Waterfront vacation rentals in Anastasia Island

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Anastasia Island

Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.

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Guest favorite
Apartment in St. Augustine Beach
4.92 out of 5 average rating, 212 reviews

Beachfront St. Augustine Escape* Pool & Ocean View

Welcome to Turtle Trace, your beachfront getaway on Anastasia Island in beautiful St. Augustine! This condo offers direct pool & beach access, sweeping ocean views, and just minutes from Historic Downtown. Perfect for families, couples, or anyone wanting the ultimate coastal escape. Why You’ll Love It 🏖 Steps to the beach & pool right outside your patio door 🌅 Enjoy amazing sunrise views over the Atlantic 🏡 Gated, beautifully maintained community 🍴 Walk to restaurants, cafes & grocery stores

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Top guest favorite
An open dining area is situated adjacent to large windows, offering a view of a vibrant sunset over the ocean. A wooden table with several chairs dominates the space, complemented by a cozy sofa nearby. Decorative elements include a wall hanging and a potted plant.
Apartment in St. Augustine Beach
4.98 out of 5 average rating, 139 reviews

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.

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Top guest favorite
A vibrant swimming pool reflects the evening sky, surrounded by well-maintained landscaping. Poolside seating includes colorful lounge chairs and a dining set, while a floating flamingo adds a playful touch. Soft lighting from string lights enhances the serene atmosphere as dusk approaches.
Home in St. Augustine
4.99 out of 5 average rating, 140 reviews

HGTV-Style Home + Pool + Walk/Bike to Attractions

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

BeachHospitalityKitchen

Top guest favorite
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.
Condo in Crescent Beach
4.99 out of 5 average rating, 144 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

BeachViewLaundry

Top guest favorite
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.
Condo in Butler Beach
4.99 out of 5 average rating, 210 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.

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Top guest favorite
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.
Apartment in St. Augustine Beach
4.96 out of 5 average rating, 115 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!

ViewBeachKitchen

Top guest favorite
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.
Guesthouse in Butler Beach
4.95 out of 5 average rating, 218 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.

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Guest favorite
A view overlooking the ocean reveals gentle waves and a clear blue sky. Green palm fronds are positioned in the foreground, while a red-roofed gazebo is visible on the beach, blending with the natural coastal landscape.
Condo in Butler Beach
4.91 out of 5 average rating, 253 reviews

What a View! Sand & Sea!

Welcome to the most beautiful white sand beach via a short wood walkway from condo over a small dune! Or drive out 4x4 only. Later take a tour of the oldest city in the US Historic St Augustine! We are a tropical small resort with a private balcony and ocean views. Two pools / hot tub / grills/tables/loungers right below condo. We are on the 3rd floor. Of course it’s for THE VIEW (August through November free cancelling/refund if a hurricane is predicted/island issues evacuation.

ViewBeachWifi

Guest favorite
A spacious resort-style pool is surrounded by modern buildings, featuring palm trees and lounge chairs for relaxation. Umbrellas provide shade over seating areas. A vibrant sunset casts warm colors across the sky, reflecting on the water's surface and enhancing the tranquil environment.
Apartment in St. Augustine
4.95 out of 5 average rating, 98 reviews

10min DT/Beach | Resort Style 2B+2B, King Beds

☀️ Top-Rated Beach Condo in St. Augustine – Now Offering Competitive Rates! ☀️ Looking for the perfect family-friendly vacation rental in Florida? You’ve found it! This luxurious 2-bedroom, 2-bathroom beach condo is nestled in a gated resort community just minutes from St. Augustine Beach and the historic downtown. Whether you’re planning a romantic getaway, a fun family vacation, or a weekend with friends, this St. Augustine Airbnb has everything you need for a 5-star experience.

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Guest favorite
A living area features a cooling ceiling fan and large windows with light-filtering curtains. A wall-mounted TV displays an aquatic scene. A light-colored coffee table sits on wooden flooring, complemented by decorative plants and a woven tray.
Condo in Butler Beach
4.77 out of 5 average rating, 282 reviews

Great 1 bedroom 1 bath condo with heated pool

Great condo in an Oceanside community You cannot see the ocean from this condo 5-10 minute walk to the beach Private boardwalk to the beach Condo is in 3rd floor must climb stairs no elevator **** Tennis courts 2 pools 1 heated Shuffle Board Gym Restaurants and bars you can walk to Pet Friendly with a $100 pet fee Only 1 dog is allowed and we must register the dog before you check in The security will not let you on the premises if the dog has not been registered Pull out couch

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Top guest favorite
The living area features comfortable seating, including a soft blue sofa and an armchair, arranged around a white coffee table. Light-colored décor and subtle greenery create a relaxed ambiance. The space is illuminated by a contemporary chandelier, with a view of the kitchen and dining area in the background.
Condo in St. Augustine Beach
4.96 out of 5 average rating, 200 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!

ViewBeachWifi

Top guest favorite
A bright living area features large floor-to-ceiling windows that provide sweeping ocean views. Comfortable seating is arranged around a central coffee table adorned with decorative items. A Smart TV is positioned for easy viewing, while a ceiling fan adds a cooling breeze.
Condo in Butler Beach
4.97 out of 5 average rating, 159 reviews

Family Beach Condo - Steps To The Sand Or Pool

Our beach condo on Crescent Beach has been our family’s haven for years, and we’re excited to share it with you! The breathtaking ocean views from our living room and balcony are just the start—enjoy a renovated kitchen, comfy bedrooms, and family-friendly touches that make this place truly special. Whether you’re here to relax, explore historic St. Augustine, or enjoy the natural beauty of Anastasia State Park, we hope you’ll create lasting memories like we have!

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