Holiday rentals with a fireplace in Anastasia Island

4.97 out of 5 average rating, 238 reviews

Private Romantic Old Florida Style Cottage

Private Romantic Cottage in flower filled garden with mature trees. Cathedral ceiling, fireplace, full kitchen, large shower with two shower heads, queen bed, lots of off street parking, two large decks, outdoor shower, maple wood floor. A perk: Free parking Spot Close to Downtown included at a different property. You have this entire property to yourself. In the serene Historic Fullerwood Neighborhood. Beautiful architectural details make this a memorable place to stay. Perfect for couples.

4.98 out of 5 average rating, 120 reviews

The Salty Seashell, Coastal Pool Home, Sleeps 8

Relaxing heated pool home in a quiet and safe neighborhood. Our home is clean and spacious located a few steps from the Intracoastal Waterway equipped with a boat launch. We are 10-mins from Old Town or the beach and less than 5 mins from restaurants, grocery stores, and shopping. Experience our lovely saltwater pool enclosed in a lanai. Our home has 3 bedrooms and two bathrooms, full kitchen, and a open family room. Each bedroom has brand new beds. Fast WIFI. Boat/Trailer/RV Friendly :-)

4.97 out of 5 average rating, 259 reviews

St Augustine Beachside Home - Walk to Beach

Time to Relax at our St Augustine canal front getaway! Great family destination just 15 min. to Historic Downtown St Augustine. Neighborhood features PRIVATE Beach Access with a less than 10 minute . walk, depending on pace, to the Beach. Boating and Fishing at your Fingertips with private, over-the-water dock and ramp to floating dock where you can tie up your own boat/kayak/jet skis. The perfect end to your beachside dream day will be watching the sunset while on your private dock.

4.94 out of 5 average rating, 199 reviews

HistoricLuxury•Designer Kitchen&Baths•Walk&Trolley

No Cleaning Fee! 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.

4.9 out of 5 average rating, 152 reviews

Luxury Vacation Experience Getaway

Beautiful Single-family home less then 5 minutes from Historic Downtown Saint Augustine. Get the Best of both worlds with all the Amenities of Downtown and the beach but without the Hussle and Bussle of intown parking and crowds. Our luxury home has you just a 8-minute drive from all Historic downtown has to offer and less then 10 minutes to Saint Augustine's beautiful beaches. Look no further for your get away stay! Weve already planned the perfect accommodations for you!

4.94 out of 5 average rating, 129 reviews

Poolside Getaway | The Good Host Stay

Wake up to palm trees swaying and coffee on the balcony. Spend sunny days floating in the heated pool, grilling on the patio, or watching the kids laugh in the game room. As evening falls, soak in the hot tub or gather by the fire pit under the stars. Every corner is designed for comfort, fun, and connection. With beachy charm, room for everyone, and the ocean just a short walk away, it’s so relaxing and complete, you may never want to leave this perfect family retreat.

Apartment in St. Augustine

5 out of 5 average rating, 106 reviews

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.

4.97 out of 5 average rating, 169 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 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, 199 reviews

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.

Guest house in St. Augustine

4.94 out of 5 average rating, 274 reviews

Sunset Casita

This is a duplex located off A1A in beautiful St. Augustine Beach. There is an oceanfront boardwalk to the beach nearby. Beach access by car is 2 blocks away. Publix, Winn Dixie and Starbucks are within walking distance as are many wonderful restaurants and shops. We are located five minutes from St. Augustine Amphitheater and 10 minutes to historic St. Augustine.

4.97 out of 5 average rating, 103 reviews

Oasis Pool House! Close to DT, Beach & Boat ramp

Dreamy backyard pool oasis in a safe, quiet family-friendly neighborhood minutes from all Saint Augustine has to offer. The HEATED pool is situated on a fenced-in double lot shaded by mature bamboo with a large grassy area. Plenty of privacy for guests and pets! Enjoy BBQing poolside on the grill and sipping your morning coffee on the screened-in patio.