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

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.

4.97 out of 5 average rating, 808 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

Vacation home in St. Augustine

A two-story blue home is framed by lush green trees. The exterior features large windows and a welcoming front porch supported by white columns. Well-kept landscaping includes a stone pathway leading to the entrance and decorative figures flanking the steps.

4.97 out of 5 average rating, 189 reviews

Historical Beauty in the Heart of St. Augustine

Amazing Location! Uptown Historic District-close to St. George st., Plaza & Fort. Large, comfortable home! Get the complete St. Augustine experience- walking distance to all historical sites, amazing restaurants/eateries, unique shops, & art galleries. This home has been recently remodeled from top to bottom. Enjoy a chef's kitchen, beautiful bedrooms, bathrooms, & off-street parking in uptown luxury. High speed internet and cable. Outdoor grill. Minutes to St. Augustine and Vilano beaches.

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.

4.94 out of 5 average rating, 217 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.

The home’s exterior is characterized by a modern architectural style with a covered front porch featuring four rocking chairs. A wide concrete path leads to the entrance, flanked by well-maintained green landscaping under a clear blue sky.

4.98 out of 5 average rating, 208 reviews

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.

4.95 out of 5 average rating, 189 reviews

The charming cottage is framed by lush greenery and a pathway leading to a welcoming front porch. The airy porch is adorned with hanging plants and a ceiling fan, inviting relaxation. Gravel landscaping enhances the surrounding gardens, offering a serene first impression.

Cottage in St. Augustine

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.

A modern kitchen is presented with sleek white cabinetry and a striking granite countertop. Stainless steel appliances are neatly arranged, and a large sink is installed in the island. A textured black backsplash complements the overall design, creating a functional cooking space.

4.93 out of 5 average rating, 171 reviews

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.

4.93 out of 5 average rating, 185 reviews

The image features a historic building in St. Augustine, adorned with multiple flags, including those of the United States, Italy, and Florida. The entrance is framed by a decorative lamp post, and pedestrians are seen walking along the pedestrian-only street, contributing to the lively atmosphere.

Loft in St. Augustine

The Sweet Spot Suite - Heart of Historic District

This newly remodeled space is in a class all by itself. Seated in the heart of St. Aug where you are right on(with a balcony hanging over) St. George Street, the pedestrian-only “strip” of the city (judged best in the country for walking). Located above the sweet spot ice cream shop and close to dining, nightlife, family-friendly activities, live music, the beach, and much more that our city offers. Please note: there is some noise related to this busy area. Check out my other listings.

Vacation home in St. Augustine

An aerial view captures the charming neighborhood surrounding Hope & Glory, with tree-lined streets and various homes. The picturesque landscape features glimpses of the nearby water and distant landmarks, including the prominent cross, symbolizing the area's historical significance.

5 out of 5 average rating, 181 reviews

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, fully fenced backyard, off-street parking, paved driveway close to downtown and excellent beaches. Prime location!

4.92 out of 5 average rating, 127 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.

The living room features a light-colored sofa adorned with blue pillows, accompanied by two armchairs. A round mirror hangs on the wall, and natural light floods the space through multiple windows. A decorative plant stands near the entrance, and a minimalist coffee table is centered in the room.

4.99 out of 5 average rating, 102 reviews

Charming Home in historic downtown, walk to it all

Our home, Casita Uva de Playa, is the perfect centrally-located home in the Historic Region of Downtown St Augustine. You can walk less than 1/2 mile into the city for a perfect breakfast biscuit, taste amazing cuban food, take in all the history, or enjoy a martini. You can also take a short 10 minute car ride to the beach. Or just relax in our quiet cottage. Your comfort and relaxation while on vacation is our priority. Come stay with us!

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.

4.96 out of 5 average rating, 201 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.

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.

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 outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

The exterior of the home features a two-story structure with a welcoming porch. Potted plants hang from the posts, and a decorative sign is positioned near the entrance. Lush greenery and various plants are arranged along the pathway leading to the front steps.

4.99 out of 5 average rating, 221 reviews

Historic St. Augustine 2/2 Duplex & Pool

4.97 out of 5 average rating, 108 reviews

Leonardi Downtown Craftsman

Superhost

The exterior of the home is showcased, featuring wooden stairs leading to the upper deck. Lush green grass surrounds the property, accented by decorative landscaping and palm trees. A paved driveway provides access to a garage, with a wooden fence offering privacy.

4.86 out of 5 average rating, 159 reviews

Carriage Manor- Next to Fountain of Youth & Beach

The front entrance features a pastel green exterior with a light purple door partially open. Two large lanterns flank the door, while lush greenery frames the pathway. A small mailbox is attached to the wall beside the door.

4.98 out of 5 average rating, 108 reviews

Walk to Everything plus Pool and bonus Cottage!

The historic home features a grand façade with white siding and tall columns supporting a covered balcony. Decorative lights and a festive wreath adorn the front entrance. A beautifully detailed wrought-iron gate opens to a landscaped pathway leading to the door.

4.95 out of 5 average rating, 475 reviews

Genovar Mansion Master Suite Private Entrance

A spacious master bedroom features a king bed with white bedding and a gray upholstered bed frame. Natural light enters through large windows with blinds. A small side table and lamp are present, along with a bench at the foot of the bed, creating a welcoming environment.

4.93 out of 5 average rating, 133 reviews

Orange St Gem | 8-min walk to St. George St & Fort

A spacious backyard is highlighted by a private round pool, surrounded by lush greenery and palm trees. An outdoor cabana features a bar area, while a well-maintained lawn adds to the inviting atmosphere. The charming pink structure complements the serene setting.

5 out of 5 average rating, 125 reviews

Pink Palms *Heated Pool* Walk to Downtown

Superhost

A charming single-story house with a light yellow exterior stands amid lush greenery. A driveway leads up to the home, bordered by neatly maintained grass and palm trees. The inviting front porch features steps leading to the entrance, framed by greenery.

Home in Lincolnville

4.87 out of 5 average rating, 348 reviews

Riberia Place - Pet Friendly & Walk to Downtown

Apartment rentals with outdoor seating

A living area is presented with refinished hardwood floors and neutral grey walls. A blue upholstered sofa faces a mounted flat-screen television above a white fireplace. Natural light enters through large windows, and a small potted plant adds a touch of green to the space.

4.96 out of 5 average rating, 420 reviews

Short Scenic walk into Historic St Augustine

A well-lit bedroom features a spacious bed dressed in white linens, accented by decorative pillows. An orange wall adds warmth to the space, complemented by a colorful piece of artwork. Two glass side tables are positioned beside the bed, with natural light filtering through a nearby window.

4.95 out of 5 average rating, 507 reviews

Charming Downtown Victorian for a Perfect Getaway

An open living area is illuminated by natural light from multiple windows, featuring light-colored walls and warm wood flooring. A gray sofa with a striped throw sits beside a round coffee table. The kitchen area contains white cabinetry and modern appliances, with a dining table set for four.

4.91 out of 5 average rating, 499 reviews

Downtown Bungalow- Walk to Downtown, Mins to Beach

A sunny courtyard is framed by two yellow apartment buildings, surrounded by well-maintained landscaping. Palm trees and shrubs add greenery, while a pathway leads through the center, enhancing the inviting outdoor space.

4.97 out of 5 average rating, 214 reviews

C5 Perfect location in city center, patio, beaches

A contemporary living space features a white daybed adorned with yellow pillows and a gray sofa with matching cushions. Light-colored wooden flooring complements a wooden coffee table at the center. Two sets of double doors lead to a bright outdoor area, enhancing the airy feel.

5 out of 5 average rating, 154 reviews

DOWNTOWN COTTAGECORE, 7 min walk to historic ctr.

A well-lit living room showcases a grey sofa with yellow accent pillows and a glass coffee table. A large television stands on a dark wood console, while a potted plant adds a touch of greenery. Natural light enters through the door leading to a small porch.

4.96 out of 5 average rating, 130 reviews

Lovely Cozy 2 BR Home in St. Augustine

The exterior of a two-story building showcases a contemporary design with a vibrant turquoise front door and matching chairs on the balcony. White wooden siding contrasts with dark railings, while lush greenery and landscaping enhance the entrance.

4.98 out of 5 average rating, 495 reviews

*2BR* Luxe Loft Close to Everything | Balcony

Apartment in Lincolnville

A charming porch area is framed by vibrant pink bougainvillea flowers. The white railing and lattice provide a bright contrast to the floral elements. A comfortable seating area with patterned cushions can be seen in the background, inviting relaxation and enjoyment of the outdoor space.

4.92 out of 5 average rating, 440 reviews

Bougainvillea way, steps to town center, romantic.

Condo rentals with outdoor seating

A light-filled living room features a cozy sectional sofa adorned with decorative cushions. A stylish coffee table sits atop a patterned rug, and a modern TV is positioned on a sleek white media console. Natural elements are introduced through plants and woven wall decor.

4.95 out of 5 average rating, 169 reviews

The Bohemian Rhapsody! In the middle of it ALL!

4.97 out of 5 average rating, 152 reviews

A brightly lit living area features a comfortable brown sofa and two accent chairs with blue cushions. A coffee table is positioned centrally, complementing the light rug beneath. The dining area is visible, showcasing a dark table set for six, with wall art enhancing the space.

Condo in Lincolnville

Middle of Historic District + Quiet at Night

4.95 out of 5 average rating, 198 reviews

A spacious bedroom is equipped with a large bed adorned with plush, blue pillows. A sliding glass door opens to a private balcony offering a scenic view. A small seating area with two chairs is visible outside. A flat-screen TV is positioned on a dresser.

Condo in Crescent Beach

After Dune Delight, BEACH FRONT w/Fishing Pier

The living room features a comfortable gray sofa facing a wall-mounted television. A round coffee table sits on a light area rug, complemented by decorative plants. Bright natural light fills the space through sliding glass doors, leading to a balcony.

4.98 out of 5 average rating, 165 reviews

Pretty walk to Old Town, Anastasia Island 2 bdrm

4.97 out of 5 average rating, 99 reviews

A view framed by lush tropical plants reveals the expansive waterway, with its calm, reflective surface. The image captures a serene outdoor space, featuring stone flooring leading towards the grassy area and water, emphasizing the natural surroundings.

Condo in Crescent Beach

Incredible Waterfront Townhome

The living room features comfortable seating, including a blue sofa and two patterned armchairs. A wooden coffee table sits centrally, complemented by side tables with lamps. Natural light fills the space through sliding glass doors, providing a view of the outdoor area.

4.91 out of 5 average rating, 145 reviews

The Octopus Sanctuary

4.91 out of 5 average rating, 113 reviews

Marina View|Camachee Harbor Waterfront Escape