Cottage holiday rentals in Anastasia Island

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Top-rated cottage rentals in Anastasia Island

Guests agree: These cottages are highly rated for location, cleanliness and more.

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Top Guest favourite

Cottage in St. Augustine Beach

Direct Oceanfront! : Sleeps 16! : Walk Everywhere!

Salty C Cottage is a beautiful 7 Bdrm, 3 Bath Oceanfront home right on Saint Augustine Beach, 5 minute walk to restaurants & bars. The Cottage is set up on two fully self contained levels that can easily accommodate 16 guests (max 14 adults) and is one of the largest rentals you'll find Oceanfront. Ample on-site parking for 6 vehicles. Includes an Outdoor Grill, Beach Chairs and Umbrellas all complimentary for our guests. Strictly No Pets / Weddings / Parties or additional visitors on-property.

FamilyLocationBathroom

4.98 out of 5 average rating, 178 reviews

Top Guest favourite

A charming two-story cottage is seen behind an ornate wrought-iron gate, framed by vibrant green grass and well-maintained landscaping. Large windows allow natural light to fill the exterior, and a cheerful yellow door adds a welcoming touch.

Cottage in Lincolnville

Walk Historic Downtown! “Blue Heaven”

Stunningly renovated cottage combines modern amenities with vintage charm... * 2 master suites with queen beds * Quiet neighborhood walking distance to explore The Nation's Oldest City * Clawfoot tubs inside and out (along with showers, of course!) * Big screened-in porch with hanging daybed * Off-street paved parking * Fully fenced backyard, Weber grill, gas fire pit * Fast Wi-Fi and Smart TV * 2 blocks to Fish Camp, Ice Plant, LaNuvelle, trolley stop * 10 minute walk to central downtown

ValueFamilyComfort

5.0 out of 5 average rating, 278 reviews

Superhost

Cottage in St. Augustine

Coastal Cottage -firepit, pet fence, kayaks, bikes

Located in the historic Lighthouse Park neighborhood, this charming 1940s coastal cottage is easy strolling distance to the Lighthouse, Alligator Farm, mini-golf, cafes & more! It is only a 0.8-mi walk to the Bridge of Lions, where you can walk over the Bay to downtown St. Augustine. You couldn't ask for a better location! It's on Anastasia Island so you're a short walk/bike/car ride from the beach & Ampitheater. It's cozy, pet & kid-friendly with a big backyard. Kayaks & bikes available!

LocationFamilyTV

4.91 out of 5 average rating, 235 reviews

Top Guest favourite

The exterior of a two-story cottage showcases wooden shingle siding and a welcoming front porch. Lush greenery and colorful plants surround the house, with potted flowers placed in the foreground. Sunlight highlights the charming architectural details against a clear blue sky.

Cottage in St. Augustine

Charming 2/2 Cottage ~ Walk to Historic Downtown

This St. Augustine home is right in the heart of quaint & historic downtown! The lovely two level cottage has an upstairs full bath and two private bedrooms each with a queen bed. Downstairs is a second full bath, as well as a living room and full kitchen. The space is perfect for 1-4 guests. A short 8-10 minute walk allows visitors to explore the many downtown historic sites, museums & restaurants. One parking spot is available on our lot. Free street parking for additional cars.

LocationValueHospitality

4.98 out of 5 average rating, 319 reviews

Guest favourite

A spacious deck overlooks a clear blue saltwater pool surrounded by lounge chairs and umbrellas. Lush greenery and palm trees frame the view of the water and dock area in the distance, creating a serene outdoor space for relaxation.

Cottage in St. Augustine

Fun Waterfront Retreat, Heated Pool, Rooftop Deck

You've found your waterfront oasis tucked under the White Birds of Paradise! This spacious retreat was formerly a commercial art gallery. Two queen beds, one full bathroom & full kitchen make for comfortable living! You have a fenced path leading you down to the beautiful waters of Salt Run where a rooftop deck & saltwater in-ground pool invites you to relax and slow down. Less than a mile to downtown St. Augustine, a little over a mile to the Amphitheater and about 3 miles to the beach.

LocationValueKitchen

4.98 out of 5 average rating, 196 reviews

Top Guest favourite

Cottage in Lincolnville

~Romantic Historic 1888 Cottage~Walk to Downtown

Come live in history! This cottage traces its roots back to humble beginnings and it still stands today as one of Lincolnville's original historic treasures. Nestled in the heart of America's oldest city, this endearing circa 1888 cottage offers an intimate, refined escape with a boutique ambiance. This is the ideal retreat for travelers seeking a romantic getaway or guests who wish to be transported to a more graceful time. Modest in scale but grand in experience.

ValueLocationLayout

5.0 out of 5 average rating, 195 reviews

Superhost

A newly renovated historic home is set against a serene natural backdrop, featuring a large deck accessible via a wooden walkway. The exterior showcases multiple arched windows and a modern roof deck, surrounded by lush vegetation and reflected in the calm waters of the marsh.

Cottage in Vilano Beach

The Shire on 1 acre marshfront with dock and Spa

One of a kind 1930s historic home, newly renovated and transformed into a beautiful secluded getaway. new luxury finishes, while holding its traditional charm. No Events allowed. Rooftop deck, sunrise views of the Atlantic ocean, Downtown, and sunsets over the river. The new dock with covered roof hosts a national geographic like eco system. It’s short walk to the beach and 3 miles to downtown St George street. Follow along @carcabaroad for weekly content of the home.

ValueFamilyBackyard

4.91 out of 5 average rating, 179 reviews

Top Guest favourite

The exterior of a one-story unit is displayed with a red metal roof and a welcoming porch. A colorful umbrella provides shade over outdoor seating. A grill is positioned nearby, and landscaped areas with flowers enhance the entrance.

Cottage in Butler Beach

Livin’ the Dream at St. Augustine Beach

Bright beachy unit with all amenities including community pool, close public beach access and essentials including bedding, towels, beach cruiser bikes and grill. Enclosed porch and outside deck are ideal for grilling out or hanging out. My home is located in Peppertree RV Resort . The public beach access is a short 10 minute walk away. The unit has parking for two vehicles with extra parking available in an overflow lot. A washer and dryer are located inside the unit.

ValueFamilyBarbecue

4.92 out of 5 average rating, 301 reviews

Top Guest favourite

A private courtyard is softly illuminated by string lights, creating a warm ambiance at night. Lush greenery, including large tropical plants, surrounds a rustic wooden dining table set on a patterned stone surface, inviting outdoor gatherings.

Cottage in St. Augustine Beach

Enchanting courtyard, quiet cottage by beach

Very comfortable, relaxed island breezy appeal. King and queen bedrooms, additional quality blow up queen mattress. Open living space with French doors leading to back deck. Spacious kitchen, dining & breakfast nook. Gorgeous private courtyard with string lights for magical night time ambiance. Expect everything you may need with complimentary wine and baked goods upon arrival. Local dining scene is incredible! No smoking inside! *See house rules for pet info.

FamilyLocationBiking

4.97 out of 5 average rating, 189 reviews

Guest favourite

A charming cottage is surrounded by lush greenery and tropical plants. The entrance features a shaded outdoor seating area with two chairs and a table, set under a red umbrella. The light-colored house is topped with a metal roof and has multiple windows, inviting natural light.

Cottage in St. Augustine

Downtown House near Flagler College & St George st

Enjoy this charming, (originally a carriage house in 1899) adorable cottage, nestled in the heart of historic downtown St Augustine! It's a rare find for its proximity. Walking distance to all of downtown and Flagler College! No driving necessary for a full complete vacation. This amazing little house has a fully stocked kitchen that opens up to a shaded deck. We do require guests be 25+ to book instantly otherwise please inquire. Please read the whole listing.

LocationValueNearby

4.89 out of 5 average rating, 243 reviews

Top Guest favourite

A cottage is set amidst lush green grass and palms, showcasing a covered porch with lattice details and colorful beach accessories. The building's exterior features a welcoming entrance, and the clear sky offers a bright, inviting atmosphere.

Cottage in St. Augustine Beach

Slice of Paradise/Harlow & Hailey's Beach Cottage

A great community of small cottages. Check out our reviews. You will enjoy time on the back deck with white lights in the evening and your own backyard. The cottage is well equipped and we pride ourselves on how it is maintained and cleaned. Incredibly convenient location to all things St. Augustine and excellent beach access. Check us out! You will not be disappointed. We would love to have you as our guests.

LocationValueOutdoor spaces

4.94 out of 5 average rating, 124 reviews

Guest favourite

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

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

FamilyLocationTV

4.89 out of 5 average rating, 113 reviews