What follows are some links that I feel will put you in touch with much of the Big Island vacation rental market. There are so many different types of rental properties for tourists and islanders alike. Many of us who live here in Kona love to "escape" to the lava fields of Kau, where unusual vacation rental properties are to be had. Check this picture out!!
Another option is around Volcano town, where vacation rentals can be had in the rain forest that surrounds Volcanoes National Park. Here is a good example:
If you want to stay in a condo in Kailua-Kona, one of the largest selections can be found at Sunquest Hawaii. If you are thinking about buying a vacation rental in an condominium complex that's close to the ocean, use this link for vacation rental pricing on over 25 condos along Alii Drive. And, of course, you can book a condo here too.
Check out Kona Bali Kai at the Castle Resorts site.
Outrigger provides two exceptional properties in Kailua-Kona: the Royal SeaCliff and Kanaloa at Kona. You can also check out Outrigger's Fairway Villas at Waikoloa Beach Resort, which is in the Kohala district north of Kona. These complexes may have units for sale. Click on Outrigger.
Kailua-Kona is the main town on the leeward side of the Big Island. As you head north into Kohala, you will have sunnier skies, drier weather and more wind. Kohala is the prime resort area of the island, and if you want to rent a condo in the Waikoloa Beach Resort, check out VacationRentals.com.
Many people I talk to use vrbo.com (which contains listings mostly by owners) to find vacation rentals here on the Big Island. Currently, vrbo.com has over 3,000 vacation rentals on the Big Island. Have a look: vrbo.com.
If you're thinking about buying a vacation rental, email me for information on this process.
Above all, have fun and good traveling!