ISLAND REAL ESTATE

What ISLAND REAL ESTATE does

Island Real Estate is a privately-held vacation rental management and real estate brokerage operating exclusively on Anna Maria Island, Florida—a single 7-mile barrier island on the state's Gulf Coast. Founded in 1970 and led by Broker/Owner Larry Chatt, the company manages a portfolio of vacation rental properties spanning beachfront homes, condominiums, pet-friendly units, and pool-equipped houses across Holmes Beach, Bradenton Beach, and Anna Maria City, while also operating a real estate sales division for property purchases and sales on the island. Day-to-day vacation rental operations are led by CEO Jodi Nichols (Island Real Estate Vacations), with Kacey Varga as Revenue Manager and Carol Bernard handling sales support; the firm employs 11–50 people across multiple on-island offices.

The company generates revenue through three streams: property management fees from owners (covering marketing, booking, guest services, maintenance, and inspections), transaction-based commissions on direct vacation rental bookings via islandreal.com, and real estate sales commissions on property transactions. Its technology stack is built on TrackHS property management software, which powers an owner portal, guest login, availability calendars, and integrated payment processing. The direct booking platform is positioned explicitly against third-party OTAs (Airbnb, VRBO) on the basis of upfront all-in pricing and on-island customer service.

Go-to-market is hybrid: a direct-to-consumer website and phone reservations channel (877-778-6066) for vacation rentals, complemented by a sales-led real estate brokerage for property transactions. Marketing relies on an extensive local content blog (~100+ articles on Anna Maria Island activities, dining, and area guides), organic social presence on Facebook/Instagram/TikTok, Google reviews, and local SEO. The firm also operates a German-language site (annamariaferienhaus.de) targeting European inbound demand, and has partnered with TripPreserver for hurricane-season trip insurance. Memberships in the Anna Maria Island Chamber of Commerce, VRMA, and FAVR round out its institutional positioning within the regional vacation rental industry.

Name

ISLAND REAL ESTATE

Legal name

Island Real Estate

Website

https://islandreal.com

Company type

Private

Founded year

1970

Operating status

Operating

Headcount range

11–50 employees

Short description

Island Real Estate is a privately-held vacation rental manager and real estate brokerage operating exclusively on Anna Maria Island, Florida. It serves individual vacation renters, property owners, and real estate buyers using a direct-booking platform, local on-island offices, and TrackHS-based property management software.

Ownership category

akta.pro rank

Product category

Vacation Rental Management

NAICS

Real Estate Property Managers (53131), Residential Property Managers (531311)

SIC

Hotels, Rooming Houses, Camps & Other Lodging Places (7000), Real Estate Agents & Managers (For Others) (6531)

akta.pro primary industry

Vacation & Short-Term Rental Management (BPAJAFAI)

akta.pro secondary industries

Beachfront & Lakefront Homes (THAMAAAF), Luxury Beachfront & Waterfront Villas (THAMAEAE)

Keywords

• Vacation rental management
• Vacation rental booking
• Real estate sales
• Property management services
• Condominium association management

Headquarters

HQ city

Holmes Beach

HQ country

United States

HQ region

North America

Offices3 records

Markets served

GTM type

B2B and B2C

Offering type

Services

Cost components

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

Revenue model

1. Vacation Rental Management: The company manages vacation rental properties on Anna Maria Island, earning revenue through property management fees from property owners. They handle marketing, booking, guest services, maintenance, and inspections for vacation homes.
2. Real Estate Sales Commissions: The company earns commissions on real estate sales transactions through their sales division. They assist buyers in finding properties and help sellers list and sell homes on Anna Maria Island.
3. Vacation Rental Booking Revenue: Revenue generated from guest bookings of vacation rental properties. Pricing varies by property, with nightly rates, cleaning fees, and taxes quoted upfront with no hidden fees.

Pricing tiers

Go-to-market motion2 records

Distribution channels4 records

Marketing channels5 records

Core offering

Island Real Estate manages and directly books vacation rental properties on Anna Maria Island, Florida, offering a portfolio of beachfront homes, condos, dog-friendly rentals, and homes with private pools. The company also provides real estate sales brokerage for island property purchases, condominium association management, and annual/long-term rentals. Guests transact exclusively via the company's own website and phone reservations, bypassing third-party platforms such as Airbnb and VRBO.

Product overview

Island Real Estate operates as a comprehensive vacation rental management company on Anna Maria Island, Florida. Their core offerings consist of a Vacation Rental Management platform and a Direct Booking Platform, supplemented by Real Estate Sales services for property purchases. The vacation rental portfolio includes various property types such as beachfront rentals, dog-friendly rentals, and homes with pools. Additional services include Condominium Association Management, Annual Rentals, and Grocery Delivery Coordination. The company serves both vacation rental guests seeking direct booking access and property owners looking to list their homes or purchase investment properties on the island.

Differentiator

Problem solved

Functional benefit

Products and services

• Vacation Rental Management Full-service vacation rental management for property owners on Anna Maria Island, including listing marketing, booking, guest services, property maintenance, cleaning between stays, and post-departure inspections.
• Anna Maria Island Vacation Rentals Bookable portfolio of vacation rental properties across Anna Maria Island, including beachfront homes, condos, houses with pools, and dog-friendly rentals, available for short-term stays.
• Direct Booking Platform Online direct-booking platform at islandreal.com that allows guests to search, filter, view availability, and book vacation rentals with no hidden fees.
• Real Estate Sales Real estate brokerage for buyers and sellers of Anna Maria Island properties, including MLS listings, agent representation, and investment property consultation.
• Condominium Association Management Management services for condominium associations on Anna Maria Island, including maintenance coordination and administrative support.
• Annual Rentals Long-term annual rental property management services for residents and seasonal visitors seeking monthly or multi-month stays on Anna Maria Island.

Quantifiable outcome

• 50+ years in the vacation rental business on Anna Maria Island
• +1 more outcomes

Named customers2 records

Segments4 records

Ideal customer profiles3 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.

• TripPreserverminorGTM or Marketing PartnerTripPreserver is a trip insurance provider that Island Real Estate frequently works with for customers visiting during hurricane season. The company recommends trip insurance to guests and works with TripPreserver for policy coverage, particularly for June 1 to November 1 hurricane season bookings where policies must be purchased before a storm is named.

Scale indicators2 records

Recent moves6 records

Expansion highlights5 records

Direct peers

• Anna Maria Vacations: Another long-established vacation rental management company operating exclusively on Anna Maria Island, with overlapping property inventory in Holmes Beach, Bradenton Beach, and Anna Maria City, and a similar direct-to-guest booking model.
• Tidewater Vacations: Anna Maria Island-based vacation rental manager offering beachfront and island home rentals with a comparable direct booking platform and concierge service model.
• Sato Real Estate: Long-standing Anna Maria Island real estate and vacation rental firm offering overlapping MLS sales, property management, and rental services in the same Holmes Beach and Bradenton Beach micro-markets.
• Mike Norman Real Estate: Anna Maria Island-focused brokerage and rental agency competing for both owner management contracts and direct guest bookings in Holmes Beach and Bradenton Beach.

Broad incumbents

• Vacasa: National full-service vacation rental management company that competes for managed properties and direct-booking traffic in coastal Florida markets, offering owners a scalable alternative to local operators.
• Evolve Vacation Rental: National vacation rental management platform focused on lower-fee, owner-friendly management; competes for the same property owner relationships on Anna Maria Island and across Florida Gulf Coast destinations.
• Airbnb: Global OTA and alternative distribution channel that Island Real Estate deliberately avoids; sets guest expectations for price transparency, search UX, and review-driven discovery that influence the company's direct booking platform design.
• VRBO (Expedia Group): Major vacation rental OTA whose commission structure and broad reach are explicitly cited by Island Real Estate as the rationale for its direct-booking positioning, making it the most direct substitute for guest acquisition.

Emerging players

• LocalVR (Local Vacation Rentals): Multi-market vacation rental management operator with a local-presence model that targets exactly the type of owner served by Island Real Estate, including Florida Gulf Coast markets.
• iTrip Vacations Anna Maria Island: Franchise-style vacation rental management company with an Anna Maria Island franchisee, offering owner management services and direct-booking listings on the same island.

Market position

Strengths4 records

Weaknesses4 records

Competitive moat4 records

Key risks5 records

Key highlights5 records

Customer concentration

• YouTubeyoutube.com/user/islandreal
• Facebookfacebook.com/IslandReal
• Instagraminstagram.com/islandrealestateami
• TikToktiktok.com/@islandrealestateami
• Xx.com/islandreal

Revenue estimate

Valuation estimate

Number of profiles

Profiles4 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 ISLAND REAL ESTATE