
Waterfront vacation rentals in Anastasia Island
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Top-rated waterfront rentals in Anastasia Island
Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.

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!

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.

Incredible Waterfront Townhome
As close to the water as you can get! Our building is considered the best in the complex which is waterfront, very private and peaceful. Perched on the Point we have fantastic views overlooking the intracoastal's oyster beds, mangroves, exotic birds, fish and bald eagles!. The sunsets are incredible. A fisherman's paradise. There is a private boat dock and a small boat ramp to launch your kayak. Watch dolphins put on a show almost daily from your lanai. The beach is right across the street!

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.

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.

Windjammer 208, Oceanfront and Riverview
Beautiful newly renovated condo in Crescent Beach, with spectacular views of the beach as well as the Matanzas river. Coffee while watching sunrise on your east balcony and wine while watching the sunset on the Windjammer fishing pier, while dolphins are entertaining you. 10 miles from historic St Augustine, a couple of miles from Marine land and a variety of restaurants close by. Flatscreen TV'S in all the rooms for your convenience when the weather does not allow you on the beach.

St Augustine Beachside Home - Walk to Beach
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 about a 10 minute walk 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.

Ocean Gallery 1/1, 2 pools
Bright, airy and beachy, this condo at Ocean Gallery pairs resort-style amenities with an exceptionally clean, stylish and comfortable condo. Perfect for a couple or one family, it sleeps up to 4 in beds (primary bed sleeps 2; pullout sofa in living area sleeps 2 additional guests - perfect for kids). You’ll be a few steps from 1 of the 2 pools, and a 5 minute leisurely stroll through the complex will take you to the beach!

Perfect location 2 Bedroom Private Hot Tub
Couples retreat, grill out in your own private courtyard while listening to the relaxing water fountain. “Wine” down and watch the sunset. Private brand new 4 person hot tub. Beautiful courtyard night lighting. 0.5 miles walking distance to the bridge of lions and historic downtown. Off-street parking. Food bars and fun within 300 feet location is directly off the downtown boulevard entrance. Special requests are available.

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.

Wade n Sea Ocean Front Condo
Bring the whole family to this ocean front condo with lots of room for fun. Wake up to spectacular sunrises every morning! Kick back and relax in the heated pool or spend lazy days on the beach. Head to Historic St Augustine which is only a few minutes away and enjoy the town.

Surf Side Six C-3
SS6C-3 Unbelievable Ocean Front Condo with Breathtaking Views
Popular amenities for Anastasia Island waterfront rentals
Waterfront apartment rentals

Oceanfront Hammock Beach Retreat

Charming Vintage Intracoastal Apartment

SEA & SALT|2-min walk Beach|2x Sparkling Pools

Updated and clean, private beach access condo

Luxury Sunset Marsh View New Remodele Easy Walk #B

< • < • Resort Style Retreat •> • >

Oceanfront Condo with Balcony!

Private Beach 2 min walk No chores! 2 Bd/1 Ba Apt
Waterfront house rentals

Ocean Village Club-First Floor Access.

Hercules by the Sea

Absolute Oceanfront: Sleeps 16: Parking for 6 Cars

Surfside House

Oceanfront, Blissful Sunrises, Beach Gear, BBQ

BYO Boat, Kayak, Golf Cart, RV

The Sculptor's House Irresistible Oceanfront Home

Hawaiian Island Escape ~ Heated Pool/Spa/Beach
Waterfront condo rentals

What a View! Sand & Sea!

Lovely 2BR/2BA Oceanview Condo, St Augustine Beach

Beachfront! Creston by the Sea, 11D!

361 Fun in the Sun | Direct Oceanfront Ground Floor

The Salty Suite Resort style condo

B207 Entire Oceanfront Condo Steps From Pool & Bch

~Heated Pool~Hot Tub~Steps to the Beach~King Bed

Summerhouse - Direct Oceanfront Corner Unit
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- Ocean Center
- Daytona International Speedway
- Crescent Beach
- EverBank Stadium
- St Augustine Amphitheatre
- Daytona Boardwalk Amusements
- VyStar Veterans Memorial Arena
- Saint Augustine Town Plan Historic District
- Kathryn Abbey Hanna Park
- Lightner Museum
- Daytona Lagoon
- St Johns Town Center
- Fountain of Youth Archaeological Park
- TPC Sawgrass
- Summer Haven st. Augustine FL
- Vilano Beach Fishing Pier
- Adventure Landing Jacksonville Beach
- University of North Florida
- Ravine Gardens State Park
- Daytona Beach International Airport
- Memorial Park
- Little Talbot
- St. Augustine Alligator Farm Zoological Park
- Daytona Beach Bandshell
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