Kid-friendly holiday rentals in Southside, Jacksonville

Golf Cart, Sun, Sand, & Island life Beach Retreat!

Cruise in Style On Our Complimentary Street Legal Golf Cart! Embrace the island life at our newly renovated beach cottage, half a mile from the sandy shores. Explore the beach, downtown Fernandina, and local eats with ease using our provided golf cart. This cozy 3-bedroom, 2-bathroom haven is coastal perfection, and pet-friendly, too! The open living space creates a gathering point for families and groups, while the screened back patio sets the scene for relaxing mornings over a cup of coffee.

NEW - The Sanctuary - A step above the rest

New Listing! Artsy Island sanctuary. Come enjoy this newly remodeled home in the middle of it all! Walking distance to historic downtown, restaurants, and bars. Brand new beds and furniture. Huge backyard. Located right off of Anastasia Blvd with great restaurants, coffee shops, pubs and fun for the Kids!Located 1 mile to the Anastasia beach state park and then a little over a mile to the beach! This is the main house with a detached apartment rented separately or all together on the property.

Paradise Retreat*Vilano Beach*Sand & Ocean Breeze

Come and escape to the Florida sun and beaches at Paradise Retreat! This completely renovated home is only a few minute's walk to the beach with access to miles of tranquil, quiet stretches of beautiful sand, abundant sea seashells and a fantastic blue ocean. It is located in a quiet residential neighborhood, perfect for bike riding and evening walks under the stars. Paradise Retreat is your peaceful getaway only minutes to everything Vilano Beach and historic Saint Augustine has to offer.

Perfect location- Cottage Retreat in historic area

This charming two story gem with a wrap around front porch is perfect for your stay while visiting historic St. Augustine. Situated within walking distance of the Fountain of Youth and the Old Town Trolley Tours, you can easily explore all the city has to offer! It’s in a perfect location near the city’s downtown area featuring Castillo de San Marcos (1 mile away) and many local shops and restaurants. Check out the featured guidebook which references many nearby points of interest.

Sweet Sandcastle Vacations: A Luxury Beach Getaway

Come enjoy your stay at Sweet Sandcastle Vacations where you will be greeted with a sweet surprise! This 3,400 sq ft, 3-story, 7 bed/3 bath luxurious rental is perfect for big family gatherings! Has beds for 10 adults and 6 kids. Free Parking for up to 8 vehicles. Situated between the Intracoastal Waterway and Beach, both just a 5 min walk away. Enjoy semi-private beach access, relax on the outdoor patio, or around our fire pit. Explore the historic city of St. Augustine 10 min away!

Updated Cottage in Heart of Town Park & Walk

Located in the Historic Abbott District of St Augustine, Florida in the heart of it all. Walk to everything, you will never need your car! This 2-bedroom cottage has all the historic charm was lovingly updated with an open floor plan is beautifully decorated and tastefully furnished. Enjoy a five-minute walk through the neighborhood to famed Castillo De San Marcos (the fort) and Historic St. George Street in the ancient “Colonial Quarter”. Extremely clean, and well-maintained.

Country Cottage 3-bedroom home with free parking

Your family will enjoy the comfort at this lovely Country Cottage and what it has to offer. The Country Cottage is a single family home that is located in a quiet, tree-lined up and coming neighborhood that's just a few blocks west from the Historical Downton St. Augustine, with a 15-minute drive to the beach and Anastasia Island. This three-bedroom, two-bathroom home sleeps 8 people and has a lovely kids room with books, toys,and more. Our outdoor space has lovely seating area.

Luxury Townhouse--1.5 block stroll to the Beach

Fleur-de-Sea is a 3 bedroom, 3.5 bath, three story townhouse located just 1.5 blocks to Jacksonville Beach with it's gorgeous white sand and amazing surfing. It is a family friendly retreat that is the perfect place to build lasting memories with your children and friends. It is an easy walk to the restaurants, bars, and shopping district of Jax Beach while maintaining enough distance for peace and relaxation. It features a backyard fire pit, games, books, and beach toys.

Country villa pool hot tub game rm pond 2.5 acres

Take it easy at this unique and tranquil getaway. Ask about our couples discount. Our villa includes pond, pool, hot tub, game room, outdoor cooking area with industrial smoker, wood burning pizza oven, and gas grill. Oyster bar, fire pit area wood included. Kitchen has 2 coffee making options, air cooker and all other essentials. Full laundry with soap and dryer sheets. Parking space for your toys and camper. Security gate w/ fence completely surrounding the property.