Buying Luxury Real Estate on the Big Island: A Step-by-Step Guide

Buying a luxury property on Hawaii Island is an exciting milestone—whether you're searching for a primary residence, second home, or income-producing vacation rental. The Big Island offers an exceptional mix of high-end resorts, gated communities, oceanfront estates, and golf course enclaves, each with its own nuances and local considerations.

This guide walks you through the Big Island luxury buying process step-by-step, including local practices, zoning considerations, and what makes purchasing in Hawaii different from the mainland.

Step 1: Define Your Luxury Lifestyle Goals

Before browsing listings, clarify how you plan to use the property:

• Primary residence

• Second home / vacation home

• Investment or short-term vacation rental (STVR)

Then narrow down preferences:

• Oceanfront vs. ocean view vs. golf course

• Condo vs. single-family home vs. estate property

• Gated community or private neighborhood

• Resort amenities vs. secluded setting

On the Big Island, many luxury buyers gravitate toward resort and high-end subdivisions such as:

• Waikoloa Beach Resort

• Mauna Lani

• Mauna Kea Resort

• Kohanaiki

• Kukio

• Hualalai

• Waikoloa Village (select gated enclaves)

• Kona Highlands

Identifying your lifestyle priorities early makes the entire process more efficient.

Step 2: Understand Hawaii Property Types & Ownership

Hawaii real estate includes ownership structures that may differ from mainland norms:

Fee Simple

You own both the structure and the land. Most luxury buyers prefer fee simple ownership.

Leasehold

You own the structure but lease the land for a set period. (Less common in luxury markets today.)

CPR (Condominium Property Regime)

A legal structure used for condos and some attached homes. Common in resort communities.

Understanding these categories helps avoid surprises later in escrow.

Step 3: Learn Local Zoning & Rental Regulations

If rental income is part of your plan, this step is critical.

Short-Term Vacation Rentals (STVR)

• Not all areas allow short-term rentals

• Some properties hold active STVR permits

• Resort-zoned communities often allow vacation rentals, but verification is essential

Always confirm:

• Zoning designation

• County rules

• Permit status (if applicable)

Luxury resort properties with existing STVR permits are especially valuable.

Step 4: Get Financially Prepared

Luxury purchases in Hawaii often require:

• Proof of funds

• Strong pre-approval from a Hawaii-based or island-experienced lender

• Understanding of jumbo loan guidelines (if financing)

Buyers should also budget for:

• Closing costs

• HOA dues (common in resorts)

• Property taxes

• Insurance (including hurricane coverage, and possibly lava or flood depending on zone)

A strong financial profile strengthens your negotiating position.

Step 5: Work With a Local Luxury Specialist

Choosing the right representation is one of the most important decisions you will make.

Partnering with a trusted local brokerage and luxury specialist ensures you have accurate guidance on pricing, zoning, rental regulations, and resort community rules.

A reputable Big Island luxury brokerage provides:

• Access to on-market and off-market opportunities

• Deep understanding of resort and high-end subdivision nuances

• Strong relationships with local escrow, title, lenders, inspectors, and attorneys

• Experienced negotiation on high-value transactions

Working with an established brokerage and experienced local agent gives you confidence that every detail of your purchase is handled professionally.

Big Island real estate is hyper-local.

A knowledgeable local agent helps you:

• Access off-market or quiet listings

• Interpret zoning and permit status

• Understand HOA rules

• Navigate resort community nuances

• Evaluate long-term value

Luxury properties often involve more moving parts than standard transactions—local expertise matters.

Step 6: Tour Properties Strategically

Luxury buyers should focus on quality, not quantity.

During tours, evaluate:

• Orientation (sun exposure, trade winds)

• Privacy and proximity to neighbors

View corridors:

• Build quality and upgrades

• HOA amenities and restrictions

Virtual tours are common for off-island buyers, but in-person visits provide valuable insight into neighborhood feel and surroundings.

Step 7: Make a Strong Offer

Offers typically include:

• Purchase price

• Earnest money deposit

• Financing or cash terms

• Contingency periods

• Requested closing date

In competitive luxury segments, clean terms and strong documentation can matter as much as price.

Step 8: Escrow, Inspections & Due Diligence

Once under contract:

• Open escrow with a Hawaii-based title and escrow company

• Complete home inspection

• Review HOA documents (if applicable)

• Verify zoning, permits, and rental status

• Secure financing and appraisal (if required)

Hawaii transactions emphasize thorough disclosure and buyer review periods.

Step 9: Closing & Recording

On closing day:

• Funds are wired

• Deed is recorded with the State of Hawaii

• Keys are released

Buyers do not typically attend closings in person. Remote notarization and courier services are common.

Step 10: After Closing Considerations

Many luxury buyers coordinate:

• Property management

• Housekeeping and maintenance

• Landscaping

• Interior design or furnishing

• Vacation rental setup (if applicable)

Your agent can provide trusted local referrals.

Why Buyers Choose Hawaii Island for Luxury Real Estate

• World-class beaches

• Championship golf courses

• Five-star resorts

• Privacy and space

• Strong second-home demand

• International buyer appeal

The Big Island offers a rare blend of natural beauty, resort lifestyle, and long-term value.

Final Thoughts

Buying luxury real estate on Hawaii Island is not just a transaction—it’s an investment in lifestyle.

With the right guidance, local expertise, and clear goals, owning a luxury property in the Big Island’s most prestigious resorts and subdivisions can be a seamless and rewarding experience. 

Thinking about buying luxury real estate on the Big Island?

I specialize in high-end resort and luxury properties across Hawaii Island and would be happy to guide you through every step.

📩 Contact me for private listings, market insights, and personalized property recommendations.