Family-friendly vacation rentals in St. Augustine

Guesthouse in St. Augustine

An outdoor seating area features multiple blue Adirondack chairs arranged around a circular stone patio, complemented by a small green table. A lamp post stands nearby, and a flag flutters gently in the breeze, surrounded by lush greenery and tall palm trees.

4.91 out of 5 average rating, 578 reviews

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).

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.

4.99 out of 5 average rating, 412 reviews

Your Home Away From Home

1,800 SF, 2 bedrooms, 2 1/2 bathrooms, on a secluded 5 acre lot just minutes from Historic Downtown and St. Augustine Beach. The home is 100% HANDICAPPED ACCESSIBLE! Convenient shopping and close by restaurants. Full kitchen, spacious living area, large bedrooms (1 with TWINKLE mattress) ceiling fans. Pet friendly! (Some restrictions apply, advance notice required!) Base rate covers up to 4 guests and there's a small upcharge for 5 or more. Motorcycle friendly! We also do live on the property!

Bungalow in St. Augustine

The living area features a light blue sectional sofa with colorful accent pillows, paired with a rustic wooden coffee table. A dining table is visible, surrounded by four chairs. Natural light streams through the windows, adorned with blue curtains, while a small door leads outside.

4.96 out of 5 average rating, 205 reviews

Ooo Laa Laaah! 4th of July open!Fenced yard.

Private, fenced in yard and private Free standing cottage in quiet neighborhood. Private, fenced in yard! Pets are welcome. Fees apply. 2 washers and dryers, internet/wifi, 2 smart TVs. All kitchen appliances. One story. The beach is a one block stroll with no major streets to cross. Keep your car at home..walk to the beach 2 minutes stroll . Downtown, St. Aug. is a 10 minute car ride. Not a condo scene. Crescent Moon cottage is in front but completely separate. Shared laundry room.

A wooden boardwalk leads to a sandy beach, framed by green vegetation on either side. The tranquil ocean stretches into the distance under a clear blue sky, with gentle waves lapping at the shore.

4.85 out of 5 average rating, 281 reviews

Sunny, family friendly Sol Mate Beach Cottage

Our renovated beach cottage is one block to the beach, walking distance to restaurants and ice cream, nightlife, public transport, family-friendly activities. Across the street is the pier, volleyball courts, splash pad and weekly Wednesday farmers market. A short drive to the oldest city in the US and a grocery store! You’ll love our adorable beach cottage because of the location, the neighborhood and the beach is gorgeous. Our place is good for couples, solo adventurers, and families.

4.87 out of 5 average rating, 217 reviews

A glass of wine rests on a decorative table, with a backdrop of city roofs and greenery. The view captures distant church spires under a bright blue sky dotted with clouds, creating a serene atmosphere for relaxation.

Condo in Lincolnville

Rooftop View | Near Eats, Waterfront & Attractions

Located in one of the best spots in the heart of town and ready to welcome you! - An awesome rooftop terrace with outdoor seating to enjoy city & bay views - Walking distance to the waterfront, shops, great local eats & attractions/activities - A short drive to groceries, several golf courses & awesome fishing spots - A fully-equipped kitchen with a dishwasher, washer/dryer & detergent provided - Good WiFi, laptop-friendly workspaces, Smart TV (connect to your own accounts)

A wooden dock extends towards a serene landscape of marsh grass and coastal trees. The house is positioned in the background, surrounded by a lush lawn beneath a clear blue sky.

4.91 out of 5 average rating, 105 reviews

Waterfront Cottage on Private Island in Preserve

Longvue is an Old Florida house set on private Medicis island in the Intracoastal Waterway surrounded by the Guana/Tolomato Matanzas National Estuarine Research Reserve (73,000 acres) and Stokes Landing Conservation Preserve (300 acres). Private floating dock with tidal access to the IWC. Very private island with 6 residences. The 10 acre island is surrounded by rivers, marsh flats and fresh water ponds. Boat/Kayak to the National Reserve and walk the trails to S. Ponte Vedra Beach.

Apartment in Lincolnville

An open-plan living area is featured, showcasing a spacious sectional sofa set against a warm orange wall. A wooden coffee table sits in the center, accompanied by a textured area rug. Natural light pours in through a large window, adjacent to the kitchen area.

4.93 out of 5 average rating, 586 reviews

1880 Victorian in Heart of Downtown

Best of both worlds with upscale renovations in a 3 story 1880 Victorian home. House is located within the heart of the Historic District. Located downtown next to restaurants, churches and historical sights. Sit outside on the front porch and enjoy your complimentary bottle of wine or your own private front and back balconies await. Second floor private apartment has a kitchen, queen bed, sectional sofa, fully equipped kitchen and large full bath. ON SITE PARKING INCLUDED!

A deck is furnished with a large dining table surrounded by comfortable chairs. Decorative elements include plants, a surfboard propped against the wall, and a woven rug. String lights are hung above, providing a warm ambiance for outdoor meals.

4.93 out of 5 average rating, 147 reviews

Designer's "Treehouse" just 4 Houses From the Sea!

The next best thing to beachfront! Grab your beach gear and walk just 2-5 mins to the quiet community beach entrance located only three houses away (this is not a popular entrance because there is NO public parking). Spend your evenings reconnecting as you roast S'mores around the fire pit. Enjoy long talks on the deck shaded in the day by the live oak trees and lit up at night with cafe lights hung overhead, all while listening to the lullaby of waves.

Apartment in St. Augustine

The living area showcases a dark leather sofa adorned with colorful pillows, paired with a light wooden coffee table. A ceiling fan hangs above, and a large television is mounted on the wall. The space features original pine flooring and a decorative non-functioning fireplace.

4.95 out of 5 average rating, 284 reviews

FREE BIKES Dog-friendly apt in the heart of St A

A beautiful, renovated, pet-friendly, first-floor apt in a historic house . A fully-stocked kitchen for cooking, beautiful bathroom, comfy bed. A shaded, shared backyard with picnic tables and charcoal bbq grills. A few minute walk to the Historic District , Francis Field and Flagler College, while still being in a quiet neighborhood. Free use of bicycles. One parking space. Pet fee is $40 per dog per stay (max of 2 dogs). No cats.

The charming exterior of the house is framed by lush greenery, with a well-maintained front yard and a white picket fence featuring decorative accents. Soft lighting highlights the inviting entrance, enhancing the serene atmosphere of the property.

4.99 out of 5 average rating, 184 reviews

Fun & Artsy 3BR/2BACottage in Downtown St. Aug

Discover serenity in this charming, hidden gem nestled in a quaint downtown neighborhood. A short stroll will lead you to vibrant festivals at Francis Field and St. Augustine's finest dining, bars, tours, and more. Art, music, and local culture are woven into the very fabric of this locale. Whether you're unwinding with a movie, savoring morning coffee in the backyard, or lounging on the front patio, we've curated the perfect escape.

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.

4.98 out of 5 average rating, 188 reviews

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

Great walkable location on a safe quiet street; Spacious and very comfortable for entertaining and relaxing. Nice touches like bikes and beach chairs. Very comfortable beds. The porches have rocking chairs too. The home is on one level which is also nice for elderly with mobility challenges. The host is very responsive, and guests say this is a convenient stay for local weddings, special events¸ and an enjoyable vacation.