
Places to stay near San Sebastian Winery
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Top-rated holiday rentals near San Sebastian Winery
Guests agree: these stays are highly rated for location, cleanliness and more.

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

Lux Coastal Cottage in Historic District
Inviting remodeled cottage boasts luxury finishes on the interior while maintaining the appeal of historic downtown Saint Augustine. Come & enjoy the authentic experience of nestling in one of the few ‘shotgun cottages’ still standing in historic Lincolnville. Offering 2 King bedrooms where you’ll relish luxury linens, memory foam mattresses, ceiling fans, large closets & custom art. Enjoy a spa-like restroom with cascading waterfall tile & pebble laid shower floor offering endless hot water.

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

Downtown HistoricLuxury • Designer Kitchen & Baths
Off Street Parking for 2 vehicles 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 Retreat in Historic Downtown. Indulge in a charming vacation rental featuring a spacious living room, gourmet kitchen, and luxury baths. 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.

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.

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

Middle of Historic District + Quiet at Night
Cordova Gold is located near the infamous Casa Monica hotel, behind the Lightner Museum & Flagler College. Walk to everything historic St. Augustine has to offer but enjoy the peaceful local neighborhood after your activities. Our condo building was built between 1885 - 1893 by Henry Flagler to serve as the servants' quarters for his Ponce de Leon Hotel, now known as Flagler College. We have 1 dedicated parking spot in our lot along with 1 off-street parking space which is very rare.

C8 Perfect location in city, balcony, free parking
Relax in this cozy and comfortable upstairs apartment with balcony. Don't worry about the struggle of downtown parking, PARKING IS FREE on site (2 designated spots 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 offer Roku TV. We have a drip coffee maker, coffee, decaf, creamers, and sugar.

Studio Apartment, king bed, Downtown St Augustine
High ceilings greet you at this second floor studio located in Historic Downtown St. Augustine. Originally built in 1910 and completely updated in 2023, this carriage house apartment is just two blocks from St. George St, walking distance to Flagler and all of downtown St Augustine. This studio has a full kitchen, king size bed and private patio. Free off street parking, so you are able to park, walk around and enjoy everything downtown has to offer.

Cute & Compact 1BR-Walk to town
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 lower level apt. has an open concept kitchen and living room area. There is a small porch that allows guests to sit outside to enjoy their morning coffee. This apt. is a one BR (queen) with master bath and is perfect for 2 guests. ** One parking space provided on site and Free street parking for additional cars

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, ...

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.
Popular amenities for holiday rentals near San Sebastian Winery
Condo rentals with Wi-Fi

Ocean Side Complex w/ Heated Pool B-15

The Bohemian Rhapsody! In the middle of it ALL!

Oceanside complex B17 1 Bed 1 Bath w/Heated Pool

Ocean Front Gem: Top Floor Corner Unit

Cozy Beach Townhome - Bikes, Garage & Pickle Ball!

Newly renovated! Steps to BEACH & POOL!

Rooftop Bay Views | Near Historical Attractions

Pretty walk to Old Town, Anastasia Island 2 bdrm
Family-friendly house rentals

SaraCasa - First Floor House 2Br/1.5Bath

Perfect One Bedroom Cottage in Lighthouse Park

Historic St. Augustine 2/2 Duplex & Pool

Calm cozy couples cottage close to Downtown & Bch

Leonardi Downtown Craftsman

Hen House Saint Augustine

Uptown Attic - Your Secret Escape

Genovar Mansion Master Suite Private Entrance
Apartment rentals with air conditioning

Home away from Home close to everything!

SeaGlass on Vilano Beach~St. Augustine, FL

Old Town "Gem"

*2BR* Luxe Loft Close to Everything | Balcony

Top Floor Loft - Park and Walk everywhere!

Clean simple and cozy home in St. Augustine

Apt A - Comfort of Home in Historic St Augustine

Bougainvillea way, steps to town center, romantic.
Other great holiday rentals near San Sebastian Winery

The Castle Cottage

2 Steps to Ice Plant, Apt in Downtown St. Aug

Historic Lemon Studio – Walkable to Downtown

192 Riberia Downtown Luxury Home

Eclectic•Colorful• Fun designer home

The Sweet Spot Suite - Heart of Historic District

Marsh Studio Anastasia Island Beach Amphitheater

The Hideaway
Destinations to explore
- EverBank Stadium
- Daytona Boardwalk Amusements
- Summer Haven st. Augustine FL
- Lightner Museum
- St Augustine Amphitheatre
- Daytona Lagoon
- Fountain of Youth Archaeological Park
- Kathryn Abbey Hanna Park
- VyStar Veterans Memorial Arena
- Adventure Landing Jacksonville Beach
- Ravine Gardens State Park
- St Johns Town Center
- Saint Augustine Town Plan Historic District
- Ocean Center
- TPC Sawgrass
- St. Augustine Alligator Farm Zoological Park
- University of North Florida
- Daytona Beach Bandshell
- Ocean Walk Shops
- Vilano Beach Fishing Pier
- Anastasia State Park
- Memorial Park
- Little Talbot
- Marineland Dolphin Adventure




