Vacation rentals in Anastasia Island

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Top-rated vacation rentals in Anastasia Island

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

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Top guest favorite
A spacious bedroom features a comfortable bed with a woven headboard, flanked by two bedside lamps. Natural light enters through a window dressed with wooden blinds. A ceiling fan circulates air, while decorative paddles add an interesting touch to the wall.
Apartment in Butler Beach
4.93 out of 5 average rating, 336 reviews

Toast Sunsets from the Wraparound Deck at a Coastal Oasis

A wonderful getaway, this property includes two airbnbs. A two story home with a detached guesthouse. These listings can be rented separately or together, if available. This listing is space is about 1,000 sq ft. You will have exclusive access to the second story apartment and wrap around porch. You will have one dedicated parking spot. There is a small backyard area with an outdoor shower that is shared with the other Airbnb. Access to the apartment is via keypad code. Were available if you need anything, but many times we only communicate with our guests through Airbnb! This Crescent Beach retreat is set back a bit from the road just 3 blocks from the ocean and 8 miles from downtown. Uber is the best way to get around without a vehicle. The Crescent Beach house is on A1A, set back a bit from the road. A1A is a moderatly busy two lane highway. However, you access the home from the backyard, which is also where you park, via a short grass road. Uber is the best way to get around if you do not have your own vehicle. This property includes two airbnbs. Each listing has one dedicated parking space in the rear of the property via a short grass backroad. The parking spaces are right next to each other.

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Top guest favorite
A spacious living area features wood-paneled walls and large glass doors, offering views of the ocean. A chandelier hangs from the ceiling. The seating area includes a comfortable couch and a dark coffee table, while a television with vibrant display adds a touch of modernity.
Condo in St. Augustine
4.92 out of 5 average rating, 118 reviews

Treehouse Artist Haven Direct Oceanfront 2br

Located along a stretch of pristine beach is this spectacular house with a beachfront location like no other. This unique home encompasses 3 separate floors. This is the middle of the 3 floors “The Artists Haven”. Inside you will find 2 bedrooms, a bath and an open plan living/dining area that opens out to a surrounding deck with seating. Enjoy uninterrupted ocean views from the wrap around deck with many places to relax & watch dolphins, sip your morning coffee or watch the pink sunsets. 1002

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Top guest favorite
Bungalow in Butler Beach
4.96 out of 5 average rating, 238 reviews

Ooo Laa Laaah Pets welcome

Private, fenced in yard and private Free standing cottage in quiet neighborhood. Private, fenced in yard! Pets are welcome. Fees apply. 2 washers and dryers, internet/wifi, 2 smart TVs. All kitchen appliances. One story. The beach is a one block stroll with no major streets to cross. Keep your car at home..walk to the beach 2 minutes stroll . Downtown, St. Aug. is a 10 minute car ride. Not a condo scene. Crescent Moon cottage is in front but completely separate. Shared laundry room.

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Top guest favorite
A panoramic view of a beach scene at sunset, featuring vibrant clouds in shades of pink, orange, and purple. The sun dips below the horizon, reflecting off the water's surface. Grassy dunes are visible in the foreground, framing the tranquil scene.
Guest suite in Butler Beach
5.0 out of 5 average rating, 376 reviews

Entire guest suite short walk to beach.

Enjoy exploring beautiful, historical St. Augustine then kick back and take it easy at this private, quiet beach retreat within a short walk to the beach. Separate keyless entry allows for self check-in. Queen size bed, fully furnished, with amenities including a Keurig coffee maker, iron, hair dryer, beach cruiser bicycles, beach chairs, towels, umbrella and gas grill for cooking out. Flat screen TVs in both the living room and bedroom with Netflix and Amazon Prime included and Free WiFi

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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 spacious living area features a light gray sectional sofa with a chaise, positioned on a natural fiber rug. A round mirror enhances the sense of space, while a dining area is visible in the background, complete with wooden chairs and a table.
Villa in St. Augustine Beach
5.0 out of 5 average rating, 129 reviews

VILLA One

The Villas are designed for short stays, long weekends or for a unique styled location for brands to shoot their products. The space features warm tones, natural finishes and local art for an effortless vibe that allows visitors to relax the second they walk in the door. Complete with two bedrooms, two bathrooms and a backyard complete with tropical landscaping, lounge area, dining and outdoor shower. One of 4 Villas located in St. Augustine Beach. Not pet friendly. @staugustinebeachvillas

LocationFamilyCleanliness

Top guest favorite
A light-filled living area is depicted, featuring a spacious couch positioned against a vibrant artwork of a clownfish. Sliding glass doors lead to a serene outdoor space, while colorful paintings adorn the walls, adding artistic charm to the room.
Guest suite in St. Augustine
4.99 out of 5 average rating, 537 reviews

Art Studio Space – Quiet – Walk to Beach

This very private studio apartment is on Anastasia Island, with its own entrance across the street to Anastasia State Park, which includes the St. Augustine Amphitheater in a quiet, friendly beach neighborhood. This ideal location is quite literally "a walk in the park" to a beautiful undeveloped Florida beach; or a 10 minute drive across the famous Bridge of Lions to historic downtown St. Augustine – with quick access to the many local attractions and great restaurants in the area.

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Top guest favorite
The exterior of Casa Coquina is presented, featuring a charming façade with rounded archways. A light blue garage door complements the neutral-colored walls. Lush greenery, including palm trees and decorative plants, enhances the inviting entryway, while a driveway leads to the garage.
Home in St. Augustine
4.99 out of 5 average rating, 136 reviews

Casa Coquina Walk to Downtown Clean Quiet Spacious

Casa Coquina offers a uniquely central location for your visit to the nation's oldest city. Located across from Salt Run Waterway & walking distance to many restaurants & entertainment, this newly renovated home offers 2 bedrooms & 2 full bathrooms, large living room, Florida room & outdoor patio. It is a 2-minute drive to Historic Downtown & 5-minute drive to our beautiful beaches. The huge tree-shaded yard is completely fenced in for child/pet safety & total privacy. Enjoy!

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Top guest favorite
A screened-in pool area features a crystal-clear water pool with a shallow entry. Two chairs, one green and one yellow, are positioned beside the pool, surrounded by natural greenery and a wooden fence. Sunlight brightens the space, creating a relaxing outdoor ambiance.
Guest suite in St. Augustine Beach
4.94 out of 5 average rating, 382 reviews

Ground floor--just 365 steps to beach!

Beautiful ground floor of a two-story house only 365 steps from one of the most beautiful beaches in the United States. Close to the Ancient City, with all its amenities and attractions. Within walking distance of great restaurants and bars. Private entrance, pool, fully furnished kitchenette with Keurig type coffeemaker, Internet, Cable TV. Two bedrooms, one with a queen bed, and the other a double Murphy bed. On-site parking for one car provided.

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Superhost
The entrance features a solid brown door with modern glass accents, welcoming guests into the cottage. A small decorative mat lies on the porch, and bright blue siding complements the entryway. Light fills the interior through visible open spaces beyond the entrance.
Cottage in Butler Beach
4.89 out of 5 average rating, 112 reviews

Tones of Blue

Just a short walk to one of St Augustine's loveliest beaches, this completely renovated 2-bedroom, 2 bath beach cottage is sharp to say the least! Well appointed with a full kitchen, washer dryer and 2 king beds. Lots of parking and a fenced outdoor seating area. Quiet neighborhood close to downtown. There is also a detached garage apartment available to rent for additional guests. Sorry but no pets or smoking

LocationFamilyCheck-in

Top guest favorite
The living area features a comfortable white sofa accompanied by a woven coffee table. A ceiling fan circulates air above, while a wall-mounted TV is positioned for easy viewing. Bright wood flooring and light walls create a spacious ambiance, complemented by a dining area in the background.
Cottage in St. Augustine
4.96 out of 5 average rating, 277 reviews

1920s Coastal Cottage | Walk to Amp & Downtown

Light-filled, historic charm meets modern coastal living. Built in the 1920s, this meticulously updated 2-bedroom, 1-bathroom cottage features original heart pine floors, walls of windows, and a breezy, open feel that instantly makes you feel at home. Nestled in the quiet, historic Lighthouse Park neighborhood, you are right between the beach and historic downtown — 5 minutes to both.

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Top guest favorite
The kitchen features modern appliances, including a refrigerator, microwave, and dishwasher. White cabinetry provides ample storage. A dining table with four chairs is positioned near the door, and a light fixture illuminates the space. A decorative rug adds a touch of warmth.
Cottage in St. Augustine Beach
4.95 out of 5 average rating, 508 reviews

Beautiful Beach Cottage

Located smack in the middle of St. Augustine Beach, this beautiful beach cottage has private access to the beach and pool. Close to the Ancient City, with all its amenities and attractions. Close to great restaurants and bars. Fully furnished kitchen with Keurig type and brewing coffeemakers, all rooms with TVs.

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Popular amenities for Anastasia Island vacation rentals

Frequently Asked Questions

  • Where is Anastasia Island located?

    Anastasia Island is just off the northeast coast of Florida, near the city of St. Augustine. It is known for its beaches, natural preserves, and relaxed coastal atmosphere.

  • When is the best time to visit Anastasia Island?

    Late spring and early fall are often suggested for comfortable weather, with temperatures ranging from about 65 to 84°F (18 to 29°C) and manageable rainfall. Cooler winters appeal to those wanting fewer crowds, while summer brings warmer days and higher humidity.

  • What are some things to do near Anastasia Island?

    Explore wide sandy beaches, visit Anastasia State Park for walking trails and native wildlife, or discover the historic St. Augustine Lighthouse and Maritime Museum. The area also has local seafood restaurants, nature preserves, and opportunities for water activities.

  • How is the weather near Anastasia Island?

    Anastasia Island experiences mild winters around 45–68°F (7–20°C), with warmer, humid summers near 90°F (32°C) and peak rainfall during late summer. Spring and fall are frequently noted for moderate temperatures and less humidity, making outdoor activities inviting.

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