Family-friendly holiday rentals in St. Augustine

4.99 out of 5 average rating, 157 reviews

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.

Home in Butler Beach

Driftmark Cabin - RV friendly, Pool + Beach!

Experience the ultimate beachside getaway at our fully renovated Airbnb, just steps away from the sun-kissed sands. This luxurious retreat offers modern comfort with a private pool and inviting hot tub, allowing you to unwind in style. The recently upgraded interior boasts premium amenities, ensuring a relaxing stay. Outside, lush turf landscaping surrounds the pool, creating an oasis of comfort. Whether you're lounging by the pool, or enjoying the beach a stone's throw away, Driftmark delivers.

4.99 out of 5 average rating, 138 reviews

HtdPool w/Arcade, Fire, GolfCart Access, 1.2 mi DT

ISLE BE BACK 🌴— brand NEW modern home! **Golf Cart Access for an additional fee Please inquire if interested!** Welcome to your ultimate St. Augustine getaway! Just 5 mins from downtown, this fun-filled retreat is perfect for families, friends, or anyone looking to relax and play. Swim in the pool, compete on the putting green, roast s'mores by the fire pit, or challenge your crew on the retro Pac-Man machine—all without leaving the house! ✔Sleeps 8 comfortably ✔Self check-in & free parking

4.91 out of 5 average rating, 248 reviews

An open-concept kitchen and dining area features a large island with a butcher block countertop and modern appliances. Bright white beams accent the ceiling, while vibrant green chairs surround a round dining table. A cozy seating area includes light-colored furniture and a flat-screen TV.

Loft in St. Augustine

Downtown •Historic Whitney House Loft•RoofTop Deck

Residential Street Parking Pass 2 Min Walk to St George Street 5 Min Drive to State Park Beach 6 Min Drive to Anastasia Fitness/Pool/Suana/Yoga High Speed Starlink Internet Luxury 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 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, 141 reviews

Pink Palms *Pool* Party ~ Walk to Downtown

🏝️ Luxurious Private Heated Pool Home In Historic Downtown and Family Friendly! - Private Heated Pool & large backyard with tons of gorgeous palms - Outdoor cabana with grill, fans, pool table, kid toys, bocce, corn hole and seating - Walking distance to the Castillo de San Marcos Fort, Fountain of Youth, Uptown shops, The Bayfront and St. George Street - Wild Peacocks in backyard 🦚 - Less than 10 mins to Vilano Beach 🌊 - Sleeps 6/ 2 King beds, 2 XL twin beds (daybed trundle) - Pet Friendly

5 out of 5 average rating, 274 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”

Stunningly renovated cottage combines modern amenities with vintage charm... * 2 master suites with queen beds * Quiet neighborhood walking distance to explore The Nation's Oldest City * Clawfoot tubs inside and out (along with showers, of course!) * Big screened-in porch with hanging daybed * Off-street paved parking * Fully fenced backyard, Weber grill, gas fire pit * Fast Wi-Fi and Smart TV * 2 blocks to Fish Camp, Ice Plant, LaNuvelle, trolley stop * 10 minute walk to central downtown

Villa in St. Augustine Beach

A spacious living area features a light gray sectional sofa with a chaise, positioned on a natural fiber rug. A round mirror enhances the sense of space, while a dining area is visible in the background, complete with wooden chairs and a table.

5 out of 5 average rating, 126 reviews

VILLA One

The Villas are designed for short stays, long weekends or for a unique styled location for brands to shoot their products. The space features warm tones, natural finishes and local art for an effortless vibe that allows visitors to relax the second they walk in the door. Complete with two bedrooms, two bathrooms and a backyard complete with tropical landscaping, lounge area, dining and outdoor shower. One of 4 Villas located in St. Augustine Beach. Not pet friendly. @staugustinebeachvillas

Townhouse in St. Augustine

An open living area with wooden beams offers panoramic ocean views through large sliding glass doors. A modern dining table is paired with high chairs, while a cozy seating arrangement features a plush sofa. A mounted TV and decor add warm touches to the space.

4.94 out of 5 average rating, 217 reviews

Penthouse Artist Haven Ocean front Penthouse

Nestled along a pristine stretch of semi-private beach is this historic artists haven offering an absolute beachfront location like no other. This unique home is split into 3 separate floors, where you will be renting the entire top penthouse level. Inside you will find open studio living with a luxe king bed and a front and rear balcony. Enjoy uninterrupted ocean views from the panoramic windows while you relax & watch dolphins play in the surf and stunning sunsets spread across the sky.

4.96 out of 5 average rating, 138 reviews

A classic 43-foot Gulf Star yacht is moored in calm waters, exhibiting a spacious deck with a covered seating area. The hull is painted in a crisp white, reflecting sunlight, while nearby masts and boats frame the picturesque marina scene.

Boat in St. Augustine

Funshine - Vacation on a 43' Gulfstar Yacht

A unique, memorable place, anything but ordinary. Try living the boating lifestyle on a classic and quaint vintage 43 foot Gulf Star yacht. Only 1.2 miles to the historical St. Augustine Bayfront and less than 10 miles to many of our gorgeous beaches. This 2-bedroom 1.5 bath beauty allows you to experience a life on a live-a-board. You will vacation within a reasonable walking distance to many of the attractions in St Augustine, a winery, distillery, several museums, many restaurants.

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, 164 reviews

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

* Built in 2023- luxe coastal furnishings & linens * Featured in 2024 Good Housekeeping Mag🌟 * 2 King Suites (1 on each floor) | 2 Queen Bedrooms | 3.5 Baths * Private Saltwater Pool & Spa/Hot Tub * Poolside Cabana | Outdoor Kitchen | Front Porch * Bikes, Beach Toys, Beach Chairs * Lush Tropical Landscaping * 0.2 miles - Gorgeous quiet beach * 5.5 miles- Historic downtown St Augustine- The oldest city in the United States! * 0.2 miles - Cap's Restaurant for sunset dinner on the water

The living area features a modern design with custom wood paneling on one wall. A leather sofa is positioned in the foreground, while a decorative coffee table and a small workstation with a chair are visible. Soft lighting highlights a piece of scenic artwork above the table.

4.97 out of 5 average rating, 126 reviews

St Augustine Entire Home, King Bed, Pet Friendly

Casita Luxe Retreat Near Historic St. Augustine – Pet-Friendly Haven! Discover this luxurious 3-bedroom, 2-bath retreat! Designed with a modern luxe aesthetic, it features custom wood paneling, a fully equipped kitchen with a chic island, and a king-size plush mattress. Enjoy the large, fenced yard, fire pit, outdoor shower, and fun family games. Pet-friendly, with Wi-Fi, smart TVs, and parking included this home offers comfort and style in an up-and-coming neighborhood. Book now!

A private saltwater pool is centrally located within a spacious patio area, surrounded by well-maintained grassy lawns. Lounge chairs are positioned alongside the pool, while tables and chairs can be seen in the background. The home features sliding glass doors providing access to the pool area.

4.97 out of 5 average rating, 105 reviews

Music on Marilyn- Steps from the Amp! •Jacuzzi•

Nights of Lights & mere seconds from the St. Augustine Amphitheater— a short bike ride to the beach and downtown, this modern escape is 3 beds and 2 baths. Welcome to Music on Marilyn! This is the quintessential St. Augustine experience. Nestled on a quiet street that dead ends to the intracoastal, walking distance to the St. Augustine Amphitheater, Lighthouse, Anastasia Park, Alligator Farm and much more! St. Augustine Beach and historic downtown are just a short bike ride away.

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.

4.99 out of 5 average rating, 123 reviews

Heated Pool/Hot Tub 1 mile to dwntn/beach

Property Highlights - Large heated Saltwater Pool (heated Nov 1-May 1) - Hot Tub - Fully Fenced Private Backyard - Open Floor Concept - 1 Mile to Downtown - 1.5 Mile to State Park Beach - Quiet Neighborhood - Newly furnished Perfect for month stays, long weekend and week vacations, and out of town wedding guests! Escape to this St. Augustine home- that is not only the perfect vacation spot, but an ideal and convenient home away from home for your out of town wedding guests.

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

4.97 out of 5 average rating, 133 reviews

Luxury pool & spa home steps to beach & 2 masters!

Apartment in St. Augustine Beach

4.89 out of 5 average rating, 211 reviews

Beachy Condo| Steps to Beach | Pools | Hot Tubs

4.94 out of 5 average rating, 140 reviews

Tide Pool | 4/3 Eclectic Escape | Pool & Rooftop

4.99 out of 5 average rating, 643 reviews

A charming two-story apartment stands above a pool area framed by lush greenery. The balcony offers a view of the pool, while the surrounding landscape features vibrant foliage and mature oak trees. The pool is bordered by textured paving stones and a patio set in the background.

Flat in St. Augustine

Villa Tizoc

4.95 out of 5 average rating, 195 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 Vilano Beach

Charming Vintage Intracoastal Apartment

4.94 out of 5 average rating, 108 reviews

Spring Summer Oasis- A Million Memories

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.

4.96 out of 5 average rating, 193 reviews

Newly renovated! Steps to BEACH & POOL!

4.98 out of 5 average rating, 342 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

Loins Bridge 0.5m away, 2 Bedroom, Private Hot Tub

Family- and pet-friendly home rentals

4.98 out of 5 average rating, 141 reviews

Flagler Cottage l 1 Block to Historic District

A charming white cottage showcases a welcoming porch adorned with hanging planters. An American flag flutters by the entrance, while a gravel pathway leads up to the home, surrounded by manicured greenery and shaded by large trees, creating a serene exterior setting.

5 out of 5 average rating, 147 reviews

Historic 1918 Cottage in Downtown St. Augustine

A comfortable living area features a large sectional sofa adorned with yellow and grey cushions. A flat-screen television hangs above a decorative fireplace. A coffee table with a small plant is centered on a textured area rug, and natural light filters through the nearby windows.

4.91 out of 5 average rating, 331 reviews

SaraCasa - First Floor House 2Br/1.5Bath

A cozy outdoor space features a wooden deck surrounding a small pool, complemented by colorful cushions and lounge chairs. Soft lighting from string lights overhead adds a warm ambiance. The area is enclosed by a wooden fence, providing privacy for guests.

4.97 out of 5 average rating, 101 reviews

Top-Rated Stay | Pool, Tiki Bar, Walk to the Beach

5 out of 5 average rating, 154 reviews

Private oasis, heated pool, exceeds expectations

4.91 out of 5 average rating, 235 reviews

Cottage in St. Augustine

Coastal Cottage -firepit, pet fence, kayaks, bikes

4.92 out of 5 average rating, 102 reviews

The Secret Garden On Locust!

4.96 out of 5 average rating, 138 reviews

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

Family-friendly home rentals with a pool

Superhost

Home in St. Augustine Beach

5 out of 5 average rating, 3 reviews

Luxury Beach Retreat, Pool Spa Sauna Yoga Studio

An outdoor pool area is framed by a spacious patio featuring lounge chairs and an outdoor dining set. The large heated pool reflects the clear blue sky, and shaded areas are created by an umbrella. The surrounding landscape includes trees and fencing for added privacy.

4.99 out of 5 average rating, 86 reviews

1 Block to Beach! Heated Pool, Near Historic Dist.

5 out of 5 average rating, 20 reviews

Pool + Fire Pit | Game Room | 1 Mile to Downtown

5 out of 5 average rating, 15 reviews

Pelicans Paradise Pool Home —Steps to Downtown

4.99 out of 5 average rating, 73 reviews

Cocktail Pool, Putt Putt, Bowling, BBQ, Nintendo

A two-story blue house features a private pool surrounded by a stone patio. White chairs and a small table are set near the pool, with additional seating visible against the home's exterior. Lush greenery borders the enclosed yard, enhancing the tranquil ambiance.

4.93 out of 5 average rating, 102 reviews

Blue Haven

5 out of 5 average rating, 44 reviews

Heated Poolside Movie Nights + Game Shed

An outdoor dining area features a wooden table with six chairs, shaded by a large tree. A small pool is visible nearby, surrounded by lounge chairs and tropical plants. A hammock can be seen draped between two posts, creating a space for relaxation.