Breezeway
Property operations and messaging platform for short-term rental and hospitality managers that automates cleaning, maintenance, inspections, and guest communication.
Best for: Short-term rental and hospitality operators coordinating cleaning, maintenance, and guest messaging at scale
Last reviewed 6/2/26
- Pricing
- Property-based, billed monthly with volume discounts for 5+ properties. Free tier for a first property; Host Essentials starts at $19/month; Essential Ops, Operations Pro, and Guest Experience suites are quote-based.
- Integrations
- Guesty, Hostaway, Streamline, Track, Avantio, OwnerRez, AppFolio, Escapia, Eviivo, Hospitable, Hostfully, Hostify, Rent Manager, 365 Villas, Airbnb, Vrbo, Cloudbeds, Mews, Oracle Opera, Lodgify, Intuit QuickBooks, Dormakaba, Igloo Home, NoiseAware, PointCentral, StayNTouch, WebRezPro, Barefoot, LiveRez, Smily
- Property types
- Short-Term Rental, Vacation Rental, Hospitality, Residential
- Geography served
- Global (used in 85+ countries)
How Breezeway uses AI[1][2]
Breezeway runs AI across property care and guest messaging, drafting suggested replies from property and reservation data and auto-generating cleaning, maintenance, and turnover tasks from reservation triggers.
- • AI-powered Suggested Replies draft responses to guest messages using deep property profiles and reservation context
- • Assist AI is built on ChatGPT generative AI to surface suggested replies inside the messaging product
- • Automated workflows generate scheduling, housekeeping, and maintenance tasks from occupancy status and reservation data
- • AI messaging sends timed guest communications such as check-in details and local recommendations
AI type: Generative AI (LLM)
API: unknown MCP: no
Key numbers[3][6]
- • Company-reported: 3,500+ clients
- • 265,000+ properties powered across 85 countries
- • more than 30 million property tasks facilitated
- • integrates with 35+ property management systems.
Credibility[3][7][8]
- Founders
- Founded and led by CEO Jeremiah (Jeremy) Gall, who previously founded vacation rental marketplace FlipKey (acquired by TripAdvisor).
- Customers
- 3,500+ clients powering operations for 265,000+ properties across 85 countries; clients include managers running from single units to 1,000+ property portfolios.
- Investors
- Resurgens Technology Partners (2026 strategic growth investment), Catalyst Investors (Series B lead), Schooner Capital (Series A lead); ~$36M+ raised across rounds including a $15M Series B (2022) and $8M Series A (2020).
Founded
2017
Headquarters
Boston, Massachusetts, USA
Stage
Private equity backed (Resurgens Technology Partners, 2026)
Employees
201-500
Sources
- Breezeway Products (AI Suggested Replies and automation)
- Skift: Breezeway launches Assist AI tool using ChatGPT
- Resurgens: Breezeway strategic growth investment (clients, properties, countries, founder, founded, HQ)
- Breezeway Pricing page (plans and per-property billing)
- Breezeway Integrations page (PMS and partner list)
- Breezeway FAQ (30M+ tasks, 90+ countries, 35+ PMS integrations)
- ShortTermRentalz: Breezeway raises $15M Series B (Catalyst Investors lead)
- VRM Intel: Q&A with founder Jeremy Gall on $8M round (Series A, Schooner Capital, FlipKey background)
- Business Wire: Breezeway Announces Strategic Growth Investment from Resurgens
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