Holiday houses 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

Private & Secluded Oceanfront Home w/ Large Deck

Welcome to a serene beachfront retreat in Ponte Vedra Beach. This home offers direct private beach access, a spacious open layout, and a huge deck with breathtaking ocean views. Plus, there are no houses behind—just a peaceful nature preserve, ensuring a quiet and relaxing stay. If you are a large group, you can book Sandy Shores II (next door) to accommodate up to 16 guests—perfect for family reunions, large gatherings, and special celebrations. LONG STAY DISCOUNTS Jan-Feb, send us an inquiry!

VILLA One

The Villas are designed for short stays, long weekends or for a unique styled location for brands to shoot their products. The space features warm tones, natural finishes and local art for an effortless vibe that allows visitors to relax the second they walk in the door. Complete with two bedrooms, two bathrooms and a backyard complete with tropical landscaping, lounge area, dining and outdoor shower. One of 4 Villas located in St. Augustine Beach. Not pet friendly. @staugustinebeachvillas

Oasis on the 18th w/ Spa, 3 Pools and pickleball

Escape to our serene World Golf Village condo, blending tropical elegance with modern comfort within a gated community This immaculate space sleeps 4 with a king bed, queen sofa bed. Fully stocked kitchenette, in-unit washer/dryer, and tranquil pool views🌴 Resort perks: 3 sparkling pools, pickleball and golf onsite, clubhouse & lush walking paths. 30 minutes from historic St. Augustine’s charm, dining & beaches Perfect for couples, solo travelers, small families, or a pet-friendly escape!

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!

Private Apartment

Unique private upstairs apartment near the beautiful Julington Creek very close to St. Johns, under majestic live oak trees offering a quiet and secluded setting, but close enough to everything you need for your next trip to Jacksonville. Short distance to great dining, beaches, shopping, St. Johns and St. Augustine! Guests will enjoy a one bedroom apartment with a fully equipped kitchen. Property access for our guests only. Complimentary beer, sodas, water and coffee! Adults only.

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 Waddle Inn

Peaceful modern farmhouse 2-bed, 1-bath private 2nd-floor suite on our 2-acre creekfront mini farm. Built in 2023, it offers high-quality linens, smart TVs, and Wi-Fi. Meet our two rescue draft horses, friendly chickens and curious turkey; guests are welcome to help feed treats. Enjoy pool, firepit and on-site kayak rentals on the creek to the St. Johns River. 30–35 minutes to beaches, NAS JAX, TPC Sawgrass and historic St. Augustine. Perfect for couples, families and remote work.

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.

Luxury Cottage with River Access

Enjoy the peaceful ambiance of this brand new luxury cottage on Julington Creek in Saint Johns County. Centrally located -- we're just a 30 minute drive to the beach, downtown Jacksonville, and St. Augustine. Amenities include a king-sized bed, two TV's, and a fully-equipped kitchen. The cottage is located at the front of our 1-acre property. Our own home is situated just across the lawn from the cottage. Guests will walk through the backyard to access the river.

Penthouse Condo in St. Augustine

The LARGEST 1 bedroom penthouse condo within the very desirable King and Bear gated community inside World Golf Village. Enjoy ultimate privacy and beautiful views! Perfect for anyone seeking a peaceful place to relax and unwind. Enjoy resort-style amenities including pool, hot tub, tennis, pickleball, salon, fitness center, and plenty of scheduled activities! This rental is set up to feel like home. Just bring your bags and the rest is taken care of.

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.