Family-friendly vacation rentals in St. Augustine

4.99 out of 5 average rating, 147 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

5.0 out of 5 average rating, 156 reviews

Private oasis, heated pool, exceeds expectations

Private retreat on 2 acres of gated land, just 20 minutes to historic downtown St. Augustine and 25 minutes to the beach. This fenced property offers a perfect blend of relaxation, fun, and comfort. Enjoy your private pool, or let the kids enjoy their own space in the pool house, featuring TV, games, and a cozy hangout area. Start your day with fresh eggs from our happy hens- an experience that feels both farm-fresh and uniquely memorable. This home is designed to make your stay unforgettable.

A charming coastal bungalow is set amidst lush green grass, surrounded by palm trees and nature. The driveway leads to the front entrance, featuring a single-car garage. The home is framed by a clear blue sky dotted with clouds, highlighting its welcoming facade.

4.95 out of 5 average rating, 237 reviews

Surfside House

This special vacation home is close to everything, making it easy to plan your visit. Ideal location across from the beach, just minutes to drive or bike into historic downtown St. Augustine. The 1950's coastal bungalow is set on Vilano Beach's historical Street. The home has been completely remodeled, plenty of parking and is pet friendly. Surfside's pet friendly beach access/parking and North Shore Community Park is 1 block away with tennis/ pickle ball courts, playground and dog park.

4.94 out of 5 average rating, 109 reviews

The Starfish Cottage

Welcome to your new home away from home! The Starfish Cottage is a 3 BR/ 2 BT home just walking distance from Downtown St. Augustine and a 10 minute drive to St. Augustine Beach!Perfect for any small family or group that wants to experience the charm of St. Augustine while living on island time! This newly remodeled home comes with all brand new appliances and furniture. It also has a fully equipped kitchen, an open living area, 2 queen beds, a twin and full bunkbed, and large outdoor patio!

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, 170 reviews

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

🌴 Featured in Good Housekeeping & Designed by HGTV-featured Builders ✨ 🏡 New 2023 Luxury Coastal Home 🛏️ 2 King Suites + 2 Queen Bedrooms 🛁 3.5 Bathrooms 💦 Private Saltwater Pool + Heated Spa/Hot Tub 🍹 Poolside Cabana & Outdoor Kitchen 🚲 Bikes, Beach chairs, Cooler & Toys included 🌿 Tropical Backyard Oasis w/ Mature Palms, Lounge Chairs, Outdoor Shower & Turf 👣 Walk 0.2 miles to the beach 🌅 Stroll 0.2 miles to Cap’s for Waterfront Sunset Dinner 🏰 10 min to Historic St. Augustine

Superhost

Two blue patio chairs are positioned on a wooden deck, facing the ocean. The expansive beach and gentle waves are visible in the background, under a clear blue sky dotted with soft clouds.

4.85 out of 5 average rating, 165 reviews

Oceanfront Barefoot Beach Retreat

Lovingly updated oceanfront cottage, located on a fabulous and quiet stretch of beach in Vilano Beach. Just ten minutes north of historic downtown St Augustine . Close enough for a quick drive to see the sights but just far enough away to get some peace and quiet ! Beautiful beach with access right off the back of this dreamy home, enjoy amazing sunrises right off the back deck or even from the master bed ! Kick off your shoes and leave your worries behind and enjoy the peace and serenity !

4.96 out of 5 average rating, 140 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.

An expansive ocean view is framed by a white railing on a sunny day. Lush green grass and tropical plants lead to the sandy beach, while waves gently lap against the shore under a clear blue sky.

4.95 out of 5 average rating, 204 reviews

Ponte Vedra Sth/Vilano Oceanfront 3Bed 2bath Pets

Nicely furnished 3 bedroom 2 full bathroom house tucked away in the dunes on Surfside Vilano Beach . 3 miles from downtown St Augustine, a half mile from Publix .The deck wraps around half the house, pretty fantastic ocean views, sunrise and river side sunsets. Each bedroom has a smart tv with Internet and a very comfortable Queen or King size bed. TPC Sawgrass is a 20 minute drive north , Daytona International Speedway 70 minutes south , 2 hours to Orlando and Busch Gardens.

4.94 out of 5 average rating, 234 reviews

Downtown • Parking for 2 + Wraparound Porch

Historic Whitney House • Newly renovated 1,700 sq ft designer home Private driveway parking for 2 • Steps to trolley & St. George Street Gourmet kitchen, 2 en-suite bedrooms, 3 luxury baths, Starlink WiFi, wrap-around porch + sunny deck. Fitness club & pool passes included. Modern luxury in the heart of historic downtown St. Augustine. Perfect for couples or small groups seeking modern luxury, easy parking, and a walkable base right in the heart of historic downtown St. Augustine.

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.

5.0 out of 5 average rating, 206 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, fully fenced backyard, off-street parking, paved driveway close to downtown and excellent beaches. Prime location!

Villa in St. Augustine Beach

5.0 out of 5 average rating, 130 reviews

VILLA ONE • 1 Block to the Ocean

One block from the ocean in St. Augustine Beach, this design-forward 2BR/2BA villa is made for easy beach stays. Warm tones, natural finishes and local art create a relaxed, laid-back feel. Outside, enjoy a private tropical backyard with lounge area, outdoor dining and outdoor shower. Walk to the beach, coffee and local favorites, with Historic Downtown just 10 minutes away. One of four individually styled St. Augustine Beach Villas. Not pet friendly. @staugustinebeachvillas

A spacious screened-in pool area features a large blue swimming pool surrounded by patio tiles. Comfortable seating arrangements with multiple chairs and a table are visible nearby, providing a relaxed space for leisure. Natural light streams in through the screened enclosure.

4.93 out of 5 average rating, 200 reviews

Heated Pool, Beach, Patio Lounge, Near Downtown

Add my home to your wishlist, click the <3 in top right corner! *Book 2 nights, get the 3rd night 30% off!* >HUGE screened in pool! Heat pool for $60/day or $350/wk. >500 steps to beach >3 TV's with streaming apps (not cable) >Lots of parking! >.5 miles to Publix grocery store >Short drive to marina, restaurants, boat rentals >Walk to intracoastal >Short drive to DT St. Aug >Washer + Dryer >BBQ Grill >3 days of supplies (TP, trash bags, etc.)

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

Apartment in St. Augustine

4.92 out of 5 average rating, 157 reviews

Cozy Garden - Sleeps 4- hottub/outdoor shower!

A spacious hot tub is centrally positioned in a private outdoor area, surrounded by a wooden privacy fence. Red Adirondack-style chairs are arranged nearby, providing a relaxed seating area. Lush greenery and palm trees enhance the serene atmosphere of the garden space.

4.93 out of 5 average rating, 131 reviews

Stay in A Castle In St. Augustine, Hot Tub, Firepl

Superhost

A newly renovated historic home is set against a serene natural backdrop, featuring a large deck accessible via a wooden walkway. The exterior showcases multiple arched windows and a modern roof deck, surrounded by lush vegetation and reflected in the calm waters of the marsh.

Cottage in Vilano Beach

4.91 out of 5 average rating, 179 reviews

The Shire on 1 acre marshfront with dock and Spa

4.99 out of 5 average rating, 162 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!

Apartment in St. Augustine

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.

4.99 out of 5 average rating, 650 reviews

Villa Tizoc

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, 200 reviews

Newly renovated! Steps to BEACH & POOL!

Condo in St. Augustine Beach

A balcony table is set for two, featuring white plates and cups, with expansive ocean views. Lush greenery and sandy beach can be seen in the distance under a clear blue sky, creating a serene and inviting outdoor space.

4.98 out of 5 average rating, 262 reviews

Ocean Front Gem: Top Floor Corner Unit

Apartment in Vilano Beach

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.

4.95 out of 5 average rating, 201 reviews

Charming Vintage Intracoastal Apartment

Family- and pet-friendly home rentals

Apartment in Vilano Beach

A spacious backyard features a stone fire pit surrounded by several comfortable Adirondack chairs. In the distance, a colorful children's playset stands beneath a sky painted in hues of pink and purple, while lush green grass stretches across the area.

4.93 out of 5 average rating, 183 reviews

BIG Backyard w/Terrace|Dining|Games | 6min2Beach

4.93 out of 5 average rating, 116 reviews

An aerial view captures a sweeping stretch of Crescent Beach shoreline, highlighting the sandy beach alongside the Atlantic Ocean. Residential and commercial buildings are visible in the nearby area, with greenery bordering the beach, showcasing the natural landscape of this coastal community.

Home in Crescent Beach

Bridgekeeper's Cottage

5.0 out of 5 average rating, 167 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!

4.98 out of 5 average rating, 114 reviews

An aerial view highlights the charming blue cottage surrounded by lush palm trees and vibrant greenery. The proximity to pristine beach waters is visible, along with neighboring coastal homes. A walkway leads from the yard to the street, emphasizing the inviting outdoor space.

Cottage in Vilano Beach

Vilano Charmer, Capo’s Cottage, 1/2 block to beach

Home in St. Augustine Beach

4.87 out of 5 average rating, 244 reviews

St. Aug Oceanfront Home w/ Heated Pool & Firepit

4.99 out of 5 average rating, 142 reviews

An aerial view of a beach house situated one block from the ocean is displayed. The coastline and sandy beach are visible, along with surrounding residential buildings and parked cars. The water shimmers under sunlight, suggesting a clear day.

Home in Butler Beach

Memory Maker - Vacation with Friends and Family

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.

5.0 out of 5 average rating, 154 reviews

Historic 1918 Cottage in Downtown St. Augustine

An enclosed lanai features a heated saltwater pool surrounded by a sleek concrete deck. Colorful lounge chairs are positioned nearby, and greenery is visible outside the mesh screens. The walls exhibit a calming light hue, contributing to a serene poolside atmosphere.

4.97 out of 5 average rating, 138 reviews

The Salty Seashell, Coastal Pool Home, Sleeps 8

Family-friendly home rentals with a pool

Apartment in St. Augustine

A serene outdoor area features a suspended basket chair, surrounded by lush greenery and sun loungers beside a sparkling pool. Umbrella-shaded tables provide shade, while the building's modern architecture stands in the background, enhancing the inviting atmosphere of the space.

4.85 out of 5 average rating, 107 reviews

Luxury Retreat in St. Augustine

A tranquil backyard area is featured, showcasing a heated pool surrounded by lush greenery. Two black chairs are positioned on the stone patio, offering a comfortable spot for relaxation. The space is enclosed by vibrant tropical plants, enhancing the private atmosphere.

4.95 out of 5 average rating, 196 reviews

Pool home oasis steps to ocean

4.98 out of 5 average rating, 161 reviews

A bright living area features large floor-to-ceiling windows that provide sweeping ocean views. Comfortable seating is arranged around a central coffee table adorned with decorative items. A Smart TV is positioned for easy viewing, while a ceiling fan adds a cooling breeze.

Condo in Butler Beach

Family Beach Condo - Steps To The Sand Or Pool

Apartment in Vilano Beach

The living area features a light-colored sectional sofa with decorative pillows, complemented by two armchairs. A coffee table rests on a soft area rug, and light filters through shutters on the windows. A ceiling fan is visible, adding a cool breeze.

4.98 out of 5 average rating, 164 reviews

Oceanfront paradise

Cottage in St. Augustine Beach

The kitchen features modern appliances, including a refrigerator, microwave, and dishwasher. White cabinetry provides ample storage. A dining table with four chairs is positioned near the door, and a light fixture illuminates the space. A decorative rug adds a touch of warmth.

4.95 out of 5 average rating, 509 reviews

Beautiful Beach Cottage

4.98 out of 5 average rating, 198 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

Superhost

5.0 out of 5 average rating, 5 reviews

Island Home • Pool • Putting Green • Walk to Amp