Pet-friendly holiday rentals in Diamondhead

Sycamore Cottage- 5 min. walk from Amtrak train!

Charmingly restored 1905 cottage. Updated, well-equipped kitchen--perfect for romantic dinners. Solid heart pine floors & cheery decor. Bathroom: claw-foot tub/shower & attached rm with 2 sinks. Two bdrms each with queen bed. Office area has futon to sleep one. Cozy front porch, plus small screened porch off kitchen door. Parking for 2+ cars on site. Back yard w/charcoal grill, table w/4 chairs, umbrella. Close to beach & fun "Depot" district. Two min drive to "old town" Bay St.Louis.

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.

New Home Waterfront Near NOLA Gulf Beach Casino

A modern vacation stay located in The Bayou Phillips Estates. This spacious 3 bedroom, 2 bathroom home features an open floor plan with vaulted ceilings, modern appliances, covered and furnished deck overlooking the Bayou with a private dock, all on a spacious acre lot surrounded by woods. Great fishing right off the private dock and direct access to The Bay. Local boat launch just a block away! Kayaks & Basketball. Less than an hour drive to New Orleans, Biloxi, Gulfport, and Long Beach.

InstaWorthy~ Luxe King Bed~ Mins to Beach

Have the Gulfport vacation of your dreams in the spacious 3BR 2Bath oasis in the tranquil neighborhood. Spend the day soaking up the sun in the private backyard, or exploring nearby attractions. ✔ 2 Comfy Bedrooms + Office Double Bed ✔ Open Design Living ✔ Fully Equipped Kitchen ✔ Back Patio (Wide-Screen Projector) ✔ Backyard ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Free Parking See more below! WE DO NOT GUARANTEE THE HOT TUB! This was t amen out of our list of amenities March, 2025.

The House in the Bay - Discounts for Longer Stays

Spacious Old Town home. Walk to everything. Get away from it all in this mid-century modern, light-filled retreat. Just three blocks from the harbor and beach, the House in the Bay is close enough to walk to restaurants, coffee shops, music and all the downtown fun. The fishing pier, boat launch, public library and grocery store are less than a mile away. Catch the breeze and relax in the shade of a registered Live Oak. Small and medium dogs allowed with prior approval.

Cozy Sea La Vie guest quarters

This space is the simplicity and privacy of guest quarters but with the bonuses of your own private living room/work space as well as a patio and fenced 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.

The Low Commotion {downtown Depot District}

The Low Commotion sits right in the life of the Historic Depot District in old town Bay St. Louis. It features a train-inspired decor blending perfectly with its location across from the train depot. The master bedroom includes a queen bed with a private bathroom and access to the back porch. The additional bedroom boasts fun built-in bunk beds. It is near an active railroad. Watching the train pass and hearing the whistle is included for no extra fee!

Charming Cottage Retreat / Downtown Pass Christian

Welcome to The Pelican’s Nest, your cozy beach escape in the heart of Pass Christian! Tucked in the quiet and charming Cottages at 2nd Street, our coastal cottage is just a short walk to the beach, restaurants, shops, and local bars. Whether you're relaxing on the front porch or heading out to explore the coast, this is the perfect home base for couples, small families, or remote workers looking for comfort, walkability, and local charm.

"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!