Family-friendly holiday 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!

Bamboo Room: King Guest Suite - Quiet Green Oasis

WEST Bay St Louis - 8mi TO DOWNTOWN! Quiet green rural alternative to major tourist areas. Comfy clean king bedroom guest suite (YOUR OWN PRIVATE: entrance, bathroom, deck, large garden, A/C) ATTACHED TO QUIET RESIDENTIAL HOME. Host lives on property. 5mi to beach & Silver Slipper Casino; 23mi to Gulfport; 55mi to New Orleans. Minutes to beaches, casinos, restaurants. Self check in. Sit outside on private deck & garden w/firepit to read, work, listen to birds & frogs, or to stargaze at night.

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!

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. 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. Not a full kitchen but Refrigerator, portable induction cooktop, microwave, coffee maker & toaster/convection oven available Charcoal grill & fire pit available

The Loft at Cypress Cottage – Steps from the Train

Location location. Beautiful updated and newly furnished loft in a Creole Cottage circa 1895 located in the middle of Old Town Bay St. Louis. Located on a safe & quiet street two blocks from Main Street. Short 5 minute walk to enjoy all the restaurants, shops, and bars that Bay St. Louis has to offer. Walking distance to the beach. Come enjoy yourself at one of the "10 Best Small Coastal Towns in America" according to USA Today. The loft at the Cypress Cottage is waiting for you.

Backyard Bungalow ~1 Mile to Beach Private Studio

Spacious yet cozy and comfy retreat - just minutes to beaches, casinos, restaurants; completely separate clean studio/guest house behind a quiet private residence in a beautiful garden setting. Queen size bed; bath w/shower; kitchenette w/ mini fridge, microwave, toaster oven, coffee maker, hot plate, dishes, cookware, utensils, sink; dining area; wifi, work area; TV, Roku w/Prime access. Off street parking adjacent to owner's driveway and private entrance with lockbox.

The Low Commotion {downtown Depot District}

The Low Commotion sits right in the life of the Historic Depot District in old town Bay St. Louis. It features a train-inspired decor blending perfectly with its location across from the train depot. The master bedroom includes a queen bed with a private bathroom and access to the back porch. The additional bedroom boasts fun built-in bunk beds. It is near an active railroad. Watching the train pass and hearing the whistle is included for no extra fee!

THE BAY RITZ - Lovely 2 Bedroom Beachfront Condo

Beautifully decorated beachfront unit in the heart of Old Town Bay St Louis, MS. Restaurants, bars & shops are only steps away from this gorgeous unit. Relax on the balcony and enjoy beautiful views of the bay, beach and surrounding areas. Gourmet kitchen fully stocked including spices. Main bedroom has king size bed. Second bedroom has queen size bed, it's own private bathroom and a kitchenette. Perfect for two couples to spread out and relax.

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!

"Chickie's Roost" family-friendly barn apartment

Rustic country charm! "Chickie's Roost" is a two story apartment like space in a barn overlooking a farm and a beautiful pecan orchard. Private entrance, upstairs is an open loft with queen bed, full bed, futon, TV, sink, microwave, refrigerator, 2 coffee makers and bathroom. Downstairs is a separate space with Roku TV and a sleeper sofa. 100 Mbps internet is available for interested teleworkers!

Charming 1-Bedroom Suite in Pass Christian

New construction, property to be fully completed July 2025. Photos will be available soon Charming 1-Bedroom Suite | Walk to Beach & Downtown Welcome to your perfect getaway in Pass Christian! This cozy 1-bedroom suite is nestled in a charming bungalow on a beautiful property featuring restaurants, boutique shops, a spa, & pool.