House 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

Fan Fave Waterfront: Lion’s Bridge & Old Town View

Our reviews set us apart. WE'D LOVE TO HOST YOU! Walk across the Bridge of Lions to downtown St. Augustine with amazing restaurants and attractions. A short walk to historic downtown, less than 1 mile to Castillo de San Marcos fort. Anastasia State Park Beach, the Alligator Farm and lighthouse are less than two miles away. Several restaurants and bars only a few blocks away. Whether going to the old fort or Flagler College, our home provides a great base for exploring an amazing part of Florida!

Genovar Mansion Rose Garden Suite Private Entrance

The direct view of a gorgeous live oak canopy on Magnoila Avenue and incredible architecture make this historic home a memorable place to stay. This romantic ground floor suite is perfect for couples with a private entrance, queen poster bed, living room,  spacious bathroom, individual climate control, heirloom antiques and reserved driveway parking spot. The home is located within the historic district, close to trolley stops and within easy walking distance to downtown. 6 minutes to the beach.

La Rêverie | Downtown Boutique, Historical Chic

Step inside La Rêverie, a distinguished 19th-century residence steeped in American heritage, meticulously restored & reimagined for today's discerning traveler. Centrally located on original coquina pillars, La Rêverie boasts cathedral ceilings suffused with sunlight and a bespoke French kitchen with chef-grade amenities. Invite guests to the sitting room, carefully designed to foster camaraderie. Choose from three plush bedrooms, each with an en-suite bath for a luxurious, yet private retreat.

Tree Tops: Where Everything is brand new

Take it easy at this unique and tranquil getaway nestled in the Tree Tops. All new appliances, furniture, electronics, sheets, and towels are found in this totally remodeled home. No expense was spared in making your stay as comfortable as possible. This is your perfect get away from the hustle and bustle of life. Enjoy your first cup of coffee on one of 3 porches. Tree Tops is also close to popular attractions, located 6 miles to Vilano Beach and 4 miles to St. Augustine’s historic district.

Historic Whitney House •Designer•Steps2Attractions

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.

St. Aug cottage, great location!

Newly updated tropical cottage close to everything in St. Augustine and steps from the Matanzas River boat ramp. This 2 bedroom, 2 bath home has wood and tile floors and a lovely screened patio to relax looking at nature and listening to the bubbling fountain. Back yard is fully fenced. 3 miles to downtown, beaches, alligator farm, or the amphitheater. Beautiful area for walking along the Matanzas river and your well loved and cared for pets are always welcome. Boat parking available.

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!

Cottage close to beach & historic downtown

Relax with the whole family at our clean, peaceful, family-friendly home in a very quiet neighborhood! Only a 10-minute drive to the beach and downtown St. Augustine without the stress of busy streets and difficult parking. Our home is set up to make you feel comfortable and relaxed. Enjoy looking at the starry sky from our front porch in the stillness and quiet of the night sky. And in the morning, grab a cup of coffee and head over to some of the nicest beaches on the west coast.

Paradise Palms Estate

Located off the popular, scenic Roscoe Boulevard this home sits directly on Cabbage Creek connecting to the Intracoastal water way. Enjoy a private dock, heated pool, spa, fire pit, hammock and oasis. This contemporary home is nestled on a private street with 300 foot long driveway on an acre and is less than a mile from the world renowned TPC golf course as well as exquisite dining, luxury shopping and the historic city of St. Augustine. Plan your escape today!

Charming Home in historic downtown, walk to it all

Our home, Casita Uva de Playa, is the perfect centrally-located home in the Historic Region of Downtown St Augustine. You can walk less than 1/2 mile into the city for a perfect breakfast biscuit, taste amazing cuban food, take in all the history, or enjoy a martini. You can also take a short 10 minute car ride to the beach. Or just relax in our quiet cottage. Your comfort and relaxation while on vacation is our priority. Come stay with us!

Historic Downtown - firepit/pet friendly/fenced-in

Our home offers the ideal combination of comfort, convenience, and style. Experience the vacation of a lifetime at our 3bd/2ba luxury home which offers a fully fenced in private backyard for pets, BBQ grill, firepit, and playground for the littles. Minutes from the best St. Augustine has to offer: • Beaches -12 mins • Castillo de San Marcos -9 mins • Alligator Farm -10 mins • Fountain of Youth -10 mins Pet fee: $20/pet/night