Vacation rentals with a fireplace in Anastasia Island

4.89 out of 5 average rating, 186 reviews

Chelsea House 3/2, sleeps 6 Free parking Downtown!

Welcome to Chelsea House. Bring your kids, your dog & your boat. It's a sizable 3-bedroom 2 bath rustic style home located on an oversized lot in a quiet residential boating community. If you're looking for something a little different, this is it! It is furnished with an eclectic collection of antiques & reproduction pieces, this home's style will reflect your visit to our nation's oldest city, the home is comfortable, relaxing & private. It is just a 10-minute drive to the Historic District.

The exterior of the two-story property is shown, surrounded by lush greenery and trees. A spacious gravel driveway leads to the home, which features a covered porch on the upper level. The lower area includes a decorative railing and opens up to a well-maintained yard.

4.89 out of 5 average rating, 110 reviews

Tree Tops: Where Everything is brand new

Take it easy at this unique and tranquil getaway nestled in the Tree Tops. All new appliances, furniture, electronics, sheets, and towels are found in this totally remodeled home. No expense was spared in making your stay as comfortable as possible. This is your perfect get away from the hustle and bustle of life. Enjoy your first cup of coffee on one of 3 porches. Tree Tops is also close to popular attractions, located 6 miles to Vilano Beach and 4 miles to St. Augustine’s historic district.

The living room is furnished with two light-colored sofas and a central coffee table, creating a spacious and inviting space. A decorative fireplace is framed by mirrors and artwork, while natural light filters in through shuttered windows and greenery adds a touch of nature.

4.94 out of 5 average rating, 221 reviews

Historic Designer Home • Luxury Baths • Steps2DWTN

Off Street Parking for 2 vehicles 2 Min. walk to St George St 5 Min drive to Anastasia State Park Beach 6 Min drive to Fitness Club/Pool High Speed Starlink Internet Luxury Retreat in Historic Downtown. Indulge in a charming vacation rental featuring a spacious living room, gourmet kitchen, and luxury baths. Immerse yourself in the rich history and vibrant culture, with its charming streets and local attractions. Whether seeking adventure or relaxation, this retreat offers the perfect base.

4.94 out of 5 average rating, 207 reviews

St Augustine Home Walk to Beach on Canal

Relax and enjoy our Island Home-Walkable to the Beach. This spacious 3 bed/2 bath Island home is located on a beautiful canal and is just a short bike ride/walk to the beach with dedicated beach access. Bring your boat, kayak or paddleboard so you can explore and fish the scenic waterways. Only 15 minutes outside of Historic Downtown St Augustine, "A Treasured Retreat" is the perfect place for making lasting memories for families, friends, beach-goers, boaters and everyone in between.

4.93 out of 5 average rating, 104 reviews

Beach Bums Paradise|Private Pool|8-min walk to BCH

Welcome to Beach Bums Paradise, where sun-kissed days and relaxation await you. Nestled in only an 8-min walk from the sandy shores, this idyllic property seamlessly blends the best of both worlds: an exquisite private pool, private hot tub, fire pit and the enchanting allure of the beach, just three short blocks away. If you dream of a vacation filled with sun-soaked days, gentle ocean waves, and blissful poolside lounging, then look no further! New private fully fenced backyard!

Condo in St. Augustine Beach

A cozy living area features soft beige furnishings and decorative blue pillows. A wooden coffee table occupies the center, while a stone fireplace adds warmth. Large sliding doors provide natural light and reveal views of the outdoors, framed by sheer curtains.

4.92 out of 5 average rating, 143 reviews

Quiet, Updated Condo - Pool, Bikes & Pickleball!

Relax at our beautifully updated 2BR/2.5BA condo in a quiet, family-friendly St. Augustine Beach community! Newly renovated guest and powder bathrooms completed for summer 2026 (not yet pictured). Enjoy easy beach access via a private boardwalk, pool, hot tub, tennis & pickleball courts, beach gear, bicycles, private balconies, and a fully stocked kitchen. Conveniently located near restaurants, shops, and historic downtown St. Augustine—perfect for your next coastal getaway!

Apartment in St. Augustine

The kitchen features modern white cabinetry and a spacious countertop with a light gray surface. Stainless steel appliances, including a microwave and stove, are visible. Natural light enters through a window, illuminating the area, while a dining table is seen nearby.

4.93 out of 5 average rating, 219 reviews

Spacious Beach Side Sanctuary King Bed & Sunny

Walk to everything! Beach side 2nd floor unit with lofted ceilings provides ample comfort for 2 couples or 1 family. 2 bedroom, 2 bath with laundry in unit & a wrap around porch. This beach home is spacious and luminous. Sunlight streams in through four sets of sliding glass doors. The decor is also bright and beachy, featuring two stone faced fireplaces (electric). Only 8 lots from the beach and has a gorgeous and newly renovated all white kitchen and dining room.

4.97 out of 5 average rating, 178 reviews

"CORAL COTTAGE" in St. Augustine near the Beach

CORAL COTTAGE is a cute little "beach house" located at St. Augustine Beach. It is tastefully decorated, newly renovated and in an ocean community. The Atlantic Ocean is just a short walk away with a crosswalk for safety. The house has a new deck and railing for sunbathing, outdoor shower, full kitchen, etc. Separate downstairs space efficiency space sleeps 3 and only for upstairs guests for an additional charge. Only shared space is the laundry room.

5 out of 5 average rating, 127 reviews

Lush greenery frames a wooden pathway leading to a sandy beach, with palm trees and residential buildings visible in the background. The sky is illuminated by soft hues of sunset, creating a serene backdrop for the coastal environment.

Condo in St. Augustine

Boutique Beachside condo with easy access to beach

Skipper’s Hideaway is a charming beachside retreat that sleeps up to six, with a king bed, queen sofa pull-out, and twin daybed with trundle. Located on the ground floor for easy access, the condo offers a partial Atlantic Ocean view from the living room window. Just steps from Crescent Beach, this peaceful spot is perfect for relaxing. For more excitement, the shops, restaurants, and nightlife of downtown St. Augustine are only a 15-minute drive away.

An inviting outdoor area features a stone fire pit surrounded by white adirondack chairs. A vibrant sunset casts warm colors over the scene, while a solar heated pool glistens nearby. Lounge chairs, umbrellas, and tropical landscaping enhance the charming ambiance.

4.97 out of 5 average rating, 106 reviews

Island Retreat: Pool/Hot Tub/Tiki Bar/Close2Beach

ISLAND RETREAT - Truly a One of a Kind Private Outdoor Living Experience! ✔ 3 Comfy Bedrooms (Extra 4th Private Sleeping Room) and 2 Full Baths ✔ Solar Heated Pool and Brand New Hot Tub ✔ Tiki Bar, Yard Games and Grill ✔ Firepit ✔ Super Close to New Beach Access Point (.25 miles) ✔ Short drive to Downtown St. Augustine (15 Min) ✔ Kids Game and Entertainment Room ✔ Equipped with 5 TVs and high speed Internet

5 out of 5 average rating, 214 reviews

A welcoming entrance displays a white front door framed by large glass panels. Two black wire chairs are positioned on either side, enhancing the space. A doormat is placed at the threshold, and a small flowerbed with bright blooms adds a touch of color to the entrance.

Villa in St. Augustine

Quiet Villa

Nestled just across the Bridge of Lions on Anastasia Island, this peaceful retreat welcomes you in. Newly renovated duplex, the space is fresh, open and natural light pours in providing a tranquil feel. Centrally located, the site is a short walk over the bridge to Historic downtown or stay on the island where nearby restaurants, Lighthouse Park, Alligator Farm and Anastasia State Park await your visit.