Holiday houses in Historic District, St. Augustine

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Top-rated holiday rentals in Historic District, St. Augustine

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Top Guest favourite
A charming view of the Italian restaurant Pizzalley's, featuring a decorative balcony adorned with hanging plants. The building’s colorful facade complements the vibrant street lined with trees and vintage-style street lamps, creating a lively atmosphere in the historic district.
Apartment in St. Augustine
4.97 out of 5 average rating, 804 reviews

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

Guest favourite
The living room is furnished with two light-colored sofas and a central coffee table, creating a spacious and inviting space. A decorative fireplace is framed by mirrors and artwork, while natural light filters in through shuttered windows and greenery adds a touch of nature.
Home in St. Augustine
4.94 out of 5 average rating, 216 reviews

Downtown Luxury • Gourmet Kitchen • STEPS 2 DTWN !

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.

Top Guest favourite
A charming guest house is presented with a front porch featuring a decorative railing. Lush greenery and a small white picket fence frame the landscaped yard, while palm trees provide shade. The exterior showcases a light color palette, with contrasting trim and a welcoming entrance.
Apartment in St. Augustine
4.95 out of 5 average rating, 371 reviews

The Rohde House, The Rohde Guest House

Our place is close to nightlife, public transport, the airport, the city square, and parks. It's good for couples, solo adventurers, business travelers, families (with kids), and furry friends (pets). Five minute walk to the "Nights of Lights", two minute walk to Francis Field event field, where many festivals, concerts and activities are held. Five minute drive to the ocean beach at Vilano. Many Restaurants and bars in walking distance, including sports bar, martini bar, Irish pub and more.

Top Guest favourite
A charming Victorian home is showcased with a bright yellow exterior, framed by lush greenery. The two-story structure features a spacious porch with white railings and decorative trim. A welcoming sign is positioned at the entrance, indicating the property's name.
Home in St. Augustine
4.93 out of 5 average rating, 267 reviews

DOWNTOWN ~ Victorian Home ~ ABOVE CUPCAKE SHOP!

Casa de San Marcos is in Saint Augustine’s historic district. You are steps away from antique shopping, food, and other attractions. The Castillo de San Marcos, Ripley’s Believe It Or Not, The Fountain of Youth, Francis Field events, The Old Jail, and much more are within blocks. Our property is located in the San Marco Shopping District and has a trolley stop nearby in the Uptown San Marco Shopping District! The apartment shares this Victorian home with LuLi’s Cupcakes on the first floor!

Top Guest favourite
A dining area is showcased with a wooden table surrounded by six chairs, featuring vibrant floral upholstery. A woven pendant light hangs above, illuminating the space. An ocean-themed mural adorns the wall, complemented by potted plants positioned nearby.
Apartment in St. Augustine
4.92 out of 5 average rating, 159 reviews

Charming Old-Florida Apartment

This darling Uptown apartment is in the thick of it! Next door to fabulous uptown shops and eateries -- including our own bodega and taproom. Walkable to bustling historic downtown, the fort, the Bridge of Lions, and the Matanzas River. Bikeable to Vilano Beach and Anastasia State Park. And a short drive to additional beaches on Anastasia Island or in Vilano. Enjoy a slice of Saint Augustine typically only enjoyed by the locals, and relax in the friendly historic Abbott Tract neighborhood.

Top Guest favourite
The exterior of a two-story cottage showcases wooden shingle siding and a welcoming front porch. Lush greenery and colorful plants surround the house, with potted flowers placed in the foreground. Sunlight highlights the charming architectural details against a clear blue sky.
Cottage in St. Augustine
4.98 out of 5 average rating, 270 reviews

Charming 2/2 Cottage ~ Walk to Historic Downtown

This St. Augustine home is right in the heart of quaint & historic downtown! The lovely two level cottage has an upstairs full bath and two private bedrooms each with a queen bed. Downstairs is a second full bath, as well as a living room and full kitchen. The space is perfect for 1-4 guests. A short 8-10 minute walk allows visitors to explore the many downtown historic sites, museums & restaurants. One parking spot is available on our lot. Free street parking for additional cars.

Top Guest favourite
The kitchen features a spacious layout with wooden cabinetry and modern appliances. A dining area is present with a round table and four chairs. Natural light enters through large windows, and a beige rug adds warmth to the hardwood floor.
Apartment in St. Augustine
4.95 out of 5 average rating, 301 reviews

Apt B - Historic District Home Away from Home

Key Lime Oasis is nestled on a tree lined residential street in historic Saint Augustine. There is lots to see and do starting a mere two block walk away, and multiple beaches within 3-4 miles. I provide 2 beach chairs, a cooler, umbrella and beach towels.. The apartment features all new appliances, a quiet back porch, French doors leading from the bedroom to a delightful bathroom with a large shower with a Bluetooth speaker. A complimentary parking pass to the city garage is provided.

Guest favourite
Apartment in St. Augustine
4.92 out of 5 average rating, 124 reviews

Cozy Garden - Sleeps 4- hottub/outdoor shower!

This is a lovely vacation home in downtown  St. Augustine. This charming retreat offers a perfect blend of modern amenities and charm, while providing an unforgettable getaway experience. This two-bedroom, one-bath home is designed for comfort and tranquility. The main bedroom features large French doors that open onto a private deck with modern decor, while the second bedroom also offers access to the private deck with a hot tub, creating an equally inviting space.

Top Guest favourite
The exterior of La Casita features a welcoming porch with seating for two, surrounded by greenery and flowering plants. The entrance is marked by a decorative clock, while the landscape includes gravel areas and a fire pit, creating an inviting outdoor atmosphere.
Home in St. Augustine
4.96 out of 5 average rating, 200 reviews

“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.

Top Guest favourite
A bright bedroom features a four-poster bed dressed in white linens. Two bedside lamps offer gentle illumination, while large windows allow natural light to fill the space. The light-colored walls and flooring create a serene atmosphere.
Apartment in St. Augustine
4.95 out of 5 average rating, 259 reviews

Lemon Street Studio (Very Walkable + Free Parking)

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

Top Guest favourite
A private back deck features a round dining table surrounded by four green chairs, all positioned beneath a large red umbrella. A hot tub is visible in the background, complemented by potted plants along the edges. Sunlight illuminates the area, enhancing the inviting outdoor space.
Home in St. Augustine
4.98 out of 5 average rating, 244 reviews

Cordova House ,In the historic downtown .

The "Cordova House", built in 1900, is the Victorian Secret of the Ancient City District, featuring covered balconies in front and back, a private back deck, high ceilings, modern kitchen, a Kohler 10 head shower, two indoor spa tubs and more. Hot tub on the back deck.Located in the heart of downtown, yet also has off-street parking for up to two cars (very rare). Nothing compares.

Top Guest favourite
An open-concept living area features a comfortable gray sofa, a coffee table, and a TV on a stand. Natural light fills the space through the windows, and a dining table with chairs is visible in the background. A patterned rug adds warmth to the wooden floor.
Home in St. Augustine
4.96 out of 5 average rating, 358 reviews

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.

Popular amenities for Historic District, St. Augustine holiday rentals

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Avg. price$257 NZD$261 NZD$275 NZD$250 NZD$242 NZD$247 NZD$245 NZD$235 NZD$230 NZD$240 NZD$292 NZD$339 NZD
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Quick stats about holiday rentals in Historic District, St. Augustine

  • Total holiday rentals

    Explore 340 holiday rentals in Historic District, St. Augustine

  • Nightly prices starting at

    Historic District, St. Augustine holiday rentals start at $122 NZD per night before taxes and fees

  • Verified guest reviews

    Over 40,030 verified reviews to help you choose

  • Family-friendly holiday rentals

    210 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 150 rentals that welcome pets

  • Holiday rentals with a pool

    40 properties feature pools

  • Rentals with dedicated workspaces

    160 properties have a dedicated workspace

  • Wi-Fi availability

    340 of Historic District, St. Augustine holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across Historic District, St. Augustine rentals

  • 4.9 Average rating

    Historic District, St. Augustine stays are highly rated by guests—averaging 4.9 out of 5!