Family-friendly vacation rentals in Diamondhead

It's 5'O-Clock Here On The Dock

If you are looking for the perfect place on the water, we got you covered at "It's 5'O-Clock Here" on the Jourdan River. Enjoy the river with countless sandbars, and hang out underneath kitchen while you watch the game. Swim off the pier and dock your boat or fish and make great memories. The award winning Jourdan River Steamer is less than a 2 minute boat ride. You can also rent pontoon boats for the family in the neighborhood. Take your boat to the popular coastal town Bay St. Louis and enjoy!

Majestic Oaks Beach Retreat

This beautiful and tranquil 3.5 acre beach retreat is located approximately 15-20 minutes from downtown Ocean Springs. Ideal for those who want to enjoy a quiet getaway but close enough to enjoy all the shopping and nightlife that Ocean Springs has to offer. Property has waterfront beach on the Mississippi Sound. It is natural and primitive. Great for launching paddle boards and kayaks. There are also two boat launches 5-7 min from property and plenty of room to park your boat at the house.

the Bird House/Center of Ocean Springs

The "Bird House," a charming 80's "Ishee Style" Bill Allen home, is located in the serenity of picturesque downtown Ocean Springs. The historic shopping & dining district of the downtown, and beautiful sugar sands of the beach are a 5 minute drive by car or a 1.5 mi walk. This house has room to sleep a family of 8, but plenty of interior & exterior space for entertaining. Visitors come for art, bicycling, bird-watching, cruising, festivals, fishing, gaming, shopping and the uncrowded beaches.

St George Cottage

Charming 1890's historic cottage in the heart of Old Town Bay St. Louis just two blocks from the marina, restaurants, shops, parks and the beach. The home has original hardwood floors, 10 ft. ceilings, an open living/dining room, full kitchen, 2 bedrooms, 1 bath and a private back porch. This cottage on St. George is one of the few side hall cottages in Bay St. Louis and was built in 1890. The cottage is within the boundaries of the Bay St. Louis Historic District. Registration #: BSL015

Cozy efficiency cottage near beach & entertainment

Cozy efficiency cottage 1 block from beach & close to old town Bay St Louis shopping & dining. Fenced private yard. Dogs welcome for $20 fee each but please notify host of # & type of dogs. Owner lives in house next to cottage but offers privacy & freedom to come and go as you please. Sleeps 2 comfortably in double bed. Twin day bed offers another sleeping space. Refrigerator, portable induction cooktop, microwave, coffee maker & toaster/convection oven. Charcoal grill & fire pit available

Beauty by the Beach

A beautiful place to enjoy the Mississippi Gulf Coast. Blocks from the beach. Casinos down the road. Premium shopping for fun and so much more in food and pleasure for you to explore and enjoy. Come visit our beautiful Mississippi Gulf Coast, and find what you love best. My home offers 3 comfortable Bedrooms and 2 bathrooms for our guests’ convenience with all of your home amenities just for you. Top bunk: Maximum 150 pounds and no small children up there. Please note pet fees for dogs.

Farm House Cottage

Step into a charming slice of Southern hospitality with "The Cottage." This adorable studio is brimming with character and Southern flair. Perfect for a romantic getaway, solo retreat, or a small family, this cozy space is your peaceful home away from home. Enjoy a fully stocked kitchen, queen-sized bed, air mattress, Wi-Fi, and a Roku TV. Located amid farmland, you can relax on the porch and watch the animals graze. A peaceful escape in a serene setting. Long term stays welcome!

Coastal Cottage | Walkable Downtown Stay

This cozy beach cottage offers a quiet, walkable stay in the heart of Pass Christian. Just a short stroll to the beach, restaurants, coffee shops, and local bars, it’s perfect for couples, small families, or remote workers. The Pelican’s Nest is part of the covted Cottages at 2nd Street community and offers easy self check-in, a fully equipped kitchen, fast WiFi, and a dedicated workspace. Relax, explore the coast, and enjoy a comfortable, convenient retreat close to everything.

Chickie's Cottage, an idyllic getaway.

Chickie's Cottage, nestled in a shady pecan orchard where horses graze, is adjacent to the 600,000 acre Stennis Space Center buffer zone. The pastures and natural surroundings include pecans and live oaks that evoke peace and tranquility. Farm life includes horses, cats and chickens who enjoy visiting guests. The farm house is one-of-a-kind; charming, comfortable, complete with unique furnishings and modern amenities such as 100 Mbps WiFi and Roku TVs.

The Dolly Suite

A Dolly-themed private suite located in the historic Bell House on Main Street. Enter your completely private suite with full bathroom from your own separate entrance on the front porch. Enjoy use of the beautiful, serene grounds that will take you back to Dolly’s home in the Mountains in Tennessee. Pour yourself a cup of ambition and start your morning on our front porch which has seven oak trees around the property.

Mermaids and Moonshine

Comfy cozy studio with lots of extras! Super comfortable bed! 15 minutes to the Beach! Close to Hancock County Fair Grounds, Stennis Space Center, Hancock Sports complex, Centrally located between Gulfport MS and Slidell LA. We are one hour from New Orleans. Come be our Guest! Enjoy the Pool, Barbecue, Fire pit and outdoor areas. This is a perfect spot if you are visiting family but want your own space!

King Suite. Sleeps 6. 2.5 Baths. No cleaning fee!

This stylish home is perfectly located just minutes from Old Town Bay St. Louis and 4 blocks from the ocean. Completely stocked with everything you need. Just pack a bag and come to the Bay! It’s awesome here! We have a fenced in private patio with a gas grill and fire pit. No cleaning fee. Pet friendly. Free parking for 4 vehicles!