Holiday Homes in Diamondhead

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Find holiday rentals that suit your style

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Apartments
Apartments
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Cabins
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Check prices for these dates

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 Jan

Our top choices for Diamondhead holiday homes

A spacious dining area with a wooden table set for four, white chairs, and a chandelier.

1. 16th and Golden in Diamondhead

16th and Golden in Diamondhead
Diamondhead
9.8 out of 10, Exceptional, (19 reviews)
"Wonderful place to stay for our whole family. We enjoyed the accommodations and especially loved the country club."
United States
Mallory D.
16th and Golden in Diamondhead
A cozy living room with a wooden ceiling, a dark leather sofa, a coffee table, and a view through an open doorway to a bedroom.

2. Drackett House by Whiskey Properties

Drackett House by Whiskey Properties
2.5 star property
Old Town Bay St Louis
9.6 out of 10, Exceptional, (48 reviews)
"Comfy beds, quiet, lovely pool. My only complaint the cottage is a bit dingy, upholstery needs a good shampoo."
United States
JANA
The price is €97
includes taxes & fees
10 Nov - 11 Nov
Drackett House by Whiskey Properties
A spacious living area with a wooden dining table, a sofa, and a large rug.

3. Relaxing Waterfront Getaway with Fenced in Pet Friendly Property

Relaxing Waterfront Getaway with Fenced in Pet Friendly Property
Bay St Louis
10.0 out of 10, Exceptional, (179 reviews)
"Great dog friendly quaint stay "
United States
Claudia
The price is €332
includes taxes & fees
8 Nov - 9 Nov
Relaxing Waterfront Getaway with Fenced in Pet Friendly Property
A row of white single-story houses with a white picket fence, each with a small porch and a flag.

4. Old Town Beach Bungalow~ 2 blocks from Main St. and Beach Blvd.

Old Town Beach Bungalow~ 2 blocks from Main St. and Beach Blvd.
Bay St. Louis
10.0 out of 10, Exceptional, (30 reviews)
"Great little vacay"
United States
Austin S.
The price is €219
includes taxes & fees
8 Nov - 9 Nov
Old Town Beach Bungalow~ 2 blocks from Main St. and Beach Blvd.
A kitchen with white cabinets, a granite countertop, a stainless steel sink, a microwave, and a stove.

5. Peaceful and Cozy 3 Bedroom house on the water in Bay St Louis! Sleeps 6.

Peaceful and Cozy 3 Bedroom house on the water in Bay St Louis! Sleeps 6.
Bay St. Louis
10.0 out of 10, Exceptional, (4 reviews)
"Most peaceful house we have stayed in. Clean, homey, and exactly what we needed! Beds super comfy. Felt like being home!"
United States
Linnea R.
Peaceful and Cozy 3 Bedroom house on the water in Bay St Louis! Sleeps 6.
A two-story house with a covered patio, outdoor seating, and a landscaped garden.

6. Waterfront Outdoor Bar, Game Room, Fire pit, Grill, Fishing Bay St. Louis Home

Waterfront Outdoor Bar, Game Room, Fire pit, Grill, Fishing Bay St. Louis Home
Bay St. Louis
10.0 out of 10, Exceptional, (10 reviews)
"We really enjoyed our stay it was a nice peaceful place with friendly neighbors. We look forward to coming back."
United States
Lucien D.
The price is €300
includes taxes & fees
10 Nov - 11 Nov
Waterfront Outdoor Bar, Game Room, Fire pit, Grill, Fishing Bay St. Louis Home
A wooden building with a balcony and a staircase leading to the entrance.

7. J & S's Pond Da Rosa A Place Apart From The Rest

J & S's Pond Da Rosa A Place Apart From The Rest
Bay St. Louis
10.0 out of 10, Exceptional, (17 reviews)
"It was perfect! We will be booking this location every time we go to Bay St. Louis."
United States
Jason M.
J & S's Pond Da Rosa A Place Apart From The Rest
A kitchen with a central island, white cabinetry, and a 'Welcome' sign.

8. Home near white sand beaches and casinos

Home near white sand beaches and casinos
Bay St Louis
10.0 out of 10, Exceptional, (114 reviews)
"Perfect little rental for our couples trip! Great location for golf-carting to town. Paul made sure everything went smoothly, and we had everything we needed."
United States
Jahnele A.
The price is €199
includes taxes & fees
16 Nov - 17 Nov
Home near white sand beaches and casinos
A two-story wooden building with a balcony, surrounded by trees and a calm water body.

9. Charming 1-bedroom house with WiFi, AC on the Bayou in beautiful Bay St. Louis

Charming 1-bedroom house with WiFi, AC on the Bayou in beautiful Bay St. Louis
Bay St. Louis
10.0 out of 10, Exceptional, (5 reviews)
"What a great place to stay. The host was amazing. "
United States
Gabrielle S.
The price is €246
includes taxes & fees
9 Nov - 10 Nov
Charming 1-bedroom house with WiFi, AC on the Bayou in beautiful Bay St. Louis
A kitchen with a large island, a dining area, and large windows with a view.

10. Waterfront Oasis w/ Dock, Sleeps 12

Waterfront Oasis w/ Dock, Sleeps 12
Bay St. Louis
10.0 out of 10, Exceptional, (13 reviews)
"Great location and great place to stay!"
United States
John G.
Waterfront Oasis w/ Dock, Sleeps 12
A two-story house with a balcony, a covered porch, and a gravel driveway.

11. Hollywood House - Luxurious New Build With 6 Seat Golf Cart!

Hollywood House - Luxurious New Build With 6 Seat Golf Cart!
Bay St. Louis
10.0 out of 10, Exceptional, (13 reviews)
"Clean, quaint accommodations. Very comfortable and accommodating. Lots of little perks. "
United States
Shaun A.
The price is €433
includes taxes & fees
1 Dec - 2 Dec
Hollywood House - Luxurious New Build With 6 Seat Golf Cart!
A balcony with two blue stools and a view of a lake surrounded by trees.

12. Waterfront Beach & Lake House w/ BBQ, deck, & more

Waterfront Beach & Lake House w/ BBQ, deck, & more
Pass Christian
9.6 out of 10, Exceptional, (16 reviews)
"Great pricing and great place!"
United States
S. John P.
The price is €239
includes taxes & fees
8 Nov - 9 Nov
Waterfront Beach & Lake House w/ BBQ, deck, & more
A dining area with a large wooden table, multiple chairs, a chandelier, and artwork on the walls.

13. Old Town Central Station - A home with charm!

Old Town Central Station - A home with charm!
Bay St. Louis
8.4 out of 10, Very good, (33 reviews)
"Loved our stay"
United States
Sheri R.
The price is €218
includes taxes & fees
1 Dec - 2 Dec
Old Town Central Station - A home with charm!
A modern kitchen with white cabinetry, a stainless steel refrigerator, wooden stools, and a central island.

14. Took the Bayt in Bay St.Louis, MS

Took the Bayt in Bay St.Louis, MS
Bay St. Louis
10.0 out of 10, Exceptional, (17 reviews)
"Great location! Will be back!"
United States
Mallory A.
The price is €420
includes taxes & fees
8 Nov - 9 Nov
Took the Bayt in Bay St.Louis, MS
A beach scene with a pier extending into the water, a boat, and a small structure on the pier.

15. Pet Friendly Home · 1.5 Private Acres · Fireplace

Pet Friendly Home · 1.5 Private Acres · Fireplace
Gulfport
9.2 out of 10, Wonderful, (5 reviews)
"Was a great place to stay. Will remember it next time we need a place to stay in Gulfport."
United States
Jeremy F.
The price is €267
includes taxes & fees
8 Nov - 9 Nov
Pet Friendly Home · 1.5 Private Acres · Fireplace
A wooden deck with a staircase leading to a covered area.

16. Isle Be Back - Pet Friendly Waterfront Camp 3Br 1.5Ba

Isle Be Back - Pet Friendly Waterfront Camp 3Br 1.5Ba
Bay St. Louis
10.0 out of 10, Exceptional, (10 reviews)
"We had a great time for the 4th of July weekend. Great location."
United States
Blaine E.
The price is €364
includes taxes & fees
8 Nov - 9 Nov
Isle Be Back - Pet Friendly Waterfront Camp 3Br 1.5Ba
A two-story house with a wooden deck, a hot tub, outdoor seating, and a pool.

17. Bay St. Louis Pool, Hot Tub, Ping Pong, Fire Pit, and Grill Waterfront Home

Bay St. Louis Pool, Hot Tub, Ping Pong, Fire Pit, and Grill Waterfront Home
Bay St. Louis
9.6 out of 10, Exceptional, (5 reviews)
"Perfect spot for a small get together for some catching up with friends."
United States
NormaMoss DarrenSr B.
Bay St. Louis Pool, Hot Tub, Ping Pong, Fire Pit, and Grill Waterfront Home
A modern kitchen with white cabinetry, a central island with stools, stainless steel appliances, and pendant lighting.

18. Waterfront Escape in Bay STL with dock,pickleball, ping pong, basketball & more!

Waterfront Escape in Bay STL with dock,pickleball, ping pong, basketball & more!
Bay St. Louis
10.0 out of 10, Exceptional, (15 reviews)
"My Family and I enjoyed our stay! The House was clean and great location. "
United States
Jessica T.
The price is €341
includes taxes & fees
9 Nov - 10 Nov
Waterfront Escape in Bay STL with dock,pickleball, ping pong, basketball & more!
A two-story house with a covered porch and a staircase leading to the upper level.

19. Peggy Sue

Peggy Sue
Pass Christian
10.0 out of 10, Exceptional, (63 reviews)
"Was a very ice rental"
United States
David W.
The price is €218
includes taxes & fees
11 Nov - 12 Nov
Peggy Sue
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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