Holiday rentals with a fireplace in St. Augustine

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.

Downtown • Historic Whitney House • Luxury Baths!

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.

The Ocean is Your Backyard - Entire House on Ocean

At our home, the ocean is literally your backyard. Come and enjoy a stay in our small slice of paradise in the quaint Flagler beach area. Located on the north private beach section of Flagler Beach (Painters Hill), you can sit right in the backyard and experience ocean living with nothing obstructing your view. It's the perfect place for a family or a couple. Our spacious 2/2 with a full kitchen, living room and dinette will comfortably fit 4 Adults plus kids for a fun filled beach vacation.

Waterfront Cottage on Private Island in Preserve

Longvue is an Old Florida house set on private Medicis island in the Intracoastal Waterway surrounded by the Guana/Tolomato Matanzas National Estuarine Research Reserve (73,000 acres) and Stokes Landing Conservation Preserve (300 acres). Private floating dock with tidal access to the IWC. Very private island with 6 residences. The 10 acre island is surrounded by rivers, marsh flats and fresh water ponds. Boat/Kayak to the National Reserve and walk the trails to S. Ponte Vedra Beach.

Music on Marilyn- Steps from the Amp! •Jacuzzi•

Nights of Lights & mere seconds from the St. Augustine Amphitheater— a short bike ride to the beach and downtown, this modern escape is 3 beds and 2 baths. Welcome to Music on Marilyn! This is the quintessential St. Augustine experience. Nestled on a quiet street that dead ends to the intracoastal, walking distance to the St. Augustine Amphitheater, Lighthouse, Anastasia Park, Alligator Farm and much more! St. Augustine Beach and historic downtown are just a short bike ride away.

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 (not yet pictured) and powder bathrooms completed for summer 2026. 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!

Oceanfront, Blissful Sunrises, Beach Gear, BBQ

Add my home to your wishlist, click the <3 in top right corner! *Book 2 nights, get the 3rd night 30% off!* >Stunning Oceanfront Home with pano ocean views >Beautifully styled >4 Smart TVs w cable and streaming apps >Parking for 4 cars >Continuous balconies >Beach gear provided (towels, chairs, umbrella) >Walk to The Reef Restaurant >Short drive to downtown + Vilano Publix >Washer + Dryer >BBQ Grill >Drip Coffee Maker >3 days of supplies (TP, trash bags, etc.)

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.

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.

1928 Coastal Bungalow w/ 2 King Beds | Walk to Amp

Welcome to Salt Run Stay — a lovingly restored 1928 beachy bungalow in the heart of St. Augustine. Ideal for couples, friends, families and solo travelers, the bungalow is walking distance to the famous Lighthouse, Salt Run Inlet, a boat launch, restaurants, cafes and the Alligator Farm. You can also easily bike to the Amphitheater, Anastasia State Park and beach, and the historic downtown area.

Flagler House short walk to Historic District

Beautiful 3bd / 2 bath home walking distance to Historic District of St Augustine and a short bike ride to the Beach, Lighthouse, Alligator Farm, Anastasia State Park, Amphitheatre and more. Escape the hustle of downtown with a short stroll over the Bridge of Lions. Enjoy the many Davis Shores farm to table eateries and St Augustine's famous seafood restaurants.

1900s Cottage in Heart of Town-walk everywhere!

Welcome to Groveside Cottage on the historic street of St. Augustine! In 1920s Grove Avenue was the home of several families of cigar makers and two cigar manufacturing companies. This charming cottage is a great mix of vintage and modern; you will be amused! We allow 1 dog, please message us - approval required before booking. Thank you!