Holiday houses in Diamondhead

5 out of 5 average rating, 3 reviews

Eagle’s Nest - Golf & Relax at DH - Pet Friendly

Kick back and relax in this calm, stylish space next door to Diamondhead Country Club - featuring two 18 hole golf courses! An easy walk or cart to the Clubhouse for dining & entertainment. Quiet condo complex with beautiful live oaks. Our recently built 2nd floor condo features 2 bedrooms with 2 bathrooms - both offering access from the bedroom. The great room features the living area, kitchen with breakfast bar, dining room and coffee/wet bar. WiFi & Smart TV’s. Well appointed and super cozy.

Guest suite in Bay St. Louis

4.98 out of 5 average rating, 174 reviews

Bamboo Room: King Guest Suite - Quiet Green Oasis

In WEST Bay St Louis! 5mi to beach & Silver Slipper Casino; 8mi to historic downtown; 23mi to Gulfport; 55mi to New Orleans. Newly renovated quiet comfy clean completely private king bedroom guest suite (YOUR OWN PRIVATE: entrance, bathroom, deck, large garden, A/C - no shared spaces/entrances) ATTACHED TO QUIET RESIDENTIAL HOUSE. Minutes to beaches, casinos, restaurants. Self check in. Sit outside on private deck & garden to read, lounge, work, listen to birds & frogs, or to stargaze at night.

Guesthouse in Bay St. Louis

4.96 out of 5 average rating, 412 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

Apartment in Bay St. Louis

5 out of 5 average rating, 250 reviews

Sweet Suite in the Bay

Enjoy your own private escape while still enjoying all the Bay has to offer. There's a lot going on in this artsy beach town, and the Sweet Suite in the Bay offers a place to relax, refresh & recharge as you get ready for more of the action! Don't be fooled by the name. You're getting more than just a 'suite'. You'll have a fully furnished detached open space with a bedroom, bathroom, kitchen and living room and a dedicated outdoor space to enjoy your morning coffee before hitting the town!

5 out of 5 average rating, 16 reviews

Sunshine Oaks - Pool & Golf!

***NEW VACATION RENTAL*** Beaches, casinos, golf courses, and much more are available when you visit the Mississippi Gulf Coast! At Sunshine Oaks you will be staying in a well-kept, artistically decorated one-bedroom, one-bathroom condo located in Diamondhead's Molokai Village. Newly renovated, at Sunshine Oaks you will find all the comforts of home and a central location. It is the perfect choice for a romantic getaway, golf trip, or vacation with the family. Book your stay today!

4.98 out of 5 average rating, 111 reviews

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, 151 reviews

Loft in Bay St. Louis

The Loft at the Cypress Cottage

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, 195 reviews

Guesthouse in Waveland

No one likes a Shady Beach

Quiet and Comfy in the Heart of Waveland/Bay St. Louis area. 1 bedroom and 1 bath 700 sq ft cottage that is as adorable as can be! Less than a mile to the beach where there is a beautiful new pier to fish from and beach volleyball. 8 minute drive to Old Bay Town. Wood floors, full service Kitchen with microwave/range/oven/refrigerator/dishwasher, gorgeous beams and unique shower! Step outside to the back yard and enjoy the peace and quiet and beautiful scenery. No Pier Pressure

4.83 out of 5 average rating, 6 reviews

Apartment in Diamondhead

18th Hole Hideaway - A Clean and Modern Condo

Escape to a serene getaway at the golf course. Our charming vacation rental offers a perfect blend of comfort and luxury, featuring access to a pristine pool, the country club, golf, tennis courts and more! Enjoy modern amenities, a fully equipped kitchen, and cozy living space designed for maximum relaxation. Sit on the balcony and enjoy your morning coffee or afternoon cocktail. Just minutes from the beach all local attractions. Pull out couch available for 2nd bed.

4.97 out of 5 average rating, 156 reviews

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.

4.87 out of 5 average rating, 175 reviews

“Fairway to Heaven” Condo on 12th hole with POOL!!

Fairway to Heaven is the perfect place for you and your family to enjoy a stay on the desirable MS Gulf Coast. You can step out on the back patio and enjoy your coffee and watch golf as our studio apartment sits on the 12th hole. There are two eighteen hole golf courses and a nearby pool just steps away to enjoy. Bring your appetite and enjoy dinner in or around Bay St. Louis. The beach is only a short drive away and New Orleans is less than one hour away.

4.98 out of 5 average rating, 373 reviews

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!

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Other great holiday rentals in Diamondhead

5 out of 5 average rating, 20 reviews

Home in Pass Christian

The Pearl Haven Cottage

KimberlyRating, 5 stars3 days ago

Paul’s little cottage was absolutely perfect for our weekend getaway. Everything was so clean and the beds are supper comfy. I loved that we were able to walk to get dinner both nights and had such a peaceful night when we returned.

Home in Diamondhead

5 out of 5 average rating, 3 reviews

Modern home on the 14th hole!

ThomasRating, 5 stars3 months ago

Good location. Very interesting modern house. Mark met us to let us in, gave us a tour, very friendly. Called him twice, he was helpful and courteous. We were two couples with plenty of room. We will be back next year (senior golf tournament) and will definitely request this unit again.

5 out of 5 average rating, 6 reviews

2BR updated dog-friendly condo with pool & tennis

SandraRating, 5 stars6 months ago

This was a very comfortable and well appointed condo. Everything we needed was there and more! The furnishings are beautiful, comfortable bedding and a great location for our needs. We will definitely book this condo for our next visit to Diamondhead.

5 out of 5 average rating, 44 reviews

Home in Kiln

Waterfront property! Private Boat Launch

MaryRating, 5 stars2 weeks ago

We cannot begin to tell you how wonderful Malarie was. She answered in a very timely manner and offered suggestions for whatever we asked for. She told us it was about 9 miles from the camp to the beach and that was very accurate. She also gave us suggestions on restaurants and we sent them one as well. The layout is amazing and it has a good atmosphere, with very comfortable furniture in every room. The kids had a great time fishing and crabbing, and every day they did not want to stop. There were more than enough games inside for the family to play together and both TVs worked very well giving us family movie night with no issue. They had enough supplies to get us through the first few days and plenty of dishes. The coffee pot was broken and when I told Malarie she immediately had one brought to us by way of DoorDash. She even included donuts for the kids and coffee. They do have several stairs to get into the camp, but it is well lit and they are in great condition. Highly recommend

4.99 out of 5 average rating, 82 reviews

Home in Bay St. Louis

Spencer's Way Beach House B with heated pool

JamesRating, 5 stars2 weeks ago

This is my second time at this place it is such a cool and relaxing spot. Pool area is fantastic for sitting and for cooking. The house is amazingly clean. She always responded promptly to any questions or comments. I will be returning again soon.

Tiny home in Bay St. Louis

4.9 out of 5 average rating, 31 reviews

Napoleon Complex

ChloeRating, 5 stars3 weeks ago

I really enjoyed my stay here! The place was very clean and super cute, just as pictured. While it’s a smaller space, the bed and shower were both surprisingly roomy and comfortable. Being so close to the beach was a major plus, and made the trip even better. The train nearby was definitely loud, but the listing mentioned it so we knew what to expect. Overall, a cozy and well-kept spot in a great location!

Townhouse in Diamondhead

4.86 out of 5 average rating, 80 reviews

Bogey Nights! Condo on golf course w/ pool

TiffanyRating, 5 stars4 months ago

I stayed here during a winter storm. So unfortunately everything around was closed so I didn’t get to enjoy the dining at the club house. Or even sitting on the back deck lol. But the pictures are 100% accurate. The place was cozy.. it’s on the 2nd floor. The stairs & railing seemed secure & safe. The bed is quite firm as some others have mentioned but I slept fine. Cute place! Meghan communicated great. Would stay again!