Family-friendly vacation rentals in Diamondhead

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Top-rated family-friendly rentals in Diamondhead

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

The image captures a serene river view with multiple docks extending into the water. Lush greenery surrounds the area, and the reflections of the trees can be seen in the calm surface. A well-maintained lawn and walking path are visible in the foreground.

Home in Kiln

4.97 out of 5 average rating, 121 reviews

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!

Top guest favorite

A single-story brick home is presented, featuring bright teal shutters and a welcoming front door. A concrete walkway leads to the entrance, surrounded by a well-maintained lawn and greenery. Flowers are positioned near the entrance, adding a touch of natural beauty.

Home in Long Beach

4.96 out of 5 average rating, 113 reviews

Gallery 101 Two blocks to the Beach

Gallery 101 is for travelers who are searching for a cozy, well- equipped home with a quirky style. The home is 2 blocks from the beach and a 15 minute walk to Long Beach shops and restaurants. The RR tracks are just north of the home and the train comes through during the day and usually twice each night. The rumbling of the train or the train whistle is something to consider before you reserve. However, if you stay anywhere in Long Beach, you will hear the train. Only 2 vehicles allowed.

Top guest favorite

A comfortable guest suite is shown, featuring a king bed with decorative pillows and a patterned quilt. A small table holds dishes and a mini fridge, while a microwave and information pamphlets are visible. Soft lighting from a nightstand lamp adds warmth to the room.

Guest suite in Bay St. Louis

4.98 out of 5 average rating, 178 reviews

Bamboo Room: King Guest Suite - Quiet Green Oasis

WEST Bay St Louis - 8mi TO DOWNTOWN! Quiet green rural alternative to major tourist areas. 5mi to beach & Silver Slipper Casino; 23mi to Gulfport; 55mi to New Orleans. 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. 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.

Top guest favorite

A charming cottage is visible, featuring grey doors framed by decorative round accents. A stone pathway leads to the entrance, bordered by a well-kept lawn. A small outdoor seating area with a table and chairs, shaded by an umbrella, complements the vibrant flower pots nearby.

Guesthouse in Bay St. Louis

4.96 out of 5 average rating, 423 reviews

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

Guest favorite

A screened-in porch features comfortable seating arranged around a round coffee table. Ceiling fans provide a cooling breeze, and large windows offer views of surrounding trees and the bay. Natural light enhances the inviting atmosphere of this outdoor space.

Cottage in Bay St. Louis

4.95 out of 5 average rating, 176 reviews

Bay Views from the Porch

Everything you need to have the perfect relaxing vacation. Ideally located just a mile and a half from downtown, golf, the beach, or the casino. You can walk, bike, or take a short car ride to do anything your heart desires. After enjoying a day at the beach, golf course, boating, visiting the local shops, or enjoying festivals, relax on your serene screened-in porch staring at the bay and enjoying a wonderful dinner, grilled to perfection. The Bay House is the perfect stay. Sorry, no pets.

Top guest favorite

A two-story house is presented, featuring a metal exterior with a covered deck on the upper level. The ground floor provides a spacious area for parking. Lush greenery, including tropical plants, defines the surrounding yard, with a clear blue sky overhead.

Home in Bay St. Louis

4.96 out of 5 average rating, 137 reviews

Waterfront w/ Boat Dock, Outdoor Kitchen, Hot Tub

Relax and unwind at Camp Who Dat! The house is perfect for entertaining with a screened porch upstairs, an outdoor kitchen downstairs, a boat dock, and hot tub. The house is a short drive to the gulf coast beaches and downtown and there is a boat launch nearby. The house has an open kitchen and living space with 2 bedrooms, 2 baths, washer/dryer, and high speed internet. The house has an outdoor lift for ADA (by request only). Bring your bikes, kayaks, jet skis, pontoon or bay boat!

Guest favorite

A charming red cottage is set against a backdrop of lush greenery. A gravel pathway leads to the entrance, flanked by flowering shrubs and trees. The cottage features a distinct gabled roof with a decorative cross, enhancing its inviting exterior.

Guest suite in Kiln

4.98 out of 5 average rating, 113 reviews

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!

Guest favorite

A bright living area is furnished with a gray sofa adorned with pillows in various shades. A round glass coffee table sits on a patterned rug. Natural light filters through multiple windows, highlighting a potted plant and a cozy reading chair positioned beside the door.

Loft in Bay St. Louis

4.93 out of 5 average rating, 158 reviews

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.

Top guest favorite

A spacious bed is dressed in a light blue quilt, flanked by two lamps on nightstands. A decorative bench with a floral pattern sits at the foot of the bed. Artwork adorns the walls, adding color to the warm yellow backdrop.

Guesthouse in Long Beach

4.98 out of 5 average rating, 161 reviews

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.

Top guest favorite

A rustic barn-style structure features a gabled roof and wooden siding, surrounded by lush greenery. Large windows allow natural light to enter, and an outdoor seating area is visible beneath the covered front porch. Fencing outlines the property, enhancing its country charm.

Barn in Picayune

4.98 out of 5 average rating, 380 reviews

"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!

Guest favorite

A comfortable living area features two armchairs and a plush sofa, arranged around a wooden coffee table. A brick fireplace serves as a focal point, complemented by a mounted television above it. Large windows allow natural light to fill the space, with a view of the screened porch.

Home in Long Beach

4.95 out of 5 average rating, 133 reviews

Cozy Coastal Cottage Near Beach & DT Long Beach

NO CHORES!! 🧹🧽 Our cozy 2BR cottage is the perfect Gulf Coast escape. You’ll have Wi-Fi, a washer/dryer, full kitchen, private bath, and a screened porch to relax on. Walk to the beach or charming downtown Long Beach, or take a short drive to casinos, the MS Aquarium, and more. Whether it’s a weekend getaway or a longer stay, this spot feels like home-easy, peaceful, and close to everything.

Guest favorite

A view is presented from a deck, showcasing a fenced yard. A tree casts gentle shade in the background, while the ground is covered with leaves and grass. The fence features alternating horizontal slats, enhancing the natural surroundings.

Apartment in Long Beach

4.93 out of 5 average rating, 149 reviews

Private Apartment 5 miles off the Beach! (B )

Want a nice getaway without all the hassle? Come stay in our fully furnished and ready to go rentals at Magic River! It has two bedrooms with queen beds in each room, a living room with a TV, full kitchen, bathroom, washer & dryer, and a deck with a mini BBQ grill. The rental comfortably sleeps 3-4 people. We are also within 15-20 minutes of the casinos!