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Family-friendly holiday rentals in Historic District, St. Augustine

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Quick stats about holiday rentals that are family-friendly in Historic District, St. Augustine

  • Total holiday rentals

    Explore 210 holiday rentals in Historic District, St. Augustine

  • Nightly prices starting at

    Historic District, St. Augustine holiday rentals start at $126 AUD per night before taxes and fees

  • Verified guest reviews

    Over 18,300 verified reviews to help you choose

  • Pet-friendly accommodation

    Find 110 rentals that welcome pets

  • Holiday rentals with a pool

    40 properties feature pools

  • Rentals with dedicated workspaces

    100 properties have a dedicated workspace

  • Wi-Fi availability

    210 of Historic District, St. Augustine holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Historic District, St. Augustine rentals

  • 4.9 Average rating

    Historic District, St. Augustine stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated family-friendly rentals in Historic District, St. Augustine

Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

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Guest favourite
A cozy bedroom is highlighted by a double bed adorned with floral bedding and decorative cushions. Soft, warm light is emitted from two bedside lamps on wooden nightstands. Artwork and photographs decorate the walls, and delicate curtains frame the window, allowing natural light to fill the space.
Apartment in St. Augustine

Victorian Era-5-10 Min Walk Downtown Attractions

PERFECT LOCATION!! Excellent accommodations to explore the City of St Augustine by foot. A 5-10 minute walk to attractions, restaurants and shopping(Beaches-State Parks 15 min drive). "The Riverside Boarding House" is a unique 1894 Victorian Historic Home. A European-Styled cozy space filled with character and charm. Small but fully functional: SEPARATE ENTRANCE, Bedroom, PRIVATE BATHROOM. A safe, quiet neighborhood with ample parking. True Victorian Experience! Couples, Singles, Children 12+.

4.9 out of 5 average rating, 547 reviews
Top Guest favourite
A two-story blue home is framed by lush green trees. The exterior features large windows and a welcoming front porch supported by white columns. Well-kept landscaping includes a stone pathway leading to the entrance and decorative figures flanking the steps.
Holiday home in St. Augustine

Historical Beauty in the Heart of St. Augustine

Amazing Location! Uptown Historic District-close to St. George st., Plaza & Fort. Large, comfortable home! Get the complete St. Augustine experience- walking distance to all historical sites, amazing restaurants/eateries, unique shops, & art galleries. This home has been recently remodeled from top to bottom. Enjoy a chef's kitchen, beautiful bedrooms, bathrooms, & off-street parking in uptown luxury. High speed internet and cable. Outdoor grill. Minutes to St. Augustine and Vilano beaches.

4.98 out of 5 average rating, 201 reviews
Guest favourite
Home in St. Augustine

The Secret Garden On Locust!

Welcome to your home away from home in downtown St. Augustine, Florida! This delightful 2-bedroom, 1-bathroom bungalow, built prior to 1900, offers a perfect blend of modern comfort and historic charm. Nestled in the prime location of the Abbot Tract Historic District, 19 Locust is just a 5-minute stroll from the storied Castillo de San Marcos and historic downtown. With the beach just a short jaunt away, you’ll have equally easy access to all the attractions this enchanting area has to offer.

4.91 out of 5 average rating, 107 reviews
Top Guest favourite
Guesthouse in St. Augustine

The Garden Casita in St. Augustine Florida

Secluded garden casita tucked away three tenths of a mile from the city gates. Take the private garden pathway to serenity's doorstep, and gain access to WIFI, free parking, and a kitchenette equipped with the basic necessities. The zen garden serves as a wonderful resting space to relax and unwind from your day. The casita features a queen size bed with luxury linens, desk nook and a full bathroom. Come find your peace at the Garden Casita on the grounds of a 100 year old private home.

4.94 out of 5 average rating, 459 reviews
Top Guest favourite
The home’s exterior is characterized by a modern architectural style with a covered front porch featuring four rocking chairs. A wide concrete path leads to the entrance, flanked by well-maintained green landscaping under a clear blue sky.
Home in St. Augustine

Newly built w/garage In The Heart of St.Augustine

Click [♡ Save] button to easily find this listing again before your dates are booked. Great walkable location on a safe quiet street; Spacious and nice for entertaining and relaxing. Bikes and beach chairs included. Very comfortable beds. The porches have rocking chairs too. The home is on one level which is also nice for elderly with mobility challenges. Guests say this is a convenient stay for local weddings, special events¸ and an enjoyable vacation. Send us a message to plan your stay.

4.98 out of 5 average rating, 223 reviews
Top Guest favourite
A dining area is showcased with a wooden table surrounded by six chairs, featuring vibrant floral upholstery. A woven pendant light hangs above, illuminating the space. An ocean-themed mural adorns the wall, complemented by potted plants positioned nearby.
Apartment in St. Augustine

Charming Old-Florida Apartment

This darling Uptown apartment is in the thick of it! Next door to fab shops/eateries -- including our own bodega, coffee shop, and taproom, plus food truck and vintage shops. Walkable to historic downtown, the fort, Bridge of Lions, and Matanzas River. Bikeable to Vilano and Anastasia State Park. And a short drive to more beaches on Anastasia Island or in Vilano. Enjoy a slice of St. Augustine typically only enjoyed by the locals, and relax in the friendly historic Abbott Tract neighborhood.

4.92 out of 5 average rating, 172 reviews
Top Guest favourite
The charming cottage is framed by lush greenery and a pathway leading to a welcoming front porch. The airy porch is adorned with hanging plants and a ceiling fan, inviting relaxation. Gravel landscaping enhances the surrounding gardens, offering a serene first impression.
Cottage in St. Augustine

Casa Verde 1885 - Walk to Downtown

Let this gem located in the historic Abbott Tract be your home away from home. Located just 2 blocks from the Downtown area and all it has to offer. This cottage was built in 1885 and retains its old-world charm while featuring modern conveniences. Whether you’re enjoying breezes from Matanzas Bay sitting on the front porch swing, or dining in the resort-like back yard featuring an outdoor bar, built-in eating area, covered porch and lounge chairs, this is an experience not to be missed.

4.95 out of 5 average rating, 201 reviews
Top Guest favourite
A modern kitchen is presented with sleek white cabinetry and a striking granite countertop. Stainless steel appliances are neatly arranged, and a large sink is installed in the island. A textured black backsplash complements the overall design, creating a functional cooking space.
Home in St. Augustine

Historic 10 Dupont Lane

In St Augustine's historic neighborhood. Completely modernized, but we kept the old charm. New everything. Included amenities bikes, BBQ, Fire pit, outdoor lounge furniture, private patio, laundry inside, Nespresso maker, coffee included, soaps and shampoos, beach essentials. Everything you need is here. Just bring your suit case. 5-10 minute walk to the center of town. Catch the trolly at the end of the street. Buy your tickets here and receive a discount. Welcome to a fun memorable stay.

4.93 out of 5 average rating, 198 reviews
Top Guest favourite
Home in St. Augustine

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.

4.94 out of 5 average rating, 233 reviews
Top Guest favourite
A charming mid-century home features a welcoming front porch with seating. Lush greenery and Spanish moss surround the property, enhancing its tranquil setting. The entrance is marked by a slate stone walkway and a decorative sign, contributing to the home's inviting appearance.
Home in St. Augustine

Charming 3 bedroom cottage, feed the peacocks!

A 15-minute walk to Old Town, this cozy mid-century home has all the modern touches while retaining its roots! Stroll down beautiful Magnolia St. to the Fountain of Youth, or stay and feed the free-roaming peacocks from the front porch! Old Town Trolley stop, and the Old City Jail are just at the end of the street. Enjoy games with the family, grilling, or hit the beach, only a 7-minute drive! Beach supplies are provided. Take advantage of the free bikes and locks for a ride to town!

4.96 out of 5 average rating, 196 reviews
Top Guest favourite
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.
Holiday home in St. Augustine

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!

5.0 out of 5 average rating, 206 reviews
Top Guest favourite
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!

Welcome to Groveside Cottage on the historic street of St. Augustine! In 1920s Grove Avenue was the home of several families of cigar makers and two cigar manufacturing companies. This charming cottage is a great mix of vintage and modern; you will be amused! We allow 1 dog, please message us - approval required before booking. Thank you!

5.0 out of 5 average rating, 167 reviews

Popular amenities for Historic District, St. Augustine family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Guest favourite
Apartment in St. Augustine

Cozy Garden - Sleeps 4- hottub/outdoor shower!

4.92 out of 5 average rating, 156 reviews
Guest favourite
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.
Home in St. Augustine

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

4.93 out of 5 average rating, 131 reviews
Top Guest favourite
An inviting exterior view of the home is presented, featuring a spacious front porch adorned with eight rocking chairs. Lush greenery and colorful plants frame the entrance, enhancing the charm of the property. A well-maintained pathway leads to the front steps, inviting guests inside.
Home in Lincolnville

Southern Comfort - Downtown|Hot Tub|Heated Pool

4.97 out of 5 average rating, 191 reviews
Top Guest favourite
A private back deck features a round dining table surrounded by four green chairs, all positioned beneath a large red umbrella. A hot tub is visible in the background, complemented by potted plants along the edges. Sunlight illuminates the area, enhancing the inviting outdoor space.
Home in St. Augustine

Cordova House ,In the historic downtown .

4.98 out of 5 average rating, 262 reviews
Guest favourite
Home in St. Augustine

Kid & Dog Haven: Poolside Fun in St. Augustine

4.91 out of 5 average rating, 124 reviews
Top Guest favourite
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.
Apartment in St. Augustine

Villa Tizoc

4.99 out of 5 average rating, 649 reviews
Top Guest favourite
The entryway features a dark blue door framed by lush greenery and vibrant pink flowers. A welcome mat lies on the wooden steps, while a light blue overhang provides shade. The house number is displayed on the wall beside the door.
Home in Lincolnville

Walk to Downtown | Hot Tub + Golf Cart

4.99 out of 5 average rating, 119 reviews
Top Guest favourite
Home in St. Augustine

Romantic Villa Clawfoot Tubs Sauna Net Bed Fire

4.99 out of 5 average rating, 103 reviews

Family- and pet-friendly home rentals

Top Guest favourite
A charming Victorian home is showcased with a bright yellow exterior, framed by lush greenery. The two-story structure features a spacious porch with white railings and decorative trim. A welcoming sign is positioned at the entrance, indicating the property's name.
Home in St. Augustine

DOWNTOWN ~ Victorian Home ~ ABOVE CUPCAKE SHOP!

4.93 out of 5 average rating, 278 reviews
Top Guest favourite
The exterior of a four-bedroom home is presented, featuring a light blue façade with a welcoming black front door. Lush greenery, including palm plants, surrounds the entrance. The porch is visible with steps leading to the door, and a well-maintained lawn adds to the inviting appearance.
Home in St. Augustine

Uptown Abode on Garnett- Dog Friendly!

4.88 out of 5 average rating, 509 reviews
Top Guest favourite
Apartment in St. Augustine

Tree Top View 2

4.96 out of 5 average rating, 278 reviews
Top Guest favourite
Apartment in St. Augustine

Apt C - Historic St. Augustine. Walk Everywhere!

4.99 out of 5 average rating, 182 reviews
Guest favourite
The living room features large windows that allow natural light to fill the space. A comfortable sectional sofa and armchairs are arranged around a round coffee table. A ceiling fan is visible, and a television is mounted on the wall. The room opens to a serene outdoor area.
Home in St. Augustine

Charming Getaway Near Fountain of Youth & Downtown

4.86 out of 5 average rating, 168 reviews
Top Guest favourite
The property's exterior is illuminated by soft lighting, highlighting the unique architecture. A decorative fountain is situated in the foreground, surrounded by manicured grass. The building features multiple windows with shutters, and an American flag is displayed near the entrance.
Apartment in St. Augustine

La Posada:Downtown Historic District. Pet Friendly

4.9 out of 5 average rating, 210 reviews
Top Guest favourite
A charming guest house is presented with a front porch featuring a decorative railing. Lush greenery and a small white picket fence frame the landscaped yard, while palm trees provide shade. The exterior showcases a light color palette, with contrasting trim and a welcoming entrance.
Apartment in St. Augustine

The Rohde House, The Rohde Guest House

4.95 out of 5 average rating, 384 reviews
Guest favourite
A comfortable living area is highlighted by a brown leather sofa and a round coffee table. A large wall-mounted television is positioned above a natural fiber rug. Potted plants add greenery to the space, complemented by light streaming through windows dressed in white blinds.
Bungalow in St. Augustine

Historic Full House 2min walk to Historic Downtown

4.92 out of 5 average rating, 255 reviews

Family-friendly home rentals with a pool

Top Guest favourite
The exterior of the home features a two-story structure with a welcoming porch. Potted plants hang from the posts, and a decorative sign is positioned near the entrance. Lush greenery and various plants are arranged along the pathway leading to the front steps.
Home in St. Augustine

Historic St. Augustine 2/2 Duplex & Pool

4.99 out of 5 average rating, 241 reviews
Top Guest favourite
Home in St. Augustine

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

4.99 out of 5 average rating, 146 reviews
Guest favourite
Covered seating is arranged around a sleek coffee table on a patio with a view of a large heated pool, accented by palm trees and umbrellas. A dining area with a table and chairs is visible, offering ample space for relaxation and enjoyment.
Condo in Lincolnville

F1, Downtown, POOL, beaches, porch, parking!

4.92 out of 5 average rating, 190 reviews
Top Guest favourite
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.
Home in St. Augustine

Pink Palms *Pool* Party ~ Walk to Downtown

5.0 out of 5 average rating, 147 reviews
Top Guest favourite
A private heated pool is surrounded by a spacious patio featuring paver stones and tropical landscaping. A wooden pergola provides shade, complemented by lounge chairs and vibrant orange seating. The cottage's white exterior is visible in the background, framed by swaying palm trees under a clear blue sky.
Home in Vilano Beach

Floridian Bungalow•2 Min Walk to Beach•Heated Pool

4.99 out of 5 average rating, 161 reviews
Top Guest favourite
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.
Home in St. Augustine

Your Home Away From Home

4.99 out of 5 average rating, 451 reviews
Guest favourite
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.
Apartment in St. Augustine

Luxury Retreat in St. Augustine

4.85 out of 5 average rating, 107 reviews
Top Guest favourite
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.
Apartment in Vilano Beach

Oceanfront paradise

4.98 out of 5 average rating, 164 reviews

Destinations to explore