Holiday 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, 797 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

5 out of 5 average rating, 225 reviews

The exterior of a two-story carriage house displays a light pink and beige striped façade, with large windows allowing natural light. Lush greenery surrounds the entrance, and a small potted plant is positioned on the porch, contributing to the welcoming appearance of the property.

Cottage in 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

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, 458 reviews

Genovar Mansion Master Suite Private Entrance

The direct view of the gorgeous live oak canopy on Magnolia Avenue and incredible architecture make this historic home a memorable place to stay. This romantic master suite is perfect for couples with a private entrance, queen poster bed, spacious bathroom with two shower heads and body jets, private balcony, individual climate control and parking spot. The home is located within the historic district, close to trolley stops and within easy walking distance to downtown. 6 minutes to the beach.

Guest house in St. Augustine

The exterior of the casita features a gabled roof with large glass windows, allowing natural light to enter. Two double doors provide access, surrounded by lush green plants and palms. A covered entryway leads to the main entrance, enhancing the inviting appearance.

4.94 out of 5 average rating, 427 reviews

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.

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, 175 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.

A light-filled living area features a soft blue sofa adorned with decorative pillows. A wooden coffee table provides a functional centerpiece, and a flat-screen television is positioned on a white console with storage baskets. The space is complemented by natural light from the nearby windows.

4.86 out of 5 average rating, 583 reviews

Catch Some Rays on your Deck -walk everywhere

Welcome to The Grove! This one bedroom unit is nestled in the heart of Historic St. Augustine- less than a mile from the City Gates and all tourist amenities! One of the highlights of this unit is the private deck patio, providing a delightful outdoor space to unwind and enjoy your morning coffee or an evening glass of wine. Feel the historic vibes as you take in the views of the surrounding architecture and immerse yourself in the unique character of the neighborhood.

A well-lit living area features a plush dark recliner and a light-colored sofa, arranged around a small coffee table. A decorative lamp adds warmth beside a window. A TV is positioned on a black stand, while framed artwork and a plant enhance the welcoming space.

4.97 out of 5 average rating, 251 reviews

Dog-friendly, Walk Everywhere apt with FREE BIKES

Come stay in this completely renovated, beautiful second floor, pet-friendly one bedroom apartment with a large fully-equipped eat-in kitchen. A spacious balcony with rocking chairs. Shared use of the fabulous back yard with picnic tables, BBQ grills, and bicycles! One parking space guaranteed. Best part: The location! About a five-minute walk to historic downtown and Flagler. Super comfy queen size 4-post bed. Pet fee is $40 per dog per stay (max of 2 dogs).

A bright kitchen area features modern appliances and wooden countertops. A dining table with four pink chairs is positioned near a window, allowing natural light to illuminate the space. Open shelves display a few kitchen essentials, contributing to a functional and welcoming atmosphere.

4.93 out of 5 average rating, 207 reviews

1-Bdrm Apt Historic St Augustine

Come enjoy this lovely carriage house apartment located in the heart of Historic Downtown St Augustine. Originally built in 1910 and completely updated in 2023. Just two blocks from St. George St, walking distance to Flagler and all of downtown St Augustine. This apartment offers one bedroom, full kitchen and private patio. Free off street parking, so you are able to park, walk around and enjoy everything downtown has to offer.

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, 195 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.

A bright sleeping area features a spacious bed with a light-colored coverlet. Flanking the bed are two bedside tables, each with a lamp providing soft illumination. The room is accented with light blue walls and a piece of serene artwork, enhancing the relaxed atmosphere.

4.98 out of 5 average rating, 290 reviews

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.

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, 357 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 outdoor seating rentals in Historic District, St. Augustine

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

A welcoming porch is highlighted by an orange umbrella providing shade. Lush greenery and potted plants surround the entrance to the cottage, which features a decorative front door. Comfortable seating is visible, creating a cozy outdoor space for relaxation.

4.92 out of 5 average rating, 197 reviews

Historic St. Augustine Cottage - Walk everywhere!

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, 218 reviews

Historic St. Augustine 2/2 Duplex & Pool

A charming mid-century home features a welcoming front porch with seating. Lush greenery and Spanish moss surround the property, enhancing its tranquil setting. The entrance is marked by a slate stone walkway and a decorative sign, contributing to the home's inviting appearance.

4.95 out of 5 average rating, 163 reviews

Charming 3 bedroom cottage, feed the peacocks!

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.

4.93 out of 5 average rating, 261 reviews

DOWNTOWN ~ Victorian Home ~ ABOVE CUPCAKE SHOP!

4.97 out of 5 average rating, 103 reviews

Leonardi Downtown Craftsman

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.

4.89 out of 5 average rating, 151 reviews

Carriage Manor- Next to Fountain of Youth & Beach

5 out of 5 average rating, 120 reviews

The sitting room features a blend of warm green and golden hues. A brown leather sofa is adorned with colorful pillows, complemented by a green accent chair. Sunlight filters through the white window blinds, illuminating a vibrant area rug and a piece of art depicting a pelican.

Home in Lincolnville

La Rêverie | Downtown Boutique, Historical Chic

A private heated pool is surrounded by a spacious patio featuring paver stones and tropical landscaping. A wooden pergola provides shade, complemented by lounge chairs and vibrant orange seating. The cottage's white exterior is visible in the background, framed by swaying palm trees under a clear blue sky.

4.99 out of 5 average rating, 137 reviews

Floridian Bungalow•2 Min Walk to Beach•Heated Pool

Apartment rentals with outdoor seating

A bright and airy bedroom features a spacious bed with a light blue blanket, flanked by matching bedside tables with lamps. A comfortable chair sits in the corner, and decorative art in shades of turquoise adorns the walls. Natural light filters through the window, enhancing the serene ambiance.

4.96 out of 5 average rating, 401 reviews

SeaGlass on Vilano Beach~St. Augustine, FL

A cozy sleeping area features a spacious bed adorned with a patterned bedspread and accented by a decorative pillow. A bedside table holds a small lamp, while a dark cabinet provides additional storage. Light filters in through a window dressed with textured blinds.

4.96 out of 5 average rating, 202 reviews

Traveler’s Nest of uptown St. Augustine with pool!

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, 148 reviews

DOWNTOWN COTTAGECORE, 7 min walk to historic ctr.

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, 486 reviews

*2BR* Luxe Loft Close to Everything | Balcony

A modern bathroom features a walk-in shower enclosed by clear glass, with tile work in earthy tones. A stylish vanity with a solid surface sink is complemented by a large mirror. Natural light filters through a window, providing a fresh and bright ambiance.

4.97 out of 5 average rating, 120 reviews

Clean simple and cozy home in St. Augustine

The kitchen and dining area feature modern gray cabinetry and stainless steel appliances. A round dining table with black chairs is positioned on a patterned area rug. Natural light enters through two windows, illuminating the space and offering a view of the neighboring buildings.

4.98 out of 5 average rating, 384 reviews

Short Scenic walk into Historic St Augustine

4.92 out of 5 average rating, 427 reviews

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.

Flat in Lincolnville

Bougainvillea way, steps to town center, romantic.

A tranquil courtyard is depicted with a tiered fountain at its center, surrounded by lush greenery and tropical plants. Two benches are positioned near the fountain, inviting relaxation. Soft light filters through the tall trees overhead, creating a serene atmosphere.

4.9 out of 5 average rating, 189 reviews

Carriage Hse in the trees, Historic St. Augustine

Apartment rentals with outdoor seating

A screened-in balcony offers views of the lush greenery and marshlands beyond. Colorful cushions adorn a comfortable seating area, while a small wooden table sits centrally. Natural light fills the space, creating a peaceful atmosphere for relaxation.

4.99 out of 5 average rating, 122 reviews

Riverfront direct views-Get it ALL in St Augustine

Apartment in St. Augustine Beach

A swimming pool is surrounded by lounge chairs, with palm trees providing shade in the background. Blue skies and scattered clouds create a bright atmosphere. The pool area features a smooth surface and a safety railing on one side.

4.84 out of 5 average rating, 267 reviews

Ocean Side Complex w/ Heated Pool B-15

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, 167 reviews

The Bohemian Rhapsody! In the middle of it ALL!

An open living area features a light-toned laminate floor and a spacious dark sofa facing a wall-mounted TV. A white coffee table sits in front of the sofa, while two wooden stools are positioned nearby. The kitchen is visible in the background, with natural light coming through the window.

4.86 out of 5 average rating, 286 reviews

Oceanside complex B17 1 Bed 1 Bath w/Heated Pool

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, 163 reviews

Pretty walk to Old Town, Anastasia Island 2 bdrm

A spacious studio features a large king bed with colorful accents complemented by tropical artwork on the walls. A cozy chaise couch sits in the corner, with vibrant orange and blue decor. Large windows reveal scenic marina views, inviting natural light into the room.

4.85 out of 5 average rating, 99 reviews

King Harbor View, Balcony, Tropical Feel

Apartment in Treasure Beach

Lush greenery frames a wooden pathway leading to a sandy beach, with palm trees and residential buildings visible in the background. The sky is illuminated by soft hues of sunset, creating a serene backdrop for the coastal environment.

5 out of 5 average rating, 116 reviews

Boutique Beachside condo with easy access to beach

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.