Holiday rentals with outdoor seating in Historic District, St. Augustine

Little Sister's Carriage House w/ Parking

Welcome to Little Sister's Carriage House, a bright and delightful historic cottage located only steps from all St. Augustine has to offer. Beautifully furnished and full of vintage touches, this home is the perfect blend of modern comfort and historic charm. With a personal garden, full vintage kitchen and tons of character, it's a one of a kind stay. Sip coffee on your porch, or take a short stroll into town. Park your car and walk everywhere! Locally operated by lifelong St. Augustinians

Historic 10 Dupont Lane

Located in the heart of historic downtown St Augustine, Florida. Walk to the sites, restaurants, night life and art galleries. A short 5 minute drive to the Vilano Beach. So much history and charm, entertain the family and friends out back in your zen like garden patio with propane fire pit, couches, dining tables and BBQ, tiki torches. It's really cool. Everything from beds to silverware is new. T.V.'s in every room. The best linens for you and yours. Nespresso Coffee. 2 parking spaces!!

The Garden Casita in St. Augustine Florida

Secluded garden casita tucked away three tenths of a mile from the city gates. Take the private garden pathway to serenity's doorstep, and gain access to WIFI, free parking, and a kitchenette equipped with the basic necessities. The zen garden serves as a wonderful resting space to relax and unwind from your day. The casita features a queen size bed with luxury linens, desk nook and a full bathroom. Come find your peace at the Garden Casita on the grounds of a 100 year old private home.

Casa Verde 1885 - Walk to Downtown

Let this gem located in the historic Abbott Tract be your home away from home. Located just 2 blocks from the Downtown area and all it has to offer. This cottage was built in 1885 and retains its old-world charm while featuring modern conveniences. Whether you’re enjoying breezes from Matanzas Bay sitting on the front porch swing, or dining in the resort-like back yard featuring an outdoor bar, built-in eating area, covered porch and lounge chairs, this is an experience not to be missed.

Updated Victorian apt in heart of downtown +VIEWS!

21 Orange Street is a bright and airy second story apartment with unparalleled views of historic downtown Saint Augustine and the bay front. Enjoy old world charm in our newly renovated circa 1860's home- furnished with modern and comfortable amenities! We are steps away from Saint George Street shopping, world class dining and lively bars. If you choose to spend your time here in a more relaxing way, you’ll love the spacious bedroom and our comfortable porch to take a break from it all.

Walk Historic Downtown! "Hope & Glory"

You'll be one block from Historic Uptown Saint Augustine's shops, eateries & attractions. Enjoy smart TVs, luxury bedding with blackout curtains in bedrooms, screened in porch, back deck, bathing cabana with outdoor shower/clawfoot tub, gas fire pit and Weber grill, game room with darts, fooseball, crafts & More. Cozy, clean & relaxing. Fabulous fully-equipped kitchen, full privacy fence, off-street parking, paved driveway close to downtown and excellent beaches. Prime location!

Casa Tranquila Comfy*Stylish*Walk Everywhere*Homey

Casa Tranquila is located on a quiet street only a blocks away from all the action in the heart of the nation's oldest city. Built in 1917 w/ 11 ft. ceilings, renovated in 2021 & is tastefully decorated & equipped with everything needed to make your stay in Historic St. Augustine a remarkable experience. Indoor dining area, updated kitchen, & an outdoor dinning on the screened in porch. Café & scones in the AM or cocktails & Tapas in the evening al fresco. See you soon.

“Little Pink House”-hidden gem in the 💗 of Uptown

Stay with us and you truly can "Have It All"!. Just steps from shopping and restaurants, yet nestled in a quiet neighborhood. Walk to St George Street, The Fort, Visitors Center, Trolley Station, Coffee Shops, The Bayfront. 7 minutes from the Beach. Relax after a day of sightseeing around the pool, and enjoy coffee or wine on the porch. Little Pink House is the guest cottage right behind Pink House Uptown Charmer. More space for your group!

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.