Airbnb your place

Places to stay near San Sebastian Winery

Book unique holiday rentals, homes and more on Airbnb

Top-rated holiday rentals near San Sebastian Winery

Guests agree: these stays are highly rated for location, cleanliness and more.

1 of 1 pages1 / 1
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, 845 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.
Flat 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
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 studio features a king-sized bed with a soft green coverlet and a cozy dark sectional sofa. Natural light enters through windows, highlighting the modern kitchen area and dining space in the background. A bathroom door is visible on the right side.
Guest house 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
A bright dining area features a round table with a fresh floral centerpiece, complemented by alternating wooden benches and a chair with a patterned seat. The adjacent kitchen showcases light-colored cabinetry and stainless steel appliances, with a large window allowing natural light to illuminate the space.
Flat in St. Augustine

Cozy & Comfy 2/2 Apt ~ Walk to Historic Downtown

This St. Augustine home is right in the heart of quaint & historic downtown! The cozy upper level apartment with a queen bed in the master bedroom with bath and double and single beds in the second bedroom with bath is perfect for 1-5 guests. A short 8-10 minute walk allows visitors to explore the many downtown historic sites, museums & restaurants. Free parking for one car on our lot. There is free street parking for additional cars (except from Nov 15th-Jan11th Nights of Lights).

4.97 out of 5 average rating, 357 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
Flat 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.
Flat 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
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

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, ...

5.0 out of 5 average rating, 158 reviews
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.
Flat in St. Augustine

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.

4.95 out of 5 average rating, 299 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

Apartment rentals with wifi

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.
Apartment in Lincolnville

Middle of Historic District + Quiet at Night

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

Island Suite l Walk to Downtown!

4.9 out of 5 average rating, 470 reviews
Guest favourite
A light-filled living room features a cozy sectional sofa adorned with decorative cushions. A stylish coffee table sits atop a patterned rug, and a modern TV is positioned on a sleek white media console. Natural elements are introduced through plants and woven wall decor.
Apartment in St. Augustine

The Bohemian Rhapsody! In the middle of it ALL!

4.94 out of 5 average rating, 177 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.
Apartment 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.
Apartment in St. Augustine

The Turtle Sanctuary

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

Walk to town, short drive to the beach.

4.87 out of 5 average rating, 172 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.
Apartment 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
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
Superhost
The kitchen is equipped with modern stainless steel appliances, including a refrigerator and dishwasher. Black cabinetry complements the white countertops. Natural light streams in from a window above the sink, adorned with a small plant, enhancing the functional layout.
Home in St. Augustine

Cozy, Pet-friendly Private House near downtown

4.85 out of 5 average rating, 386 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
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
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
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 private heated pool is surrounded by a spacious patio featuring paver stones and tropical landscaping. A wooden pergola provides shade, complemented by lounge chairs and vibrant orange seating. The cottage's white exterior is visible in the background, framed by swaying palm trees under a clear blue sky.
Home in Vilano Beach

Floridian Bungalow•2 Min Walk to Beach•Heated Pool

4.99 out of 5 average rating, 161 reviews

Apartment rentals with air conditioning

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

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

4.97 out of 5 average rating, 836 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.
Flat in St. Augustine

*2BR* Luxe Loft Close to Everything | Balcony

4.98 out of 5 average rating, 509 reviews
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.
Flat in St. Augustine

Victorian Era-5-10 Min Walk Downtown Attractions

4.9 out of 5 average rating, 547 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.
Flat in St. Augustine

Beach Charm in Downtown St. Augustine.

4.91 out of 5 average rating, 408 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.
Flat in St. Augustine

Updated Victorian apt in heart of downtown +VIEWS!

4.96 out of 5 average rating, 415 reviews
Guest favourite
A cozy bedroom features a wooden sleigh bed dressed with white pillows and a patterned blanket. Soft light emanates from wall sconces, while a stained glass lamp adds colorful accents. A large window is adorned with dark curtains, allowing gentle light to filter through.
Flat in St. Augustine

Pub Life

4.97 out of 5 average rating, 202 reviews
Guest favourite
Flat in St. Augustine

Cozy Garden - Sleeps 4- hottub/outdoor shower!

4.92 out of 5 average rating, 156 reviews
Top guest favourite
Flat 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
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

4.9 out of 5 average rating, 693 reviews
Top guest favourite
The cottage exterior features a welcoming white facade with a covered porch and steps leading to the front door. Lush greenery and a stone wall border the pathway, while trees provide shade, creating a serene atmosphere near the entrance.
Cottage in St. Augustine

1900s Cottage in Heart of Town-walk everywhere!

5.0 out of 5 average rating, 167 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, 201 reviews
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
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
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
Guest favourite
A charming cottage is surrounded by lush greenery and tropical plants. The entrance features a shaded outdoor seating area with two chairs and a table, set under a red umbrella. The light-colored house is topped with a metal roof and has multiple windows, inviting natural light.
Cottage in St. Augustine

Downtown House near Flagler College & St George st

4.89 out of 5 average rating, 243 reviews
Top guest favourite
Guest house in St. Augustine

The Garden Casita in St. Augustine Florida

4.94 out of 5 average rating, 459 reviews