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Diamondhead Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Diamondhead vacation rentals

A corridor leading to a dining area with a view of a green lawn and parked cars.

1. Cozy 1-bedroom condo in lovely Diamondhead with AC

Cozy 1-bedroom condo in lovely Diamondhead with AC
Diamondhead
10.0 out of 10, Exceptional, (3 reviews)
"Clean and cute"
United States
Southern S.
$203 nightly
The price is $222
Oct 20 - Oct 21
Total with taxes and fees
Cozy 1-bedroom condo in lovely Diamondhead with AC
A kitchen with white cabinets, a coffee maker, and a framed pineapple picture.

2. Relax & Golf - Oakview Condo II at Diamondhead - cozy, new. Walk to the Club

Relax & Golf - Oakview Condo II at Diamondhead - cozy, new. Walk to the Club
Diamondhead
10.0 out of 10, Exceptional, (3 reviews)
"Clean house. Good location. Cheaper than the hotel we originally planned to stay at. I will book again soon and you should too"
United States
Donald W.
$260 nightly
The price is $284
Oct 19 - Oct 20
Total with taxes and fees
Relax & Golf - Oakview Condo II at Diamondhead - cozy, new. Walk to the Club
A modern kitchen with stainless steel appliances, a large island with bar stools, and a dining area with a view of the outdoors.

3. Upstairs Luxe Style Condo at Diamondhead Country Club - Walk to the Clubhouse

Upstairs Luxe Style Condo at Diamondhead Country Club - Walk to the Clubhouse
Diamondhead
10.0 out of 10, Exceptional, (3 reviews)
"Clean, great communication and a perfect location if you’re golfing in Diamondhead!"
United States
Mackenzie L.
$276 nightly
The price is $300
Oct 18 - Oct 19
Total with taxes and fees
Upstairs Luxe Style Condo at Diamondhead Country Club - Walk to the Clubhouse
A modern kitchen with a central island, stainless steel appliances, and a dining area with a red chair.

4. Monthly Discount! Near the Golf Course - Diamondhead Country Club at 228Vacay

Monthly Discount! Near the Golf Course - Diamondhead Country Club at 228Vacay
Diamondhead
$304 nightly
The price is $331
Oct 18 - Oct 19
Total with taxes and fees
Monthly Discount! Near the Golf Course - Diamondhead Country Club at 228Vacay
A spacious dining area with a wooden table set for four, white chairs, and a chandelier.

5. 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.
$426 nightly
The price is $445
Oct 12 - Oct 13
Total with taxes and fees
16th and Golden in Diamondhead
A spacious living room with a brown leather sofa, a round wooden dining table with six chairs, and a large window with blinds.

6. Another Adventure awaits your Arrival. Charming 2 Bed / 2 Bath with Hangar!

Another Adventure awaits your Arrival. Charming 2 Bed / 2 Bath with Hangar!
Diamondhead
10.0 out of 10, Exceptional, (1 review)
"Great host!"
United States
Ben G.
$432 nightly
The price is $471
Oct 13 - Oct 14
Total with taxes and fees
Another Adventure awaits your Arrival. Charming 2 Bed / 2 Bath with Hangar!
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.

7. 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, (44 reviews)
"Good for a quick stay "
United States
CINDY
$90 nightly
The price is $98
Nov 2 - Nov 3
Total with taxes and fees
Drackett House by Whiskey Properties
A spacious living room with hardwood floors, a brown leather sofa, a recliner, and a spiral staircase.

8. Carroll House Cottages

Carroll House Cottages
3.0 star property
Bay St Louis
9.0 out of 10, Wonderful, (330 reviews)
"The property was clean, quaint and conveniently located near everything. We will be returning in the future."
United States
Carla
$190 nightly
The price is $207
Oct 14 - Oct 15
Total with taxes and fees
Carroll House Cottages
A courtyard with palm trees and string lights, surrounded by a building with a covered patio area.

9. Pass Bungalows

Pass Bungalows
4.5 star property
Pass Christian
10.0 out of 10, Exceptional, (51 reviews)
"The atmosphere was very great. The bungalows were very nice and clean. Only complaint was the pool closing at dark."
United States
Sean
$185 nightly
The price is $207
Oct 13 - Oct 14
Total with taxes and fees
Pass Bungalows
A dining area with a round wooden table, white chairs, and a vase of flowers. There is a white sofa and a small white table with a lamp. The room has wooden flooring, white walls, and a ceiling with recessed lighting.

10. Cozy 2-bedroom cottage near Bay Saint Louis Harbor

Cozy 2-bedroom cottage near Bay Saint Louis Harbor
Bay St. Louis
10.0 out of 10, Exceptional, (132 reviews)
"Lovely little cottage. Very convenient and very comfortable."
United States
Lisa
$191 nightly
The price is $208
Oct 18 - Oct 19
Total with taxes and fees
Cozy 2-bedroom cottage near Bay Saint Louis Harbor
A house with a porch, steps, and a small garden area with plants and a potted plant.

11. Quaint Cottage, Walk to Beach and Old Town Bay St. Louis

Quaint Cottage, Walk to Beach and Old Town Bay St. Louis
Bay St Louis
9.8 out of 10, Exceptional, (90 reviews)
"Precious cottage in a wonderful location close to all Old Town BSL has to offer! The host was lovely and helpful. We’ll be back!"
United States
Nanette S.
$221 nightly
The price is $241
Oct 14 - Oct 15
Total with taxes and fees
Quaint Cottage, Walk to Beach and Old Town Bay St. Louis
A kitchen with a central island, white cabinetry, and a 'Welcome' sign.

12. 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.
$197 nightly
The price is $215
Oct 12 - Oct 13
Total with taxes and fees
Home near white sand beaches and casinos
A beach house interior with a kitchen, dining area, and a view of the beach.

13. BAY-CAY Getaway, Beaching, Casinos, Swim, Grill, Chill, Memories!

BAY-CAY Getaway, Beaching, Casinos, Swim, Grill, Chill, Memories!
Bay St. Louis
9.8 out of 10, Exceptional, (67 reviews)
"Great place to stay! Convenient to restaurants, buccaneer park, silver slipper casino and much much more! Beautiful view and accommodations!"
United States
lisa c.
$210 nightly
The price is $229
Oct 12 - Oct 13
Total with taxes and fees
BAY-CAY Getaway, Beaching, Casinos, Swim, Grill, Chill, Memories!
A wooden building with a balcony and a staircase leading to the entrance.

14. 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, (16 reviews)
"It was perfect! We will be booking this location every time we go to Bay St. Louis."
United States
Jason M.
$369 nightly
The price is $402
Oct 12 - Oct 13
Total with taxes and fees
J & S's Pond Da Rosa A Place Apart From The Rest
A view through a window with a wooden frame, overlooking a grassy area with trees and a body of water.

15. 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, (178 reviews)
"Fantastic place for peace, quiet and tranquility - enjoyed the views from the back - Kim is a fantastic host - 2nd to none ! Will definitely come back !"
United States
Marle D.
$333 nightly
The price is $363
Nov 1 - Nov 2
Total with taxes and fees
Relaxing Waterfront Getaway with Fenced in Pet Friendly Property
A two-story house with a covered porch and a small balcony.

16. The Pass Picture Book

The Pass Picture Book
3.0 star property
Pass Christian
10.0 out of 10, Exceptional, (1 review)
$158 nightly
The price is $177
Oct 12 - Oct 13
Total with taxes and fees
The Pass Picture Book
A spacious living room with a neutral color palette, a chandelier, a television, and a kitchen in the background.

17. Beauty and The Bay

Beauty and The Bay
Bay St. Louis
9.4 out of 10, Exceptional, (22 reviews)
"Great place to stay"
United States
Ronnie G.
$254 nightly
The price is $277
Oct 30 - Oct 31
Total with taxes and fees
Beauty and The Bay
A row of white single-story houses with a white picket fence, each with a small porch and a flag.

18. 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.
$223 nightly
The price is $243
Nov 8 - Nov 9
Total with taxes and fees
Old Town Beach Bungalow~ 2 blocks from Main St. and Beach Blvd.
A kitchen with a large island, a dining area, and large windows with a view.

19. 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.
$484 nightly
The price is $528
Oct 12 - Oct 13
Total with taxes and fees
Waterfront Oasis w/ Dock, Sleeps 12
A kitchen with white cabinets, a wooden island, a sink, and a window with plants.

20. My Bay Cottage Beach House

My Bay Cottage Beach House
Bay St. Louis
10.0 out of 10, Exceptional, (12 reviews)
"Perfect location."
United States
Kidd T.
$284 nightly
The price is $310
Oct 12 - Oct 13
Total with taxes and fees
My Bay Cottage Beach House
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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Top Diamondhead Hotel Reviews

Hollywood Casino Gulf Coast

Hollywood Casino Gulf Coast

10/10 Excellent
"Room was clean and the staff was very helpful and friendly."
Norman 5-night trip
Posted 16 hours ago
Hollywood Casino Gulf Coast

Find out more about Diamondhead

Everything you need to know about Diamondhead vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Diamondhead vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Diamondhead vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Diamondhead vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Diamondhead. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Diamondhead in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $98 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Diamondhead rentals

At Expedia, we put the best Diamondhead vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Diamondhead rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Diamondhead vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Diamondhead. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Diamondhead?

Yes, you can find vacation rentals near popular attractions in Diamondhead, or you can select a more secluded option if you'd like a relaxing place to stay. Diamondhead is known for its casinos and seafood restaurants. Make sure you have time to check out the golf courses and coffeehouses during your trip.

What's the top vacation rental in Diamondhead?

Drackett House by Whiskey Properties: This vacation home rental near Diamondhead is located in the historical district and has an outdoor pool, a terrace, and free WiFi to put you at ease in your new surroundings. This vacation rental also comes with free parking to give you added peace of mind. You can relax into your vacation with a private yard and a hot tub.

How many vacation rentals are there in Diamondhead?

Choose from 17 Expedia vacation rentals in Diamondhead for a memorable vacation.

What’s there to see and do in Diamondhead?

Enjoy the area's cultural attractions such as Thou Art Gallery & GIfts, or get outdoors into nature at a spot like Gulfport SportsPlex. In the larger area, you’ll find Diamondhead Country Club and Hollywood Casino.

What’s a vacation rental in Diamondhead like?

A vacation rental is a private property where you can stay for several days or longer in Diamondhead. Vacation rentals provide amenities such as kitchens and laundry facilities so you'll have a home away from home. If you're concerned about cleanliness, a vacation rental can offer a sense of privacy away from shared hotel elevators and busy front desks while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great choice for family trips.