Upstay
Upstay is a privately held, Orlando-based vacation rental property manager founded in 2019 that curates and operates 245 properties across the US, Costa Rica, and Canada, offering full-service management — design, cleaning, 24/7 support, and 65+ OTA distribution — to leisure travelers and homeowner clients.
- Company typePrivate
- Founded2019
- HeadquartersOrlando, United States
- Headcount101–250
- GTM typeB2B and B2C
- OfferingServices
What Upstay does
Upstay Inc. is a privately held, Delaware-incorporated vacation rental property management company founded in 2019 and headquartered in the Orlando metro area (Winter Garden, FL), with an additional operational presence in Kissimmee, FL. The company curates and manages a portfolio of 245 hand-picked vacation rental properties across the United States (Orlando, Austin TX, South Padre Island, Silverthorne CO), Costa Rica, and Canada (Calgary, Toronto, Kitchener, Ontario), serving leisure travelers — primarily families and groups seeking proximity to theme parks and resort-style amenities — alongside an owner-side customer segment.
Upstay's core offering is full-stack property management, spanning in-house interior design, turnkey furnishing, professional photography, multi-platform distribution across 65+ online booking channels (Airbnb, VRBO, Booking.com, Expedia, Agoda), 24/7 guest support, professional cleaning, and maintenance. Operations run on the Guesty property management system, and a third-party "AI Catalog by Kismet" is embedded on property pages as an AI-powered booking storefront. The product surface also includes themed-room inventory (Disney, Harry Potter, Jurassic Park, Star Wars, Hollywood, sports) and free city and resort guidebooks used as content marketing to drive direct bookings.
The business model combines transaction-level short-term rental revenue with property management fees charged to owners (marketed as "reduced" management fees generating "above-market returns"), plus ancillary fees (cleaning $99-$349, pet $49-$139, pool heating) and an interior design services vertical. Distribution is hybrid: direct via upstay.com and a dedicated owner portal (owners.upstay.com), and indirect via major OTAs. The company is independently owned with no disclosed external funding, parent company, or M&A history, and the leadership bench is thin in public records — only co-founder and CEO Andrew Lenjosek is identified by name.
Upstay firmographics
Firmographics- Name
- Upstay
- Legal name
- Upstay Inc.
- Website
- https://upstay.com
- Company type
- Private
- Founded year
- 2019
- Operating status
- Operating
- Headcount range
- 101–250 employees
- Short description
- Upstay is a privately held, Orlando-based vacation rental property manager founded in 2019 that curates and operates 245 properties across the US, Costa Rica, and Canada, offering full-service management — design, cleaning, 24/7 support, and 65+ OTA distribution — to leisure travelers and homeowner clients.
- Ownership category
- akta.pro rank
Upstay industry classification
Industry- Product category
- Vacation Rental Property Management
- NAICS
- General Rental Centers (53231)
- SIC
- Real Estate Agents & Managers (For Others) (6531), Hotels, Rooming Houses, Camps & Other Lodging Places (7000)
- akta.pro primary industry
- Full-Service Vacation Rental Property Management (BPAJAIAA)
- akta.pro secondary industries
- Family & Group-Friendly Rentals (Large Homes, Multi-Unit Compounds) (THAGANAI), Villas & Luxury Estates (THAMAAAC), Professional/Managed Inventory Vacation Rental Marketplaces (THAMALAB)
Keywords
Where Upstay is headquartered
LocationHeadquarters
- HQ city
- Orlando
- HQ country
- United States
- HQ region
- North America
Offices2 records
Markets served
Upstay business model
Business model- GTM type
- B2B and B2C
- Offering type
- Services
- Cost components
- Personnel, Operations, Marketing or Sales, Technology or R&D, Infrastructure
Revenue model
- Short-Term Rental Transactions: Revenue generated from short-term rental fees charged to guests who book vacation properties through Upstay's platform. The company acquires rights and interests in accommodation for the onward supply to travelers staying in the United States and other countries.
- Property Management Services: Services provided to property owners including interior design, furnishing, cleaning, repairs, and property management. Upstay manages the entire vacation rental process and provides above-market returns for homeowners through reduced property management fees and investment analysis.
Pricing tiers
| Model | Billing | Price |
|---|---|---|
| Unit Pricing | Pay-as-you-go | Budget-friendly vacation rentals from $99/night |
| Unit Pricing | Pay-as-you-go | Mid-range family homes $200-$500/night |
| Unit Pricing | Pay-as-you-go | Luxury group accommodations $500-$1,500+/night |
Go-to-market motion2 records
Distribution channels8 records
Marketing channels7 records
Upstay product offering
Product offeringCore offering
Upstay curates and manages a portfolio of hand-picked vacation rental properties in destinations such as Orlando, Austin, Costa Rica, and Canada, offering themed rooms and premium amenities. For property owners, it provides end-to-end property management including interior design, turnkey furnishing, professional photography, listing distribution across 65+ online booking platforms (Airbnb, VRBO, Booking.com, Expedia, Agoda), 24/7 guest support, cleaning, and maintenance. For guests, it delivers a direct-booking platform with curated themed vacation homes and AI-powered discovery via Kismet.
Product overview
Upstay is a vacation rental property management company founded in 2019 that operates a curated portfolio of hundreds of hand-picked vacation rental properties across popular destinations including Orlando, Austin, Costa Rica, Canada, and South Padre Island. The core offering is full-stack property management — from interior design and furnishing to professional photography, listing distribution across 65+ online booking platforms, 24/7 guest support, professional cleaning, and maintenance. Upstay differentiates through themed vacation rentals featuring immersive themed rooms (Disney, Harry Potter, Jurassic Park, underwater/Ocean, Hollywood, and sports themes) and complementary City and Resort Guidebooks for guests. Properties are listed on major OTAs (Airbnb, VRBO, Booking.com, Expedia, Agoda) as well as via direct booking through the Upstay website and an AI-powered storefront powered by Kismet. The company also offers interior design services and property investment analysis for homeowners.
Differentiator
Problem solved
Functional benefit
Products and services
- Vacation Rental Property Management
- Interior Design Services
- Themed Vacation Rentals (Themed Homes)
- Upstay Direct Booking Platform
Quantifiable outcome
- 65+ online booking platforms used to list each property
- +2 more outcomes
Companies that use Upstay
Customer profileNamed customers6 records
Segments4 records
Ideal customer profiles4 records
Upstay technology and API
TechnologyTechnology focussed Yes
API detail
- Has API
- No
- API docs
- API detail
Core technology
AI maturity
App detail
Integration1 record
AI capability1 record
Feature3 records
Upstay partnerships and signals
Strategic signalPartnerships
Seven partnerships are on record, tiered core, major, strategic and operational.
- AirbnbcoreUpstay properties are listed on Airbnb's marketplace, reaching millions of potential travelers. Each property uses professional photography and tailored descriptions to maximize visibility on the platform.
- VRBO (HomeAway)coreProperties distributed through VRBO's vacation rental marketplace, part of the Expedia Group family of travel brands.
- Booking.comcoreProperties listed on Booking.com's extensive accommodation network, one of the world's leading travel e-commerce platforms.
- ExpediamajorProperties distributed through Expedia's travel platform, providing access to Expedia's large customer base of leisure and business travelers.
- AgodamajorProperties listed on Agoda's platform, particularly valuable for international travelers and Asian market access.
- KismetstrategicAI-powered booking engine and storefront integration providing intelligent property discovery, dynamic pricing, and enhanced booking experience for guests.
- GuestyoperationalProperty management system used for operations including reservations, guest communication, cleaning management, and multi-platform synchronization.
Scale indicators5 records
Recent moves6 records
Expansion highlights4 records
Upstay competitors and assessment
Company assessmentBroad incumbents
- Sonder: Hospitality operator offering short and extended-stay apartments and vacation rentals. Adjacent model with tech-driven property management; competes for leisure and extended-stay demand overlapping with Upstay's portfolio.
- Airbnb: Dominant vacation rental marketplace that controls the largest share of Upstay's third-party distribution. Operates a much broader platform but increasingly encroaches on host services, making it both a channel partner and indirect competitor.
- Marriott Homes & Villas: Loyalty-integrated whole-home rental offering from a major global hotel brand. Targets the same premium leisure traveler segment with professionally managed upscale homes in leisure destinations.
Direct peers
- AvantStay: Tech-enabled vacation rental manager with curated, design-forward properties in leisure destinations including Austin and other markets overlapping with Upstay. Comparable premium positioning and full-service property management.
- Vacasa: Largest U.S. vacation rental property manager with full-service offerings (interior design, multi-platform distribution, 24/7 support). Direct competitor for property owners in Orlando and other markets; comparable business model, though at significantly greater scale.
- TurnKey Vacation Rentals: Full-service vacation rental property manager emphasizing local market presence, professional cleaning, and guest experience. Directly comparable model targeting owners in similar resort and leisure markets.
- Casago: Vacation rental property management franchise operating in resort markets including Orlando and other Florida destinations. Directly competes for the same homeowner inventory and guest segments in core geographies.
- Evolve Vacation Rental: Full-service vacation rental manager with national footprint and similar hands-on property management model. Competes for the same property owners and employs a comparable tech-enabled approach to distribution and guest experience.
Others
- Guesty: Property management system provider whose platform Upstay uses for operations. Comparable ecosystem participant but enables rather than competes with managers; useful proxy for tech stack direction in the category.
Emerging players
- Kasa: Tech-forward apartment and vacation rental operator that has expanded into short-term rental management in leisure markets. Partial overlap with Upstay in design-forward, professionally managed short-term rentals.
Market position
Strengths4 records
Weaknesses4 records
Competitive moat4 records
Key risks6 records
Key highlights7 records
Customer concentration
Upstay social profiles
Digital presenceUpstay financial estimates
Financial estimateRevenue estimate
Valuation estimate
Upstay leadership team
Management profileNumber of profiles
Profiles1 record
Upstay funding detail
Funding detailFunding overview
Funding rounds
Investors
Funding detail is available on the Subscription and Enterprise plan.Contact sales →
Upstay M&A and investment
M&A and investmentM&A
Investments
M&A and investment is available on the Subscription and Enterprise plan.Contact sales →
Frequently asked questions about Upstay
What does Upstay do?
Upstay curates and manages a portfolio of hand-picked vacation rental properties in destinations such as Orlando, Austin, Costa Rica, and Canada, offering themed rooms and premium amenities. For property owners, it provides end-to-end property management including interior design, turnkey furnishing, professional photography, listing distribution across 65+ online booking platforms (Airbnb, VRBO, Booking.com, Expedia, Agoda), 24/7 guest support, cleaning, and maintenance. For guests, it delivers a direct-booking platform with curated themed vacation homes and AI-powered discovery via Kismet.
Is Upstay a public or private company?
Upstay is a private company. It is classified as founder individual operated bootstrapped and is currently operating.
When was Upstay founded?
Upstay was founded in 2019. It employs 101 to 250 people.
Where is Upstay based?
Upstay is headquartered in Orlando, United States, in the North America region.
How does Upstay make money?
Two revenue lines are on record. Short-Term Rental Transactions are the primary driver. The others are property Management Services.
Who are Upstay's main competitors?
Broad incumbents on record are Sonder, Airbnb and Marriott Homes & Villas. Direct peers are AvantStay, Vacasa, TurnKey Vacation Rentals, Casago and Evolve Vacation Rental. Guesty is listed as an others. Kasa is listed as an emerging player.
Does Upstay have an API?
No public API is recorded for Upstay.
What industry is Upstay in?
Upstay's product category is Vacation Rental Property Management. Its primary akta.pro industry code is BPAJAIAA, Full-Service Vacation Rental Property Management, with a secondary code of THAGANAI, Family & Group-Friendly Rentals (Large Homes, Multi-Unit Compounds). Its NAICS code is 53231 and its SIC code is 6531.