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.

Guest house 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

4.92 out of 5 average rating, 308 reviews

A serene landscape is captured with a vibrant sunset glowing over a vast marsh area. Lush greenery and a variety of trees frame the scene, casting soft shadows on the ground. The sky features scattered clouds, creating a picturesque backdrop of natural beauty.

Cottage in Bay St. Louis

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.

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

Guest house in Long Beach

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.

4.98 out of 5 average rating, 172 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.

4.99 out of 5 average rating, 150 reviews

A rustic cottage with a covered front porch is surrounded by lush green grass and trees. The warm wooden structure features a sloped roof, brick chimney, and vibrant foliage highlighting the calming natural landscape.

Farm stay in Picayune

Chickie's Cottage, an idyllic getaway.

Chickie's Cottage, nestled in a shady pecan orchard where horses graze, is adjacent to the 600,000 acre Stennis Space Center buffer zone. The pastures and natural surroundings include pecans and live oaks that evoke peace and tranquility. Farm life includes horses, cats and chickens who enjoy visiting guests. The farm house is one-of-a-kind; charming, comfortable, complete with unique furnishings and modern amenities such as 100 Mbps WiFi and Roku TVs.

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!

4.92 out of 5 average rating, 165 reviews

Flat in Pass Christian

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

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.

Popular amenities for Diamondhead family-friendly rentals

Kitchen

Wifi

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

5 out of 5 average rating, 22 reviews

An aerial view showcases a spacious property featuring a fenced-in pool area with lounge chairs and palm trees. The house is raised on stilts, with a wraparound balcony that offers seating. Surrounding greenery enhances the open landscape, providing a serene outdoor space.

Home in Waveland

Waveland Beach Cottage 213

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.

Apartment in Gulfport

4.8 out of 5 average rating, 137 reviews

Walk 2 Beach on Gulfport/Biloxi border, 2 pools

4.85 out of 5 average rating, 99 reviews

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

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

Apartment 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

4.96 out of 5 average rating, 118 reviews

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.

Home in Bay St. Louis

The Row on State_351

Guest house in Long Beach

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.

4.91 out of 5 average rating, 160 reviews

The Cottage at Pino (Low clean fee)

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

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.

Guest house in Gulfport

Tucked Away & Cozy

Apartment in Bay St. Louis

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.

4.97 out of 5 average rating, 214 reviews

The Low Commotion {downtown Depot District}

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.

Flat in Long Beach

Private Apartment 5 miles off the Beach! (B )

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

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

4.98 out of 5 average rating, 145 reviews

A heated saltwater pool is surrounded by a spacious deck, illuminated by soft outdoor lighting. Comfortable lounge chairs line the poolside, while a table with colorful seating is positioned nearby. A fire feature adds warmth to the space, creating a cozy gathering area.

Home in Bay St. Louis

Spencer’s Way Beach House A with heated pool

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

5 out of 5 average rating, 102 reviews

A spacious, open living area features a comfortable sectional sofa and a wooden coffee table. Light-colored walls complement the tiled floor, while a dining table is visible in the background. Large windows allow natural light to fill the space, creating a bright atmosphere.

Apartment in Long Beach

Lovely Long Beach Condo With Pool and Beach View!

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

Townhouse in Mississippi City

The exterior showcases a two-story townhouse with a light blue and yellow facade. Each unit features a porch with seating, and balconies on the second floor. Lush greenery serves as a backdrop, contributing a natural aspect to the community setting.

4.88 out of 5 average rating, 206 reviews

2-min to BEACH~Game room~Pool~Gated community~Deck