Family-friendly vacation rentals in St. Augustine

4.99 out of 5 average rating, 146 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.

4.94 out of 5 average rating, 236 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.

5.0 out of 5 average rating, 278 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

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

4.96 out of 5 average rating, 139 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, 233 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.

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

The outdoor area features a heated pool surrounded by comfortable lounge chairs and shaded umbrellas. A spacious patio includes additional seating and a tranquil atmosphere, enhanced by palm trees and bright blue skies.

5.0 out of 5 average rating, 201 reviews

Don’t You Wanna? Heated Pool & SPA 4Bed & 3Bath

Don't You Wanna...4 Bedroom, 3 Bath with HEATED POOL, SPA, and Outdoor Shower located in the heart of Vilano Beach of historic St. Augustine, FL. Our conveniently located home allows you to bring family and friends to share memories with a nice sunset or sunrise just down the street at the third street beach access point. Want to have a nice dinner at one of the most popular restaurants in all of St. Augustine? Walk around the corner to Cap's On The Water for great dining.

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

One of a kind 1930s historic home, newly renovated and transformed into a beautiful secluded getaway. new luxury finishes, while holding its traditional charm. No Events allowed. Rooftop deck, sunrise views of the Atlantic ocean, Downtown, and sunsets over the river. The new dock with covered roof hosts a national geographic like eco system. It’s short walk to the beach and 3 miles to downtown St George street. Follow along @carcabaroad for weekly content of the home.

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

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

Apartment in St. Augustine

4.92 out of 5 average rating, 156 reviews

Cozy Garden - Sleeps 4- hottub/outdoor shower!

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, 649 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

Condo in St. Augustine Beach

A cozy living area features soft beige furnishings and decorative blue pillows. A wooden coffee table occupies the center, while a stone fireplace adds warmth. Large sliding doors provide natural light and reveal views of the outdoors, framed by sheer curtains.

4.92 out of 5 average rating, 153 reviews

Quiet, Updated Condo - Pool, Bikes & Pickleball!

Family- and pet-friendly home rentals

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, 153 reviews

Historic 1918 Cottage in Downtown St. Augustine

An open-concept living area features a comfortable gray sofa, a coffee table, and a TV on a stand. Natural light fills the space through the windows, and a dining table with chairs is visible in the background. A patterned rug adds warmth to the wooden floor.

4.96 out of 5 average rating, 384 reviews

Downton Abbottry 2/2 - 5 Min Walk To City Gates

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, 163 reviews

Oceanfront Barefoot Beach Retreat

A light-filled living area features a modern TV console with a large screen and decorative accents. The space includes a comfortable sofa, two armchairs, and a dining area with a table and chairs, seamlessly connecting to the fully equipped kitchen.

4.91 out of 5 average rating, 171 reviews

Sunshine by historic downtown & the beach

4.91 out of 5 average rating, 107 reviews

The Secret Garden On Locust!

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

The exterior of Casa Coquina is presented, featuring a charming façade with rounded archways. A light blue garage door complements the neutral-colored walls. Lush greenery, including palm trees and decorative plants, enhances the inviting entryway, while a driveway leads to the garage.

4.99 out of 5 average rating, 136 reviews

Casa Coquina Walk to Downtown Clean Quiet Spacious

Bungalow in St. Augustine

4.9 out of 5 average rating, 124 reviews

Historic 12 Dupont Lane A

Family-friendly home rentals with a pool

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, 195 reviews

Pool home oasis steps to ocean

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

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, 508 reviews

Beautiful Beach Cottage

A serene outdoor space features a clear, in-ground heated pool surrounded by natural landscaping. Comfortable lounge chairs and a shaded dining area under an umbrella offer inviting spots for relaxation. A tree provides added greenery nearby, creating a tranquil, private environment.

4.87 out of 5 average rating, 127 reviews

Brand NEW Beach House with HEATED pool!

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

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, 451 reviews

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