Cottage vacation rentals in Anastasia Island

Lakefront cottage and dock★Free bikes & paddleboat

Bring your fishing gear or small boat to enjoy a fun getaway at the Captain's Cottage with a dock on Lake Stella. Key-less entry allows for self check-in and welcomes you to this comfortable clean 962 sq. ft. space with two queen size beds, one bathroom, full kitchen, florida room, and a fenced-in backyard. A paddle boat is provided. Three kayaks and 2 bicycles are also available! Or you can bring your boat and go fishing! Enjoy swimming, lovely sunsets and strolls around the beautiful lake.

Unique mid-century modern Lemon Tree Cottage

Bright and cheery Mid-Century modern inspired cottage located in the northern section of St. Augustine. Tucked away on a quiet street, only 2 miles from the heart of historic downtown and 2.5 miles away from the pristine Vilano Beach. All new tile flooring, countertops, fridge and stove, bathroom vanity, linens and area rugs. Meticulously curated to be a unique and fun stay with vintage decor. Great Value Stay for a single family home while being close to downtown. Plenty of off street parking.

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!

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 & 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.

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 * Fenced yard, Weber grill, gas fire pit * Fast Wi-Fi and Smart TV * 2 blocks to Fish Camp, Ice Plant and LaNuvelle * 10 minute walk to central downtown St Augustine

~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. Discreet in scale but grand in experience.

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.

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.

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.

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.

Couples Boho Bungalow close to Beach and Downtown

Enjoy St. Augustine – the nation’s oldest city – and everything it has to offer from this cozy, Boho themed 1 bed / 1 bath getaway. Located near the heart of the city, it is close enough to walk to the historic St. George Street while also maintaining privacy and quiet comfort. With new, modern amenities, a back porch, a yard, and ample dedicated parking, this home is everything you could want on your trip to beautiful St. Augustine, Florida.

Island Style Guest Cottage

The island style guest cottage and bath house are in a quiet suburban neighborhood. There is an off street parking area reserved for the guest that is large enough to fit a vehicle with a trailer. The cottage is located close to downtown St Augustine, St Augustine beach, and St Augustine Amphitheatre, and just far enough away to get away from the congestion there. It is only 5 or 6 miles to all of those spots.