Family-friendly 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

Condo near Downtown St Augustine/beach/golf

Relax with family at this peaceful quiet condo on 3rd floor Recently renovated, close to historic downtown St. Augustine & beaches & golf. Pets Welcome.Has lobby pool & hot tub, & a full health spa open to the public. AT&T Fiber wifi, two smart tv’s, full kitchen w/all needed to prepare meals, coffee maker & coffee/tea included. Lots of walking trails. Laterra Condominiums is inside The King & The Bear 24/7 gated community. The King & The Bear Golf Club is open for play at their posted rates.

Private oasis, heated pool, exceeds expectations

Private retreat on 2 acres of gated land, just 20 minutes to historic downtown St. Augustine and 25 minutes to the beach. This fenced property offers a perfect blend of relaxation, fun, and comfort. Enjoy your private pool, or let the kids enjoy their own space in the pool house, featuring TV, games, and a cozy hangout area. Start your day with fresh eggs from our happy hens- an experience that feels both farm-fresh and uniquely memorable. This home is designed to make your stay unforgettable.

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.

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 FL Home with Pool, Hot tub & Luxury Master

This is a lovely family home in the Mandarin area of Jacksonville which has undergone many renovations and upgrades. The master boasts its own, ensuite, tv, fireplace and sitting area, as well as a private entrance from the pool and hot tub area. The house itself has newer furnishings, flooring, modern decor, a large fenced in backyard, pickle ball court and firepit. Located in a safe South East Suburb of Jacksonville, not far from shopping, beaches and many other Florida attractions.

Mandarin. Modern and Cozy!

Single-family house located in Mandarin, one of the best, quietest, safest, and most beautiful neighborhoods in Jacksonville.Driveway for 4+ cars. Fully equipped kitchen and the living room TV with local channels, and Netflix. The large Florida room with TV with local channels and Netflix. Fast Internet, jacuzzi tub. I offer a long-term stay discount. The house is conveniently located near Interstate 295 and I-95. Many nearby restaurants. Walmart, Publix, and Winn Dixie are close by

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!

Luxurious Ranch House 63 Acres w/ Pool

Perfect Family Getaway! Our spacious, fully equipped home offers comfort and memorable experiences. Enjoy the private backyard pool overlooking 63 acres of natural beauty. Explore the farm and see chickens, goats, cows, sheep, horses, turkeys, — and you may even spot wild deer wandering through. Whether you’re looking to reconnect with nature or simply unwind in a peaceful setting, this is the perfect destination. Swim, gather by the fire, bbq or stroll the tranquil farm grounds.

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.

Pet Friendly Studio w/ Private Fenced Yard

Welcome to the newly renovated Pop's Garage! If you've stayed with us before, you'll love the upgrades to our kitchen, the bathroom and the new floors throughout. Plus, we now feature a new, memory-foam King bed and sleeper sofa to accommodate parties of 4. The pet-friendly space includes a private and secure fenced-in area, allowing your canine to stretch out and explore. Discover the perfect balance of comfort and convenience at this one-of-a-kind vacation rental

Peaceful Getaway in the Heart of Jacksonville

Unwind in this peaceful 3BR, 2BA Jacksonville getaway! Enjoy bright, inviting spaces, a fully equipped kitchen, and cozy bedrooms. Step into the tranquil backyard—perfect for morning coffee, yoga, or listening to the cheerful sounds of birds. Less than 15 mins to downtown, beaches, and NAS. St. Augustine, St. Johns, and Amelia Island are nearby. Only 2 mins to major highways, local shops, dining, and entertainment!