Family-friendly vacation rentals in Historic District, St. Augustine

Guesthouse in St. Augustine

A pool area is showcased with a clear blue pool surrounded by a stone patio. Two lounge chairs are positioned on one side, complemented by a thatched umbrella. A covered seating area can be seen in the background, adding to the inviting ambiance of the outdoor space.

4.98 out of 5 average rating, 169 reviews

Historic St. Augustine 2/1 Cottage & Pool

About this space: Welcome to this poolside cottage located in Historic St. Augustine. This cottage is close and within walking distance to all the fun downtown has to offer. It is also a short drive to the beaches! This cottage has 2 bedrooms and 1 full bathroom, living room, kitchen and direct access to the pool. This space: This is a detached cottage located behind the main house Guest access: Keyless code entry Other things to note: Please keep in mind that the pool is a shared space :)

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, 772 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

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.

4.91 out of 5 average rating, 174 reviews

Historic St. Augustine Cottage - Walk everywhere!

*OLD FLORIDA: A charming 1920s bungalow in a peaceful neighborhood. *WALKABLE to everything old town *PRIVATE PARKING. (BEWARE: “Street parking” means first come/first served). *FIRE PIT (wood provided) *BIKES *HAMMOCK *OUTDOOR SHOWER: hot/cold *BBQ grill: charcoal provided This cozy 1 bed/1 bath has a queen bed, a living room with daybed/trundle, fully stocked kitchen, W/D, TV, WiFi, Dogs allowed: $100 fee. Located only 0.4 miles from downtown—(check distance when others say “walkable”)

A cozy living area is highlighted by a neutral-toned sofa and a wooden coffee table, all set on a textured area rug. A large mirror adds depth while soft natural light filters through the windows. A small plant and decorative items enhance the inviting feel.

4.97 out of 5 average rating, 238 reviews

Uptown Attic - Your Secret Escape

Located in the desirable Uptown District in Historical Downtown St. Augustine, this charming early 1900’s home is the perfect local experience. Featuring alley access to a private driveway with a designated one car parking spot, this newly renovated apartment is steps from all of the city’s hot spots. Guests can easily walk or bike to all of the famous tourist attractions, fantastic dining, and even the area’s famous beaches. This cozy space is also the perfect escape to just stay in and relax.

Guesthouse 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.

4.95 out of 5 average rating, 406 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.

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.

4.92 out of 5 average rating, 137 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.

Place to stay in St. Augustine

A stone fountain stands at the center of a lush courtyard, surrounded by vibrant green ferns and tropical plants. A wooden bench is positioned nearby, offering a tranquil space for relaxation amid the serene sounds of cascading water.

4.92 out of 5 average rating, 942 reviews

Moon Over the Courtyard in the Historic District

You have found your cozy oasis tucked under an ancient Oak tree in a private, lush tropical Courtyard in the Historic District of St Augustine. Sit by the fountain, feed the roaming tortoises day or enjoy the fire and the 1000's of tiny lights reflected on the tree canopy by night. This small studio and exemplifies the appeal of tiny living: compact, clean, efficient, and convenient. The Courtyard is a short walk from all of the Historic Districts Shops, Restaurants and Attractions.

The exterior of the house features a wrap-around porch with white railings, complemented by shaded areas and lush landscaping. A brick pathway leads up to the entrance, framed by palm trees and greenery, showcasing a welcoming facade against a clear blue sky.

4.99 out of 5 average rating, 216 reviews

Downtown • Historic Luxury • DesignerKitchen&Baths

Off Street Parking 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 3-BR Retreat in Historic Downtown. Indulge in a charming vacation rental featuring a spacious living room, gourmet kitchen, and luxury bath. 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.

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, 154 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, full privacy fence, off-street parking, paved driveway close to downtown and excellent beaches. Prime location!

A cozy living area features a comfortable sofa paired with a light-colored armchair and a round coffee table. Natural light flows through multiple windows, illuminating the space. The full kitchen is visible, showcasing modern appliances and blue cabinetry, complemented by woven wall decor.

4.96 out of 5 average rating, 208 reviews

Charming 1 Bedroom apt, Historic St Augustine

You will love this newly remodeled one bedroom apartment in Historic 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 with king size bed, full kitchen and private patio. Free off street parking, so you are able to park, walk around and enjoy everything downtown has to offer.

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.

4.98 out of 5 average rating, 222 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.

A light and airy bedroom features a spacious bed dressed in white bedding. Two decorative starfish are displayed on the wall above the bed, while large windows with flowing curtains allow natural light to brighten the space. Two woven chairs are positioned beside the bed.

4.97 out of 5 average rating, 1,042 reviews

Sea Star Studio (Very Walkable + Free Parking)

Two blocks from the fort and the heart of downtown, this charming studio attached to our home has its own private entrance and tiny fenced in yard. Our driveway provides parking and is located in a quaint historic neighborhood. This bright, updated retreat is perfect for couples looking to walk to the nearby sights and is just a 10 minute drive to our nearest beach.

Popular amenities for Historic District, St. Augustine family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A large heated saltwater pool presents a curved design with a spa area seamlessly integrated. The pool area is surrounded by pavers and features vibrant turquoise lounge chairs. Lush greenery and decorative planters enhance the tranquil outdoor setting, enclosed by a white privacy fence.

5 out of 5 average rating, 101 reviews

Heated Pool/Hot Tub 1 mile to dwntn/beach

Camper/RV in St. Augustine

A comfortable seating area features a yellow couch adorned with decorative throw pillows inspired by The Beatles. The large windows allow ample natural light, while soft gray curtains frame the view. A small side table complements the space, enhancing the cozy atmosphere.

4.88 out of 5 average rating, 188 reviews

Yellow Submarine II

A hot tub is positioned on the deck, offering a view of the ocean and white sandy beach in the distance. Two houses flank the view, while lounge chairs are visible in the shared yard, contributing to the inviting outdoor space.

4.96 out of 5 average rating, 192 reviews

Luxurious Oceanfront Home

A comfortable living area is showcased with a gray sofa adorned with decorative pillows. A glass coffee table sits in front, accented by a floral arrangement. Two windows provide natural light, and stylish curtains frame the view. A small bookshelf stands against the wall.

4.94 out of 5 average rating, 156 reviews

Charming Vintage Intracoastal Apartment

An expansive backyard features a refreshing saltwater pool and a hot tub, surrounded by lush turf landscaping. A two-story building with a wooden staircase overlooks the serene outdoor space, framed by palm trees and vibrant plants. Lounge chairs are positioned nearby for relaxation.

4.98 out of 5 average rating, 119 reviews

Driftmark Cabin - RV friendly, Pool + Beach!

Condo in St. Augustine Beach

The living area features comfortable seating, including a soft blue sofa and an armchair, arranged around a white coffee table. Light-colored décor and subtle greenery create a relaxed ambiance. The space is illuminated by a contemporary chandelier, with a view of the kitchen and dining area in the background.

4.95 out of 5 average rating, 155 reviews

Newly renovated! Steps to BEACH & POOL!

An inviting outdoor pool area features a heated pool surrounded by lounge chairs and a large umbrella. Soft lighting illuminates the space, highlighting the wooden fencing and lush greenery in the background.

4.98 out of 5 average rating, 173 reviews

"Once Upon A Tide" Beach House *Heated Pool* King

4.98 out of 5 average rating, 295 reviews

A private hot tub is set in a serene outdoor area surrounded by greenery and wood paneling. The tub is equipped with a cover and nearby is a container holding spa towels, providing a relaxing space for guests.

Villa in St. Augustine

Perfect location 2 Bedroom Private Hot Tub

Family- and pet-friendly home rentals

A two-story house is presented with a classic design, featuring large windows with green trim. Two small chairs are positioned on the porch, which is adorned with soft white curtains. Lush greenery surrounds the exterior, creating a welcoming entryway.

4.85 out of 5 average rating, 209 reviews

Uptown Classic 2 | Effortless Exploration of STA

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.

4.97 out of 5 average rating, 191 reviews

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

Superhost

A bright living area features a large sofa adorned with decorative pillows, accompanied by a glass coffee table. A television is positioned on a dark wood console, while tropical-themed wallpaper adds a colorful backdrop. Natural light streams through the windows, enhancing the inviting space.

4.79 out of 5 average rating, 428 reviews

Old Town Charm

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.

4.92 out of 5 average rating, 145 reviews

Historic 10 Dupont Lane

The image captures a serene beach at sunset, where the sun is partially obscured by clouds, creating soft orange and blue hues in the sky. Tall grasses sway gently in the foreground, framing the scene of the calm ocean waves reflecting the fading light.

4.89 out of 5 average rating, 740 reviews

Beach and Serenity

The kitchen is equipped with modern stainless steel appliances, including a refrigerator and dishwasher. Black cabinetry complements the white countertops. Natural light streams in from a window above the sink, adorned with a small plant, enhancing the functional layout.

4.85 out of 5 average rating, 348 reviews

Cozy, Pet-friendly Private House near downtown

A spacious studio features a king bed with a patterned blanket, complemented by a cozy sofa and armchair. A kitchenette is visible in the background, along with a modern ceiling fan overhead. Large windows allow natural light to fill the room.

4.98 out of 5 average rating, 356 reviews

Cozy studio 15 min to beaches & historic downtown

An outdoor cabana area is presented, featuring a pool table and bar seating alongside a private heated pool. Surrounding lush turf and palm trees create a serene environment. The space is illuminated by recessed lighting, enhancing the inviting vibe for relaxing and entertaining.

5 out of 5 average rating, 105 reviews

Welcome to Pink Palms - Heated Pool - Walk to DT

Family-friendly home rentals with a pool

Condo 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.

4.85 out of 5 average rating, 260 reviews

Ocean Side Complex w/ Heated Pool B-15

The exterior of a single-story house is displayed, featuring a sloped roof and an inviting entryway. Green grass surrounds the home, complemented by mature trees and landscaped bushes. A concrete driveway leads up to the entrance, providing accessible access.

4.99 out of 5 average rating, 424 reviews

Your Home Away From Home

4.86 out of 5 average rating, 272 reviews

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.

Condo in St. Augustine

Oceanside complex B17 1 Bed 1 Bath w/Heated Pool

4.98 out of 5 average rating, 189 reviews

A spacious deck overlooks a clear blue saltwater pool surrounded by lounge chairs and umbrellas. Lush greenery and palm trees frame the view of the water and dock area in the distance, creating a serene outdoor space for relaxation.

Cottage in St. Augustine

Fun Waterfront Retreat, Heated Pool, Rooftop Deck

4.92 out of 5 average rating, 160 reviews

Covered seating is arranged around a sleek coffee table on a patio with a view of a large heated pool, accented by palm trees and umbrellas. A dining area with a table and chairs is visible, offering ample space for relaxation and enjoyment.

Condo in Lincolnville

F1, Downtown, POOL, beaches, porch, parking!

A spacious entryway leads into an open concept living area with natural light highlighting the wood flooring. The inviting space includes a modern kitchen visible in the background, a comfortable seating arrangement, and access to a staircase.

5 out of 5 average rating, 152 reviews

Southern Charmer w/Pool - Walk to Everything!

5 out of 5 average rating, 112 reviews

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.

Condo in Treasure Beach

Boutique Beachside condo with easy access to beach