Vacation–Connections.com Direct-from-Owner Hawaii Vacation Listings

Connecting you to paradise: Hawaii's top vacation rentals.

Click on a listing to request a reservation. We feature listings in Hawaii, California, and Nevada.
Dates Available (mm/dd/yy) Property Size/
Occupancy 		Location Price (USD)
06/12/26 – 06/19/26 Kona Coast Resort 1BR/4 Big Island $599
06/20/26 – 06/27/26 Hilton Hawaiian Village - Kalia Tower 1BR/4 Oahu $1,699
06/20/26 – 06/27/26 Imperial Hawaii Resort (Waikiki Beach Walk) 1BR/6 Oahu $899
06/21/26 – 06/28/26 Kona Coast Resort 2BR/6 Big Island $899
06/21/26 – 06/28/26 Hawaiian Princess at Makaha 2BR/6 ⓘ Oahu $1,899
06/28/26 – 07/05/26 Hilton Waikoloa Beach Resort - Bay Club 1BR/4 ⓘ Big Island $1,399
06/29/26 – 07/05/26 Hilton Kaanapali Beach Club 1BR Maui $1,199
07/02/26 – 07/09/26 Hilton Waikoloa Beach Resort - Kohala Suites 2BR/6 Big Island $1,499
07/03/26 – 07/10/26 Kona Coast Resort 1BR/4 Big Island $999
07/04/26 – 07/11/26 Waikiki Banyan 1BR/4 Oahu $999
07/10/26 – 07/17/26 Hilton Kaanapali Beach Club 1BR Maui $1,599
07/17/26 – 07/24/26 Hilton Waikoloa Beach Resort - Kings Land 1BR/4 ⓘ Big Island $1,499
07/24/26 – 07/31/26 Hilton Waikoloa Beach Resort - Bay Club 2BR/6 ⓘ Big Island $1,599
07/24/26 – 07/31/26 Hilton Hawaiian Village -Grand Islander 1BR/4 Oahu $1,899
07/29/26 – 08/05/26 Hilton Kaanapali Beach Club 1BR Maui $1,199
07/31/26 – 08/07/26 Hilton Hawaiian Village -Grand Islander 1BR/4 Oahu $1,899
08/02/26 – 08/09/26 Hawaiian Princess at Makaha 2BR/6 Oahu $1,750
08/02/26 – 08/09/26 Hilton Kaanapali Beach Club 1BR Maui $1,599
08/02/26 – 08/09/26 Hilton Kaanapali Beach Club 1BR Maui $1,699
08/07/26 – 08/14/26 Hilton Hawaiian Village -Grand Islander 1BR/4 ⓘ Oahu $2,199
08/07/26 – 08/14/26 Kuleana Club (Best Kept Secret - Jewel of West Maui) 1BR/4 ⓘ Maui $899
08/07/26 – 08/14/26 Cliffs Club (Princeville) 1BR LOFT/6 Kauai $1,299
08/14/26 – 08/21/26 Hilton Waikoloa Beach Resort - Kings Land 1BR/4 Big Island $1,750
08/21/26 – 08/28/26 Hilton Kaanapali Beach Club 1BR Maui $1,699
08/29/26 – 09/05/26 Hilton Waikoloa Beach Resort - Kings Land 1BR/4 Big Island $1,699
08/30/26 – 09/06/26 Hawaiian Princess at Makaha 2BR/6 Oahu $1,750
09/04/26 – 09/11/26 Maui Schooner 2BR Maui $1,299
09/05/26 – 09/12/26 Hawaiian Princess at Makaha 2BR/6 Oahu $1,750
09/05/26 – 09/12/26 Kona Coast Resort 2BR/6 Big Island $1,899
09/06/26 – 09/13/26 Hawaiian Princess at Makaha 1BR/4 Oahu $999
09/11/26 – 09/18/26 Hilton Hawaiian Village -Grand Islander 1BR/4 Oahu $1,799
09/13/26 – 09/20/26 Hilton Kaanapali Beach Club 1BR Maui $1,599
09/13/26 – 09/27/26 Hilton Kaanapali Beach Club 1BR Maui $1,599
09/20/26 – 09/27/26 Hawaiian Princess at Makaha 1BR/4 Oahu $999
10/10/26 – 10/17/26 Hilton Hawaiian Village -Grand Islander 2BR/6 Oahu $2,799
10/23/26 – 10/30/26 Hilton Waikoloa Beach Resort - Kings Land 1BR/4 Big Island $1,799
10/24/26 – 10/31/26 Hilton Waikoloa Beach Resort - Kings Land 1BR/4 Big Island $1,399
11/08/26 – 11/15/26 Waikiki Marina Resort at ILIKAI Studio/4 Oahu $999
11/21/26 – 11/28/26 Kona Hawaiian Resort 2BR/6 Big Island $1,599
11/28/26 – 12/05/26 Hilton Waikoloa Beach Resort - Kings Land 2BR/6 Big Island $2,799
12/04/26 – 12/11/26 Holua Resort at Mauna Loa Village 1BR/4 Big Island $1,899
12/13/26 – 12/20/26 Hilton Waikoloa Beach Resort - Kings Land 1BR/4 Big Island $2,099
12/19/26 – 12/26/26 Sweetwater at Alii Kai 2BR/6 Kauai $1,799
12/19/26 – 12/26/26 Waikiki Banyan by Sweetwater 1BR/4 Oahu $1,899
12/25/26 – 01/01/27 Wyndham Ka Eo Kai 2BR/6 ⓘ Kauai $1,999
12/26/26 – 01/02/27 Waikiki Banyan by Hawaiian Holidays 1BR/4 Oahu $1,799
12/26/26 – 01/02/27 Waikiki Banyan by Sweetwater 1BR/4 Oahu $1,899
12/26/26 – 01/02/27 Lawai Beach Resort (Poipu) 1BR/4 Kauai $1,899
12/27/26 – 01/03/27 Maui Schooner 1BR/4 Maui $1,799
12/31/26 – 01/07/27 Wyndham Bali Hai Villas 2BR/6 ⓘ Kauai $1,999
12/31/26 – 01/07/27 Wyndham Ka Eo Kai Studio/2 Kauai $1,299