Waterfront holiday rentals in Anastasia Island

4.89 out of 5 average rating, 415 reviews

Waterfront Fisherman’s Treasure at Crescent Beach

Enjoy waking up in a quiet Treasure Beach neighborhood having coffee on the screened-in back porch, or enjoy the dock, watching a variety of birds, wildlife and fish jumping in the canal. All you need is a pole. Take a 5 minute ride from the house to ocean access and walk our beautiful Crescent Beach. A short drive away, there's shopping, entertainment and great restaurants in St. Augustine (Oldest City in the USA). We look forward to your stay and know you will make memories to last a lifetime.

Apartment in St. Augustine

4.99 out of 5 average rating, 168 reviews

SeaPlace, Ocean View, Poolside 2/3 Walk to Beach

Beautiful St. Augustine Beach ocean and pool views from this 2/2.5 townhouse style condo, just steps to the beach. Come enjoy everything this vibrant city has to offer. 2 quiet bedrooms and bathrooms upstairs. 2 private balconies. Downstairs is a full kitchen, dining area for 6 (or well lit workspace), half bathroom, living area w/ new 65" TV, 10 minutes from historic downtown. Family friendly resort community w/ pools, tennis, pickleball and bocce’ ball courts. Beach chairs & towels provided.

4.9 out of 5 average rating, 214 reviews

Canal Home, Dock, BBQ, Walk to Beach, Fishing

Save my home to your wishlist, click the <3 in top right corner! *Book 2 nights, get the 3rd night 30% off!* > Canal front home with new dock! > Walk to Butler Bch and the IC waterway! > Neighborhood beach walkover > Dog friendly - up to 2 dogs under 20 lbs *WITH nightly fee* > Fully fenced yard > Fully equipped kitchen > Safe neighborhood > 2 Smart TVs (LR + Master Bdm) > Fish in the canal > Keurig > Private parking > Minutes from boat ramp > 3 days of supplies! (TP, trash bags, pods, etc)

4.87 out of 5 average rating, 192 reviews

Ocean Front Private Getaway in St. Augustine Beach

Just a few short steps from the ocean and 10 minutes from downtown St. Augustine, this unique, 1970s original PINK, three-story A-Frame home is ready to host your next vacation, bachelorette party, or any other getaway you have in mind! Its bright, cheerful interior is perfect for popping mimosas in the morning, or enjoying a beautiful beach day from your own private beach access. Stay for the weekend or stay for the season and create lasting memories of a lifetime - I can't wait to host you!

5 out of 5 average rating, 125 reviews

Waterfront - Lion’s Bridge & Old Town View

Walk across the Bridge of Lions to downtown St. Augustine with amazing restaurants and attractions. Half a mile to historic downtown! Less than 1 mile to the Castillo de San Marcos fort. Anastasia State Park Beach, the world famous Alligator Farm and Zipline, and the lighthouse are less than two miles away. Several restaurants and bars only a few blocks away. Whether going to the old fort, lighthouse or Flagler College, our home provides a great base for exploring an amazing part of Florida!

4.98 out of 5 average rating, 182 reviews

Cottage in St. Augustine

Fun Waterfront Retreat, Heated Pool, Rooftop Deck

You've found your waterfront oasis tucked under the White Birds of Paradise! This spacious retreat was formerly a commercial art gallery. Two queen beds, one full bathroom & full kitchen make for comfortable living! You have a fenced path leading you down to the beautiful waters of Salt Run where a rooftop deck & salt water in-ground pool invites you to relax and slow down. Less than a mile to downtown St. Augustine, a little over a mile to the Amphitheater and about 3 miles to the beach.

Apartment in St. Augustine Beach

4.97 out of 5 average rating, 221 reviews

Ocean Front Gem: Top Floor Corner Unit

Top floor, direct ocean front, corner unit with elevator and beautiful unobstructed views of the beach from both bedrooms, living room, dining room, kitchen and private balcony. We have upgraded the condo and believe it to be the best condo in St Augustine Ocean and Racquet Resort. We also offer the condo immediately next door for rent, Ocean Front Escape: https://www.airbnb.com/h/saint-augustine-oceanfrontescape. Our checkin process is contact free. We use a Nest lock on the front door.

Guest house in St. Augustine

4.94 out of 5 average rating, 156 reviews

Heated Pool Beach Bungalow Steps to the Ocean

Beautiful brand new in 2022 en-suite Bungalow beach side! Perfect for a romantic get a way or just one person, just 600 steps to the beach. Five minutes to the St Augustine pier and 10 minutes to the oldest city in the US, Historic Downtown St Augustine. Not only do you have the most comfortable bed to fall into, a 50" TV, recliners and an amazing heated pool. Beautiful beach sunrises, fishing, hiking, Concerts at the Amphitheater. For your safety you have an electronic keyless entry.

Apartment in St. Augustine

4.96 out of 5 average rating, 190 reviews

Ocean Front Condo only Steps to the Beach.

Self-Check-In, Covid-19 Protocol Cleaning Utilized, Ground level, oceanfront unit w/ 2 bedrooms/2 baths at Sea Place, a quaint seaside community. Has updated kitchen & walk-in shower, washer/dryer, wifi, cable & covered patio. Amenities: 2 pools (not heated), tennis, racquetball, & beach access; 4 beach chairs & umbrella provided. Located near shops, restaurants & historic St. Augustine. 2 nights min stay. Max: 4 guests. No pets (per HOA), smoking or parties please. No BBQ grill per HOA.

4.97 out of 5 average rating, 247 reviews

St Augustine Beachside Home - Walk to Beach

Time to Relax at our St Augustine canal front getaway! Great family destination just 15 min. to Historic Downtown St Augustine. Neighborhood features PRIVATE Beach Access with a less than 10 minute . walk, depending on pace, to the Beach. Boating and Fishing at your Fingertips with private, over-the-water dock and ramp to floating dock where you can tie up your own boat/kayak/jet skis. The perfect end to your beachside dream day will be watching the sunset while on your private dock.

Apartment in St. Augustine Beach

4.95 out of 5 average rating, 140 reviews

Newly renovated! Steps to BEACH & POOL!

Our little slice of paradise is situated in the heart of St. Augustine Beach right on A1A Beach Blvd. Our unit, recently renovated, is just steps from the beach and closest building to the pool! 2 outdoor pools (1 heated in winter), 5 hot tubs & tennis courts. Perfect location to enjoy our beautiful beaches & all that Anastasia Island has to offer! Historic St. Augustine is less than 7 miles away. Unit is equipped with everything you need for a perfect beach vacation!