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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Top guest favorite

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

4.99 out of 5 average rating, 140 reviews

Spencer’s Way Beach House A with heated pool

Come and relax with the family at our newly constructed beach themed home. Blocks away from the center of Bay St. Louis and the beach. The Bay has a small little city Key West vibe , with boutiques, antique shops, great restaurants with live music. We Invite you to stay at our cozy Place and have a wonderful time. There is also a new HEATED salt water pool with barbecue area, fridge & sink. Bar area with television and blue tooth speakers for your enjoyment. The pool is shared by both units.

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, 179 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, 428 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

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, 141 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 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

4.94 out of 5 average rating, 285 reviews

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.

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, 114 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!

Top guest favorite

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

4.99 out of 5 average rating, 195 reviews

Cozy Sea La Vie guest quarters

This private guest quarters is attached to the main house with the simplicity of your own bedroom, bathroom, living room and work space as well as a patio with a fence-backyard. Park right at your private entrance located on the street that leads you to the beach. Centrally located 2 miles from the hospitality center of downtown Gulfport which includes many places of entertainment such as the new aquarium, Jones park and Island View Casino. Beautiful and private residential street.

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, 163 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 cozy cottage is nestled beneath the sprawling branches of an aged tree, providing shade. The entrance features large glass doors, leading to a covered patio with outdoor seating. Lush greenery and blooming flowers frame the property's surroundings, inviting relaxation and tranquility.

Guesthouse in Bay St. Louis

4.9 out of 5 average rating, 431 reviews

Palm Cottage - Old Town Bay St. Louis

BSL Permit No. 099. Newly renovated studio filled with all you need for the perfect vacation: private patio, kitchenette, big BBQ, wash/dryer, TV with cable, Wi-fi, private parking, jacuzzi tub, more. Walk to beach, shops, restaurants, train depot, Main Street antiques. This is a studio cottage with queen bed and sofa bed in the same room. This cottage is walkable from the Amtrak station - or if you would like a ride from the station, please contact us.

Top guest favorite

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

4.97 out of 5 average rating, 102 reviews

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!

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, 382 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!

Top guest favorite

A light-filled living and dining area showcases a soft pink sofa paired with a round coffee table. The well-equipped kitchen features olive green cabinetry, stainless steel appliances, and a dining table with wooden chairs. Decorative wall art enhances the inviting atmosphere.

Cottage in Pass Christian

4.99 out of 5 average rating, 166 reviews

2nd Street Cottage: Walk to Beach & Shops

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.