Holiday rentals in St. Augustine

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

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.

Perfect location 2 Bedroom Private Hot Tub

Couples Retreat Near Downtown St. Augustine. 0.5 miles from the Bridge of Lions. Enjoy a secluded courtyard, relaxing water fountain, and new 4-person hot tub. Wine down and watch the sunset in a peaceful setting after a exploring. Off-street parking is included. Restaurants, bars, coffee shops, and local favorites are only steps away. Perfect for a romantic getaway, weekend escape, or special occasion. Special requests and accommodations are available to help make your stay unforgettable.

St Augustine Entire Home, King Bed, Pet Friendly

Casita Luxe Retreat Near Historic St. Augustine – Pet-Friendly Haven! Discover this luxurious 3-bedroom, 2-bath retreat! Designed with a modern luxe aesthetic, it features custom wood paneling, a fully equipped kitchen with a chic island, and a king-size plush mattress. Enjoy the large, fenced yard, fire pit, outdoor shower, and fun family games. Pet-friendly, with Wi-Fi, smart TVs, and parking included this home offers comfort and style in an up-and-coming neighborhood. Book now!

Art Studio Space – Quiet – Walk to Beach

This very private studio apartment is on Anastasia Island, with its own entrance across the street to Anastasia State Park, which includes the St. Augustine Amphitheater in a quiet, friendly beach neighborhood. This ideal location is quite literally "a walk in the park" to a beautiful undeveloped Florida beach; or a 10 minute drive across the famous Bridge of Lions to historic downtown St. Augustine – with quick access to the many local attractions and great restaurants in the area.

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.

192 Riberia Downtown Luxury Home

Summary: Located in historic Lincolnville neighborhood is this stunning luxury home perched along the tidal marshes of Oyster Creek and just steps from St. Augustine’s historic district. This unique home features a gourmet kitchen, an open living area with Netflix included, a handy workspace, 2 king bedrooms each with a full bath, queen memory foam sleeper sofa and stunning views out to the marsh from the custom windows and decked patio.

St. George Historic Bungalow

Come stay at this St. George Historic 1915 Bungalow featured in the well known book, The Houses of St. Augustine. Enjoy being in one of the city’s most pleasant and distinctive neighborhoods. Be reminded of the history that surrounds you as horse carriages stroll by while you enjoy your coffee or wine on the large front porch. The house borders on the lovely Maria Sanchez Lake that inhabits many birds year round.

Short Scenic walk into Historic St Augustine

Stay in Style on Anastasia Island Step into timeless elegance at this fully renovated 1920s apartment. Nestled in the heart of historic Davis Shores, this beautiful retreat blends old Florida charm with modern comfort. 🌴 Perfect Location Walk across the Bridge of Lions to the cobblestone streets, shops, and restaurants of historic St. Augustine. Surrounded by local cafés, parks, and coastal scenery.

Historic Full House 2min walk to Historic Downtown

I'm a lovely old home called La Casita in historic St. Augustine. Nice to meet ya! Flagler had me built to house his crew. I’m certified historic and charming too. I'm right downtown where you need to be so close to everything you'll want to see— The fort, the lighthouse, and all the rest. I’d be delighted if you were my guest. Comfort and peace is a phone call away. Please say yes. I want you to stay. 

1920s Coastal Cottage | Walk to Amp & Downtown

Light-filled, historic charm meets modern coastal living. Built in the 1920s, this meticulously updated 2-bedroom, 1-bathroom cottage features original heart pine floors, walls of windows, and a breezy, open feel that instantly makes you feel at home. Nestled in the quiet, historic Lighthouse Park neighborhood, you are right between the beach and historic downtown — 5 minutes to both.

Apt A - Comfort of Home in Historic St Augustine

Charming apartment in the historic district (within a short 3-4 miles from multiple beaches with an updated bathroom and kitchen. The kitchen has new appliances, cupboards and quartz countertop. My favorite part of this apartment is the porch where you can relax, enjoy your morning and evening beverages, watch horse drawn carriages and mingle with our neighbors...