Diamondhead Vacation Rentals

Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

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.
$185 nightly
The price is $201
Nov 16 - Nov 17
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.
$241 nightly
The price is $263
Nov 9 - Nov 10
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, (4 reviews)
"Clean, great communication and a perfect location if you’re golfing in Diamondhead!"
United States
Mackenzie L.
$271 nightly
The price is $295
Nov 16 - Nov 17
Total with taxes and fees
Upstairs Luxe Style Condo at Diamondhead Country Club - Walk to the Clubhouse
A spacious dining area with a wooden table set for four, white chairs, and a chandelier.

4. 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.
$395 nightly
The price is $412
Nov 9 - Nov 10
Total with taxes and fees
16th and Golden in Diamondhead
A courtyard with palm trees and string lights, surrounded by a building with a covered patio area.

5. Pass Bungalows

Pass Bungalows
4.5 star property
Pass Christian
9.8 out of 10, Exceptional, (58 reviews)
"Would definitely recommend I Enjoyed my stay!"
United States
Matha
$171 nightly
The price is $191
Nov 9 - Nov 10
Total with taxes and fees
Pass Bungalows
A spacious room with a wooden floor, a spiral staircase, and a dining area with a chandelier.

6. Carroll House Cottages

Carroll House Cottages
3.0 star property
Bay St Louis
9.4 out of 10, Exceptional, (331 reviews)
"The property was clean, quaint and conveniently located near everything. We will be returning in the future."
United States
Carla
$189 nightly
The price is $206
Nov 12 - Nov 13
Total with taxes and fees
Carroll House Cottages
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, (48 reviews)
"Comfy beds, quiet, lovely pool. My only complaint the cottage is a bit dingy, upholstery needs a good shampoo."
United States
JANA
$92 nightly
The price is $100
Nov 10 - Nov 11
Total with taxes and fees
Drackett House by Whiskey Properties
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.

8. 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, (136 reviews)
"Lovely little cottage. Very convenient and very comfortable."
United States
Lisa
$184 nightly
The price is $201
Nov 29 - Nov 30
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.

9. 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, (92 reviews)
"The property is pet friendly as well"
United States
Cary B.
$216 nightly
The price is $235
Nov 12 - Nov 13
Total with taxes and fees
Quaint Cottage, Walk to Beach and Old Town Bay St. Louis
A beach house interior with a kitchen, dining area, and a view of the beach.

10. 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, (69 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.
$200 nightly
The price is $218
Nov 9 - Nov 10
Total with taxes and fees
BAY-CAY Getaway, Beaching, Casinos, Swim, Grill, Chill, Memories!
A cozy living room with a sofa, a television, and a dining area with a table and chairs.

11. Walk to Gulfport Beach! Coastal Studio Getaway

Walk to Gulfport Beach! Coastal Studio Getaway
3.0 star property
Gulfport
$230 nightly
The price is $257
Nov 9 - Nov 10
Total with taxes and fees
Walk to Gulfport Beach! Coastal Studio Getaway
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.
$243 nightly
The price is $267
Nov 9 - Nov 10
Total with taxes and fees
Waterfront Beach & Lake House w/ BBQ, deck, & more
A row of white single-story houses with a white picket fence, each with a small porch and a flag.

13. 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.
$216 nightly
The price is $235
Nov 9 - Nov 10
Total with taxes and fees
Old Town Beach Bungalow~ 2 blocks from Main St. and Beach Blvd.
A bedroom with a bed, a ceiling fan, and a window with curtains.

14. Beautiful studio close to the beach!

Beautiful studio close to the beach!
Gulfport
9.2 out of 10, Wonderful, (52 reviews)
"As always, everything was amazing! The apartment is always spotless and the hosts are always super responsive and accommodating!"
United States
Kelsie H.
$131 nightly
The price is $144
Nov 9 - Nov 10
Total with taxes and fees
Beautiful studio close to the beach!
A two-story house with a covered porch and a small balcony.

15. The Pass Picture Book

The Pass Picture Book
3.0 star property
Pass Christian
10.0 out of 10, Exceptional, (1 review)
$138 nightly
The price is $154
Dec 9 - Dec 10
Total with taxes and fees
The Pass Picture Book
A spacious living area with a wooden dining table, a sofa, and a large rug.

16. 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
$326 nightly
The price is $355
Nov 13 - Nov 14
Total with taxes and fees
Relaxing Waterfront Getaway with Fenced in Pet Friendly Property
A kitchen with a central island, white cabinetry, and a 'Welcome' sign.

17. 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.
$194 nightly
The price is $211
Nov 16 - Nov 17
Total with taxes and fees
Home near white sand beaches and casinos
A dining area with a large wooden table, multiple chairs, a chandelier, and artwork on the walls.

18. 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.
$205 nightly
The price is $224
Nov 16 - Nov 17
Total with taxes and fees
Old Town Central Station - A home with charm!
A two-story wooden structure with a balcony, outdoor seating, and a covered area.

19. New cottage blocks from the beach; pets OK! Firepit! Grill! EV Charger! 65” TV

New cottage blocks from the beach; pets OK! Firepit! Grill! EV Charger! 65” TV
Waveland
10.0 out of 10, Exceptional, (13 reviews)
"Excellent amenities and location. We had a great time and would stay again."
United States
Alex L.
$253 nightly
The price is $276
Nov 17 - Nov 18
Total with taxes and fees
New cottage blocks from the beach; pets OK! Firepit! Grill! EV Charger! 65” TV
A modern kitchen with a central island, bar stools, and a hanging light fixture.

20. Coastal 1BR with Pool - Near Beach

Coastal 1BR with Pool - Near Beach
Pass Christian
10.0 out of 10, Exceptional, (18 reviews)
"Perfect little getaway"
United States
Jenny S.
$219 nightly
The price is $228
Nov 9 - Nov 10
Total with taxes and fees
Coastal 1BR with Pool - Near Beach
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

An indoor swimming pool with lounge chairs and tables, surrounded by wooden pillars and red lockers.
Ramada by Wyndham Diamondhead I-10/Gulfport

Ramada by Wyndham Diamondhead I-10/Gulfport

Ramada by Wyndham Diamondhead I-10/Gulfport
Diamondhead

10/10 Excellent

Great location.
United States
Jackie
Reviewed May 29, 2025
Ramada by Wyndham Diamondhead I-10/Gulfport

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 $100 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.

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.

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