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

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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)
03/07/26 – 03/14/26 Hilton Hawaiian Village -Grand Waikikian 2BR/6 Oahu $2,399
03/08/26 – 03/15/26 Wyndham Mauna Loa Village (Holua) 2BR/6 Big Island $1,499
03/08/26 – 03/15/26 Paniolo Greens (Waikoloa) 2BR/6 Big Island $999
03/08/26 – 03/15/26 Cliffs Club (Princeville) 4BR/10 Kauai $1,599
03/20/26 – 03/27/26 Maui Schooner 2BR/6 Maui $1,599
03/20/26 – 03/27/26 Wyndham Bali Hai Villas (Princeville) 1BR/4 Kauai $1,099
03/21/26 – 03/28/26 Maui Schooner 2BR/6 Maui $1,599
03/22/26 – 03/29/26 Holua Resort at Mauna Loa Village 2BR/6 Big Island $1,295
03/22/26 – 03/29/26 Marriott Maui Ocean Club 1BR/4 Maui $2,950
03/28/26 – 04/04/26 Maui Schooner 2BR/6 Maui $1,599
03/28/26 – 04/04/26 Maui Lea at Maui Hill 1BR Maui $1,599
03/28/26 – 04/04/26 Wyndham Mauna Loa Village 2BR/6 Big Island $1,699
03/29/26 – 04/05/26 Wyndham Mauna Loa Village 2BR/6 Big Island $1,599
03/29/26 – 04/05/26 Hilton Kokulani (on Waikiki Beach Walk) 1BR/4 Oahu $1,595
03/29/26 – 04/05/26 Aloha Towers 1BR/4 Oahu $1,050
03/29/26 – 04/05/26 Wyndham Bali Hai Villas (Princeville) 2BR/6 Kauai $1,399
03/29/26 – 04/05/26 Cliffs Club (Princeville) 1BR/2 Kauai $899
04/03/26 – 04/10/26 Wyndham Kona Hawaiian Resort 2BR/6 Big Island $1,399
04/05/26 – 04/12/26 Kona Coast Resort 2BR/6 Big Island $999
04/10/26 – 04/17/26 Wyndham Kona Hawaiian Resort 2BR/6 Big Island $1,699
04/17/26 – 04/24/26 Hilton Hawaiian Village - Lagoon Tower 3BR/10 Oahu $3,999
04/18/26 – 04/25/26 Hilton Hawaiian Village - Lagoon Tower 1BR/4 Oahu $1,999
04/18/26 – 04/25/26 Wyndham Royal Sea Cliff (Kona oceanfront) 2BR/6 Big Island $2,450
04/24/26 – 05/01/26 Maui Lea at Maui Hill 2BR/6 Maui $1,750
04/26/26 – 05/03/26 Sea Mountain (Pahala - South Point) 2BR/6 Big Island $1,499
04/26/26 – 05/03/26 Hilton Kokulani (on Waikiki Beach Walk) 1BR/4 Oahu $1,799
05/01/26 – 05/08/26 Hilton Kokulani (on Waikiki Beach Walk) 1BR/4 Oahu $1,799
05/01/26 – 05/08/26 Hilton Waikoloa Beach Resort - Kohala Suites 2BR/8 Big Island $2,199
05/09/26 – 05/16/26 Hilton Hawaiian Village -Grand Islander 1BR/4 Oahu $1,999
05/09/26 – 05/16/26 Hilton Hawaiian Village - Kalia Tower 1BR/4 Oahu $1,799
05/22/26 – 05/29/26 Hilton Hawaiian Village - Kalia Tower 1BR/4 Oahu $1,899
05/22/26 – 05/29/26 Lawai Beach Resort (Poipu) 2BR/6 Kauai $1,499
06/05/26 – 06/12/26 Lawai Beach Resort (Poipu) 1BR/4 Kauai $1,499
06/05/26 – 06/12/26 Hilton Waikoloa Beach Resort - Bay Club 1BR/4 Big Island $1,999
06/07/26 – 06/14/26 Hilton Waikoloa Beach Resort - Bay Club 1BR/4 Big Island $1,399
06/14/26 – 06/21/26 Hawaiian Princess at Makaha 2BR/6 Oahu $1,899
06/21/26 – 06/28/26 Hawaiian Princess at Makaha 2BR/6 Oahu $1,899
06/27/26 – 07/04/26 Hilton Hawaiian Village - Kalia Tower 1BR/4 Oahu $1,999
06/28/26 – 07/05/26 Kahana Beach Resort Studio/4 Maui $999
07/03/26 – 07/10/26 Holua Resort at Mauna Loa Village 1BR/4 Big Island $1,599
07/10/26 – 07/17/26 Imperial Hawaii Resort (Waikiki Beach Walk) 1BR/6 Oahu $1,199
07/17/26 – 07/24/26 Imperial Hawaii Resort (Waikiki Beach Walk) 1BR/6 Oahu $1,199
07/17/26 – 07/24/26 Hilton Waikoloa Beach Resort - Kings Land 1BR/4 Big Island $1,699
07/24/26 – 07/31/26 Hilton Hawaiian Village -Grand Islander 1BR/4 Oahu $2,199
07/28/26 – 08/05/26 Kona Islander 1BR/4 Big Island $1,499
07/31/26 – 08/07/26 Hilton Hawaiian Village -Grand Islander 1BR/4 Oahu $2,199
08/05/26 – 08/12/26 Kona Islander 1BR/4 Big Island $1,499
08/07/26 – 08/14/26 Hilton Hawaiian Village -Grand Islander 1BR/4 Oahu $2,199
08/13/26 – 08/20/26 Cliffs Club (Princeville) 1BR LOFT/6 Kauai $1,599
08/14/26 – 08/21/26 Hilton Kaanapali Beach Club 1BR Maui $1,699
08/21/26 – 08/28/26 Hilton Kaanapali Beach Club 1BR Maui $1,699
08/22/26 – 08/29/26 Kona Coast Resort 1BR/4 Big Island $1,199
09/03/26 – 09/10/26 Maui Lea at Maui Hill 2BR Maui $1,599
09/05/26 – 09/12/26 Kona Coast Resort 2BR/6 Big Island $1,899
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
12/04/26 – 12/11/26 Holua Resort at Mauna Loa Village 1BR/4 Big Island $1,899
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