Holiday rentals in St. Johns County

1920 Carriage House on Riverfront Estate- Weddings

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

Nocatee Family Retreat - Game Room & Cozy Lanai

✔ 15 minutes to Mickler's Beach! ✔ Pool Table, Ping Pong Table & Dart Board ✔ Screened Lanai with Fire Table ✔ Family Games & Beach Gear ✔ Fully Equipped Kitchen ✔ Washer & Dryer ✔ Outdoor Grill ✔ Stroller, Pack 'n Play, High Chair & Toys Relaxing Retreat in the Heart of Nocatee in Ponte Vedra! Family-Friendly & Close to Everything! Enjoy your morning coffee on the screened-in lanai, sit by the fire with a glass of wine, or explore the nearby shops, dining, beaches and golf just minutes away.

St. Augustine Sanctuary 3 Pools Spa & Pickleball!

Escape to this tropical paradise spa-style resort with sparkling pool views and resort-style amenities! Newly renovated spacious studio unit features a wet bar kitchen and overlooks the renowned King and Bear golf course. Whether you're looking to improve your golf game, explore historic St. Augustine, or indulge in a rejuvenating spa day, this condo offers everything you need. Enjoy access to three heated pools, a hot tub, tennis courts, a clubhouse, a full-service spa, and a fitness center!

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.

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.

Historic Home in Downtown St. Augustine

The Triay-Hall house is one of the oldest Spanish Colonial houses in St. Augustine. It was recently fully restored and offers two bedrooms and two bathrooms. One bedroom/bathroom downstairs and the primary bedroom and en-suite bathroom is upstairs along with the Kitchen. The private courtyard is a serene oasis away from the busy streets of St. Augustine. The location is in the heart of downtown and the house comes with dedicated parking. Walking distance to the shops and restaurants.

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!

Bright Modern King Bed Pool Historic St Augustine

Experience St. Augustine from this stylish 1-bedroom apartment designed with professionals and remote workers in mind. With a comfortable King bed, high-speed Wi-Fi, a smart TV, and a private balcony, this space offers the ideal balance of productivity and relaxation during your stay. Whether you are in town for work, an extended assignment, a relocation stay, or simply visiting the oldest city in the U.S., you will enjoy a comfortable home base close to everything you need.

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.

Brand New Sunny Family Home Stay

Escape to our sunny, family-friendly haven just 15 minutes from historic downtown St. Augustine! This brand-new home features 3 bedrooms, 2.5 bathrooms, and spacious living areas with stylish new furnishings. Clean, comfortable, and thoughtfully equipped, it’s your perfect vacation retreat. Whether you’re seeking relaxation or adventure, our home has something for everyone. Book your stay today and enjoy the charm and beauty of St. Augustine from your own private oasis!

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.

Downton Abbottry 2/2 - 5 Min Walk To City Gates

Enjoy this charming 1910 Sears & Roe Buck catalog home that has been meticulously maintained home just a 5 minute walk to the City Gates and downtown. You have a private back patio space to enjoy coffee in the morning or a glass of wine in the evening. Or just take a leisurely stroll to many fine restaurants that St Augustine has to offer.