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

Apt C - Historic St Augustine Charm and Comfort

Nestled on a quiet residential street, this apartment in the trees is just a block from the start of restaurants, shops, bars and historic sites and just 3-4 miles from multiple beaches. We provide 2 beach chairs, cooler, umbrella and towels. A few amenities of this renovated apartment include a back deck, a massage chair, upscale appliances, designed to provide deep R&R after a day of sightseeing and beach play. Access to the apartment is via the staircase on the west side of the building.

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.

Historical Cottage in Heart of Town! Park & Walk

Welcome to Groveside Cottage on one of historic streets of St. Augustine! In 1920s Grove Avenue was the home of several families of cigar makers and two cigar manufacturing companies. This lovingly restored cottage offers modern comforts while maintaining the character and charm of a circa 1900 home. Our coziest porch and fenced courtyard are great for a cup of coffee or a glass of wine to enjoy outdoors. Park and walk to discover all the wonderful things this historic downtown has to offer!

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.

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, full privacy fence, off-street parking, paved driveway close to downtown and excellent beaches. Prime location!

Lovely 1bdrm apt in Historic St Augustine

Check out our beautiful upstairs apartment in Historic St Augustine! The space is newly remodeled and so lovely! Originally built in 1910 and completely updated in 2023. Just two blocks from St. George St, walking distance to Flagler and all of downtown St Augustine. This one bedroom, king bed and pull out sofa, full kitchen and bath as well as a balcony to enjoy the sights. Free off street parking, so you are able to park, walk around and enjoy everything downtown has to offer.

"The Pink House" Uptown St Augustine Charmer

Visit Historic St. Augustine & truly "Have It All!!" Walk to downtown sights, trolley, fort from your expansive secluded oasis. Our lovingly decorated and well stocked home features a wraparound porch. Spacious outdoors, shared amongst just 4 rental properties, with resort-quality pool+cabana, multiple seating areas, argentine grill, hammocks. Book our co-listings upstairs - "The Attic" or guest cottage "The Little Pink House" to add another bed + bath for your group!

Uptown Classic Bungalow Comfy Walk Everywhere

The Uptown Bungalow is located on a quiet street only a block away from all the action in the heart of the nation's oldest city. Built in 1910 the unit has been renovated, is tastefully decorated ,and is equipped with everything you will need to make your stay in St. Augustine a great experience. Dine in the kitchen or an outdoor patio set on the screened in porch where the guests can enjoy a café & scones in the AM or in the evenings cocktail & Hors d'oeuvres.

Historic Full House 2min walk to Historic Downtown

I'm a lovely old home called La Casita in historic St. Augustine. Nice to meet ya! Flagler had me built to house his crew. I’m certified historic and charming too. I'm right downtown where you need to be so close to everything you'll want to see— The fort, the lighthouse, and all the rest. I’d be delighted if you were my guest. Comfort and peace is a phone call away. Please say yes. I want you to stay.