Family-friendly holiday rentals in St. Augustine

A vibrant swimming pool reflects the evening sky, surrounded by well-maintained landscaping. Poolside seating includes colorful lounge chairs and a dining set, while a floating flamingo adds a playful touch. Soft lighting from string lights enhances the serene atmosphere as dusk approaches.

4.99 out of 5 average rating, 105 reviews

Designer•As Seen on HGTV•Pool•Luxury Kitchen&Baths

No Cleaning Fee! 3 Min Drive/ 15 Min Walk to Historic Downtown 2 Min Drive to the St Augustine Amphitheater 2 Min Drive to the Anastasia State Park Beach 1 Min. Drive to Anastasia Fitness Club/Suana-Steam Rm/Pool. Looking to get away from the hustle & bustle of the city? This designer home with an amazing pool is the perfect place to recharge. Downtown & the scenic beaches in Anastasia State Park are just a minutes away. With spacious living & modern amenities, the Home offers maximum comfort

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, 385 reviews

St. Augustine Studio*Private Entrance & Bath*Bikes

A private studio designed from a garage conversion, located in the up-and-coming West King District. Separate entry with keyless lock welcomes you to this comfortable, clean space with a queen size bed, your own bathroom, kitchenette, and 2 available parking spaces in the driveway. Mini-split AC cools and heats the studio comfortably. High speed internet, flat-screen tv with Netflix for relaxing after a day of sightseeing. Bicycles for exploring our historic downtown less than 2 miles away.

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, 236 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.

A living space features a white sofa adorned with a patterned throw, complemented by a rustic wooden coffee table. A large round mirror and star decorations hang on the walls, while a ceiling fan adds functionality. Doorways lead to adjacent rooms, including a bathroom.

4.98 out of 5 average rating, 492 reviews

Winter Hawk Hideout

15 minutes from ol' St Augui. Located in the heart of this typical Florida woods and nested by oaks that saw the Seminole War as we are walking distance from Ft Peyton and 2 miles away from where Osceola was captured. The house sits on half acre of gardens and the decor is ranch, asian and whimsical .The goal is for you to feel transported away for a while. I do have 2 very small, well behaved and quiet dogs and one never seen cat. They do not have access to your quarters or are allowed in.

Treehouse in St. Augustine

A three-tiered fountain is situated in a lush tropical garden, surrounded by various palm and fern plants. Water flows gently from the top tier and cascades down to the basin below, creating a peaceful ambiance in this serene outdoor space.

4.93 out of 5 average rating, 545 reviews

courtyardtreehouseinthehistoricdistrict

You have found your cozy oasis tucked in a (Real) Treehouse lodged in Ancient Oak. Set in a lush tropical garden in the historic district. It’s a minimalist’s dream, exemplifying the appeal of tiny living: compact, clean, efficient and 2 1/2 blocks to the historic districts shopping and restaurants. Relax on the Sun Deck, Rain Deck or in the Courtyard’s Tropical Garden The day time peaceful beauty is only eclipsed by the the nighttime display of laser lights projected onto the oaks canopy.

Campervan/Motorhome 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

28' Vintage Airstream we call the Yellow Submarine, enjoy this unique experience inspired by The Beatles and furnished with IKEA. The queen bed in a separate bedroom offers comfort and privacy and 1 of 3 tvs. Full bathroom, separate shower, fully equipped kitchen, thermostatically controlled AC & space heaters. A short 6 minute Uber into downtown or 8 minutes to Viano. Beach. Our 5 star reviews love,location, privacy, firepit, and hottub, private outdooor shower and covered patio with tv.

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, 149 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.

A panoramic view of a beach scene at sunset, featuring vibrant clouds in shades of pink, orange, and purple. The sun dips below the horizon, reflecting off the water's surface. Grassy dunes are visible in the foreground, framing the tranquil scene.

5 out of 5 average rating, 306 reviews

Entire guest suite short walk to beach.

Enjoy exploring beautiful, historical St. Augustine then kick back and take it easy at this private, quiet beach retreat within a short walk to the beach. Separate keyless entry allows for self check-in. Queen size bed, fully furnished, with amenities including a Keurig coffee maker, iron, hair dryer, beach cruiser bicycles, beach chairs, towels, umbrella and gas grill for cooking out. Flat screen TVs in both the living room and bedroom with Netflix and Amazon Prime included and Free WiFi

Guest house in St. Augustine

A bright living area features a black leather sofa paired with textured cushions, complemented by a low coffee table. A television is positioned on a console, and windows allow natural light to fill the space. Artwork adorns the walls, adding character to the room.

4.99 out of 5 average rating, 109 reviews

Comfortable and Gently Disney.

Take it easy at this unique and tranquil getaway. Whether you're here for a short stay or here to explore.... There's something for the princess at heart and for the adventurer. There's a comfortable hybrid mattress for two plus an extra memory foam mattress for two and a tent with a crib size memory foam pillow. Kitchenette is nicely equipped. A fireplace for ambiance under the TV. The bathroom has all the necessities with a walk-in shower. Relax on the patio under the sun and stars.

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.

4.88 out of 5 average rating, 737 reviews

Beach and Serenity

6 BLOCKS to BEACH, off of the intercostal! Studio apartment, sleeps up to 4. Quiet neighborhood, close to all. Several restaurants/shops within walking distance. Beach bikes included, perfect for bike rides along the beach. Private entrance off of porch, which includes chairs to relax in, beach toys, towels, chairs. *yes, we are pet friendly, however, ONE PET PER STAY WITH APPROVAL *also, we cannot split weekends, so please book accordingly, fridays and Saturdays booked together

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, 351 reviews

Cozy studio 15 min to beaches & historic downtown

Outstanding location + amenities, 15 minutes to beaches + historic downtown (Nights of Lights!) minutes walk to the intercostal w/ piers, boat ramps, perfect for pleasant walks w/ swings + benches. Close to shopping/dining. Quiet, friendly neighborhood, ample parking-trailers & boats welcome. Kid friendly w/ toys, pack & play + more. Laundry, walk-in shower, private entrance. Private deck w/ cheerful seating. Well equipped kitchenette. Easy drive to theme parks, Daytona + more.

5 out of 5 average rating, 144 reviews

A charming historic cottage features a welcoming front porch with seating. The entrance is framed by intricate light fixtures and is approached via a patterned brick pathway. Lush greenery offers a serene backdrop, contributing to the inviting atmosphere of the home.

Cottage in Lincolnville

~Romantic Historic 1888 Cottage~Walk to Downtown

Come live in history! This cottage traces its roots back to humble beginnings and it still stands today as one of Lincolnville's original historic treasures. Nestled in the heart of America's oldest city, this endearing circa 1888 cottage offers an intimate, refined escape with a boutique ambiance. This is the ideal retreat for travelers seeking a romantic getaway or guests who wish to be transported to a more graceful time. Discreet in scale but grand in experience.

Popular amenities for St. Augustine family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

The night view features a pool illuminated by soft blue lights, surrounded by palm trees. Relaxing lounge chairs line the poolside, and the building's windows reflect warm light, suggesting a welcoming ambiance. A fountain adds a tranquil element to the setting.

4.94 out of 5 average rating, 134 reviews

My HOUSE is your HOUSE

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

Pool/Hot Tub Home 1 mile to downtown/beach

A balcony view showcases a serene pool surrounded by lush green palm trees and well-maintained grounds. Comfortable outdoor seating is positioned near a glass table, while the sky features fluffy clouds and hints of blue.

4.93 out of 5 average rating, 117 reviews

Spanish Colonial Design One Bedroom Condominium

4.94 out of 5 average rating, 155 reviews

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.

Flat in St. Augustine

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, 117 reviews

Driftmark Cabin - RV friendly, Pool + Beach!

Apartment 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, 152 reviews

Newly renovated! Steps to BEACH & POOL!

Holiday 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, 110 reviews

Sun Seekers Beach House- Steps from Butler Beach

A well-maintained outdoor pool area is framed by palm trees and lush green landscaping. The sparkling blue pool features a central fountain and is surrounded by loungers, creating a serene environment for relaxation.

4.86 out of 5 average rating, 295 reviews

Full Condo in St. Augustine’s World Golf Village

Family- and pet-friendly home rentals

5 out of 5 average rating, 225 reviews

A charming two-story cottage is seen behind an ornate wrought-iron gate, framed by vibrant green grass and well-maintained landscaping. Large windows allow natural light to fill the exterior, and a cheerful yellow door adds a welcoming touch.

Cottage in Lincolnville

Walk Historic Downtown! “Blue Heaven”

A modern living area is shown, featuring a comfortable blue sofa and a light gray rug. A wooden table with black chairs is visible in the foreground. The kitchen area includes dark cabinetry and stainless steel appliances, while a wall-mounted television adds to the space's functionality.

4.99 out of 5 average rating, 106 reviews

Beach Getaway - Upstairs

4.97 out of 5 average rating, 190 reviews

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.

Flat in St. Augustine

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

4.89 out of 5 average rating, 613 reviews

The living area features soft turquoise walls and light hardwood flooring. A spacious white sofa is complemented by green accent pillows. A wall-mounted television and decorative surfboards add character to the space. Natural light fills the room through the window, creating a bright atmosphere.

Bungalow in Lincolnville

The Hideaway

Guest suite in Treasure Beach

A serene waterfront view is captured at sunset, showcasing a pool surrounded by lush grass and palm trees. A shaded seating area is positioned next to the pool, overlooking the water where boats can be seen in the distance.

4.92 out of 5 average rating, 616 reviews

Waterfront suite, Dogs are cool no pet fee

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.

5 out of 5 average rating, 110 reviews

Walk 2 Beach | Game Room | Firepit |Heat/Salt Pool

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, 344 reviews

Cozy, Pet-friendly Private House near 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, 104 reviews

Pink Palms - Heated Mermaid Pool & Cabana - Downtn

Family-friendly home rentals with a pool

A well-lit outdoor living space features a heated pool surrounded by smooth pavers. Several adirondack chairs are positioned nearby for seating, and a dining table is set for outdoor meals. String lights illuminate the area, creating a cozy ambiance.

4.97 out of 5 average rating, 117 reviews

Luxury heated pool home steps from the beach!

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, 422 reviews

Your Home Away From Home

4.98 out of 5 average rating, 188 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

A private balcony features two light-colored chairs and a round table, providing views of the ocean and a nearby pool. The scenery includes lush greenery and a clear sky, while birds can be seen flying in the distance.

4.85 out of 5 average rating, 286 reviews

Direct Oceanfront ~ Fantastic Views!

The living area is furnished with a comfortable sofa and armchair, providing a relaxed seating space. A media console holds a television, and large sliding doors lead to a private balcony. Natural light fills the room, highlighting a neutral color palette.

4.92 out of 5 average rating, 336 reviews

Oceanside complex M33 1 Bed 1 Bath w/Heated Pool

A comfortable living area is highlighted by a textured armchair and a sleek coffee table. A large flat-screen TV is mounted on the wall above a stylish cabinet, while sliding glass doors provide access to the balcony, allowing natural light to fill the space.

4.95 out of 5 average rating, 123 reviews

Bring the boat! 2 Bedroom Steps from the Beach

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, 109 reviews

Boutique Beachside condo with easy access to beach