
Holiday rentals with a pool in Diamondhead
Find and book unique homes with a pool on Airbnb
Quick stats about holiday rentals with a pool in Diamondhead

Total holiday rentals
Explore 20 holiday rentals in Diamondhead

Nightly prices starting at
Diamondhead holiday rentals start at $89 SGD per night before taxes and fees

Verified guest reviews
Over 700 verified reviews to help you choose

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

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 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!
Top-rated rentals with a pool in Diamondhead
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

Beautiful Long Beach Condo with Ocean View+Pool!
Pristine condo right on Beach Blvd. Grab your flip flops and walk across the street to the beach and enjoy the beautiful sunsets. Stainless steel appliances, granite counter tops, and Flat Screens in each room. Our condo has a beautiful beach view from 2nd story balcony. Long Beach is the hidden gem of the Mississippi Gulf Coast. Hop in the car and visit the sights in Gulfport, Biloxi, Ocean Springs, Pass Christian, and Bay St Louis. All are filled with great shops, restaurants, and museums.

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.

*Pelican Pass* Golf/Fish/Swim / Incredible water v
Located in prestigious timber ridge community this water front home has it all! A community that features the Pass Christian Isle golf course, a swimming pool, and a large boat launch. Pelican Pass is a 3 bedroom 3 full bathroom home on the canal featuring its own private boat launch/lift and a bonus game room. Enjoy panoramic water views from our spacious deck or from most rooms in the house with fishing right from the on site dock. Each room in the house features brand new smart tvs and

Pool, Hot Tub, Game Area, Waterfront Bay St. Louis
Relax in this spacious home in Bay St. Louis and enjoy the private pool and hot tub. This home is located on a quiet dead end road and features plenty of space to spread out, relax, and entertain. There is plenty of outdoor seating to enjoy while watching the kids play in the pool, fish from the back yard, or enjoy the fire pit. Cook on the grill and enjoy amenities like the bicycles, beanbag toss, ping pong, beach toys and more. This home is perfect for your next getaway so don't wait.

Main St BSL: Private Pool & Golf Cart | Sleeps 10
****Now with private heated pool added May 2023**** Welcome to Hidden Paradise on the Bay, a 3 bedroom 2 1/2 bath curated cottage on Main Street in the heart of old town Bay Saint Louis, MS. 2 blocks from the marina and steps away from shopping and restaurants. Take the complimentary golf cart to the beach or for coffee and antiquing, take in a parade or cruising the coast right from the front porch swing. This family friendly home has a private pool and fire pit area for entertaining!

Shell House Estate Bungalow
We are located on the Gulf of Mexico. A private beach is out your front door along with Fishing and Sailing. We are also a short distance from Casinos, as well as many family-friendly activities. This is a three acre 170 year old private estate property with 500 year old registered live oak trees. The Bungalow also has a covered parking space. THE POOL HOUSE sleeps 6 two in one room and 4 in the other room. BUNGALOW sleeps 4 two in one room and 2 in the other room. See photos.

Golfer's Getaway! Modern Diamondhead Condo
Lanai Village Community | In-Unit Laundry | Casinos & Dining Nearby | Private Deck Secure your slice of Gulf Coast living at this Diamondhead vacation rental. Spend the afternoons lounging by the community pool and the evenings exploring the vibrant shops and bars of nearby Bay St. Louis. This contemporary condo offers a crisp, airy layout designed for slow mornings and relaxing sunset drinks as the palms sway. Don't let the weekend pass you by — book your Lanai Village retreat now!

Spencer's Way Beach House B with heated pool
Come and relax with the family at our newly constructed beach themed home. Blocks away from the center of Bay St. Louis and the beach. The Bay has a small city Key West vibe, with boutiques, antique shops, great restaurants with live music. Beautiful new HEATED saltwater pool with cabana, barbecue area, refrigerator and sink, bar with TV, blue tooth speakers for your enjoyment. We invite you to stay at our cozy place and have a good time. Pool is shared with both units.

Beach Bungalow - Private Pool+Walk to Town & Beach
Uniquely sophisticated and charmingly luxurious beach house with a private saltwater pool in Bay St. Louis' Historic District. Experience all that Bay St. Louis has to offer from this cozy, beautifully appointed bungalow located 1/2 a block from the beach and walkable to a vibrant downtown. Located about a 30 minute drive to Stennis Space Center and less than an hour drive to New Orleans. Across the Bay Bridge, discover neighboring towns of Mississippi’s “Secret Coast".

Private Pool, One minute to Beaches!
Experience the charm of Old Town Bay St. Louis, just a short 5 minutes away! Indulge in the delights of local restaurants, boutique shopping, thrilling fishing adventures, and so much more! Indulge in our fully equipped kitchen, lounge by the pool, and BBQ in your private oasis. Rest soundly in our cozy beds. Book now for the ultimate getaway! Don't miss out on this unforgettable experience! Book now and secure your slice of paradise! Your dream getaway awaits.

Heated Pool! Petite Retreat in The Pass
The Petite Retreat in The Pass A Serene, Sublime, Self-Contained Vacation Rental The Petite Retreat in The Pass in Pass Christian, Mississippi offers upscale lodging with a heated pool and a full array of amenities to keep the whole family happy without ever leaving the property! Wake up to stunning sunrises over the golf course to the east and enjoy striking sunsets over the bayou to the west. Nature's bounty surrounds this magical home.

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!
Popular amenities for Diamondhead rentals with a pool
House rentals with a pool

Southern Charm-Beach Front BSL with Saltwater Pool

Coastal Oasis - Heated Pool, Walk to Beach!

Waterfront Comfort With Pool - Sleeps 8!

Family Home "Lone Star Cabana" Shared Pool!

The View | Waterfront • Pool • Paradise •Golf Cart

Henley House - Enjoy Pool, Old Town or Beach

The Boat House Bay St. Louis

Waterfront Escape w/ Pool, Dock & Bayou Views
Apartment rentals with a pool

Blue Heaven Condo on the Beach!

Gorgeous Oceanview 3BR Luxury Condo - "Latitude"

Contemporary Biloxi Condo for 2 - Oak Shores

Beautiful Views Biloxi Beach Condo

The Ritz

Beautiful Biloxi Getaway Beach Condo!

Gulf Coast Retreat-Short/Long term VA welcome

Biloxi Beach Condo @ 2046 Beach Blvd, Biloxi
Other holiday rentals with a pool

"116 On the Green"

Lacey's Coastal Cabana - Charming & Quiet Condo

Diamond on the Gulf

Beautiful condo on Golf Course

Vibez on the Lanai at Diamondhead

1BR/1BA w/POOL & Golf - Sunshine Oaks

Waveland Beach Cottage 213

The Abode - A Guest House with Tropical Pool
When is the best time to visit Diamondhead?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $113 SGD | $119 SGD | $114 SGD | $123 SGD | $129 SGD | $137 SGD | $121 SGD | $107 SGD | $109 SGD | $145 SGD | $124 SGD | $123 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 |
Destinations to explore
- New Orleans Holiday rentals
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- Destin Holiday rentals
- Gulf Shores Holiday rentals
- Orange Beach Holiday rentals
- Birmingham Holiday rentals
- Pensacola Holiday rentals
- Columbus Holiday rentals
- Baton Rouge Holiday rentals
- Fort Walton Beach Holiday rentals
- Santa Rosa Island Holiday rentals
- Mobile Holiday rentals
- Biloxi Beach
- Fontainebleau State Park
- Mississippi Coast Coliseum & Convention Center
- Ocean Springs Beach
- Ship Island
- Lakefront Arena
- Mississippi Aquarium
- Ship Island Excursions
- Gulf Islands Waterpark
- Shaggy's Biloxi Beach
- English Turn Golf & Country Club
- Jones Park
- Big Play Entertainment Center
- Hollywood Casino
- Hard Rock Casino
- Buccaneer State Park
- Biloxi Lighthouse
- Golden Nugget Casino Presidential Suite
- Finishline Performance Karting
- Infinity Science Center
- De Soto National Forest





