My Maui Short Term Rental Condo (in Hotel Zoning) went from Airbnb to FEMA and back. How much rental income do I expect now that it is going back onto the short term rental market?

Hawaii's ultra-luxury real estate market has produced some of the highest-priced home sales in the country. This video breaks down the ten largest residential real estate sales in Hawaii's history, from Jeff Bezos $78 million purchase in La Perouse Bay, Maui, to record-setting sales on Oahu, Kauai, and the Big Island. This breakdown follows a conversation with a reporter from Bloomberg News about trends in Maui's luxury real estate market. Using over twenty years of MLS sales data across all four major Hawaiian islands, this video looks at how Hawaii's luxury real estate market, defined as homes and condos selling for three million dollars or more, has changed since 2005, and how that compares to the ultra-luxury market, defined here as sales of fifteen million dollars or more. In this video: the ten most expensive residential real estate sales in Hawaii history, how many homes in Hawaii have ever sold for more than thirty million dollars, luxury and ultra-luxury real estate trends on Maui, Oahu, Kauai, and the Big Island, why Maui's share of Hawaii's luxury real estate market has declined in recent years, how inflation affects long-term luxury real estate sales data, and why now may be a good time for luxury buyers to consider purchasing in Hawaii.

Lahaina Rebuild Update: The First 5 Businesses Returning to Front Street (July 2026). The latest Lahaina rebuild update on the commercial core along Front Street! In this video, we break down the major announcements from Maui County regarding the very first commercial building permits issued since the 2023 wildfires. Want to support the work I do on this channel? Consider joining as a member. Link below to membership options: https://www.youtube.com/channel/UCyMhPInDNkisrxa1j0vtoKQ/join Facebook - https://www.facebook.com/jesse.g.wald Instagram - https://www.instagram.com/jesse.g.wald/ FAQ: Which businesses are returning to Front Street in Lahaina? As of July 2026, Maui County has officially issued five commercial building permits for the permanent rebuilding of Lahaina’s historic Front Street. Additionally, a temporary marketplace called ʻUlu o Lele is currently under construction at the former Outlets of Maui site. Expected to open in Fall 2026, it will feature 17 modular retail units and 8 food trucks to provide an interim, rotating home for displaced Lahaina businesses while the permanent concrete-and-wood rebuilding continues. #maui #lahaina #lahainafire

Lahaina Maui Hawaii - Two years and ten months after the August 2023 Lahaina fire, this driving tour shows the full picture of recovery across residential and commercial neighborhoods. From areas with significant rebuilding progress to streets that remain largely unchanged, see exactly where Lahaina stands today. Get an honest, unfiltered look at the recovery timeline and judge the progress yourself.

Lahaina Maui, Hawaii new Drone Tour. How did Lahaina fair during Hurricane Lala? In this video I share a full Drone Aerial Tour of Lahaina Town so you can see for yourself. I will also share informative updates on Lahaina's Recovery from the Lahaina Fire... more than 3 years after the Fire.

Lahaina Maui, HI - Recovery Update July 2026. Nearly 3 years after the fire, Front Street finally opens for a blessing ceremony. While no Commercial Buildings are under construction, we are seeing some progress in the area.

Maui condo prices have fallen 29% from their peak, with the median sale price dropping from $920,000 to $650,000, while single-family home prices are down 8% — so is the Maui real estate crash finally over? In this October 2026 Maui real estate market update, I break down 20 years of MLS data on pending sales, closed sales, inventory, and median prices, and introduce my new newsletter highlighting the best Maui real estate deals.

Maui's Luxury Real Estate Auctions - 4 Incredible Homes are going to auction this week !!! One in Wailea, Two on Maui's West Side and One on Maui's North Shore.

Maui Luxury Home Tour - 65 Wili Okai Way - a 5-acre, 5-bedroom luxury estate above Lahaina, Maui, listed at $9.5M and selling via Concierge Auctions with opening bids starting around $4.5M. Maui real estate broker Jesse Wald breaks down the property, the location, and exactly how the luxury auction process works.

Maui's new HOTEL zoning is approved. The Maui County Council voted yes to Bill 88 in a 7 - 2 vote, creating H-3 and H-4 zoning categories that let qualifying short-term rentals survive the Bill 9 phaseout. Maui broker Jesse Wald breaks down what it means for STR owners, condo buyers, and the road ahead.

Is a Maui short-term rental condo still a good investment after Bill 9? Here are the 4 factors every buyer should weigh before purchasing a vacation rental condo on Maui. In this video, Maui real estate broker and short-term rental investor Jesse G. Wald breaks down the 4 factors to consider before buying a short-term rental on Maui — with a focus on Hotel-Zoned properties, which are unaffected by Bill 9's phase-out of apartment-zoned STRs.

Is Maui's Luxury Home Market Crashing ??? Let's look at the recent Luxury Auctions to analyze the numbers.

Maui's Short Term Rental Ban - Update May 2026. New Hotel Zoning took one small step forward this week.

Maui short-term rental ban update: the County just released its first list of apartment-zoned condos that could convert to the new H-3 and H-4 hotel zoning and keep operating as vacation rentals. We break down every property named in Resolutions 26-110 and 26-111 across West Maui, South Maui, and Mā'alaea.

How much rental income are short term rentals making on Oahu? Are Hawaii AirBnB's profitable in 2026? In this video I share my actual rental income for one of my STR's.