Masters in Business
Masters in Business

At The Money: Grab Your Summer Rental Soon!!

It’s not too late to get your summer rental! But many of the prime locations have already been snapped up. On this episode, Barry speaks with Jonathan Miller, partner at Street Matrix and founder and President of Miller Samuel. They discuss what is going on with summer rentals, and what it means for

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Episode Summary

Executive Summary: The discussion centers on summer beach and second-home rental markets, especially the Hamptons, and finds they remain active but are normalizing after the pandemic frenzy. Demand is increasingly last-minute, skewed toward higher-income buyers/renters, and influenced by elevated mortgage rates, while construction and trades remain busy. The segment frames these markets as luxury consumption rather than a clear economic leading indicator.

Main Topics: Summer rental market as a consumer signal (Priority: 5/5): Jonathan Miller argues beach and summer rentals reflect discretionary spending and economic confidence, especially among affluent households. Normalization after pandemic frenzy (Priority: 5/5): The market remains active but is less frenzied than in the prior two to three years, with rents high but no longer at record levels. Last-minute booking behavior ('Amazonification') (Priority: 4/5): Consumers increasingly search for and book rentals on demand, weakening older seasonal timing rules and boosting post-Memorial Day traffic. K-shaped demand and wealth skew (Priority: 5/5): Demand is strongest in luxury and upper-tier markets, while middle- and lower-tier second-home demand is softer due to rate sensitivity. Mortgage rates and second-home affordability (Priority: 4/5): Rising rates make both buying and renting second homes more expensive, constraining the broader market and reducing inventory. Construction boom and trade congestion (Priority: 4/5): High-end renovation and rebuild activity is strong across vacation markets, with trades fully booked and local traffic congestion creating the 'trade parade.' COVID's lasting impact on second homes (Priority: 3/5): The pandemic expanded second-home use via remote work and Zoom, but also made demand more unpredictable and last-minute.

Key Arguments: Summer rentals are best understood as luxury consumption, not a standalone economic indicator; they reflect the spending power already present in the broader economy. The market is not weak, but it is normalizing from an exceptionally frenetic pandemic-era environment. Higher interest rates push more people to rent rather than buy, which reduces inventory and can support rents. Second-home demand is increasingly concentrated among higher-income households and linked to Wall Street compensation and other affluent income streams. Modern consumers expect on-demand access to rentals, making last-minute booking more common than the old practice of reserving a season months in advance. COVID and remote work extended the usefulness of second homes, but the market is now more unpredictable and less forecastable. Construction activity remains strong because many properties are being rebuilt or upgraded rather than simply maintained, especially in premium vacation areas.

Data Points: Hamptons rental inventory: 4,500 rentals available - Active listings mentioned on Out East for the Hamptons market East Hampton rentals: 1,077 available - Subset of Hamptons inventory cited as still available for summer Southampton rentals: 889 available - Subset of Hamptons inventory cited as still available for summer Luxury seasonal rental: $2.5 million - Example of an ultra-high-end Hamptons seasonal rental including chef and maid service Monthly luxury rental: $1.25 million - Example of what buyers might pay for July in lieu of the full season Monthly luxury rental: $1 million - Example of what buyers might pay for August in lieu of the full season Rental market timing: After Memorial Day and likely after July 4th - Speaker says demand still appears after traditional booking deadlines

Pivotal Quotes: "It's called Amazonified or Amazified... you just open your iPhone and you, you know, start looking at it." — Jonathan Miller: Describing the shift toward last-minute, on-demand rental searching and booking "I don't see it as an economic indicator because where the demand is emanating from is probably already the economic indicator to focus on." — Jonathan Miller: Explaining why summer rentals are better viewed as a consumption/luxury market than a leading macro signal "It's not a weak market, it's more normalizing, I think, is a fair description." — Jonathan Miller: Characterizing the post-pandemic state of summer second-home rentals

Implications: Expect more last-minute booking, continued strength in luxury vacation markets, and softer demand in mid-tier segments. Higher rates and wealth concentration will keep the market bifurcated.

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About Masters in Business

Barry Ritholtz speaks with the people that shape markets, investing and business.

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