Winning Holidays

What Winning Holidays does

Winning Holidays is a privately held Australian holiday accommodation booking platform and property management operator headquartered in Australia. The company aggregates 500+ properties across 16+ Australian regions plus Otago, New Zealand, operating under 28 wholly-owned regional sub-brands including Coffs Holiday Rentals, Your Luxury Escape, Weekenda, Verve Vacation Rentals, and Noosa Holiday Rentals. Its core product is a web-based booking marketplace featuring property search, availability calendars, and online reservation, supporting diverse accommodation types (apartments, cabins, cottages, duplexes, glamping, holiday houses, townhouses, villas) and specialty categories (accessible, pet-friendly, beachfront, waterfront, golf, prestige retreats, couples).

The company generates revenue through two streams: (1) transaction-based commissions or fees on holiday property bookings made through the platform, and (2) managed services revenue from property owners, including listing management, guest coordination, cleaning and maintenance coordination, and dynamic pricing optimization. Property owners access management tools via a dedicated homhero.com.au portal. The platform also integrates Klook affiliate partnerships for activities recommendations at destinations, creating a secondary commercial channel.

The company has grown primarily through acquisition of regional property management businesses, consolidating their local brands and inventory under a unified digital platform. Marketing is digital-first, leveraging SEO-optimized destination landing pages, content marketing via blog, and organic social presence on Facebook, Instagram, and LinkedIn. No AI/ML capabilities, patents, or proprietary technology beyond the booking platform are disclosed. The website is built and maintained by third-party technology partner spIT.

Name

Winning Holidays

Legal name

Winning Holidays

Website

https://winningholidays.com.au

Company type

Private

Operating status

Operating

Headcount range

11–50 employees

Short description

Winning Holidays is an Australian private holiday accommodation platform aggregating 500+ properties across 16+ regions in Australia and New Zealand under 28 regional brands, serving travelers via online booking and property owners via full-service management.

Ownership category

akta.pro rank

Product category

Vacation Rental Accommodation

NAICS

Traveler Accommodation (7211)

SIC

Hotels, Rooming Houses, Camps & Other Lodging Places (7000), Services-To Dwellings & Other Buildings (7340)

akta.pro primary industry

Metasearch & Aggregator Platforms for Vacation Rentals (THAMALAC)

akta.pro secondary industries

Full-Service Vacation Rental Property Management (THAMAKAA), Marketing, Photography & Listing Optimization Services (THAMAKAM), Luxury Vacation Rental Marketplaces (Curated/Verified Villas) (THAMALAH), Co-Host / On-the-Ground Operations & Guest Services (BPAJAIAI)

Keywords

• Holiday accommodation booking
• Vacation rental marketplace
• Property management services
• Short-term rental platform
• Australian holiday homes

Headquarters

HQ city

Nelson Bay

HQ country

Australia

HQ region

Oceania

Markets served

GTM type

B2C

Offering type

Services

Cost components

Personnel, Operations, Marketing or Sales, Technology or R&D

Revenue model

1. Holiday property bookings (Guest revenue share): Revenue generated from commission or fees on holiday property bookings made through the Winning Holidays platform. Guests pay for accommodation stays ranging from budget to luxury properties.
2. Property management services: Services provided to property owners including listing management, guest coordination, cleaning, maintenance coordination, and dynamic pricing optimization. Revenue derived from management fees charged to property owners.

Distribution channels3 records

Marketing channels7 records

Core offering

Winning Holidays operates a holiday home accommodation booking platform aggregating 500+ rental properties across 16 Australian regions plus Otago, New Zealand, under 28 regional brands. The platform enables travelers to search, filter, and book vacation properties ranging from budget apartments to luxury villas. It also provides property management services to owners including listing management, guest coordination, cleaning, maintenance coordination, and dynamic pricing optimization.

Product overview

Winning Holidays is a holiday home accommodation marketplace operating across 16 destination regions in Australia and New Zealand, including Byron, Central Coast, Coffs Coast, Gold Coast, Great Ocean Road, Hunter Valley, Lake Macquarie, Magnetic Island, Melbourne, Mornington Peninsula, Newcastle, Noosa, Northern Rivers, Otago, Port Stephens, and Sunshine Coast. The platform offers a unified booking system for various accommodation types (Apartments, Cabins, Cottages, Duplexes, Glamping, Holiday Houses, Townhouses, Villas) and specialty categories (Accessible, Affordable, Beachfront, Boat Parking, Golf, Holidays for Couples, Pet Friendly, Prestige Retreats, Waterfront). The company also provides property management services for owners and partners with Klook for activities booking. The platform is branded as incorporating multiple regional brands including Coffs Holiday Rentals, Prestige Holiday Homes, Verve Vacation Rentals, Best of Magnetic, Noosa Holiday Rentals, Port Stephens Accommodation, Great Ocean Road Holidays, Brown & Co, Your Luxury Escape, Weekenda, Holiday Coffs Coast, A Perfect Stay NSW, Boutique Stays, Caloundra Holiday Centre, Host Angel, Kingscliff Accommodation, Coast Holiday Management, Go Coastal, Divine Property Management, Relaxaway Holiday Homes, Spinnaker Bay Apartments, The Butler, and Staysouth.

Differentiator

Problem solved

Functional benefit

Products and services

• Holiday Accommodation Booking Platform

Segments4 records

Ideal customer profiles2 records

Technology focussed No

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Feature3 records

Partnerships

One partnership is on record.

• KlookminorGTM or Marketing PartnerAffiliate partnership with Klook for travel activities and Things To Do recommendations. Winning Holidays integrates Klook activity links on their platform to provide guests with local experience recommendations at various destinations including Brisbane, Byron Bay, Gold Coast, Great Ocean Road, Hunter Valley, Jervis Bay, Mornington Peninsula, Newcastle, Port Stephens, South Coast, Sunshine Coast, and New Zealand.

Scale indicators3 records

Recent moves6 records

Expansion highlights4 records

Broad incumbents

• Vrbo: Expedia-owned vacation rental marketplace that powers Stayz in Australia. Competes broadly for the same property manager and guest pool as Winning Holidays at a national and global scale.
• Airbnb: Global dominant P2P vacation rental marketplace with strong Australian presence across every region Winning Holidays operates in. Competes for both guest bookings and owner listings, with materially larger marketing and brand budgets.
• Booking.com: Global OTA with an extensive vacation rental offering alongside hotels. Competes for inbound tourist bookings to the same Australian destinations, including alternative accommodations and apartments.

Emerging players

• YourStay: Emerging Australian short-term rental management and booking platform focused on the premium segment. Competes in a similar niche (quality-managed holiday homes) and could overlap with Winning Holidays' Prestige Retreats category.

Direct peers

• MadeComfy: Australian technology-enabled short-term rental manager providing end-to-end services to property owners. Competes with Winning Holidays' property management arm and owner-portal offering, particularly in Sydney and key metro markets.
• Hometime: Australian full-service short-term rental property manager and platform, offering co-hosting, dynamic pricing, and cleaning services. Direct competitor for property owners and operates in overlapping Australian markets.
• Stayz: Australia's leading vacation rental marketplace under the VRBO/Expedia Group umbrella, offering direct booking of holiday homes across the same coastal regions Winning Holidays serves. Closest direct competitor for guest bookings and owner acquisition.

Others

• Guesty: Property management SaaS platform used by vacation rental managers globally. Adjacent comparison to Winning Holidays' own Homhero-based owner portal and could be a competitive or partnership threat to in-house property management technology.
• Mr & Mrs Smith: Curated luxury hotel and villa booking platform with a curated-verified model. Comparable to Winning Holidays' Prestige Retreats and luxury villa/Prestige Holiday Homes positioning at the upper end of the holiday rental market.
• Hostaway: Channel manager and PMS for vacation rental managers, offering unified inbox, dynamic pricing, and multi-channel distribution. Comparable technology infrastructure to what Winning Holidays would need to scale beyond its regional brand portfolio.

Market position

Strengths5 records

Weaknesses5 records

Competitive moat3 records

Key risks5 records

Key highlights6 records

Customer concentration

• Facebookfacebook.com/WinningHolidays
• LinkedInau.linkedin.com/company/winning-holidays
• Instagraminstagram.com/winning.holidays
• Xx.com/winningholidays

Revenue estimate

Valuation estimate

Number of profiles

Subsidiaries22 records

Funding overview

Funding rounds

Investors

Funding detail is available on the Subscription and Enterprise plan.Contact sales →

M&A

Investments

M&A and investment is available on the Subscription and Enterprise plan.Contact sales →

Frequently asked questions about Winning Holidays