Search Deals onDiamondhead Vacation Packages
Diamondhead Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Centennial Plaza Resort Gulfport
Price was $614, price is now $491 per person
$491
per person
Nov 12 - Nov 16
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Gulfport (GPT)
Book a stay at this golf hotel in Gulfport. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Gulfport Beach and Island View Casino are located nearby.
Handsboro Pointe Condo & Suites
Price was $776, price is now $627 per person
$627
per person
Nov 12 - Nov 16
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Gulfport (GPT)
Stay at this apartment in Gulfport. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Mississippi Coast Coliseum and Convention Center and Gulfport Beach are located nearby.
The Pass Picture Book
Price was $1,238, price is now $1,071 per person
$1,071
per person
Nov 25 - Nov 29
found 6 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Gulfport (GPT)
Stay at this cottage in Pass Christian. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Thou Art Gallery & GIfts and War Memorial Park are located nearby.
The Markham Hotel
Price was $639, price is now $554 per person
$554
per person
Nov 12 - Nov 16
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Gulfport (GPT)
Stay at this hotel in Gulfport. Enjoy free parking, an outdoor pool, and 2 bars/lounges. Popular attractions Gulfport Beach and Island View Casino are located nearby.
The hotel was amazing, from the staff to the room. We enjoyed our stay and we will be staying again. The hotel gave such a luxury feel without the price tag that usually goes with the big luxury hotels!
Reviewed on Oct 11, 2026
The Inn at Long Beach
Price was $617, price is now $539 per person
$539
per person
Nov 12 - Nov 16
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Gulfport (GPT)
Book a stay at this beach hotel in Long Beach. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Island View Casino and Gulfport Beach are located nearby.
Landing Furnished Apartments Ocean Springs - Gulf Hills
Price was $587, price is now $512 per person
$512
per person
Nov 13 - Nov 15
found 17 hours ago
Roundtrip flight included
Orlando (MCO) to Gulfport (GPT)
Stay at this apartment in Ocean Springs. Enjoy an outdoor pool, an in-room coffeemaker, and air conditioning. Popular attractions Beau Rivage Casino and Biloxi Beach are located nearby.
Best than I could’ve ever expected.
Reviewed on Jul 11, 2026
Scarlet Pearl Casino Resort
Price was $641, price is now $574 per person
$574
per person
Nov 12 - Nov 16
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Gulfport (GPT)
Book a stay at this business-friendly hotel in D'Iberville. Enjoy free WiFi, free parking, and 4 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Beau Rivage Casino and Biloxi Beach are located nearby.
Porter Condos
Price was $680, price is now $615 per person
$615
per person
Dec 4 - Dec 7
found 14 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Gulfport (GPT)
Stay at this condo in Ocean Springs. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Beau Rivage Casino and Biloxi Beach are located nearby.
This is a really nice property in a great location. Parking is easy for trucks and cars, but would be challenging if you are towing a trailer. Easy access to beach, casinos in Biloxi, and Ocean Springs shop area. Host was very helpful and responsive. We enjoyed our stay.
Reviewed on Oct 6, 2026
Diamondhead Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Fri, Dec 11 - Mon, Dec 14
TPA
Tampa Intl.
GPT
Gulfport - Biloxi Intl.
$127 Roundtrip, found 1 day ago
$127
Roundtrip
found 1 day ago
Thu, Nov 5 - Sun, Nov 8
MSP
Minneapolis - St. Paul Intl.
GPT
Gulfport - Biloxi Intl.
$237 Roundtrip, found 2 hours ago
$237
Roundtrip
found 2 hours ago
Wed, Nov 11 - Tue, Nov 17
ATL
Hartsfield-Jackson Atlanta Intl.
GPT
Gulfport - Biloxi Intl.
$279 Roundtrip, found 1 hour ago
$279
Roundtrip
found 1 hour ago
Sat, Nov 21 - Wed, Dec 2
BOS
Logan Intl.
GPT
Gulfport - Biloxi Intl.
$321 Roundtrip, found 22 hours ago
$321
Roundtrip
found 22 hours ago
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