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Cottage vacation 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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Guest favorite
Cottage in St. Augustine
4.86 out of 5 average rating, 180 reviews

Pet Friendly Getaway 3 Blocks to Old City-Unit A

Welcome to your perfect retreat! This cozy and stylish property is ideally located three blocks from the historic Old City, where you can explore charming streets. Plus, the Atlantic Ocean is just 3 miles away, offering easy access to beautiful beaches for relaxation or adventure. Amphitheatre 1.5 miles away. This location has it all and is on A1A and many local restaurants and bars. Enjoy comfortable, modern amenities in a well-appointed space, making it the perfect base for your next getaway.

Top guest favorite
Cottage in St. Augustine
5 out of 5 average rating, 267 reviews

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

Guest favorite
Cottage in St. Augustine
4.92 out of 5 average rating, 225 reviews

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!

Top guest favorite
Cottage in St. Augustine
4.98 out of 5 average rating, 193 reviews

Perfect Waterfront Retreat w/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 & salt water 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.

Top guest favorite
A charming, light green cottage features a welcoming front porch with white railings and steps. The surrounding area is landscaped with shrubs and trees. A paved walkway leads to a fenced yard, providing a sense of privacy and comfort.
Cottage in St. Augustine
4.99 out of 5 average rating, 107 reviews

Location! Stylish Downtown Cottage Getaway

Charming and centrally-located 2 Bedroom Cottage. Only a 12 min walk to the Historic Core so park your car and enjoy a beautiful stroll Downtown! After a day spent sightseeing you will appreciate the comfort of this little getaway. The open floor plan w/vaulted ceilings in the main space has a well equipped Kitchen, Dining space, Living Room w/TV plus work space. Two comfy Queen Beds w/TV and a roomy walk in shower round out the space. Relax on the porch swing or patio w/fenced yard.

Top guest favorite
The inviting entrance of the historic cottage features a well-lit doorway framed by charming potted plants. A small outdoor seating area is visible, set with a table and chairs, while warm light spills from the interior windows, enhancing the welcoming ambiance.
Cottage in St. Augustine
5 out of 5 average rating, 180 reviews

~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.

Guest favorite
Cottage in St. Augustine
4.91 out of 5 average rating, 173 reviews

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.

Top guest favorite
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 St. Augustine
4.92 out of 5 average rating, 291 reviews

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.

Top guest favorite
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
4.97 out of 5 average rating, 185 reviews

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.

Guest favorite
Cottage in St. Augustine
4.82 out of 5 average rating, 386 reviews

Sea La Vie Beach Studio.

Our renovated studio is on a quiet cul-de-sac, one block from the beach! It is one side of a duplex and is perfectly located within walking distance to restaurants, family-friendly activities, nightlife, and public transport. It is across the street from the pier and the piers weekly farmers market. It is a short drive to historic downtown St Augustine. The neighborhood is quiet and safe. Our place is good for couples, solo adventurers and business travelers.

Top guest favorite
Cottage in St. Augustine
4.93 out of 5 average rating, 115 reviews

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.

Guest favorite
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 St. Augustine
4.89 out of 5 average rating, 105 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

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