
Places to stay near San Sebastian Winery
Book unique vacation rentals, homes, and more on Airbnb
Top-rated vacation rentals near San Sebastian Winery
Guests agree: these stays are highly rated for location, cleanliness, and more.

The St Augustine Tiny House - park and walk 2 town
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 await

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

Uptown Attic - Your Secret Escape
Located in the desirable Uptown District in Historical Downtown St. Augustine, this charming early 1900’s home is the perfect local experience. Featuring alley access to a private driveway with a designated one car parking spot, this newly renovated apartment is steps from all of the city’s hot spots. Guests can easily walk or bike to all of the famous tourist attractions, fantastic dining, and even the area’s famous beaches. This cozy space is also the perfect escape to just stay in and relax.

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 convenient and 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. *Guests must be quiet as sound carries easily to our other 2 studios.

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.

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.

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.

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

HistoricLuxury•Designer Kitchen&Baths•Walk&Trolley
No Cleaning Fee! 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.

~Romantic Historic 1888 Cottage~Walk to Downtown
Come live in history! This cottage traces its roots back to humble beginnings and it still stands today as one of Lincolnville's original historic treasures. Nestled in the heart of America's oldest city, this endearing circa 1888 cottage offers an intimate, refined escape with a boutique ambiance. This is the ideal retreat for travelers seeking a romantic getaway or guests who wish to be transported to a more graceful time. Discreet in scale but grand in experience.

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.

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, ...
Popular amenities for vacation rentals near San Sebastian Winery
Condo rentals with wifi

The Bohemian Rhapsody! In the middle of it ALL!

Middle of Historic District + Quiet at Night

Newly renovated! Steps to BEACH & POOL!

King Suite With Balcony & View Of Lightner Museum

Historic Building with Bay Views & City Access

Pretty walk to Old Town, Anastasia Island 2 bdrm

Boutique Beachside condo with easy access to beach

Walk to town, short drive to the beach.
Family-friendly house rentals

Historic St. Augustine Cottage - Walk everywhere!

Close to downtown, 3BR,6Beds,Movies, Ping Pong,Fun

Perfect One Bedroom Cottage in Lighthouse Park

Historic St. Augustine 2/2 Duplex & Pool

Calm cozy couples cottage close to Downtown & Bch

Genovar Mansion Master Suite Private Entrance

“La Casita” A Charming Uptown St Augustine Cottage

Cozy, Pet-friendly Private House near downtown
Apartment rentals with air conditioning

Charming 1 Bedroom apt, Historic St Augustine

Downtown Victorian..Charming and Cozy

Charming Old-Florida Apartment

Villa Tizoc

Experience Downtown / 2 Balconies / LUX BATH

*2BR* Luxe Loft Close to Everything | Balcony

Bougainvillea way, steps to town center, romantic.

Dog-friendly, Walk Everywhere apt with FREE BIKES
Other great vacation rentals near San Sebastian Winery

Palo Haus 1918 Cottage in Downtown St. Augustine

Cozy 2BR on Charlotte St. Downtown St. Augustine

New! Hot Tub! Walk to Historic District! Fire Pit!

Historic Home in Downtown St. Augustine

Funshine - Vacation on a 43' Gulfstar Yacht

St. Augustine Studio*Private Entrance & Bath*Bikes

1 Block to Dtown!☆Kitchen☆Free Parking☆Super Clean

Cozy studio 15 min to beaches & historic downtown
Destinations to explore
- Ponte Vedra Beach
- TIAA Bank Field
- Summer Haven st. Augustine FL
- Old A1A Beach
- Daytona Beach Boardwalk and Pier
- Daytona Lagoon
- Vilano Beach
- Boneyard Beach
- Crescent Beach
- Kathryn Abbey Hanna Park
- Lightner Museum
- Fountain of Youth Archaeological Park
- Butler Beach
- Pablo Creek Club
- Eagle Landing Golf Club
- Adventure Landing Jacksonville Beach
- MalaCompra Park
- Matanzas Beach
- Amelia Island State Park
- St. Augustine Alligator Farm Zoological Park
- Worlds Most Famous Beach Daytona Beach
- Ravine Gardens State Park
- Jungle Hut Park
- Old Salt Park
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes