average rating, 509 reviews
Guest favourite
A bright living space features a comfortable dark blue sofa adorned with decorative pillows. A round dining table is accompanied by white chairs, while a sleek cabinet provides storage. Two patterned poufs sit on a striped rug, and light enters through windows adorned with soft shades.
Apartment in St. Augustine

Top Floor Loft - Park and Walk everywhere!

4.96 out of 5 average rating, 169 reviews
Guest favourite
The living area features a comfortable sofa, accompanied by a wooden side table. Artwork adorns the walls, and natural light filters through the windows. A decorative door leads to the porch area, enhancing the room's inviting layout.
Apartment in Lincolnville

Bougainvillea way, steps to town center, romantic.

4.92 out of 5 average rating, 454 reviews
Top Guest favourite
Apartment in St. Augustine

Apt C - Historic St. Augustine. Walk Everywhere!

4.99 out of 5 average rating, 182 reviews

Other great holiday rentals near San Sebastian Winery

Top Guest favourite
Cottage in Lincolnville

~Romantic Historic 1888 Cottage~Walk to Downtown

5.0 out of 5 average rating, 195 reviews
Top Guest favourite
The sitting room features a blend of warm green and golden hues. A brown leather sofa is adorned with colorful pillows, complemented by a green accent chair. Sunlight filters through the white window blinds, illuminating a vibrant area rug and a piece of art depicting a pelican.
Home in Lincolnville

La Rêverie | Downtown Boutique, Historical Chic

5.0 out of 5 average rating, 147 reviews
Top Guest favourite
A living area features a modern, light-toned sofa paired with a round coffee table. Natural light filters through large windows adorned with red curtains. The open floor plan leads to a dining area, highlighting a connection between spaces with exposed wooden beams.
Home in Lincolnville

Historic Lincolnville Retreat!

4.98 out of 5 average rating, 130 reviews
Top Guest favourite
A two-story blue home is framed by lush green trees. The exterior features large windows and a welcoming front porch supported by white columns. Well-kept landscaping includes a stone pathway leading to the entrance and decorative figures flanking the steps.
Holiday home in St. Augustine

Historical Beauty in the Heart of St. Augustine

4.98 out of 5 average rating, 202 reviews
Top Guest favourite
Guest suite in St. Augustine

Cozy 2BR on Charlotte St. Downtown St. Augustine

4.97 out of 5 average rating, 342 reviews
Top Guest favourite
Tiny home in St. Augustine

City Limit Casita/ New Tiny Home

4.93 out of 5 average rating, 131 reviews
Guest favourite
A charming coastal house is depicted with a traditional exterior, featuring dark shingles and a welcoming porch. A staircase leads to the entrance. The background is graced with a colorful sunset, casting soft light over the surrounding greenery and homes.
Home in Vilano Beach

Oceanfront Rustic Cottage by the Sea

4.93 out of 5 average rating, 120 reviews
Top Guest favourite
Guesthouse in St. Augustine

The Garden Casita in St. Augustine Florida

4.94 out of 5 average rating, 460 reviews