Family-friendly holiday 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

KitchenFamilyValue

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.

KitchenFamilyBiking

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, 168 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

FamilyIndoor spacesDecor

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.

5.0 out of 5 average rating, 129 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

FamilyKitchenParks

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

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 !

Indoor spacesFamilyValue

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.

KitchenIndoor spacesWifi

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.

KitchenFamilyParking

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.

FamilyIndoor spacesAccess

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

4.9 out of 5 average rating, 178 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.

FamilyKitchenAccess

4.96 out of 5 average rating, 108 reviews

An outdoor dining area is placed on a wooden deck, featuring a white table and six striped chairs. A vibrant red umbrella offers shade, while the expansive view of the sandy beach and ocean stretches in the background, under a clear blue sky.

Flat in Vilano Beach

Magic Beach House in Vilano Beach

Welcome to Vilano and magic shell beach! This delightful oceanfront beach house is a 3 bedroom, 2 bath, 1800 sq. ft. space that sits above 2 lower units. All entrances are private and the grand upper deck belongs solely to you and your party. Enjoy the view of gorgeous sunrises, frolicking dolphins and the ever-changing waves, water, and sky as you relax in this perfect location steps from the beach and a close 5 minute drive into the Historic City of St Augustine.

Indoor spacesKitchenValue

Apartment in Butler Beach

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.

4.97 out of 5 average rating, 159 reviews

Family Beach Condo - Steps To The Sand Or Pool

Our beach condo on Crescent Beach has been our family’s haven for years, and we’re excited to share it with you! The breathtaking ocean views from our living room and balcony are just the start—enjoy a renovated kitchen, comfy bedrooms, and family-friendly touches that make this place truly special. Whether you’re here to relax, explore historic St. Augustine, or enjoy the natural beauty of Anastasia State Park, we hope you’ll create lasting memories like we have!

FamilyIndoor spacesCleanliness

4.97 out of 5 average rating, 115 reviews

A light-filled kitchen features modern appliances, including an oven and a large dining table. Windows offer a view of the ocean, while natural light highlights the white cabinetry and rustic decor. The space is complemented by potted plants and hanging light fixtures.

Cottage in Ponte Vedra

Cane Cottage Oceanfront Oasis

Cane Cottage was renovated in 2018-2019 after extensive damage from multiple hurricanes. Our vision was to bring this old Florida beach cottage back to its original charm while also adding new life and modern amenities. From the outdoor entertaining spaces to the lavish interior finishes this AirBnB makes for the perfect beach retreat. Well designed and functional home with many well-thought-out touches.

FamilyKitchenPets

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 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, 261 reviews

Ocean Front Gem: Top Floor Corner Unit

FamilyKitchenLayout

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, 109 reviews

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

FamilyKitchenLocation

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, 200 reviews

Newly renovated! Steps to BEACH & POOL!

FamilyKitchenPool

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!

KitchenFamilyPool

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

KitchenIndoor spacesHospitality

4.92 out of 5 average rating, 156 reviews

Flat in St. Augustine

Cozy Garden - Sleeps 4- hottub/outdoor shower!

Indoor spacesFamilyShared spaces

4.93 out of 5 average rating, 144 reviews

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

FamilyIndoor spacesComfort

The exterior of the coastal home is adorned with blue siding under a clear sky. Palm trees flank the driveway, adding a tropical touch. A spacious front yard features lush greenery and an inviting walk path leading to the entrance.

4.93 out of 5 average rating, 115 reviews

2 Masters-Heated Pool & Spa+1 min Walk to Beach

FamilyIndoor spacesCheck-in

Family- and pet-friendly home rentals

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!

FamilyKitchenComfort

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”

FamilyKitchenLocation

4.83 out of 5 average rating, 237 reviews

A charming A-frame beach house is set against a backdrop of clouds, featuring a spacious deck with outdoor seating. A grassy area with coastal vegetation surrounds the home, while a barbecue grill and shaded pergola enhance the outdoor space. Neighboring buildings are visible in the distance.

Home in Ponte Vedra

The Pink Seahorse - Beachfront Modern A-Frame

FamilyKitchenGrill

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, 235 reviews

Surfside House

FamilyIndoor spacesCleanliness

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.

4.92 out of 5 average rating, 198 reviews

Heated Pool, Beach, Patio Lounge, Near Downtown

KitchenIndoor spacesTV

Apartment in St. Augustine

A spacious living area features wood-paneled walls and large glass doors, offering views of the ocean. A chandelier hangs from the ceiling. The seating area includes a comfortable couch and a dark coffee table, while a television with vibrant display adds a touch of modernity.

4.92 out of 5 average rating, 118 reviews

Treehouse Artist Haven Direct Oceanfront 2br

FamilyIndoor spacesShared spaces

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

FamilyIndoor spacesAccuracy

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

Indoor spacesFamilyAccess

Family-friendly home rentals with a pool

A private heated pool is surrounded by a spacious patio designed for relaxation. Comfortable lounge chairs are positioned nearby, alongside a well-maintained yard with decorative plants. The pool house features a playful mermaid mural on its exterior, adding a touch of charm to the outdoor space.

4.93 out of 5 average rating, 162 reviews

Splash & Explore

KitchenIndoor spacesDecor

4.85 out of 5 average rating, 106 reviews

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.

Flat in St. Augustine

Luxury Retreat in St. Augustine

Indoor spacesKitchenLaundry

4.98 out of 5 average rating, 164 reviews

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.

Flat in Vilano Beach

Oceanfront paradise

Indoor spacesFamilyBathroom

A modern home is surrounded by a well-kept backyard featuring a private pool and spacious patio. Comfortably arranged lounge chairs provide a relaxing spot. The exterior showcases light-colored siding and elevated balconies, with palm trees dotting the landscape for a tropical feel.

4.89 out of 5 average rating, 114 reviews

Sunset Cove 2 - Pool - Sea Views - Walkable

FamilyIndoor spacesLaundry

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

Indoor spacesFamilyGetting around

Luxe

Villa in Vilano Beach

5.0 out of 5 average rating, 14 reviews

Vilano Villa| Walk 2 Beach | Water View | Wellness

KitchenIndoor spacesGetting around

Superhost

5.0 out of 5 average rating, 4 reviews

Island Home • Pool • Putting Green • Walk to Amp

FamilyIndoor spacesTV

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.