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

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

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Guest favourite

Guest house in St. Augustine

4.99 out of 5 average rating, 326 reviews

Winery, Distillery, Chocolate, & Pizza

Winery, Distillery, Chocolate Factory, Pizza and historic downtown St Augustine all in walking distance. San Sebastian Winery .2 miles 4 minute walk Carmelo's Pizza .2 miles 4 minute walk Whetstone Chocolates .3 miles 5 minute walk St Aug Distillery .4 miles 9 minute walk Historic St George Street .5 miles 10 minute walk Fountain of Youth 1.4 miles 8 minute bike Beach - Anastasia State Park 3 miles 16 minute bike *****This private cottage is for 2 people only and no pets***** Enjoy your stay

28 May – 4 Jun

€ 151 per night

Guest favourite

Flat in St. Augustine

4.97 out of 5 average rating, 172 reviews

Tree Top View 2

This spacious tree-top apt overlooks a seldom used and quiet street. The private balcony has a view to majestic live oaks, a home to many squirrels and birds. A perfect place to sip a steaming mug of coffee in the morning or a glass of wine as the sun goes down. This apartment offers a king bed with a separate living area and an equipped kitchen. An easy walk into historic downtown St. Augustine, with it's many delicious eateries and tourist sites. We also rent the adjacent apt Tree Top View 1.

8–15 Sep

€ 139 per night

Guest favourite

Guest house in St. Augustine

4.95 out of 5 average rating, 296 reviews

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.

9–16 Sep

€ 151 per night

Guest favourite

Flat in St. Augustine

4.96 out of 5 average rating, 293 reviews

Updated Victorian apt in heart of downtown +VIEWS!

21 Orange Street is a bright and airy second story apartment with unparalleled views of historic downtown Saint Augustine and the bay front. Enjoy old world charm in our newly renovated circa 1860's home- furnished with modern and comfortable amenities! We are steps away from Saint George Street shopping, world class dining and lively bars. If you choose to spend your time here in a more relaxing way, you’ll love the spacious bedroom and our comfortable porch to take a break from it all.

21–28 Aug

€ 140 per night

Guest favourite

Guest suite in St. Augustine

4.97 out of 5 average rating, 300 reviews

Genovar Mansion Rose Garden Suite Private Entrance

The romantic view of a gorgeous live oak canopy and incredible architecture make this historic home a memorable place to stay. This ground floor suite of four rooms is perfect for couples with a private entrance, queen poster bed, living room, spacious bathroom, individual climate control, heirloom antiques and parking spot. The home is located within the historic district, close to trolley stops and within easy walking distance to downtown. It is one of the finest homes in St Augustine.

31 Aug – 7 Sep

€ 147 per night

Guest favourite

Loft in St. Augustine

4.95 out of 5 average rating, 99 reviews

The Sweet Spot Suite - Heart of Historic District

This newly remodeled space is in a class all by itself. Seated in the heart of St. Aug where you are right on(with a balcony hanging over) St. George Street, the pedestrian-only “strip” of the city (judged best in the country for walking). Located above the sweet spot ice cream shop and close to dining, nightlife, family-friendly activities, live music, the beach, and much more that our city offers. Please note: there is some noise related to this busy area. Check out my other listings.

8–15 Apr

€ 162 per night

Guest favourite

Flat in St. Augustine

4.92 out of 5 average rating, 138 reviews

C4 Close to beaches, downtown, history, parking!

Relax in this cozy and comfortable Upstairs apartment with patio. Don't worry about the struggle of downtown parking, PARKING IS FREE on site (1 designated spot for your apartment). So many nearby attractions just steps (or a trolley ride) from the door including shopping on St. George St, restaurants and sandy beaches where you can rent paddle boards, kayaks, small sailboats and more. Netflix, Hulu, Roku, CNN, FOX, E, Bravo, HGTV, TLC, History, A&E, USA, Travel, and much more.

30 Sep – 7 Oct

€ 146 per night

Guest favourite

Guest suite in St. Augustine

4.98 out of 5 average rating, 302 reviews

St. Augustine Studio*Private Entrance & Bath*Bikes

A private studio designed from a garage conversion. Separate key-less entry allows for self check-in and welcomes you to this comfortable, clean space with a queen size bed, your own bathroom, kitchenette, and 2 available parking spaces in the driveway. Mini-split AC cools and heats the studio comfortably. High speed internet, flatscreen television with Netflix for relaxing after a day of sightseeing. 2 bicycles for exploring our historic downtown less than 2 miles away.

11–18 Oct

€ 109 per night

Guest favourite

Flat in St. Augustine

4.99 out of 5 average rating, 111 reviews

2-Bdrm Apt in Downtown St Aug

Beautiful, large two-bedroom first floor apartment in Historic St Augustine. This space is newly remodeled and perfect for larger family stays or remote workers! Large dining table, a den that offers a quiet space to work and sofa bed, and large kitchen make this space perfect for your stay! We have free parking on site, so you are able to park and walk around to enjoy the local sights such as the Castillo de San Marcos, St George Street, and the St Augustine Marina!

23–30 Oct

€ 190 per night

Guest favourite

Home in St. Augustine

4.95 out of 5 average rating, 146 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.

7–14 Mar

€ 153 per night

Guest favourite

Flat in St. Augustine

4.95 out of 5 average rating, 310 reviews

Comfort of Home in St Augustine

Charming apartment in the historic district with a completely updated bathroom with a deep soaking tub and a separate shower, double vanity, Carrera marble tile. The kitchen is new as well with all new appliances, cupboards and quartz countertop. My favorite part of this apartment is the large front porch where you can relax, enjoy your morning and evening beverages, people watch and mingle with the neighbors...

3–10 Aug

€ 155 per night

Guest favourite

Guest house in St. Augustine

4.92 out of 5 average rating, 749 reviews

Moon Over the Courtyard in the Historic District

You have found your cozy oasis tucked under tall shade trees in a private, lush tropical courtyard in the Historic District of St Augustine. This is a new, small studio and exemplifies the appeal of tiny living: compact, clean, efficient, and convenient. Walk, bike or have a pedi cab/golf cart pick you up outside your door.

13–20 Oct

€ 79 per night