Family-friendly holiday rentals in St. Augustine

4.99 out of 5 average rating, 147 reviews

HtdPool w/Arcade, Fire, GolfCart Access, 1.2 mi DT

ISLE BE BACK 🌴— brand NEW modern home! **Golf Cart Access for an additional fee Please inquire if interested!** Welcome to your ultimate St. Augustine getaway! Just 5 mins from downtown, this fun-filled retreat is perfect for families, friends, or anyone looking to relax and play. Swim in the pool, compete on the putting green, roast s'mores by the fire pit, or challenge your crew on the retro Pac-Man machine—all without leaving the house! ✔Sleeps 8 comfortably ✔Self check-in & free parking

5.0 out of 5 average rating, 156 reviews

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.

A charming coastal bungalow is set amidst lush green grass, surrounded by palm trees and nature. The driveway leads to the front entrance, featuring a single-car garage. The home is framed by a clear blue sky dotted with clouds, highlighting its welcoming facade.

4.95 out of 5 average rating, 237 reviews

Surfside House

This special vacation home is close to everything, making it easy to plan your visit. Ideal location across from the beach, just minutes to drive or bike into historic downtown St. Augustine. The 1950's coastal bungalow is set on Vilano Beach's historical Street. The home has been completely remodeled, plenty of parking and is pet friendly. Surfside's pet friendly beach access/parking and North Shore Community Park is 1 block away with tennis/ pickle ball courts, playground and dog park.

The outdoor area features a private saltwater pool with a custom spa, surrounded by lush tropical landscaping. A spacious cabana is included, with comfortable seating beneath flowing white drapes. A shaded umbrella is positioned beside the pool, enhancing the relaxation space.

4.99 out of 5 average rating, 170 reviews

New Lux Home 4bd/3.5ba+HotTub+SaltPool+Walk2Beach

🌴 Featured in Good Housekeeping & Designed by HGTV-featured Builders ✨ 🏡 New 2023 Luxury Coastal Home 🛏️ 2 King Suites + 2 Queen Bedrooms 🛁 3.5 Bathrooms 💦 Private Saltwater Pool + Heated Spa/Hot Tub 🍹 Poolside Cabana & Outdoor Kitchen 🚲 Bikes, Beach chairs, Cooler & Toys included 🌿 Tropical Backyard Oasis w/ Mature Palms, Lounge Chairs, Outdoor Shower & Turf 👣 Walk 0.2 miles to the beach 🌅 Stroll 0.2 miles to Cap’s for Waterfront Sunset Dinner 🏰 10 min to Historic St. Augustine

4.96 out of 5 average rating, 140 reviews

A classic 43-foot Gulf Star yacht is moored in calm waters, exhibiting a spacious deck with a covered seating area. The hull is painted in a crisp white, reflecting sunlight, while nearby masts and boats frame the picturesque marina scene.

Boat in St. Augustine

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.

An expansive ocean view is framed by a white railing on a sunny day. Lush green grass and tropical plants lead to the sandy beach, while waves gently lap against the shore under a clear blue sky.

4.95 out of 5 average rating, 204 reviews

Ponte Vedra Sth/Vilano Oceanfront 3Bed 2bath Pets

Nicely furnished 3 bedroom 2 full bathroom house tucked away in the dunes on Surfside Vilano Beach . 3 miles from downtown St Augustine, a half mile from Publix .The deck wraps around half the house, pretty fantastic ocean views, sunrise and river side sunsets. Each bedroom has a smart tv with Internet and a very comfortable Queen or King size bed. TPC Sawgrass is a 20 minute drive north , Daytona International Speedway 70 minutes south , 2 hours to Orlando and Busch Gardens.

4.94 out of 5 average rating, 234 reviews

Downtown • Parking for 2 + Wraparound Porch

Historic Whitney House • Newly renovated 1,700 sq ft designer home Private driveway parking for 2 • Steps to trolley & St. George Street Gourmet kitchen, 2 en-suite bedrooms, 3 luxury baths, Starlink WiFi, wrap-around porch + sunny deck. Fitness club & pool passes included. Modern luxury in the heart of historic downtown St. Augustine. Perfect for couples or small groups seeking modern luxury, easy parking, and a walkable base right in the heart of historic downtown St. Augustine.

A charming mid-century home features a welcoming front porch with seating. Lush greenery and Spanish moss surround the property, enhancing its tranquil setting. The entrance is marked by a slate stone walkway and a decorative sign, contributing to the home's inviting appearance.

4.96 out of 5 average rating, 197 reviews

Charming 3 bedroom cottage, feed the peacocks!

A 15-minute walk to Old Town, this cozy mid-century home has all the modern touches while retaining its roots! Stroll down beautiful Magnolia St. to the Fountain of Youth, or stay and feed the free-roaming peacocks from the front porch! Old Town Trolley stop, and the Old City Jail are just at the end of the street. Enjoy games with the family, grilling, or hit the beach, only a 7-minute drive! Beach supplies are provided. Take advantage of the free bikes and locks for a ride to town!

Guest favourite

A serene outdoor area features a suspended basket chair, surrounded by lush greenery and sun loungers beside a sparkling pool. Umbrella-shaded tables provide shade, while the building's modern architecture stands in the background, enhancing the inviting atmosphere of the space.

Flat in St. Augustine

4.85 out of 5 average rating, 107 reviews

Luxury Retreat in St. Augustine

Escape to Isla Antiguas in St. Augustine, FL, and indulge in luxury at this stunning 2-bed, 2-bath Airbnb. Perfectly designed for comfort and style, this upscale retreat offers a fully equipped kitchen, elegant living spaces, and plush bedrooms. Enjoy top-tier amenities, including a sparkling pool, fitness center, and scenic surroundings. Just minutes from historic downtown and pristine beaches, this getaway is ideal for relaxation and adventure. Book now for an unforgettable stay!

Villa in St. Augustine Beach

5.0 out of 5 average rating, 130 reviews

VILLA ONE • 1 Block to the Ocean

One block from the ocean in St. Augustine Beach, this design-forward 2BR/2BA villa is made for easy beach stays. Warm tones, natural finishes and local art create a relaxed, laid-back feel. Outside, enjoy a private tropical backyard with lounge area, outdoor dining and outdoor shower. Walk to the beach, coffee and local favorites, with Historic Downtown just 10 minutes away. One of four individually styled St. Augustine Beach Villas. Not pet friendly. @staugustinebeachvillas

Guest favourite

A tranquil backyard area is featured, showcasing a heated pool surrounded by lush greenery. Two black chairs are positioned on the stone patio, offering a comfortable spot for relaxation. The space is enclosed by vibrant tropical plants, enhancing the private atmosphere.

4.95 out of 5 average rating, 196 reviews

Pool home oasis steps to ocean

Cottage style home with comfortable porches to enjoy sound of ocean waves breaking on the front and back porches. Pool in the back yard (heated by request for $50 per day) cookshed, fenced with lush trees and woods to the east. The inside looks large with high wood ceilings and multiple windows and glass doors to the beautiful pool area. Located on a dead end street in a family neighborhood with 5 star restaurants nearby. Fifteen minute drive to downtown St. Augustine.

A spacious screened-in pool area features a large blue swimming pool surrounded by patio tiles. Comfortable seating arrangements with multiple chairs and a table are visible nearby, providing a relaxed space for leisure. Natural light streams in through the screened enclosure.