Family-friendly holiday rentals in St. Augustine

Captain's Quarters Tiny House

Welcome to our newly spacious and private renovated bathroom with our outdoor shower. See photos! This Tiny House has all you need for a cozy, private stay while visiting St. Augustine. The Tiny House sits on 3/4 acres. You will feel the tranquility of this magical property and only 10 minutes to Vilano Beach or the Historic Downtown. The studio is equipped with a sink, toilet, kitchenette, coffee/tea. Commune with nature in your Private Exotic Outdoor Shower, hottub (closed July & August).

Genovar Mansion Rose Garden Suite Private Entrance

The direct view of a gorgeous live oak canopy on Magnoila Avenue and incredible architecture make this historic home a memorable place to stay. This romantic ground floor suite is perfect for couples with a private entrance, queen poster bed, living room,  spacious bathroom, individual climate control, heirloom antiques and reserved driveway parking spot. The home is located within the historic district, close to trolley stops and within easy walking distance to downtown. 6 minutes to the beach.

SeaGlass on Vilano Beach~St. Augustine, FL

Beach & Ocean lovers retreat- Steps to ocean, close to historic area, walk to grocery/waterfront dining/roof top cocktails Gem w/lots of outdoor living. Bright, spacious cottage-style apartment w/kitchenette (No oven/stove). Fenced/gated large property. Short 1 min walk to lovely quiet beach! Convenient walkable beach neighborhood. Short Uber ride to historic district. Perfect for couple (baby up to 2yrs welcome) solo traveler, Flagler College parents. Close for Night of Lights visitors.

Oceanside Condo-2 pools, 5 hot tubs, pickleball

A newly renovated 4-bed beach condo decorated with a peaceful ocean theme will be the perfect beach house for your St. Augustine stay! With 2 swimming pools, 5 jacuzzis, tennis & pickleball courts, & private walkways to the beach, this centrally located spot will have you both entertained and relaxed while on vacation. The nautical tri-bunk room is fun for the family, the classic coastal master bedroom is serene, & the martini bar adds a festive element. You'll always remember this vacation!

courtyardtreehouseinthehistoricdistrict

You have found your cozy oasis tucked in a (Real) Treehouse lodged in Ancient Oak. Set in a lush tropical garden in the historic district. It’s a minimalist’s dream, exemplifying the appeal of tiny living: compact, clean, efficient and 2 1/2 blocks to the historic districts shopping and restaurants. Relax on the Sun Deck, Rain Deck or in the Courtyard’s Tropical Garden The day time peaceful beauty is only eclipsed by the the nighttime display of laser lights projected onto the oaks canopy.

MarshMellow-Island Guest Suite Beach Amphitheater

Your own cozy guest suite with private entry. Lovely little bedroom and beautiful bathroom . Private porch and sitting area. Located adjacent our guest studio but the suite is entirely yours and private. These two share a lush garden path, but have separate porches and entrances. The MarshMellow is a well thought out accommodation that has everything we think you'll need for a lovely stay in St. Augustine. A 20 minute stroll to the Amp and short drive or bike to the beaches or downtown.

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.

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 !

Walk Historic Downtown! “Blue Heaven”

Stunningly renovated cottage combines modern amenities with vintage charm... * 2 master suites with queen beds * Quiet neighborhood walking distance to explore The Nation's Oldest City * Clawfoot tubs inside and out (along with showers, of course!) * Big screened-in porch with hanging daybed * Off-street paved parking * Fenced yard, Weber grill, gas fire pit * Fast Wi-Fi and Smart TV * 2 blocks to Fish Camp, Ice Plant and LaNuvelle * 10 minute walk to central downtown St Augustine

Cozy studio 15 min to beaches & historic downtown

Outstanding location + amenities, 15 minutes to beaches + historic downtown (Nights of Lights!) Minutes walk to the intercostal w/ piers, boat ramps, perfect for pleasant walks. Close to lots of shopping + dining. Quiet, friendly neighborhood, ample parking-trailers & boats welcome. Kid friendly w/ toys, pack & play + more. Laundry, walk-in shower, private entrance. Private deck w/ cheerful seating. Well equipped kitchenette. Easy drive to theme parks, Daytona + more.

Charming 1 Bedroom apt, Historic St Augustine

You will love this newly remodeled one bedroom apartment in Historic St. Augustine. 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 apartment offers one bedroom with king size bed, full kitchen and private patio. Free off street parking, so you are able to park, walk around and enjoy everything downtown has to offer.

Perfect One Bedroom Cottage in Lighthouse Park

One bedroom one bath cozy cottage vibe! Perfect couples retreat. This is one half of a duplex. The second half is currently vacant. Excellent location. 5 blocks to the lighthouse. 1 mile to historic downtown. 1.3 miles to the Amphitheater. 0.8 miles to Anastasia State park. 3 miles to the St. Augustine Beach Pier. Walking distance to many great restaurants and bars, mini golf, and boutique shops! Walk or bike to downtown!