Pillow Homes, a technology-driven hospitality company for vacation rentals, opened in San Diego on June 23 amid projections that the city has become the nation’s fastest-growing vacation-rental market in the country. San Francisco-based Pillow has declared that it is pioneering on-demand property management, taking care of all the work that goes into “hosting” guests in a home from platforms like Airbnb, VRBO and Homeaway.
In downtown San Diego, average short-term rental income is $3,365, double the average long-term income of $1,716 a month. In Ocean Beach, short-term is $3,407 versus $1,831 long-term. In La Jolla, it’s $3,987 versus $2,671, and in Coronado, it’s $4,111 versus $2,865. In Pacific Beach, short-term rental income averages a whopping $4,896 per month, almost triple the $1,761 of long-term rental income.
San Diego reportedly has more than 12,000 short-term vacation rentals.
Pillow is designed to help San Diegans optimize their income from short-term home rentals without actually hosting guests. The company offers homeowners two ways to earn income from their homes. The standard pay-per-booking option means homeowners pay a fee of 15 percent of their rental income for Pillow’s management services, roughly half the price of most competitors, which routinely charge anywhere from a 25 to 40 percent fee. This option reportedly offers homeowners more flexibility in set available dates for their property.
Pillow has also introduced a fixed income-guarantee, the first of its kind. Under this model, homeowners lock in a predetermined monthly rental income. Using criteria including location, number of bedrooms and amenities, the company seeks to predict occupancy and daily pricing. “Now, from Seattle to San Diego, Pillow is helping homeowners make more money from their biggest asset: their homes,” said Pillow CEO Sean Conway. “Vacation home rentals will earn San Diegans a much greater return, actually double and triple what they’d get for long-term rentals.”
Every Pillow home comes with standardized amenities and guest support to increase the supply of vacation-rental properties, for corporate or vacation needs. The company’s online services include a proprietary pricing algorithm and booking engine, listing optimization and marketing and customer service before, during and after a stay. Local services include house cleaning and preparation, guest support, key exchange, maintenance and repairs.
The service also currently operates in the San Francisco Bay Area, Sonoma, Napa Valley and Los Angeles and plans to open in nine more cities within this year following the Seattle launch.
The company’s management team includes Conway and president and co-founder Justin Miller.








