
Family-friendly holiday 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.

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.

Beach Getaway
Full studio (388 sf) near Keesler, across from the beach, restaurants, and shopping. There is a public bus stop on the corner & shuttles for the casinos. Wifi with small smart TV. Let yourself in with keyless entry then go for a swim, enjoy coast seafood, or join the excitement at a casino. Make yourself at home and feel safe with security lighting and no stairs. My place is good for couples and solo adventurers. No trailer parking allowed. Max. occupancy is 2: violation results in eviction.

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.

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

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!

Bay-Cay Getaway! Beaching-Casino-Grilling-Swimming
Everybody needs a vacation in the Bay and on the beach, right? We would love for you and your family to visit “BAY-CAY” Getaway!! This is a beautiful home/cottage located 2 blocks from the beach. You are a 2-3 minute walk from the sandy beach and an awesome fishing pier. The Silver Slipper Casino, with its award winning buffet, is just 1 mile away. You are also 1 mile from Buccaneer State Park and can enjoy the wave pool. The heart of downtown Bay St. Louis is seven miles from our home.

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.

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.

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!

Coastal Cottage in Downtown Pass Christian
The Pelican’s Nest is your cozy beach retreat in the heart of Pass Christian. Nestled in the charming Cottages at 2nd Street, it’s a short stroll to the beach, restaurants, shops, and local bars. Enjoy coffee on the front porch or explore the coast—perfect for couples, small families, or remote workers seeking comfort, walkability, and local charm.
Popular amenities for Diamondhead family-friendly rentals
Family-friendly home rentals with a hot tub

3 Acre Estate Heated Pool, Hot Tub, Boat/Fish Dock

The Corr'al Reef - Brand New!

Beach Cottage 1800's Nola style cottage

Coastal Comfort w/Hot Tub & Fire Pit

Walk 2 Beach on Gulfport/Biloxi border, 2 pools

Hot Tub | Golf | Bar | Games

*Luxury Home* Hot Tub/Outdoor Fireplace/EV Charger

Art House w/indoor jacuzzi! one block to downtown
Family- and pet-friendly home rentals

The Cottage at Pino (Low clean fee)

Old Town Cottage

Beach View Bungalow

Tucked Away & Cozy

InstaWorthy~ Luxe King Bed~ Mins to Beach

Peggy Sue

Cozy Sea La Vie guest quarters

Beach Life-Walk to Old Town! Weekly Discount
Family-friendly home rentals with a pool

Beautiful Biloxi Getaway Beach Condo!

Rose Beach House, Sleep 8, Swim Pool, Gated (91A)

The Ritz

Come and "Stay Awhile" at Oak Shores

*Pelican Pass* Golf/Fish/Swim / Incredible water v

Shell House Estate Bungalow

Blue Heaven Condo on the Beach!

A stay so inviting, you won’t want to leave
Quick stats about holiday rentals that are family-friendly in Diamondhead
Total rentals
30 properties
Nightly prices starting at
€ 51 before taxes and fees
Total number of reviews
790 reviews
Pet-friendly rentals
10 properties allow pets
Rentals with a pool
10 properties have a pool
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Destinations to explore
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- Beachfront rentals Diamondhead
- Family-friendly rentals Hancock County
- Family-friendly rentals Mississippi
- Family-friendly rentals United States
- Biloxi Beach
- Gulfport Beach, MS
- Gulf Island National Seashore
- Fontainebleau State Park
- Mississippi Aquarium
- English Turn Golf & Country Club
- Waveland Beach
- Buccaneer State Park
- Grand Bear Golf Club
- Money Hill Golf & Country Club
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- East Beach
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- Long Beach Pavilion
- The Preserve Golf Club
- Beach Park Pier
- Get Wet
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