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, 171 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, 774 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 bright living area features large windows that allow natural light to fill the space. A comfortable couch and a wooden coffee table are positioned centrally, complemented by a dining table surrounded by white chairs. A ceiling fan adds ventilation to the airy room.

4.9 out of 5 average rating, 241 reviews

Lovely 1bdrm apt in Historic St Augustine

Check out our beautiful upstairs apartment in Historic St Augustine! The space is newly remodeled and so lovely! 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 one bedroom, king bed and full sized bed pull out sofa, full kitchen and bath as well as a balcony to enjoy the sights. Free off street parking, so you are able to park, walk around and enjoy everything downtown has to offer.

Guest suite in St. Augustine

A charming entrance to a cozy guest suite is framed by lush greenery and wooden structures. A wooden deck leads up to the door, which is complemented by a decorative orange light fixture. The surrounding plants enhance the natural ambiance.

4.97 out of 5 average rating, 156 reviews

MarshMellow-Island Guest Suite nights of lights

Your own cozy guest suite with private entry. Lovely little bedroom and beautiful bathroom . Private porch and sitting area. Located adjacent our guest studio but the suite is entirely yours and private. These two share a lush garden path, but have separate porches and entrances. The MarshMellow is a well thought out accommodation that has everything we think you'll need for a lovely stay in St. Augustine. A 20 minute stroll to the Amp and short drive or bike to the beaches or downtown.

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, 138 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 decorative three-tiered fountain is set within a lush tropical courtyard, surrounded by dense greenery and tropical plants. Stone benches are positioned near the fountain, inviting guests to sit and enjoy the serene ambiance of the outdoor space.

4.88 out of 5 average rating, 1,038 reviews

The Courtyard Studio in the Historic District

You have found your cozy oasis tucked under an Ancient Shady Oak trees in a private, lush tropical courtyard in the Historic District of St. Augustine. It is a minimalist's dream and exemplifies the appeal of tiny living : compact, clean, efficient, and convenient. A short walk to all of the Shops, Restaurants and Attractions. Enjoy and relax in the courtyard cool by day and at night the tree canopy is lit by hundreds of tiny laser lights at night. Solar powered/low carbon footprint.

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, 220 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.

A sunlit courtyard is surrounded by cheerful yellow two-story buildings, featuring balconies and inviting entryways. Lush greenery and palm trees enhance the outdoor space, complemented by a manicured lawn and decorative plants. A wrought iron fence outlines the property.

4.93 out of 5 average rating, 176 reviews

C4 Close to beaches, downtown, history, parking!

Relax in this cozy and comfortable Upstairs apartment with patio. Don't worry about the struggle of downtown parking, PARKING IS FREE on site (1 designated spot for your apartment). So many nearby attractions just steps (or a trolley ride) from the door including shopping on St. George St, restaurants and sandy beaches where you can rent paddle boards, kayaks, small sailboats and more. We have a drip coffee maker, coffee, decaf, creamers, and sugar. We offer Roku TV.

The living area showcases a dark leather sofa adorned with colorful pillows, paired with a light wooden coffee table. A ceiling fan hangs above, and a large television is mounted on the wall. The space features original pine flooring and a decorative non-functioning fireplace.

4.95 out of 5 average rating, 311 reviews

FREE BIKES Dog-friendly apt in the heart of St A

A beautiful, renovated, pet-friendly, first-floor apt in a historic house . A fully-stocked kitchen for cooking, beautiful bathroom, comfy bed. A shaded, shared backyard with picnic tables and charcoal bbq grills. A few minute walk to the Historic District , Francis Field and Flagler College, while still being in a quiet neighborhood. Free use of bicycles. One parking space. Pet fee is $40 per dog per stay (max of 2 dogs). No cats.

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.

4.95 out of 5 average rating, 221 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.

5 out of 5 average rating, 120 reviews

The cottage exterior features a welcoming white facade with a covered porch and steps leading to the front door. Lush greenery and a stone wall border the pathway, while trees provide shade, creating a serene atmosphere near the entrance.

Cottage in St. Augustine

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!

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 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, 160 reviews

Charming Vintage Intracoastal Apartment

Guesthouse in St. Augustine

An outdoor seating area features multiple blue Adirondack chairs arranged around a circular stone patio, complemented by a small green table. A lamp post stands nearby, and a flag flutters gently in the breeze, surrounded by lush greenery and tall palm trees.

4.91 out of 5 average rating, 595 reviews

Captain's Quarters Tiny House

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.

4.96 out of 5 average rating, 157 reviews

Newly renovated! Steps to BEACH & POOL!

Superhost

A cozy living area is highlighted by a textured sofa and a cream-colored armchair, with a throw blanket casually draped over it. Large windows allow natural light to fill the space, and double doors provide access to additional rooms.

4.82 out of 5 average rating, 110 reviews

Beach and Serenity house

Vacation home in St. Augustine

A spacious living area features a brown leather couch centered on a light-colored coffee table. Natural light fills the room from large windows, highlighting the open layout that connects to the kitchen and dining area. Decorative artwork and plants add subtle touches of character.

5 out of 5 average rating, 112 reviews

Sun Seekers Beach House- Steps from Butler Beach

4.98 out of 5 average rating, 300 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

4.91 out of 5 average rating, 105 reviews

A charming cottage is framed by lush palm trees and tropical plants. A white picket fence surrounds the front yard, providing a welcoming entrance. The home's metal roof and light exterior complement the clear blue sky, creating an inviting curb appeal.

Cottage in St. Augustine

The Coconut Cottage. Hot Tub. Walk To Beach

The outdoor area features a private saltwater pool with a custom spa, surrounded by lush tropical landscaping. A spacious cabana is included, with comfortable seating beneath flowing white drapes. A shaded umbrella is positioned beside the pool, enhancing the relaxation space.

4.99 out of 5 average rating, 130 reviews

2023 Lux Home 4bd/3.5ba+HotTub+SaltPool+Walk2Beach

Family- and pet-friendly home rentals

A spacious sleeping area features a large king-sized bed dressed in crisp white linens, complemented by a couch with a light patterned cover. Natural light filters through the windows, which are dressed in soft curtains, illuminating the warm wooden flooring.

4.77 out of 5 average rating, 177 reviews

Palmetto Loft w/ Balcony 2 blocks from Lighthouse!

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, 192 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

Superhost

A scenic view of the Bridge of Lions at sunset, featuring vibrant orange and pink hues in the sky. The bridge's lights are illuminated, reflecting in the calm water below, creating a serene atmosphere. Silhouettes of birds are seen in the distance.

Tiny homes in St. Augustine

4.88 out of 5 average rating, 233 reviews

Cheerful Studio by LionsBridge,short🚶‍♀️to downtown.

Guest suite in St. Augustine

An inviting studio space features a queen size bed with a patterned blanket, surrounded by natural light. A kitchenette area is visible in the background, providing essential amenities. A small seating area with colorful cushions is arranged beside the bed, enhancing the room's functional layout.

4.98 out of 5 average rating, 389 reviews

St. Augustine Studio*Private Entrance & Bath*Bikes

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, 353 reviews

Cozy, Pet-friendly Private House near downtown

Bungalow in St. Augustine

A cozy living area features a blue sofa adorned with several pillows. A coffee table rests on a patterned rug, and light streams through large window blinds that brighten the space. Decorative wall art adds character to the neutrally painted walls.

4.92 out of 5 average rating, 380 reviews

Uptown Classic Bungalow Comfy Walk Everywhere

Guest suite in St. Augustine

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, 360 reviews

Cozy studio 15 min to beaches & historic downtown

Family-friendly home rentals with a pool

4.99 out of 5 average rating, 117 reviews

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.

Condo in St. Augustine

Riverfront direct views-Get it ALL in St Augustine

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, 263 reviews

Ocean Side Complex w/ Heated Pool B-15

4.86 out of 5 average rating, 278 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

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, 427 reviews

Your Home Away From Home

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

Bungalow in St. Augustine Beach

A sparkling pool is surrounded by lounge chairs, offering a refreshing retreat. Lush greenery and open fields create a serene backdrop, while a distant building is visible, adding to the tranquil setting.

4.9 out of 5 average rating, 113 reviews

Barefoot Bungalow St. Augustine Beach

5 out of 5 average rating, 113 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

An inviting pool area features lounge chairs and a vibrant mural, while an outdoor dining space with a large table is prepared for gatherings. Inside, a serene bedroom showcases soft colors and modern furnishings. A playful bunk room is also designed for fun and relaxation.