Waterfront vacation rentals in Anastasia Island

A screened-in back porch features a round dining table surrounded by four wicker chairs. The red deck flooring contrasts with the green lawn visible beyond glass panels. A peaceful canal is seen in the background, with trees lining the opposite bank.

4.89 out of 5 average rating, 464 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.

A spacious waterfront deck offers lounge seating with blue cushions, set against a vibrant sunset sky filled with pink and orange hues. A hammock is positioned nearby, with palm trees framing the stunning view of the water and docks in the background.

5 out of 5 average rating, 150 reviews

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!

A vibrant pink flamingo float is positioned in a clear swimming pool, surrounded by manicured palm trees. In the background, a sunny outdoor space features teal chairs and a matching umbrella, contributing to a relaxed atmosphere.

4.99 out of 5 average rating, 134 reviews

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

The living room features a sliding glass door that provides a direct view of the beach. A comfortable sofa is positioned near a coffee table, while a side table and chair complement the seating arrangement. Natural light brightens the space, enhancing coastal decor.

4.99 out of 5 average rating, 137 reviews

361 Fun in the Sun | Direct Oceanfront Ground Floor

Direct Oceanfront, ground floor flat unit, no stairs. Located in Crescent Beach at Summerhouse. Family oriented complex located on over 25 acres with four pools and large grass areas. Highly desired 2 bedroom unit. This property is ground level and directly oceanfront. Flat style layout not a townhouse, there are two steps to the front door but otherwise no stairs. Sliding door opens directly to covered back porch. Please see our our other property 461 More Fun in the Sun, 3 Bedroom

Apartment in St. Augustine Beach

A screened lanai offers a comfortable wooden bench, with a vibrant mural piece on the wall. The space provides sweeping views of the lush greenery and palm trees beyond, as the sun rises over the horizon, creating a serene outdoor retreat.

4.95 out of 5 average rating, 108 reviews

Oceanfront Bliss: Beach Views

Welcome to your oceanfront oasis in St. Augustine Beach! Featuring a spacious king suite, a comfy queen bedroom with twin trundle, and a sleeper sofa, it offers stunning sunrise views, a modern boho surfer’s vibe, and an updated chef’s kitchen. Steps to one of the best beaches in the east coast and walk to lively local restaurants and bars, it’s minutes to St. Augustine’s Nights of Lights, Amphitheater, and more! This isn’t just a vacation rental—it’s your personal seaside escape. Book now!

A well-maintained landscape showcases vibrant green grass and neatly trimmed shrubs, with palm trees lining the pathway. An expansive view of the ocean is visible in the background, framed by a boardwalk leading to the beach. Two residential buildings are seen in the scene.

4.99 out of 5 average rating, 205 reviews

SeaPlace Ocean & Pool Views, 2/3 Steps to Beach

Beautiful St. Augustine Beach ocean & pool views from this 2/2.5 townhouse style condo steps to the beach. Come enjoy everything this vibrant city has to offer. Two quiet bedrooms and bathrooms upstairs. 2 private balconies. Downstairs is a full kitchen, dining area for 6, half bathroom, living area w/ newer 65" TV. 10 minutes from historic downtown. Family friendly resort community w/ pools, tennis, pickleball, basketball and bocce’ ball courts. Book now and let the island magic begin.

4.98 out of 5 average rating, 341 reviews

A private hot tub is set in a serene outdoor area surrounded by greenery and wood paneling. The tub is equipped with a cover and nearby is a container holding spa towels, providing a relaxing space for guests.

Villa in St. Augustine

Loins Bridge 0.5m away, 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.

Guesthouse in St. Augustine

A tranquil outdoor space features a well-maintained heated pool surrounded by lush greenery and colorful flowers. Seating areas with black Adirondack chairs are positioned around the pool, offering a peaceful setting. A covered patio stands in the background, complementing the inviting atmosphere.

4.95 out of 5 average rating, 209 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.

A serene sunset is captured over calm waters, reflecting warm hues of orange, pink, and purple. The horizon is lined with subtle clouds, enhancing the tranquil scene. The peaceful atmosphere invites relaxation and appreciation of nature's beauty.

5 out of 5 average rating, 126 reviews

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.

A screened-in balcony offers views of the lush greenery and marshlands beyond. Colorful cushions adorn a comfortable seating area, while a small wooden table sits centrally. Natural light fills the space, creating a peaceful atmosphere for relaxation.

4.99 out of 5 average rating, 129 reviews

Riverfront direct views-Get it ALL in St Augustine

Do not compromise-Just get it all! This is the hidden gem you were waiting to find. Only a few minutes from historic downtown and the area's best beaches, The Conquistador offers 3 swimming pools, tennis, tennis/pickleball courts, trails, a fishing pier, playgrounds, BBQ area, pavilion and plenty of space to roam and relax under the amazing Oak canopy. The beach or Downtown a mere 12 minute drive. Stay in your very private condo and enjoy the gorgeous views of the Manatee River.

A wooden walkway leads from a grassy area to the sandy beach, flanked by two benches on either side. The beach is visible in the distance, with gentle waves and a clear blue sky above.

4.95 out of 5 average rating, 317 reviews

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.

Lush greenery frames a wooden pathway leading to a sandy beach, with palm trees and residential buildings visible in the background. The sky is illuminated by soft hues of sunset, creating a serene backdrop for the coastal environment.