Cottage holiday rentals in Anastasia Island

4.87 out of 5 average rating, 171 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.

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.

5 out of 5 average rating, 256 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

A charming cottage is positioned amidst a landscaped yard with lush green grass. The exterior features light-colored siding and a welcoming front porch. Decorative plants and a mature tree are visible, framed by a clear blue sky and a few wispy clouds.

4.98 out of 5 average rating, 130 reviews

Driftwood Cottage by the Sea

Great couples' getaway! Beautifully appointed cottage, just steps to the beach. Miles of beaches to walk, run or just sit in place and enjoy. Grocery stores, restaurants and shops a 5-minute walk away. Or, a 5-minute drive into the heart of St. Augustine, a charming Old World town filled with historic sites, unique restaurants, museums and art galleries. Our weather is usually great all year round but don't let a little rain, cold or wind spoil your visit. Adjust your attire accordingly.

4.93 out of 5 average rating, 216 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!

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.

4.98 out of 5 average rating, 191 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.

The entrance features a welcoming design with a vibrant pink door, flanked by wooden shutters. A rocking chair sits on the porch beside a potted plant. The doormat displays a cheerful message, inviting guests into the cottage.

4.99 out of 5 average rating, 104 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.

A charming historic cottage features a welcoming front porch with seating. The entrance is framed by intricate light fixtures and is approached via a patterned brick pathway. Lush greenery offers a serene backdrop, contributing to the inviting atmosphere of the home.

5 out of 5 average rating, 172 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.

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.

4.92 out of 5 average rating, 168 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.

Superhost

4.82 out of 5 average rating, 381 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.

A bright living area combines modern and Boho styles, featuring a yellow sofa and patterned area rug. A wall-mounted television offers entertainment. The open kitchen includes white cabinetry and bar seating, complemented by natural light from nearby windows.

4.98 out of 5 average rating, 296 reviews

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.

An aerial view highlights the charming blue cottage surrounded by lush palm trees and vibrant greenery. The proximity to pristine beach waters is visible, along with neighboring coastal homes. A walkway leads from the yard to the street, emphasizing the inviting outdoor space.

4.98 out of 5 average rating, 106 reviews

Vilano Charmer, Capo’s Cottage, 1/2 block to beach

Charming 3/2 beach cottage located in the historic Surfside Community of Vilano. Once this home belonged to the Capo Family who brought visitors from downtown St Augustine across the Intercoastal on a ferry to the beach in the 1920’s. Today, you can enjoy the vintage vibe, with modern conveniences. Only 2 min walk to Surfside Beach! Under new ownership, formerly an Airbnb for many years. One small dog will be considered.

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.