Waterfront holiday rentals in St. Johns County

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!

View · Beach · Parks

Surfside Six, Direct Oceanfront, Beachfront

BEST spot to watch the sunrise, (and moonrise) on St Augustine Beach from every room in the condo and from the two direct beach front balconies! CORNER UNIT! TOP FLOOR! One balcony off the upstairs corner primary bedroom suite, walk in closet and ocean view King size beds in each bedroom. Anytime is a good time to be on the beach in St. Augustine! Winter Spring, Summer, or Fall! Besides being steps from the beach there are plenty of local eateries,great food, live music within walking distance.

Beach · View · Accuracy

Charming Guest House on Riverfront Estate Weddings

Pretty Guest House situated on majestic 5 acre riverfront estate on the St. John’s River with park-like grounds filled with colorful azaleas, ancient oak and hickory trees, dripping in Spanish moss. Sit back and watch and listen to incredible hawks and bald eagles overhead! Wake up to a magical sunrise each day! Bass Pro Shop did a photo shoot here for their Spring 2025 catalogue! Owners home is on the property and they are always available. 45 minutes to JAX Beaches. 35 min to St. Augustine.

River · View · Layout

DesignerHGTV•Pool•Walk/Bike to Attractions•Island

Off Street Parking 3 Min Drive/ 15 Min Walk to Historic Downtown 2 Min Drive to the St Augustine Amphitheater 2 Min Drive to Anastasia State Park Beach 1 Min Drive to Anastasia Fitness Club/Suana-Steam Rm/Pool Looking to get away from the hustle & bustle of the city? This designer home with an amazing pool is the perfect place to recharge. Downtown & the scenic beaches in Anastasia State Park are just a minutes away. With spacious living & modern amenities, the Home offers maximum comfort

Beach · Pets · Long stay

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.

Beach · View · Pets

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.

View · Getting around · Indoor spaces

Perfect location 2 Bedroom Private Hot Tub

Couples Retreat Near Downtown St. Augustine. 0.5 miles from the Bridge of Lions. Enjoy a secluded courtyard, relaxing water fountain, and new 4-person hot tub. Wine down and watch the sunset in a peaceful setting after a exploring. Off-street parking is included. Restaurants, bars, coffee shops, and local favorites are only steps away. Perfect for a romantic getaway, weekend escape, or special occasion. Special requests and accommodations are available to help make your stay unforgettable.

Beach · View · Checkout

King bed, Lake View, sleeps 8, 6 TVs, Public Pool

Escape to our cozy retreat! You'll unwind in style with up to 6 beds in our safe neighborhood, close to Publix and restaurants. You'll explore nearby beaches, parks and attractions or day trip to St. Augustine and Orlando. You'll enjoy serene lake views and backyard fishing. You'll love our top-notch amenities, including a recreational pool with slide, lap pool, basketball, fitness center and playground. You'll create unforgettable memories - book now! We look forward to hosting you.

Beach · View · Amenities

Cozy 2BR on Charlotte St. Downtown St. Augustine

Beautifully renovated 2BR apartment boasts a prime downtown in the historic district of St. Augustine!!! Easily walk to plenty of restaurants, shops, and local attractions. After fun- field day, you can relax on one of the two balconies overlooking charming Charlotte Street or kick back in an open living area furnished with a plush sofa and 45" TV. Whip up tasty meals in the well-equipped kitchen, outfitted with stainless steel appliances. The apartment sleeps up to four guests.

Beach · View · Decor

Luxury Golf & Spa condo in Beautiful St. Augustine

Beautiful 1 bedroom pristine condo unit has it all. Comfortable king size bed, privacy, full bathroom with roman bathtub, washer/dryer, full kitchen with all the utensils you will need, two flat screen tv's, fast free wifi, private balcony overlooking lush gardens with a fountain. The Laterra resort boasts a plethora of amenities right outside your doorstep. Heated pool, pool with waterfall feature, hot tub, tennis courts, award winning Golf and restaurants nearby!

Beach · View · Cleanliness

Oceanfront, Blissful Sunrises, Beach Gear, BBQ

Add my home to your wishlist, click the <3 in top right corner! *Book 2 nights, get the 3rd night 30% off!* >Stunning Oceanfront Home with pano ocean views >Beautifully styled >4 Smart TVs w cable and streaming apps >Parking for 4 cars >Continuous balconies >Beach gear provided (towels, chairs, umbrella) >Walk to The Reef Restaurant >Short drive to downtown + Vilano Publix >Washer + Dryer >BBQ Grill >Drip Coffee Maker >3 days of supplies (TP, trash bags, etc.)

Beach · View · Value

St. George Historic Bungalow

Come stay at this St. George Historic 1915 Bungalow featured in the well known book, The Houses of St. Augustine. Enjoy being in one of the city’s most pleasant and distinctive neighborhoods. Be reminded of the history that surrounds you as horse carriages stroll by while you enjoy your coffee or wine on the large front porch. The house borders on the lovely Maria Sanchez Lake that inhabits many birds year round.

View · Beach · Pets