Family-friendly holiday rentals in St. Johns County

Downtown St. Augustine Luxury • Steps 2 Trolley!

Off Street Parking 6 Min. walk to St George St 4 Min drive to Gym/Pool 1 Min to Community Pool 7 Min drive to the beach Luxury 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. Book your stay now and embark on an unforgettable journey

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.

courtyardtreehouseinthehistoricdistrict

You have found your cozy oasis tucked in a (Real) Treehouse lodged in Ancient Oak. Set in a lush tropical garden in the historic district. It’s a minimalist’s dream, exemplifying the appeal of tiny living: compact, clean, efficient and 2 1/2 blocks to the historic districts shopping and restaurants. Relax on the Sun Deck, Rain Deck or in the Courtyard’s Tropical Garden The day time peaceful beauty is only eclipsed by the the nighttime display of laser lights projected onto the oaks canopy.

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

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.

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.

Amazing Views + Beachfront | Fire Pit + Hammocks

Experience serenity at this beachfront Ponte Vedra Beach home! Just steps from the sand, enjoy sweeping ocean views, soothing waves, and breathtaking sunrises. Stylish coastal design and cozy touches make it perfect year-round. Ideally located between St. Augustine and Jacksonville, with easy access to historic sites, golf, and dining. A peaceful retreat for families and friends to relax, recharge, and soak in the Atlantic coast.

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!

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.