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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.

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Guest favorite
Apartment in St. Augustine Beach

Beachfront St. Augustine Getaway-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

ViewBeachTV

4.92 out of 5 average rating, 212 reviews
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

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.

ViewBeachAccuracy

4.98 out of 5 average rating, 139 reviews
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

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

BeachSleep qualityParking

4.99 out of 5 average rating, 140 reviews
Top guest favorite
A sandy beach extends towards the horizon, meeting rolling waves under a clear blue sky. Dune grass sways gently in the foreground, with a wooden boardwalk leading to the shore. Beach chairs and umbrellas are visible in the distance, indicating a welcoming recreational area.
Condo in Crescent Beach

Pelican Inlet 2 Bedroom Condo Steps from the Beach

Enjoy this newly renovated 2 bedroom 2 bath condo for your dream getaway. This is a ground floor unit in the "B" building which means you are just steps to the beautiful Crescent Beach, Matanzas Inlet, pool, tennis courts, pickleball, and more. Just bring your swimsuit. Condo includes beach towels, chairs, boogie and skim boards, beach toys, 2 kayaks, paddleboard, pickleball paddles and tennis racquets. You'll be just a short drive from historic St. Augustine with it's many attractions.

BeachRiverGrill

4.92 out of 5 average rating, 181 reviews
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

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.

ViewBeachWifi

4.99 out of 5 average rating, 210 reviews
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

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!

ViewBeachLaundry

4.96 out of 5 average rating, 115 reviews
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

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.

BeachViewAir conditioning

4.95 out of 5 average rating, 219 reviews
Guest favorite
A vibrant view shows lush green lawns and palm trees leading to the outdoor pool area, with the ocean visible in the background. Two white buildings frame the scene under a clear blue sky, emphasizing the serene coastal atmosphere.
Condo in Butler Beach

Heated Pool, Ocean Views, Beach, Playground, BBQ

Save my home to your wishlist by clicking on the heart in the upper right corner! *Book 3 nights, get the 4th night 30% off!* >100 Steps from the beach! >Ocean and Pool Views! >Indoor heated pool, outdoor unheated pool, jacuzzi! >Sauna, tennis, racquetball, fitness center >Downtown St. Augustine is a 17 minute drive >Cable TV and streaming apps. Fast Wifi. >Drip coffee maker >Washer + Dryer in the condo >Spacious private patio >2-3 days of supplies provided (TP, trash bags, pods, etc)

ViewBeachCleanliness

4.87 out of 5 average rating, 129 reviews
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

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.

BeachViewAccess

4.91 out of 5 average rating, 253 reviews
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

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

ViewBeachBiking

4.77 out of 5 average rating, 282 reviews
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

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!

ViewBeachAccess

4.96 out of 5 average rating, 200 reviews
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

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!

BeachViewLocation

4.98 out of 5 average rating, 160 reviews

Popular amenities for Anastasia Island waterfront rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Waterfront apartment rentals

Top guest favorite
Apartment in St. Augustine Beach

Beachside Studio

BeachViewWifi

4.99 out of 5 average rating, 232 reviews
Guest favorite
A serene outdoor area features a suspended basket chair, surrounded by lush greenery and sun loungers beside a sparkling pool. Umbrella-shaded tables provide shade, while the building's modern architecture stands in the background, enhancing the inviting atmosphere of the space.
Apartment in St. Augustine

Luxury Retreat in St. Augustine

BeachRiverAir conditioning

4.85 out of 5 average rating, 107 reviews
Superhost
A heated pool is positioned at the foreground, surrounded by a spacious deck featuring lounge chairs and outdoor tables. A grassy area is situated near the pool, while the condo units with balconies are visible in the background. Bright umbrellas provide shade for guests.
Apartment in Crescent Beach

Oceanfront Condo with Balcony!

BeachViewWalkability

4.78 out of 5 average rating, 140 reviews
Top guest favorite
A comfortable living area features a beige sofa with decorative pillows positioned opposite a wooden coffee table. A recliner chair is nearby. The kitchen area includes modern appliances and seating at the counter. Palm tree artwork adorns the walls, enhancing the coastal ambiance.
Apartment in Vilano Beach

The Turtle Nest, a delightful Oceanfront getaway

ViewBeachGrill

4.99 out of 5 average rating, 150 reviews
Top guest favorite
A welcoming living room features a comfortable couch and accent chairs with geometric patterns. A wooden coffee table sits in the center, surrounded by light-colored walls and wood flooring. Natural light enters from sliding glass doors that lead to a private balcony, enhancing the spacious feel.
Apartment in Butler Beach

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

BeachViewSleep quality

4.94 out of 5 average rating, 120 reviews
Guest favorite
The living area features a comfortable sofa, accompanied by a wooden side table. Artwork adorns the walls, and natural light filters through the windows. A decorative door leads to the porch area, enhancing the room's inviting layout.
Apartment in Lincolnville

Bougainvillea way, steps to town center, romantic.

BeachViewBiking

4.92 out of 5 average rating, 454 reviews
Top guest favorite
The living area features a light-colored sectional sofa with decorative pillows, complemented by two armchairs. A coffee table rests on a soft area rug, and light filters through shutters on the windows. A ceiling fan is visible, adding a cool breeze.
Apartment in Vilano Beach

Oceanfront paradise

ViewBeachAccuracy

4.98 out of 5 average rating, 164 reviews
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

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

RiverBeachAmenities

4.95 out of 5 average rating, 98 reviews

Waterfront house rentals

Top guest favorite
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.
Home in Butler Beach

Waterfront Fisherman’s Treasure at Crescent Beach

ViewRiverLaundry

4.89 out of 5 average rating, 471 reviews
Top guest favorite
The exterior of the house features a two-story structure with a spacious upper deck, which is shaded by two large blue umbrellas. Brightly colored plants line the base of the home, complementing the fresh coastal aesthetic.
Home in St. Augustine Beach

Beachside, Pool, Super Clean, steps 2 beach, 5star

ViewBeachLocation

4.98 out of 5 average rating, 112 reviews
Guest favorite
A charming coastal house is depicted with a traditional exterior, featuring dark shingles and a welcoming porch. A staircase leads to the entrance. The background is graced with a colorful sunset, casting soft light over the surrounding greenery and homes.
Home in Vilano Beach

Oceanfront Rustic Cottage by the Sea

BeachViewNearby

4.93 out of 5 average rating, 120 reviews
Guest favorite
A living area is featured with a light yellow wall and large windows allowing natural light. A blue sofa and a recliner are arranged around a circular coffee table. A television is mounted on a white console, with framed artwork adorning the walls.
Home in Butler Beach

Ocean Village Club-First Floor Access.

BeachFamilyAmenities

4.83 out of 5 average rating, 115 reviews
Top guest favorite
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.
Home in St. Augustine

Fan Fave Waterfront: Lion’s Bridge & Old Town View

RiverViewSleep quality

5.0 out of 5 average rating, 154 reviews
Top guest favorite
A charming coastal bungalow is set amidst lush green grass, surrounded by palm trees and nature. The driveway leads to the front entrance, featuring a single-car garage. The home is framed by a clear blue sky dotted with clouds, highlighting its welcoming facade.
Home in Vilano Beach

Surfside House

ViewBeachCondition

4.94 out of 5 average rating, 236 reviews
Guest favorite
Two wooden chairs are positioned on a grassy area, facing a canal with trees in the background. A small wooden table is placed between the chairs. A white dog rests nearby, as two guests sit back, enjoying drinks while watching the scenery.
Home in Butler Beach

Crescent Beach House

BeachViewGetting around

4.88 out of 5 average rating, 216 reviews
Top guest favorite
The view from open cabana doors reveals a sandy beach with inviting turquoise beach chairs arranged facing the ocean. A colorful umbrella and a thatched cabana roof are visible, framing the serene waters and cloudy sky beyond.
Home in Vilano Beach

MARE Florida Direct Beachfront St Augustine/JAXNEW

ViewBeachAccess

4.92 out of 5 average rating, 111 reviews

Waterfront condo rentals

Guest favorite
A small balcony is furnished with two wooden chairs, offering a direct view of the sandy beach and the ocean beyond. The blue sky and gentle waves are visible, while grasses and beachgoers can be seen in the foreground.
Condo in St. Augustine Beach

Surf Side Six C-3

BeachViewWifi

4.93 out of 5 average rating, 129 reviews
Top guest favorite
A sunlit indoor pool area features large glass doors that open to an outdoor pool surrounded by palm trees. Comfortable lounge chairs are positioned around the poolside, creating a relaxing space for guests. A hot tub is visible in the foreground, enhancing the inviting atmosphere.
Condo in Butler Beach

Ocean Gallery 1/1, 2 pools

ViewBeachLocation

5.0 out of 5 average rating, 295 reviews
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

361 Fun in the Sun | Direct Oceanfront Ground Floor

ViewBeachTV

4.99 out of 5 average rating, 144 reviews
Top guest favorite
A view framed by lush tropical plants reveals the expansive waterway, with its calm, reflective surface. The image captures a serene outdoor space, featuring stone flooring leading towards the grassy area and water, emphasizing the natural surroundings.
Condo in Crescent Beach

Incredible Waterfront Townhome

RiverViewValue

4.97 out of 5 average rating, 117 reviews
Top guest favorite
Condo in St. Augustine Beach

Sunrise Special | Steps to Beach | Ocean Front

BeachViewCheckout

4.9 out of 5 average rating, 162 reviews
Top guest favorite
A view of the inviting swimming pool area is captured, featuring a large pool and a smaller hot tub surrounded by lounge chairs. The beach stretches out beyond, meeting the calm Atlantic Ocean under a clear blue sky, with palm trees framing the scene.
Condo in Crescent Beach

B207 Entire Oceanfront Condo Steps From Pool & Bch

ViewBeachLaundry

4.94 out of 5 average rating, 112 reviews
Top guest favorite
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.
Condo in Crescent Beach

Windjammer 208, Oceanfront and Riverview

RiverBeachBiking

4.99 out of 5 average rating, 130 reviews
Guest favorite
Condo in St. Augustine Beach

Oceanfront Condo! Located at Pier Park!

ViewBeachWalkability

4.86 out of 5 average rating, 114 reviews

Destinations to explore