Holiday rentals with outdoor seating in St. Johns County

Enchanted Oaks Estate-Weddings -Carriage House

1920 Carriage House on lush private estate. Renovated and charming! Situated on secluded, majestic 6 acre riverfront property on the St. John’s River. Enjoy park like grounds filled with azaleas, ancient oak and hickory trees, dripping in Spanish moss. Sit back and watch and listen to hawks and bald eagles overhead! Wake up to a magical sunrise each day! See the manatees lazily grazing! Bass Pro Shop shot their Spring Catalogue here! Owners home is on the property and they are always available

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

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 • Historic Whitney House • Luxury 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.

Penthouse Artist Haven Ocean front Penthouse

Nestled along a pristine stretch of semi-private beach is this historic artists haven offering an absolute beachfront location like no other. This unique home is split into 3 separate floors, where you will be renting the entire top penthouse level. Inside you will find open studio living with a luxe king bed and a front and rear balcony. Enjoy uninterrupted ocean views from the panoramic windows while you relax & watch dolphins play in the surf and stunning sunsets spread across the sky.

The Pink Seahorse - Beachfront Modern A-Frame

Fabulously updated 1970 a-frame on the beach with many modern and luxury touches throughout. The lowest level is equipped with a queen size bed room, a sitting area (futon converts to a bed as well) with TV and a bathroom. The main level has a queen bedroom, bathroom, very comfortable living area with dining table to seat eight, the modern kitchen equipped with everything you need for a short or long stay! The upstairs loft has two queen beds and a twin day bed. Outside, the ocean awaits!

St Augustine Entire Home, King Bed, Pet Friendly

Casita Luxe Retreat Near Historic St. Augustine – Pet-Friendly Haven! Discover this luxurious 3-bedroom, 2-bath retreat! Designed with a modern luxe aesthetic, it features custom wood paneling, a fully equipped kitchen with a chic island, and a king-size plush mattress. Enjoy the large, fenced yard, fire pit, outdoor shower, and fun family games. Pet-friendly, with Wi-Fi, smart TVs, and parking included this home offers comfort and style in an up-and-coming neighborhood. Book now!

The Shire on 1 acre marshfront with dock and Spa

One of a kind 1930s historic home, newly renovated and transformed into a beautiful secluded getaway. new luxury finishes, while holding its traditional charm. No Events allowed. Rooftop deck, sunrise views of the Atlantic ocean, Downtown, and sunsets over the river. The new dock with covered roof hosts a national geographic like eco system. It’s short walk to the beach and 3 miles to downtown St George street. Follow along @carcabaroad for weekly content of the home.

Cane Cottage Oceanfront Oasis

Cane Cottage was renovated in 2018-2019 after extensive damage from multiple hurricanes. Our vision was to bring this old Florida beach cottage back to its original charm while also adding new life and modern amenities. From the outdoor entertaining spaces to the lavish interior finishes this AirBnB makes for the perfect beach retreat. Well designed and functional home with many well-thought-out touches.

MARE Florida Direct Beachfront St Augustine/JAXNEW

Beachy eclectic shabby chic decor Awesome patio overlooking the beach Amazing cabana with dining table and Adirondack chairs. Chaise sun lounges Beach chairs, beach towels and umbrella for the beach Super close to night of lights downtown St Augustine that offers great restaurants, shopping and night life Ask about our snowbird specials for monthly stays. Time to get Out of the cold and on the beach:)

Cozy River Retreat w/ Hot Tub and an Amazing View

Cozy Waterfront Retreat with Stunning Sunsets Near Downtown St. Augustine Welcome to your perfect getaway! This fully renovated one-bedroom, one-bathroom home offers breathtaking water views and unforgettable sunsets. Perfect for honeymooners, anniversaries, or a quiet couples getaway where time slows down. Located just 20 minutes from the historic charm and vibrant culture of downtown St. Augustine.

1900s Cottage in Heart of Town-walk everywhere!

Welcome to Groveside Cottage on the historic street of St. Augustine! In 1920s Grove Avenue was the home of several families of cigar makers and two cigar manufacturing companies. This charming cottage is a great mix of vintage and modern; you will be amused! We allow 1 dog, please message us - approval required before booking. Thank you!