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!

Seaside Sanctuary with Breathtaking Ocean Views

Steps from the water, New Build in Gulfport! Escape and enjoy stunning beach sunrise/sunsets from one of the two decks overlooking the Gulf or simply cross Beach Blvd and put your toes in the white sand beach. Well appointed, 2 story, 2 bedroom home located directly on Beach Blvd overlooking the ocean and pristine white sand beaches. Less than 2 miles from downtown Gulfport, Jones Park, and Island view Casino or a 25 min walk. Located between Biloxi and Bay St. Louis and < 1.5 hr to NOLA

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

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!

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.

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.

Adorable Cottage, walk to everything

This historic, seaside community, Old Town Bay St. Louis, is a favorite for travelers seeking a beautiful, relaxing, romantic destination. The Carroll House Cottages are located in the heart of Old town. Safely walk our tree lined streets, past beautiful, historic, southern homes to everything that Old town Bay St. Louis has to offer; beaches, antique shops, boutiques, art galleries, waterfront dining, and entertainment.

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!

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.

Lake House with beautiful view.

Come and relax at our cozy 2 bedroom/1 bath lake house. Two canoes, a peddle boat, and a fire pit for your enjoyment, a 30 amp RV connection, covered patio with rope lighting, hot tub, patio furniture, a park bbq grill, everything you need to cook and serve up to 10 people, washer/dryer, smart TV, Internet, and modern kitchen.