Holiday rentals with a fireplace in Anastasia Island

Super4 bedrooms, walk everywhere, free parking.

A beautiful Victorian-style home built in 1915 and completely renovated in 2018. Located two blocks from the St. Augustine historic district with its bars, world-renown restaurants and shopping. 4 bedrooms, 2 new bathrooms, new kitchen. The front porch, complete with rocking chairs, is perfect for relaxing with a glass of wine after a long day of sightseeing. The location is terrific, and the house has all the amenities and toiletries you need. Pet fee is $40 per dog per stay (max of 2 dogs).

Red Door Revival - lg 4bd, 3ba sleeps 10 downtown

Newly renovated, spacious downtown victorian with master on main and a second master upstairs, along with 2 other bedrooms and another full bath. Large front bdrm offers queen bed and full bunks for kids, bachelorette parties, etc. A second property next door (121 Twine) offers 2 more bdrms and baths for wedding parties, family reunions, and other large groups. Extra lg covered back deck w/ceiling fan and gas grill provides plenty of seating for everyone. Park your cars and walk to everything.

The Charlotte House- Pool & Hot Tub St Augustine

Ideal setting on a serene residential street in the heart of downtown St. Augustine, this home offers a picturesque retreat adjacent to Maria Sanchez Lake. Whether you're planning a relaxing getaway, a special celebration, or a rejuvenating staycation, this charming property has it all. Bask in the Florida sun by the pool & unwind in the hot tub after a day of adventure. You'll be just a short stroll away from shops, attractions, restaurants, and bars, with the beaches just a quick drive away.

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.

Comfortable and Gently Disney.

Take it easy at this unique and tranquil getaway. Whether you're here for a short stay or here to explore.... There's something for the princess at heart and for the adventurer. There's a comfortable hybrid mattress for two plus an extra memory foam mattress for two and a tent with a crib size memory foam pillow. Kitchenette is nicely equipped. A fireplace for ambiance under the TV. The bathroom has all the necessities with a walk-in shower. Relax on the patio under the sun and stars.

Prince Road Castillo Book Your home away

Located in the quintessential tree lined, safe, neighborhood, Little Castillo is a newly renovated 4 bedroom home located 15 minutes from the Beach, 15 minutes from the Historic District and less than 15 minutes to over 30 restaurants. In addition to two electric fireplaces, the house boasts a curving staircase, 8 chandeliers, a professional clothes steamer, lighted makeup mirrors and two floor length mirrors. Outside guests will find a hot tub, fenced yard, fire pit and a screened porch.

Private Romantic Retreat Mins DWTN Beach

Newly remodeled and beautifully furnished in a romantic, fresh & modern style, private entrance to the suite has an open living area, fireplace (electric), huge modern gourmet kitchen, bar area accented by wall art. Central air/heat, private master bedroom, spacious bath tub, 1.5 bathrooms & step in shower, living room, dining area, office space/workstation, 2 patios (covered front patio and private fenced in back patio) and a private parking spot in shared driveway.

Fun & Artsy 3BR/2BACottage in Downtown St. Aug

Discover serenity in this charming, hidden gem nestled in a quaint downtown neighborhood. A short stroll will lead you to vibrant festivals at Francis Field and St. Augustine's finest dining, bars, tours, and more. Art, music, and local culture are woven into the very fabric of this locale. Whether you're unwinding with a movie, savoring morning coffee in the backyard, or lounging on the front patio, we've curated the perfect escape.

Cozy Escape w/Fire Pit & Gazebo!

You’ll love the location of this beautiful, cozy home; in proximity to beaches like Hammock Beach, Crescent Beach, and Flagler Beach. This open floor plan home has everything you need. Enjoy a gazebo that seats 10+people, a fire pit, outdoor cooking space with gas grill, large yard, hammock and lovely screened in porch with plenty of seating and a tv! We also welcome furry friends and understand they are family too!