Cottage vacation rentals in Anastasia Island

~Romantic Historic 1888 Cottage~Walk to Downtown

Come live in history! This cottage traces its roots back to humble beginnings, built by freedmen and still stands today as one of Lincolnville's original historic treasures. Nestled in the heart of America's oldest city, this endearing historic 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.

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.

119 Kings Ferry Way Historic Cottage

Absolute treasure in the heart of the Lincolnville Historic District. Ideal private and peaceful location within walking distance of great restaurants and historic sites, and FREE on site parking. Our other two side-by-side Cottages are available for groups of up to a total of eight adult guests who want to be in close proximity but also want privacy. Experience one of the most authentically restored century old cottages in the area. Perfect for extended stays or short visits.

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.

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.

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.

Oceans 11: Steps from the Ocean, Quiet Beach

Magical Oceanside Beach Cottage with Original Hardwood Floors. Antique Charm mixed w/ modern convenience. Quiet, clean beaches. 3rd house back from the Ocean on St. Augustine's most desirable beach. North of the "A" Street Ramp, so there are NO cars driving on our beach. East side of beach blvd so No streets to cross… state park beaches also within walking distance. Follow us on In-sta-gram for pics & local tips @happyhoppervacation

Beachcomber Oasis

The quintessential 1930s beach cottage - loaded with charm inside and out while updated for comfort and convenience. Home features amazing outdoor space - fully fenced for privacy.There are multiple outdoor dining and gathering areas, lush tropical gardens, and an elevated deck with a peek at the ocean when standing. Walking distance to local grocery, shops, restaurants, minutes to downtown St.Augustine and just steps to the beach!!