A tree sculpture with multiple branches and figures on it, set against a sunset sky with clouds and the ocean in the background.

Diamondhead Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Diamondhead vacation rentals

1. 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.
The price is CA $126
CA $405 total
includes taxes & fees
Oct 19 - Oct 20
Relax & Golf - Oakview Condo II at Diamondhead - cozy, new. Walk to the Club

2. 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.
The price is CA $120
CA $324 total
includes taxes & fees
Oct 13 - Oct 14
Cozy 1-bedroom condo in lovely Diamondhead with AC

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.
The price is CA $167
CA $439 total
includes taxes & fees
Oct 15 - Oct 16
Upstairs Luxe Style Condo at Diamondhead Country Club - Walk to the Clubhouse

4. Cozy 1st Floor Condo /w Full Washer/Dryer - Lacey's Coastal Cabana

Cozy 1st Floor Condo /w Full Washer/Dryer - Lacey's Coastal Cabana
Diamondhead
10.0 out of 10, Exceptional, (14 reviews)
"Perfect spot"
United States
Jennifer H.
The price is CA $291
CA $359 total
includes taxes & fees
Oct 4 - Oct 5
Cozy 1st Floor Condo /w Full Washer/Dryer - Lacey's Coastal Cabana

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

Monthly Discount! Near the Golf Course - Diamondhead Country Club at 228Vacay
Diamondhead
The price is CA $192
CA $497 total
includes taxes & fees
Oct 18 - Oct 19
Monthly Discount! Near the Golf Course - Diamondhead Country Club at 228Vacay

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.
The price is CA $355
CA $665 total
includes taxes & fees
Oct 2 - Oct 3
Another Adventure awaits your Arrival. Charming 2 Bed / 2 Bath with Hangar!

7. Pass Bungalows

Pass Bungalows
4.5 star property
Pass Christian
9.8 out of 10, Exceptional, (47 reviews)
"Beautiful"
United States
Theresa
The price is CA $146
CA $283 total
includes taxes & fees
Oct 13 - Oct 14
Pass Bungalows

8. Drackett House by Whiskey Properties

Drackett House by Whiskey Properties
2.5 star property
Old Town Bay St Louis
9.4 out of 10, Exceptional, (43 reviews)
"Good for a quick stay "
United States
CINDY
The price is CA $114
CA $142 total
includes taxes & fees
Nov 1 - Nov 2
Drackett House by Whiskey Properties

9. 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
The price is CA $96
CA $293 total
includes taxes & fees
Oct 4 - Oct 5
Cozy 2-bedroom cottage near Bay Saint Louis Harbor

10. 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
The price is CA $138
CA $298 total
includes taxes & fees
Oct 15 - Oct 16
Carroll House Cottages

11. Pool & Spa Complete! Luxury Quiet Retreat, Bay Views.

Pool & Spa Complete! Luxury Quiet Retreat, Bay Views.
Bay St. Louis
10.0 out of 10, Exceptional, (29 reviews)
"This place is awesome, great for a guys golf trip! Blake took great care of us and was responsive to a couple small issues that came up. Highly recommend!"
United States
Scotty M.
The price is CA $702
CA $1,671 total
includes taxes & fees
Oct 21 - Oct 22
Pool & Spa Complete! Luxury Quiet Retreat, Bay Views.

12. Bream Street retreat. New home in BSL on the water with boat launch. Sleeps 10.

Bream Street retreat. New home in BSL on the water with boat launch. Sleeps 10.
Bay St. Louis
10.0 out of 10, Exceptional, (19 reviews)
"Great relaxing place."
United States
Betty M.
The price is CA $255
CA $602 total
includes taxes & fees
Oct 15 - Oct 16
Bream Street retreat. New home in BSL on the water with boat launch. Sleeps 10.

13. 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)
"We wanted peace and quiet with quick access to local activities and downtown and that’s what we gotGreat value and nice accomodations. "
United States
Patrick B.
The price is CA $248
CA $569 total
includes taxes & fees
Oct 12 - Oct 13
J & S's Pond Da Rosa A Place Apart From The Rest

14. 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.
The price is CA $234
CA $524 total
includes taxes & fees
Oct 2 - Oct 3
Relaxing Waterfront Getaway with Fenced in Pet Friendly Property

15. My Bay Cottage Beach House

My Bay Cottage Beach House
Bay St. Louis
10.0 out of 10, Exceptional, (12 reviews)
"Cozy clean cottage, love how it is decorated. Great location, responsive property manager. Enjoyed our stay!"
United States
Anonymous traveller
The price is CA $220
CA $439 total
includes taxes & fees
Oct 13 - Oct 14
My Bay Cottage Beach House

16. 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, (12 reviews)
"Clean, quaint accommodations. Very comfortable and accommodating. Lots of little perks. "
United States
Shaun A.
The price is CA $362
CA $726 total
includes taxes & fees
Oct 13 - Oct 14
Hollywood House - Luxurious New Build With 6 Seat Golf Cart!

17. 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 CA $310
CA $695 total
includes taxes & fees
Oct 26 - Oct 27
Took the Bayt in Bay St.Louis, MS

18. Creole Bungalow - 2 Bedroom 2 Bath with golf cart

Creole Bungalow - 2 Bedroom 2 Bath with golf cart
Bay St. Louis
10.0 out of 10, Exceptional, (32 reviews)
"Loved this place, will definitely stay again!"
United States
Thomas W.
The price is CA $319
CA $689 total
includes taxes & fees
Oct 13 - Oct 14
Creole Bungalow - 2 Bedroom 2 Bath with golf cart

19. The Pass Picture Book

The Pass Picture Book
3.0 star property
Pass Christian
10.0 out of 10, Exceptional, (1 review)
The price is CA $264
CA $295 total
includes taxes & fees
Oct 2 - Oct 3
The Pass Picture Book

20. PRIVATE POOL, BACKYARD OASIS, CLOSE TO BEACHES!!

PRIVATE POOL, BACKYARD OASIS, CLOSE TO BEACHES!!
Bay St Louis
10.0 out of 10, Exceptional, (113 reviews)
"Everything that was listed was there!! Great place to stay and would stay there again. Very comfortable space for our whole family of six to stay. Can’t wait to return!!"
United States
Sarah F.
The price is CA $211
CA $617 total
includes taxes & fees
Oct 25 - Oct 26
PRIVATE POOL, BACKYARD OASIS, CLOSE TO BEACHES!!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Diamondhead Hotel Reviews

Find out more about Diamondhead

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Diamondhead. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.