
Holiday rentals in Diamondhead
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Top-rated holiday rentals in Diamondhead
Guests agree: these stays are highly rated for location, cleanliness and more.

Gallery 101 Two blocks to the Beach
Gallery 101 is for travelers who are searching for a cozy, well- equipped home with a quirky style. The home is 2 blocks from the beach and a 15 minute walk to Long Beach shops and restaurants. The RR tracks are just north of the home and the train comes through during the day and usually twice each night. The rumbling of the train or the train whistle is something to consider before you reserve. However, if you stay anywhere in Long Beach, you will hear the train. Only 2 vehicles allowed.

Beach Getaway
Full studio (388 sf) near Keesler, across from the beach, restaurants, and shopping. There is a public bus stop on the corner & shuttles for the casinos. Wifi with small smart TV. Let yourself in with keyless entry then go for a swim, enjoy coast seafood, or join the excitement at a casino. Make yourself at home and feel safe with security lighting and no stairs. My place is good for couples and solo adventurers. No trailer parking allowed. Max. occupancy is 2: violation results in eviction.

Bamboo Room: King Guest Suite - Quiet Green Oasis
WEST Bay St Louis - 8mi TO DOWNTOWN! Quiet green rural alternative to major tourist areas. 5mi to beach & Silver Slipper Casino; 23mi to Gulfport; 55mi to New Orleans. Comfy clean king bedroom guest suite (YOUR OWN PRIVATE: entrance, bathroom, deck, large garden, A/C) ATTACHED TO QUIET RESIDENTIAL HOME. Host lives on property. Minutes to beaches, casinos, restaurants. Self check in. Sit outside on private deck & garden w/firepit to read, work, listen to birds & frogs, or to stargaze at night.

Waterfront w/ Boat Dock, Outdoor Kitchen, Hot Tub
Relax and unwind at Camp Who Dat! The house is perfect for entertaining with a screened porch upstairs, an outdoor kitchen downstairs, a boat dock, and hot tub. The house is a short drive to the gulf coast beaches and downtown and there is a boat launch nearby. The house has an open kitchen and living space with 2 bedrooms, 2 baths, washer/dryer, and high speed internet. The house has an outdoor lift for ADA (by request only). Bring your bikes, kayaks, jet skis, pontoon or bay boat!

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!

The Loft at Cypress Cottage – Steps from the Train
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.

Historic Cottage in Old Town Bay St Louis
This one-bedroom historic cottage in Old Town Bay St Louis named Leo's House is the ideal spot in the Bay. It is a peaceful retreat in the heart of Old Town Bay St Louis. The cottage is just steps from the best shopping, restaurants, and nightlife that Bay St Louis has to offer. Once you arrive at Leo's House, you have no reason to get back in your car. The cottage is short walking distance to the beach, Bay St Louis Municipal Harbor, and shops and restaurants. BSL028

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.

InstaWorthy~ Luxe King Bed~ Mins to Beach
Have the Gulfport vacation of your dreams in the spacious 3BR 2Bath oasis in the tranquil neighborhood. Spend the day soaking up the sun in the private backyard, or exploring nearby attractions. ✔ 3 Comfy Bedrooms ✔ Open Design Living ✔ Fully Equipped Kitchen ✔ Back Patio (Wide-Screen Projector) ✔ Backyard ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Free Parking See more below! WE DO NOT GUARANTEE THE HOT TUB! This was taken out of our list of amenities March, 2025.

Mermaids and Moonshine
Comfy cozy studio with lots of extras! Super comfortable bed! 15 minutes to the Beach! Close to Hancock County Fair Grounds, Stennis Space Center, Hancock Sports complex, Centrally located between Gulfport MS and Slidell LA. We are one hour from New Orleans. Come be our Guest! Enjoy the Pool, Barbecue, Fire pit and outdoor areas. This is a perfect spot if you are visiting family but want your own space!

"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!

King Suite. Sleeps 6. 2.5 Baths. No cleaning fee!
This stylish home is perfectly located just minutes from Old Town Bay St. Louis and 4 blocks from the ocean. Completely stocked with everything you need. Just pack a bag and come to the Bay! It’s awesome here! We have a fenced in private patio with a gas grill and fire pit. No cleaning fee. Pet friendly. Free parking for 4 vehicles!
Popular amenities for Diamondhead holiday rentals
Other great holiday rentals in Diamondhead

Southern Comfort

No Stairs! Next door to Golfing & near the beach!

Studio in lake setting close to pool and clubhouse

Bogey Nights! Condo on golf course w/ pool

Cute Cottage in the Country - Unit B

18th Hole Hideaway - A Clean and Modern Condo

Beautiful condo on Golf Course

Sunshine Oaks - Pool & Golf!
When is the best time to visit Diamondhead?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $144 SGD | $145 SGD | $148 SGD | $145 SGD | $125 SGD | $145 SGD | $157 SGD | $144 SGD | $140 SGD | $146 SGD | $129 SGD | $129 SGD |
| Avg. temp | 11°C | 13°C | 16°C | 20°C | 24°C | 27°C | 28°C | 28°C | 26°C | 21°C | 15°C | 12°C |
Frequently Asked Questions
Do house rentals in Diamondhead have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Diamondhead. Enjoy a tailored experience with all the comforts you desire.
Do condo rentals in Diamondhead have wifi?
Absolutely! We offer over 10 condo rentals with wifi in Diamondhead. Enjoy a tailored experience with all the comforts you desire.
Are there Diamondhead condo rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 condo rentals with pools in Diamondhead, available on Airbnb. Make a splash and soak up the sun in style!
Do house rentals in Diamondhead have a kitchen?
Absolutely! We offer over 10 house rentals with a kitchen in Diamondhead. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Diamondhead?
Diamondhead has more than 10 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in house rentals in Diamondhead?
Experience the best of Diamondhead with our house rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
What are the most popular amenities for Condo Rentals in Diamondhead?
Enhance your stay in our Condo Rentals with the most popular amenities: over 10 homes with a kitchen, over 10 homes with wifi, over 10 homes with free parking, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do condo rentals in Diamondhead have free parking?
Absolutely! We offer over 10 condo rentals with free parking in Diamondhead. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Diamondhead?
Four-legged friends are welcome in Diamondhead. Choose from more than 20 vacation rentals for guests traveling with pets.
Are there condo rentals with a dedicated workspace in Diamondhead?
Yes! Work meets play with ease at over 10 condo rentals in Diamondhead featuring dedicated workspaces. Stay connected and productive in your home away from home.
Quick stats about holiday rentals in Diamondhead

Total holiday rentals
Explore 50 holiday rentals in Diamondhead

Nightly prices starting at
Diamondhead holiday rentals start at $65 SGD per night before taxes and fees

Verified guest reviews
Over 1,300 verified reviews to help you choose

Family-friendly holiday rentals
30 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Holiday rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
50 of Diamondhead holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Diamondhead rentals

4.9 Average rating
Diamondhead stays are highly rated by guests – averaging 4.9 out of 5!
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