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!

Restored Farmhouse AKA “The Old House”

Welcome to the "Old House"! Escape to this beautifully restored farmhouse, where comfort meets charm. With 3 cozy bedrooms, 2 modern bathrooms, and plenty of space to accommodate up to 8 guests, it's ideal for a relaxing retreat. Start your mornings on the front porch, sip your coffee, and enjoy the peaceful view of neighboring farm animals. The new kitchen is perfect for preparing meals. Located just a short drive to local attractions, you're close while still nestled in a tranquil setting.

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.

Bay Views from the Porch

Enjoy easy access to the beach, restaurants, shopping, and local attractions from our comfortable coastal home. Everything you need to have the perfect relaxing vacation. Ideally located just over a mile from downtown. For an even better vacation experience, we offer an optional 6-passenger golf cart rental exclusively for our guests at discount prices. It’s one of the best ways to explore the area, avoid parking hassles, and enjoy cruising around town during your stay. Sorry, no pets.

Cutie by the Bay

Cutie by the bay is just 4.5 miles from white sand beaches and The Silver Slipper Casino. 7.5 miles to historic downtown Bay St Louis, 23 miles to Gulfport, 53 miles to New Orleans. This unique little house offers high speed internet, 1 bathroom, 1 queen bed, 2 futon couches, full sized refrigerator, washer, dryer and many other amenities. Outside you can enjoy a fire pit under a solar lighted pergola. Or hang out under the beautiful live oak tree. Sit back, relax and enjoy your stay.

Waterfront Game Room Ping Pong Outdoor Bar Home

Relax and enjoy this waterfront home minutes from Old Town Bay St. Louis and the beach! This home is located on a quiet road and features plenty of space to entertain, relax, spread out and even fish from the back yard. Entertain at the outdoor bar area or relax on the deck or outdoor seating area with friends and family. Cook on the grill and enjoy amenities like the Ping Pong Table, bicycles, beanbag toss, beach toys, darts, and more. This home is perfect for your next getaway!

Coastal Cottage | Steps to Beach, Shops & Dining

Experience the charm of Pass Christian at The Pelican’s Nest, a cozy beach cottage in the beautiful Cottages at 2nd Street community. Tucked along a quiet street less than two blocks from the beach, it’s the perfect place to slow down and enjoy the laid-back Mississippi Gulf Coast. Walk to restaurants, coffee shops, boutiques, neighborhood bars, and the harbor. After a day at the beach or exploring the coast, return to your peaceful cottage to relax and unwind.

Coastal Oasis - Heated Pool, Walk to Beach!

Bring the whole family to enjoy a beach vacation on beautiful MS Coast. Just 5 minutes to the shops and restaurants in downtown Bay St. Louis, the West Inn Beach club is it's own private oasis. 3 blocks to beach, private pool, ping pong, outdoor living room/tv, yard games, 600 sq ft. of screened in porches. Sleeps 12! We offer the pool to be heated November - March for an additional fee. Please inquire.

Beach Bay&RiverMansion Private boat Ramp On water

Prime location. Balconies on all 4 sides. Water front ,Game Room, over looks the Jordan River & The BayNo loud music 8 min golf cart ride downtown Bay St Louis. 9 min to beach Game Room. Sleeps 15 private boat launch. Free 2 Kyac Hot Tub Salt water Pool. Pool can be heated. Breath taking views. . The only place where the beach bay and River meets. THE BEST OPEN FLOOR PLAN IN BAY ST LOUIS

Oak Coastal Retreat! Fire Pit! Golf Cart Included!

**Welcome to Oak Coastal Retreat** Your serene Gulf getaway awaits at Oak Coastal Retreat, a stunning vacation rental nestled in the heart of historic Bay St. Louis. Just a stone's throw from the pristine beach and only a few minutes' stroll from the vibrant downtown area, this property offers an enchanting blend of convenience, comfort, and coastal charm.

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!

T-Bohn Bayou Bungalow

Studio cabin guesthouse with all the conveniences of home. Nothing fancy, but simple country living located in Kiln, Mississippi - a small rural town 15-30 minutes from Bay St. Louis, Waveland, Gulfport, Long Beach, and Biloxi. Easy access to great local restaurants, breweries, parks, museums, and other attractions.