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

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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
The living room is furnished with two light-colored sofas and a central coffee table, creating a spacious and inviting space. A decorative fireplace is framed by mirrors and artwork, while natural light filters in through shuttered windows and greenery adds a touch of nature.
Home in St. Augustine
4.94 out of 5 average rating, 218 reviews

Historic Whitney House •Designer•Steps2Attractions

Off Street Parking for 2 vehicles 2 Min. walk to St George St 5 Min drive to Anastasia State Park Beach 6 Min drive to Fitness Club/Pool High Speed Starlink Internet Luxury Retreat in Historic Downtown. Indulge in a charming vacation rental featuring a spacious living room, gourmet kitchen, and luxury baths. 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.

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.
Flat in St. Augustine
4.95 out of 5 average rating, 376 reviews

The Rohde House, The Rohde Guest House

Our place is close to nightlife, public transport, the airport, the city square, and parks. It's good for couples, solo adventurers, business travelers, families (with kids), and furry friends (pets). Five minute walk to the "Nights of Lights", two minute walk to Francis Field event field, where many festivals, concerts and activities are held. Five minute drive to the ocean beach at Vilano. Many Restaurants and bars in walking distance, including sports bar, martini bar, Irish pub and more.

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
4.98 out of 5 average rating, 211 reviews

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.

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
4.93 out of 5 average rating, 176 reviews

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.

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
4.95 out of 5 average rating, 171 reviews

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!

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
5 out of 5 average rating, 185 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!

Top guest favourite
The exterior of La Casita features a welcoming porch with seating for two, surrounded by greenery and flowering plants. The entrance is marked by a decorative clock, while the landscape includes gravel areas and a fire pit, creating an inviting outdoor atmosphere.
Home in St. Augustine
4.96 out of 5 average rating, 203 reviews

“La Casita” A Charming Uptown St Augustine Cottage

La Casita is located in the Uptown Shopping District. We have darling coffee shops just at the end of the block. Shopping and a convenience store too. We are just 2 blocks from the trolley shop snd visitors center..and, just a 10 min walk to downtown and the fort! We are just a 2 min walk to Francis Field, where many festivals are held. A 7 minute drive to Vilano beach! We are in a quiet and charming neighborhood.

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
4.98 out of 5 average rating, 250 reviews

Cordova House ,In the historic downtown .

The "Cordova House", built in 1900, is the Victorian Secret of the Ancient City District, featuring covered balconies in front and back, a private back deck, high ceilings, modern kitchen, a Kohler 10 head shower, two indoor spa tubs and more. Hot tub on the back deck.Located in the heart of downtown, yet also has off-street parking for up to two cars (very rare). Nothing compares.

Guest favourite
A charming blue cottage is surrounded by lush greenery. The front porch features decorative railings and shutters, while the vibrant yellow front door stands out. The brick pathway leads to an inviting entryway, with large windows allowing natural light to fill the space.
Home in St. Augustine
4.89 out of 5 average rating, 161 reviews

Historic Uptown 2 Level Cottage - Walk to Town

Step into an 1880s Blue Bell cottage where whimsical Alice in Wonderland decor meets a private movie loft with reclining seats. You'll enjoy your morning coffee by the fountain courtyard, then walk just three blocks to Castillo de San Marcos or two blocks to Ripley's. It's designed for guests who want historic St. Augustine at their doorstep without sacrificing modern comfort.

Top guest favourite
A modern kitchen features white cabinetry and stainless steel appliances. A central island with two stools provides additional seating. Natural light floods the space through multiple windows, highlighting the quartz countertop and decorative vase of flowers on the counter.
Flat in St. Augustine
4.94 out of 5 average rating, 389 reviews

Apt A - Comfort of Home in Historic St Augustine

Charming apartment in the historic district (within a short 3-4 miles from multiple beaches with an updated bathroom and kitchen. The kitchen has new appliances, cupboards and quartz countertop. My favorite part of this apartment is the porch where you can relax, enjoy your morning and evening beverages, watch horse drawn carriages and mingle with our neighbors...

Top guest favourite
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.
Home in St. Augustine
4.96 out of 5 average rating, 361 reviews

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

Enjoy this charming 1910 Sears & Roe Buck catalog home that has been meticulously maintained home just a 5 minute walk to the City Gates and downtown. You have a private back patio space to enjoy coffee in the morning or a glass of wine in the evening. Or just take a leisurely stroll to many fine restaurants that St Augustine has to offer.

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
5 out of 5 average rating, 141 reviews

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!

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

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Avg. price$238 SGD$252 SGD$255 SGD$241 SGD$243 SGD$238 SGD$243 SGD$223 SGD$228 SGD$228 SGD$283 SGD$321 SGD
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Quick stats about holiday rentals that are family-friendly in Historic District, St. Augustine

  • Total holiday rentals

    Explore 190 holiday rentals in Historic District, St. Augustine

  • Nightly prices starting at

    Historic District, St. Augustine holiday rentals start at $102 SGD per night before taxes and fees

  • Verified guest reviews

    Over 17,530 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 100 rentals that welcome pets

  • Holiday rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    100 properties have a dedicated workspace

  • Wifi availability

    190 of Historic District, St. Augustine holiday rentals include wifi 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!