Kid-friendly holiday rentals in Southside, Jacksonville

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.

Luxury Beach Getaway w/ Heated Pool & Game Room

Recently built gorgeous 5-bedroom beach house with heated pool and game room with pool table, foosball, dart, shuffleboard, and ping pong. Living rooms on each level. Great for families. Gourmet chef's kitchen with 5 burner gas stove. Cable TV with all movie channels provided. Includes a putting green, bocci court, outdoor dining under the covered patio and a smart TV. BIKES INCLUDED PET FRIENDLY: We warmly welcome four-legged CANINE friends. No cats, please. (They don't like the beach!)

Southern Comfort - Downtown|Hot Tub|Heated Pool

The Southern Comfort is a 4BR/3.5BA home located right in the heart of Downtown St. Augustine on the famous King Street. High-end, designer touches will be found in all features of the home with respect to the 110+ year old character preserved in the 2020 renovation. Centrally located with a blend of privacy, convenience and a modern luxury design. Private, sparkling heated pool and hot tub with lounges perfect for lazy days by the water. #1 Vacation Rental in Downtown St. Augustine.

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.