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

Balcony apt on USA’s oldest Street (St. George St)

"The Heart of St. Augustine" Voted #1 Airbnb in St Augustine by Trip 101, # 5 Top 10 Airbnb's in St. Augustine" by Territory Supply and in the "Top 15 Best Airbnb's in Florida" by Road Affair. Live music, scrumptious food, craft drinks, and the hustle and bustle of people walking the historic St. George St, all surround you. Relax and people watch from your balcony. Sightseeing, restaurants, trolley stop and nightlife are steps away. This apt is in the center of it all. NYE is a 3 night min

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

Historic Designer Home • Luxury Baths • Steps2DWTN

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.

Newly built w/garage In The Heart of St.Augustine

Click [♡ Save] button to easily find this listing again before your dates are booked. Great walkable location on a safe quiet street; Spacious and nice for entertaining and relaxing. Bikes and beach chairs included. Very comfortable beds. The porches have rocking chairs too. The home is on one level which is also nice for elderly with mobility challenges. Guests say this is a convenient stay for local weddings, special events¸ and an enjoyable vacation. Send us a message to plan your stay.

Historic 10 Dupont Lane

In St Augustine's historic neighborhood. Completely modernized, but we kept the old charm. New everything. Included amenities bikes, BBQ, Fire pit, outdoor lounge furniture, private patio, laundry inside, Nespresso maker, coffee included, soaps and shampoos, beach essentials. Everything you need is here. Just bring your suit case. 5-10 minute walk to the center of town. Catch the trolly at the end of the street. Buy your tickets here and receive a discount. Welcome to a fun memorable stay.

Casa de Flora B Relaxed Elegance in St Augustine

Built in 1927 and located in Uptown St Augustine this apartment has heart of pine floors, 9 ' ceilings, private parking in back and a kitchen ready for preparing a snack or meal. It has been completely updated and is within walking distance to most attractions. Soft robes, towels and sheets help you to unwind and relax. Cable TV, WiFi, and a bedside radio/cd player are provided for your entertainment along with a large selection of movies and books.

“La Casita” A Charming Uptown St Augustine Cottage

La Casita is located in the Uptown Shopping District. We have darling coffee shops just at the end of the block. Shopping and a convenience store too. We are just 2 blocks from the trolley shop snd visitors center..and, just a 10 min walk to downtown and the fort! We are just a 2 min walk to Francis Field, where many festivals are held. A 7 minute drive to Vilano beach! We are in a quiet and charming neighborhood.

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. 

Seahorse Studio (Very Walkable + Free Parking)

Located just a few blocks from all that downtown has to offer, the Seahorse Studio is the perfect way to enjoy your trip to St Augsutine. Less than a 10 minute walk to St George Street, the Castillo de San Marcos, the Bayfront, and Flagler College. The studio welcomes you with free off-street parking, a private entrance and yard, and a stylish space to relax after hitting the town.

Urban Magic l Arcade Machine l Walk to Town

A 2 bedroom/2 bathroom historic home with a modern flair: -> Arcade machine with 100+ games including Pac Man -> Pet friendly for 1 dog (see additional info below) -> Private, enclosed back patio -> Off-street parking for 3 cars -> 1 Block from Trolley Stop at Mission Nombre de Dios -> Short walk to top boutiques and shopping district -> Vilano Beach 5 minutes drive away

Downton Abbottry 2/2 - 5 Min Walk To City Gates

Enjoy this charming 1910 Sears & Roe Buck catalog home that has been meticulously maintained home just a 5 minute walk to the City Gates and downtown. You have a private back patio space to enjoy coffee in the morning or a glass of wine in the evening. Or just take a leisurely stroll to many fine restaurants that St Augustine has to offer.

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!