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

Total vacation rentals
Explore 20 vacation rentals in Diamondhead

Nightly prices starting at
Diamondhead vacation rentals start at $97 CAD per night before taxes and fees

Verified guest reviews
Over 700 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space and kid-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of Diamondhead vacation 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.

Robin’s Nest A Golfers Delight
Welcome to Robin’s Nest located in Molokai Vlg, Diamondhead MS. Golf course, & country club walking distance away. Updated, 1 bdrm condo located on the second floor.Adjustable, queen size bed, guests say is the very “best” and a queen sofa sleeper. 3-4 guests total. Full kitchen,bath with soaking tub. Pool is gorgeous & steps away. Green space, historic oak trees and lots of deer, birds and nature to enjoy! Casinos & Beaches approx 12 min NOLA approx 45 min If shows not avail for a date, msg us

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.

Family Home "Lone Star Cabana" Shared Pool!
Welcome to the Lone Star Cabana—your cheerful coastal escape! Thoughtfully designed to offer tranquility and comfort, this one-of-a-kind retreat is part of the charming Once Upon a Tide Villas, featuring five individual units. Inside, you'll find cozy accommodations perfect for unwinding after a day of exploring. Whatever the reason for your trip we know you'll enjoy The Lone Star Cabana! Note: This is one of five units at Once Upon a Tide Villas. Common areas may be shared with other guests.

*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

Southern Charm-Beach Front BSL with Saltwater Pool
New Saltwater Pool Spring 2026! Unwind in delightful Olde Town Bay St Louis at our Southern Charm beachfront paradise. Gorgeous modern home-Southern Charm at its finest! Two story 3br, 3.5 bath, Sleeps 6, washer dryer wifi and cable, if you dare leave the majestic views from our old world front porch rocking chairs.. Walk the beach, fish the pier or walk to local restaurants shops bars and enjoy! Ask about adding on our Guest Cottage for up to 4 additional guests at a small nightly rate

Gorgeous Oceanview 3BR Luxury Condo - "Latitude"
Welcome to “Latitude”, your dream vacation getaway on the 13th floor of the luxurious Legacy Towers in Gulfport MS. This newly renovated condo includes top-of-the-line finishes and offers breathtaking ocean views that will leave you speechless. Whether it’s waking up every morning and enjoying your coffee while watching the sunrise over the Gulf or relaxing on the balcony while sipping a glass of Champaign witnessing the stunning sunsets, this condo has much to offer and will not disappoint!

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!

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".

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.

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.

Coastal Oasis - Heated Pool, Walk to Beach!
Bring the whole family to enjoy a beach vacation on beautiful MS Coast. Just 5 minutes to the shops and restaurants in downtown Bay St. Louis, the West Inn Beach club is it's own private oasis. 3 blocks to beach, private pool, ping pong, outdoor living room/tv, yard games, 600 sq ft. of screened in porches. Sleeps 12! We offer the pool to be heated November - March for an additional fee. Please inquire.
Popular amenities for Diamondhead rentals with a pool
House rentals with a pool

Heated Pool! Petite Retreat in The Pass

Waterfront Comfort With Pool - Sleeps 8!

Henley House - Enjoy Pool, Old Town or Beach

The View | Waterfront • Pool • Paradise •Golf Cart

Waterfront Escape w/ Pool, Dock & Bayou Views

The Shack

Fabulous Waterfront Getaway!

The Boat House Bay St. Louis
Condo rentals with a pool

Blue Heaven Condo on the Beach!

Beach Getaway

Beautiful Views Biloxi Beach Condo

Sunny Beachfront Biloxi Condo w/ Resort Amenities!

The Ritz

Contemporary Biloxi Condo for 2 - Oak Shores

Biloxi Beach Condo @ 2046 Beach Blvd, Biloxi

Ground Floor Beach & Casino Getaway!
Other vacation rentals with a pool

Diamond on the Gulf

Lacey's Coastal Cabana - Charming & Quiet Condo

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

Pool & Spa - Luxury Retreat With Bay Views

Relaxing 5-Bedroom Home with Outdoor Pool and Bar

7BR Mississippi Gulf Coast | Heated Pool & Balcony

Cottage At The Campground

Coastal Comfort - Pool - 1 Block from Beach
When is the best time to visit Diamondhead?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $124 CAD | $131 CAD | $125 CAD | $135 CAD | $142 CAD | $150 CAD | $132 CAD | $117 CAD | $120 CAD | $158 CAD | $136 CAD | $135 CAD |
| 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 Vacation rentals
- Panama City Beach Vacation rentals
- Destin Vacation rentals
- Gulf Shores Vacation rentals
- Orange Beach Vacation rentals
- Miramar Beach Vacation rentals
- Birmingham Vacation rentals
- Pensacola Vacation rentals
- Lower Grand Lagoon Vacation rentals
- Columbus Vacation rentals
- Baton Rouge Vacation rentals
- Santa Rosa Island Vacation rentals
- Biloxi Beach
- Fontainebleau State Park
- Mississippi Coast Coliseum & Convention Center
- Ocean Springs Beach
- Ship Island
- Lakefront Arena
- Mississippi Aquarium
- Gulf Islands Waterpark
- Shaggy's Biloxi Beach
- English Turn Golf & Country Club
- Jones Park
- Big Play Entertainment Center
- Hollywood Casino
- Hard Rock Casino
- Biloxi Lighthouse
- Buccaneer State Park
- Golden Nugget Casino Presidential Suite
- Finishline Performance Karting
- Infinity Science Center
- De Soto National Forest
- Ship Island Excursions





