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Family-friendly holiday rentals in Diamondhead

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Quick stats about holiday rentals that are family-friendly in Diamondhead

  • Total holiday rentals

    Explore 20 holiday rentals in Diamondhead

  • Nightly prices starting at

    Diamondhead holiday rentals start at €70 per night before taxes and fees

  • Verified guest reviews

    Over 910 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 of Diamondhead holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Diamondhead rentals

  • 4.9 Average rating

    Diamondhead stays are highly rated by guests – averaging 4.9 out of 5!

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 favourite
Home in Kiln

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!

4.95 out of 5 average rating, 148 reviews
Guest favourite
A spacious game room is showcased with a green felt pool table at the forefront. The area is covered and features a ceiling fan above, with a variety of seating options visible in the background alongside large windows that allow natural light to fill the space.
Home in Pass Christian

Green Lake House, GamE RooM, Sleep 10, Beach

Experience resort-style living at our vibrant and colorful vacation house! Our passion for the arts is reflected in every corner, creating a fun and comfortable atmosphere for your stay. Our back patio overlooks a serene lake, and we're only three blocks away from the sandy beach. LOCATION is key, and we've got you covered - our house is the farthest away from the noisy active train, ensuring a peaceful and restful sleep. Note: We have a strict NO PETS policy due to a severe HEALTH allergies

4.9 out of 5 average rating, 111 reviews
Top guest favourite
Home in Bay St. Louis

Pool, Hot Tub, Game Area, Waterfront Bay St. Louis

Relax in this spacious home in Bay St. Louis and enjoy the private pool and hot tub. This home is located on a quiet dead end road and features plenty of space to spread out, relax, and entertain. There is plenty of outdoor seating to enjoy while watching the kids play in the pool, fish from the back yard, or enjoy the fire pit. Cook on the grill and enjoy amenities like the bicycles, beanbag toss, ping pong, beach toys and more. This home is perfect for your next getaway so don't wait.

4.91 out of 5 average rating, 164 reviews
Guest favourite
A cyclist is seen riding along a scenic path by the beach, with sandy areas on one side and lush greenery on the other. The horizon is marked by calm waters under a partly cloudy sky, creating a peaceful coastal ambiance.
Home in Pass Christian

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.

4.92 out of 5 average rating, 381 reviews
Guest favourite
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

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!

4.97 out of 5 average rating, 141 reviews
Top guest favourite
Cottage in Pass Christian

Coastal Cottage | Walk 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.

4.98 out of 5 average rating, 246 reviews
Guest favourite
The exterior of the multi-level house features a private pool surrounded by a safety fence. A shaded seating area and outdoor dining space are visible beneath the house, with green grass extending around the property. Tall trees provide natural shade and enhance the outdoor space.
Home in Waveland

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.

4.84 out of 5 average rating, 134 reviews
Guest favourite
A large outdoor swimming pool is surrounded by a stone patio, featuring a clear blue water surface. Lush greenery and tall trees provide shade in the background, enhancing the tranquil atmosphere. A basketball hoop is positioned nearby, adding a recreational element to the space.
Guest suite in Kiln

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!

4.96 out of 5 average rating, 118 reviews
Top guest favourite
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

"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!

4.98 out of 5 average rating, 426 reviews
Top guest favourite
The exterior of the property is highlighted, showcasing a spacious deck illuminated by soft lights. A luxurious hot tub and saltwater pool are visible in the foreground, surrounded by lounge chairs and neatly arranged patio tiles, creating an inviting outdoor space.
Home in Bay St. Louis

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

4.87 out of 5 average rating, 120 reviews
Top guest favourite
A spacious backyard features a fire pit surrounded by several comfortable seating options. An outdoor dining area with an umbrella provides shade, while a well-kept lawn and tall trees enhance the inviting outdoor space.
Home 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.

4.96 out of 5 average rating, 121 reviews
Top guest favourite
Guest house in Kiln

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.

4.89 out of 5 average rating, 222 reviews

Popular amenities for Diamondhead family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Top guest favourite
The exterior of the lake house features a wide covered porch with rocking chairs set beside a dining table. Large windows provide views of the surrounding greenery. A canoe is secured on a rack to the right, enhancing the outdoor recreation appeal.
Cottage in Saucier

Lake House with beautiful view.

4.96 out of 5 average rating, 112 reviews
Top guest favourite
A balcony view features two chairs and a small table with a decorative item. The vibrant sunset casts shades of pink and orange over the horizon, creating a serene backdrop against the calm Gulf waters.
Apartment in Gulfport

Gorgeous Oceanview 3BR Luxury Condo - "Latitude"

4.99 out of 5 average rating, 141 reviews
Top guest favourite
A private pool is highlighted in the outdoor space, surrounded by neatly trimmed greenery and tropical plants. The pool area is furnished with lounge chairs, and a covered patio provides another seating option, blending relaxation and comfort in a serene environment.
Home in Gulfport

Pool & Hot Tub Oasis! | Mins to Beach! | Sleeps 6

4.95 out of 5 average rating, 98 reviews
Guest favourite
The living room features a modern design with a large flat-screen television mounted above a decorative fireplace. Soft seating arrangements include a light-colored couch and armchair, complemented by a round coffee table. Natural light streams through the large windows, enhancing the inviting atmosphere.
Home in Gulfport

Luxury Home: 1 Block to Beach, Hot Tub, EV Charger

4.95 out of 5 average rating, 125 reviews
Top guest favourite
The exterior of a historic cottage is displayed, featuring a charming pathway of pavers leading to a welcoming entry. Lush greenery includes tall cypress trees and vibrant flower beds with pink and white blossoms, framed by well-maintained shrubs and a gravel area for added texture.
Cottage in Biloxi

Beach Cottage 1800's Nola style cottage

4.98 out of 5 average rating, 163 reviews
Top guest favourite
Home in Diamondhead

Bayside Retreat - 2450 sq ft w/dock & fire pit

5.0 out of 5 average rating, 27 reviews
Top guest favourite
Home in Pass Christian

The View | Waterfront • Pool • Paradise •Golf Cart

5.0 out of 5 average rating, 33 reviews
Superhost
Home in Gulfport

Gulf View, Pool + Jacuzzi, Outdoor Bar + Games

5.0 out of 5 average rating, 4 reviews

Family- and pet-friendly home rentals

Top guest favourite
A spacious living area is shown, featuring a comfortable sectional sofa arranged around a coffee table. An entertainment center houses a large television. A staircase is visible in the background, leading to the upper level. Neutral tones create a calming environment.
Townhouse in Bay St. Louis

No cleaning fee. Sleep 6/3BR /2.5BA. Pets allowed.

4.97 out of 5 average rating, 144 reviews
Top guest favourite
The exterior of the building features a modern design with large windows framed in muted tones. A welcoming seating area is situated on the porch, complemented by minimalist lighting fixtures. Decorative planters add greenery, and the pathway leads to the entrance of the unit.
Apartment in Bay St. Louis

The Low Commotion {downtown Depot District}

4.97 out of 5 average rating, 235 reviews
Top guest favourite
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.
Guest house in Bay St. Louis

Cozy efficiency cottage near beach & entertainment

4.96 out of 5 average rating, 464 reviews
Guest favourite
The exterior of the home is framed by vibrant pink azalea flowers. Two large windows line the front, allowing natural light to fill the interior. The structure features a combination of siding and a screened porch, set against a clear blue sky.
Home in Bay St. Louis

The House in the Bay - Discounts for Longer Stays

4.9 out of 5 average rating, 116 reviews
Guest favourite
A modern home is elevated on stilts, surrounded by trees and grass. Below, a private dock extends into calm water, with scenic reflections of the house and greenery. The structure features multiple outdoor spaces and is partially sheltered by an awning, enhancing the tranquil setting.
Home in Bay St. Louis

New Home Waterfront Near NOLA Gulf Beach Casino

4.86 out of 5 average rating, 136 reviews
Top guest favourite
The charming house features a well-lit exterior with a white facade and multiple large windows. Soft lighting highlights the landscaped area, which includes plants and stone pathways. A welcoming front porch is visible, creating an inviting entry to the home.
Home in Bay St. Louis

Cutest Damn House in the Bay with new Golf Cart

4.9 out of 5 average rating, 222 reviews
Top guest favourite
Holiday home in Bay St. Louis

Main St BSL: Private Pool & Golf Cart | Sleeps 10

4.95 out of 5 average rating, 107 reviews
Guest favourite
A charming two-story house is elevated on stilts, featuring a light blue exterior and a distinctive arched window. A set of steps leads to the front porch, surrounded by lush green grass and trees, creating a peaceful outdoor setting.
Home in Pass Christian

Peggy Sue

4.83 out of 5 average rating, 144 reviews

Family-friendly home rentals with a pool

Top guest favourite
A shaded outdoor lounge area is featured, furnished with a dark sectional sofa adorned with red cushions. A coffee table is placed centrally, accompanied by a bottle of wine and a floral arrangement. The background showcases a private pool surrounded by greenery.
Home in Bay St. Louis

Private Pool, One minute to Beaches!

4.96 out of 5 average rating, 169 reviews
Top guest favourite
A well-maintained estate is set on expansive green grounds, featuring a charming two-story house with multiple windows. Towering live oak trees provide shade, and a manicured lawn is adorned with small ornamental plants. A pathway leads from the driveway to the inviting property entrance.
Bungalow in Long Beach

Shell House Estate Bungalow

4.92 out of 5 average rating, 272 reviews
Guest favourite
Apartment in Biloxi

Beach Getaway

4.85 out of 5 average rating, 297 reviews
Top guest favourite
The charming beach house is surrounded by lush greenery and features a well-maintained garden area. A gravel path leads to the entrance, with welcoming steps leading up to a covered porch adorned with ceiling fans. A picket fence encloses the inviting front yard.
Home in Bay St. Louis

Beach Bungalow - Private Pool+Walk to Town & Beach

4.99 out of 5 average rating, 109 reviews
Guest favourite
A serene beachfront scene captures gentle waves lapping at the sand, with footprints trailing along the shoreline. The sun is seen rising above the horizon, casting warm colors across the sky. Nearby buildings are faintly visible against the coastal backdrop.
Flat in Biloxi

Biloxi Beach House

4.87 out of 5 average rating, 157 reviews
Top guest favourite
The living area features a spacious white sectional sofa adorned with blue accent pillows. A dining table with chairs is positioned nearby, complemented by light fixtures overhead. The backdrop consists of a kitchen visible in the distance, with white cabinetry and appliances.
Apartment in Long Beach

Blue Heaven Condo on the Beach!

4.92 out of 5 average rating, 122 reviews
Top guest favourite
An open living area is presented with a spacious sofa and coordinating armchairs. Large windows invite natural light, complementing the light-colored walls and tiled flooring. A dining table with chairs is visible, alongside a kitchen area featuring a coastal-inspired design.
Apartment in Long Beach

Beautiful Long Beach Condo with Ocean View+Pool!

4.97 out of 5 average rating, 162 reviews
Top guest favourite
Flat in Diamondhead

Lacey's Coastal Cabana - Charming & Quiet Condo

5.0 out of 5 average rating, 47 reviews

When is the best time to visit Diamondhead?

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