Private suite holiday rentals in Anastasia Island

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Top-rated Self-Contained Units in Anastasia Island

Guests agree: These Self-Contained Units are highly rated for location, cleanliness and more.

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Top Guest favourite

A serene waterfront view is captured at sunset, showcasing a pool surrounded by lush grass and palm trees. A shaded seating area is positioned next to the pool, overlooking the water where boats can be seen in the distance.

Guest suite in Butler Beach

4.93 out of 5 average rating, 696 reviews

Waterfront suite, Dogs are cool no pet fee

Newly remodeled, waterfront suite. See dolphins, Osprey, and more frolicking in our amazing backyard overlooking the Matanzas river, & did I mention the breathtaking sunsets. 6 minute drive to Crescent Beach, one of the most beautiful beaches in Florida. Close to downtown historic St Augustine 20 min, Amphitheater concert venue is 15 min. Private entrance, full on suite bath, fishing dock, kitchenette, pool, ample free parking & internet included. Professional pool cleaning is on Mondays.

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Top Guest favourite

A living space features a white sofa adorned with a patterned throw, complemented by a rustic wooden coffee table. A large round mirror and star decorations hang on the walls, while a ceiling fan adds functionality. Doorways lead to adjacent rooms, including a bathroom.

Guest suite in St. Augustine

4.98 out of 5 average rating, 557 reviews

Winter Hawk Hideout

15 minutes from ol' St Augui. Located in the heart of this typical Florida woods and nested by oaks that saw the Seminole War as we are walking distance from Ft Peyton and 2 miles away from where Osceola was captured. The house sits on half acre of gardens and the decor is ranch, asian and whimsical .The goal is for you to feel transported away for a while. I do have 2 very small, well behaved and quiet dogs and one never seen cat. They do not have access to your quarters or are allowed in.

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Top Guest favourite

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 favourite

A charming two-story house is depicted with a red exterior and white railings. The image shows a pathway leading to the entrance, framed by lush greenery. A covered porch is visible on the second level, with a ceiling fan enhancing the inviting atmosphere.

Guest suite in Lincolnville

4.91 out of 5 average rating, 144 reviews

Historic w/ Parking BYO Bikes, Golf Cart, Kayaks

1/1 with private entry in a 100+ yr old house w/ large porch & fenced yard. This special place is close to everything & easy to plan your visit to historic downtown or miles of sandy beaches. Located in Lincolnville & walking distance to old town, restaurants, & waterfront parks. Rental bikes & scooters are at the end of Riberia or BYO (don’t forget a lock!) Also, nearby trolly stops and romantic horse drawn carriages are all great ways to explore. Park now has pickleball & b-ball courts.

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Top Guest favourite

A spacious studio features a king bed with a patterned blanket, complemented by a cozy sofa and armchair. A kitchenette is visible in the background, along with a modern ceiling fan overhead. Large windows allow natural light to fill the room.

Guest suite in St. Augustine

4.98 out of 5 average rating, 446 reviews

Cozy Studio 15 mins to Beaches & Historic Downtown

Outstanding location & amenities, 15 minutes to beaches, St. Augustine Amphitheater and historic downtown in a quiet, friendly neighborhood. Minutes walk to the intercostal, w/ piers & boat ramps, gorgeous views, perfect for walks. Close to lots of shopping & dining. Ample parking-trailers & boats welcome. Kid friendly w/ toys, pack & play + more. Laundry, walk-in shower, private entrance. Private deck w/ cheerful seating. Well equipped kitchenette. Easy drive to theme parks, Daytona + more.

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Guest favourite

A queen-sized bed is prominently featured, made of light wood with an elegant headboard. Crisp white linens are complemented by striped pillows. Natural light enters through the dual windows adorned with neutral-toned shades, accentuating the serene ambiance of the room.

Guest suite in St. Augustine

4.97 out of 5 average rating, 237 reviews

Bamboo Hideaway

Welcome to Bamboo Hideaway, a romantic getaway located under a canopy of over 10 ancient Live oak trees and sky high bamboo! Located less than 2 miles from Vilano beach and 2 miles from the heart of downtown, BH is located in one of St Augustine's most beautiful historic neighborhoods. The apartment is situated over the owner's detached garage and boasts a private entrance with a lush courtyard of tropical plants and its own outdoor shower to rinse off in after a long day at the beach.

ValueFamilyLong stay

Top Guest favourite

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, 533 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 favourite

An airy living area features a light blue wall, a plush sofa positioned in front of a flat-screen TV, and decorative artwork. A small black table rests in the center, complemented by vibrant flowers. A breakfast bar with four black chairs is visible alongside a granite countertop.

Guest suite in St. Augustine

4.97 out of 5 average rating, 341 reviews

Cozy 2BR on Charlotte St. Downtown St. Augustine

Beautifully renovated 2BR apartment boasts a prime downtown in the historic district of St. Augustine!!! Easily walk to plenty of restaurants, shops, and local attractions. After fun- field day, you can relax on one of the two balconies overlooking charming Charlotte Street or kick back in an open living area furnished with a plush sofa and 45" TV. Whip up tasty meals in the well-equipped kitchen, outfitted with stainless steel appliances. The apartment sleeps up to four guests.

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Guest favourite

The image captures a serene beach at sunset, where the sun is partially obscured by clouds, creating soft orange and blue hues in the sky. Tall grasses sway gently in the foreground, framing the scene of the calm ocean waves reflecting the fading light.

Guest suite in Butler Beach

4.89 out of 5 average rating, 794 reviews

Beach and Serenity

6 BLOCKS to BEACH, off of the intercostal! Studio apartment, sleeps up to 4. Quiet neighborhood, close to all. Several restaurants/shops within walking distance. Beach bikes included, perfect for bike rides along the beach. Private entrance off of porch, which includes chairs to relax in, beach toys, towels, chairs. *yes, we are pet friendly, however, ONE PET PER STAY WITH APPROVAL *also, we cannot split weekends, so please book accordingly, fridays and Saturdays booked together

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Top Guest favourite

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, 380 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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Top Guest favourite

Guest suite in St. Augustine

4.95 out of 5 average rating, 802 reviews

Sheepdog Hideway - on Anastasia Island near Amp!

Welcome to your relaxing island retreat on Anastasia Island, just minutes from the St. Augustine Amphitheatre and Anastasia State Park. This cozy private suite is attached to family home, however it has its own entrance and no shared inside space for complete privacy. Enjoy complimentary beach cruiser bikes for a 1.5-mile ride to the beach or 3 miles to historic downtown. We do have two friendly dogs on site, but then can be kept away if requested.

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Top Guest favourite

The exterior of the suite is shown, featuring a spacious lawn and a well-kept facade. Several outdoor chairs and a decorative wreath are positioned beside large windows, allowing natural light to fill the interior. Lush greenery and palm trees frame the property.

Guest suite in St. Augustine

4.98 out of 5 average rating, 150 reviews

Álvarez Sánchez Suite

Located on beautiful Anastasia Island, our beautiful suite is walking distance to historic St Augustine via the Bridge of Lions and biking distance to St Augustine Beach. You will fell in love with St. Augustine and the Davis Shores neighborhood right over the Bridge of Lions on Anastasia Island. Come and enjoy the real island experience with our local beaches, restaurants, people,ghost stories, or simply sitting outside under our blue skies.

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