Family-friendly holiday rentals in Diamondhead

Guest suite in Bay St. Louis

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.

4.98 out of 5 average rating, 185 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.

A spacious elevated home is surrounded by lush greenery, featuring a screened-in lower level with seating. Two sets of stairs lead up to the bright exterior, showcasing multiple windows and a cozy outdoor area with a fire pit and benches.

4.98 out of 5 average rating, 209 reviews

Old Town Home Outdoor Bar Game Area Quiet Location

Relax in this centrally located Home near Old Town Bay St. Louis. Our relaxing home is located on a quiet dead end road and is only 5 minutes from Old Town Bay St. Louis and one block from the Ocean. Beaches and plenty of places to throw a fishing pole off the sea wall are right around the corner. You will enjoy the extra amenities we've added such as a pool table, ping pong table, Basketball Goal, Cornhole boards, Darts, Firepit and Grill. We also have beach supplies and bicycles for you.

Guesthouse in Bay St. Louis

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.

4.96 out of 5 average rating, 436 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

4.98 out of 5 average rating, 124 reviews

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!

4.93 out of 5 average rating, 175 reviews

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

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.

4.86 out of 5 average rating, 190 reviews

The exterior of the cottage features a blue facade with red accents. A covered porch is supported by white railings, providing a welcoming entrance. Lush greenery surrounds the property, enhancing the outdoor space. A pathway leads from the porch to the yard.

Cottage in Bay St. Louis

Historic Cottage in Old Town Bay St Louis

This one-bedroom historic cottage in Old Town Bay St Louis named Leo's House is the ideal spot in the Bay. It is a peaceful retreat in the heart of Old Town Bay St Louis. The cottage is just steps from the best shopping, restaurants, and nightlife that Bay St Louis has to offer. Once you arrive at Leo's House, you have no reason to get back in your car. The cottage is short walking distance to the beach, Bay St Louis Municipal Harbor, and shops and restaurants. BSL028

4.98 out of 5 average rating, 172 reviews

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

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.

Guest suite in Bay St. Louis

A charming sleeping area features floral wallpaper and a spacious bed dressed in soft linens. A unique light fixture hangs above the bed, and a decorative bench is placed at the foot. A television is mounted on the wall opposite the bed, and natural light enters through the nearby door.

5 out of 5 average rating, 108 reviews

The Dolly Suite

A Dolly-themed private suite located in the historic Bell House on Main Street. Enter your completely private suite with full bathroom from your own separate entrance on the front porch. Enjoy use of the beautiful, serene grounds that will take you back to Dolly’s home in the Mountains in Tennessee. Pour yourself a cup of ambition and start your morning on our front porch which has seven oak trees around the property.

4.97 out of 5 average rating, 108 reviews

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!

4.97 out of 5 average rating, 398 reviews

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!

Apartment in Pass Christian

4.92 out of 5 average rating, 165 reviews

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.

4.88 out of 5 average rating, 194 reviews

Guesthouse 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.

Popular amenities for Diamondhead family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

An aerial view captures the expansive 3-acre estate surrounded by lush greenery and the winding Wolf River. The house is positioned centrally, with a large yard dotted by red seating. The nearby marshlands and river create a scenic backdrop, enhancing the natural beauty of the area.

4.95 out of 5 average rating, 152 reviews

Our Hot Tub WORKS, Heated Pool, boat dock pets ok

Superhost

An outdoor kitchen area features a thatched roof and bar seating, surrounded by tropical landscaping. A patio with multiple lounge chairs invites relaxation, while a fire pit area enhances the gathering space. String lights overhead create a charming ambiance for evening enjoyment.

Apartment in Bay St. Louis

4.79 out of 5 average rating, 48 reviews

Suite - "Knome Dome" with Shared Pool

Superhost

5 out of 5 average rating, 4 reviews

Milo Beach House·Steps to Beach· Hot Tub+Fire Pit

Superhost

The living room features two brown leather sofas paired with round blue poufs. A wooden coffee table sits in the center, adorned with decorative items. Large arched windows allow ample natural light, with sheer curtains providing a soft ambiance.

Condo in Gulfport

4.8 out of 5 average rating, 137 reviews

Walk 2 Beach on Gulfport/Biloxi border, 2 pools

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.

4.85 out of 5 average rating, 99 reviews

Beach Bay&RiverMansion Private boat Ramp On water

4.96 out of 5 average rating, 118 reviews

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* Hot Tub/Outdoor Fireplace/EV Charger

Condo in Mississippi City

A sandy beach scene features a welcoming sign marking the Mississippi Gulf Coast. Palm trees are scattered along the shoreline, and a gazebo is visible in the distance under a partly cloudy sky. Soft waves can be seen lapping against the shore.

4.95 out of 5 average rating, 126 reviews

Agape Bay - Sienna on the Coast Unit 102

4.91 out of 5 average rating, 64 reviews

The exterior of the Beach House showcases a light-colored structure elevated on pillars with a stairway leading to a spacious front porch. The porch features a white railing and is complemented by large windows that allow for natural light.

Home in Waveland

The Beach House

Family- and pet-friendly home rentals

A living area is showcased with a leather sofa adorned with decorative cushions. A wooden coffee table rests between the seating and a vintage rug adds a pop of color to the wooden floor. Natural light filters through the window, illuminating framed photographs on the wall.

4.96 out of 5 average rating, 118 reviews

The Row on State_351

4.91 out of 5 average rating, 372 reviews

A front porch with wooden flooring features two chairs and a rocking chair, surrounded by greenery. The view includes a garden area beyond the porch, showcasing other homes and a hint of the neighborhood ambiance.

Cottage in Bay St. Louis

Old Town Cottage

5 out of 5 average rating, 26 reviews

A spacious living area features a comfortable sofa arranged around a round coffee table. Natural light enters through large glass doors leading to an outdoor area. A decorative cabinet and framed artworks adorn the walls, while a ceiling fan adds to the inviting ambiance.

Townhouse in Diamondhead

Highpoint Haven, Base Rate $175/night

4.96 out of 5 average rating, 139 reviews

A bright bedroom is furnished with a four-poster bed dressed in white bedding, accompanied by two bedside tables with lamps. A cozy rug is positioned at the foot of the bed, and a small shelving unit adds storage space. Soft ceiling fans contribute to airflow.

Guesthouse in Gulfport

Tucked Away & Cozy

A waterfront home is depicted, featuring a two-story structure with a red exterior and a spacious deck. The deck overlooks a calm canal with docks on either side. Nearby homes and lush greenery are visible, along with an expansive view of the water extending towards the horizon.

4.88 out of 5 average rating, 114 reviews

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

5 out of 5 average rating, 211 reviews

A private patio area is depicted with a brick patio, featuring a set of comfortable seating arrangements. Cushioned chairs and a glass coffee table are surrounded by plants, creating an inviting outdoor space for relaxation and leisure.

Guest suite in Gulfport

Cozy Sea La Vie guest quarters

4.93 out of 5 average rating, 150 reviews

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

Private Apartment 5 miles off the Beach! (B )

A charming beach house in a refreshing shade of turquoise is depicted. The structure features a well-maintained front porch with a small potted plant next to the entrance. Two windows allow natural light to enter, surrounded by lush green landscaping.

4.9 out of 5 average rating, 147 reviews

Beach Life-Walk to Old Town! Weekly Discount

Family-friendly home rentals with a pool

A spacious vacation home is set within a natural landscape, featuring a fenced heated pool. Umbrellas provide shade around the pool area, while palm trees frame the exterior. The home's multiple decks overlook the surrounding greenery and can be accessed via outdoor stairs.

4.93 out of 5 average rating, 100 reviews

Heated Pool! Petite Retreat in The Pass

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.

4.99 out of 5 average rating, 90 reviews

Beach Bungalow - Private Pool+Walk to Town & Beach

4.91 out of 5 average rating, 160 reviews

The inviting exterior of The Cottage showcases a well-maintained facade with a light and dark color scheme. A pathway leads to the front door, bordered by potted plants. The cozy porch provides shade, while a spacious yard is visible beyond, framed by a privacy fence.

Guesthouse in Long Beach

The Cottage at Pino (Low clean fee)

4.96 out of 5 average rating, 26 reviews

A cottage is set in a spacious outdoor area, surrounded by greenery. The screened-in porch is visible, providing a shaded space. The white exterior of the cottage contrasts with the natural surroundings, while bushes line the path leading to the entrance.

Cabin in Bay St. Louis

Cottage At The Campground

An in-ground swimming pool is surrounded by lounge chairs, set within a landscaped area. A screened-in porch is furnished with vibrant cushions and seating, offering a relaxed outdoor gathering space. The exterior of the house displays a two-story design with steps leading to the entrance.

4.92 out of 5 average rating, 37 reviews

The Boat House Bay St. Louis

4.92 out of 5 average rating, 257 reviews

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

4.93 out of 5 average rating, 101 reviews

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.

Condo in Long Beach

Blue Heaven Condo on the Beach!