Holiday Isle Properties

What Holiday Isle Properties does

Holiday Isle Properties, Inc. is a privately held, owner-operated vacation rental management company headquartered at 842 Highway 98 East, Destin, Florida, founded in 1985. The company manages a portfolio of beachfront condominiums, standalone beach homes, townhomes, and villas across Destin, Okaloosa Island, and Miramar Beach on Florida's Gulf Coast, with unit sizes ranging from one-bedroom condos up to six-bedroom beach homes accommodating 15+ guests. Core product lines include beachfront rentals, condo rentals, home rentals, luxury rentals (marketed via the "The 100 Collection™" sub-brand), and specialized verticals such as pet-friendly, boat-dock, and snowbird extended-stay rentals; beach chair and umbrella service is included with select properties.

The company's technology stack relies on the third-party TrackHS platform for its direct-booking website, providing real-time availability calendars, property search, online reservations, and owner-facing tools. Holiday Isle operates a direct-to-consumer go-to-market model with no third-party booking distribution; reservation channels are limited to its website (www.holidayisle.net), a toll-free phone line (1-800-837-5102), and an online contact form. Marketing is anchored on a content-marketing blog covering Destin attractions and seasonal events, supplemented by Facebook, Twitter/X, YouTube, and a monthly email newsletter, with the explicit objective of driving organic, fee-free direct bookings rather than OTA traffic.

Revenue is generated via transaction fees on nightly and weekly vacation rental bookings, with seasonal pricing variations across a portfolio that includes properties at resorts such as SeaCrest, Alerio, Oceania, Mainsail, Silver Beach, Jade East, Shoreline Towers, and Destin Pointe. The company emphasizes a Best Price Guarantee positioning that claims 5%-20% savings versus third-party booking platforms. Employee count is stated at 11-50, and ownership is independent with no disclosed parent, investors, or subsidiaries; revenue figures are not publicly disclosed.

Name

Holiday Isle Properties

Legal name

Holiday Isle Properties, Inc.

Website

https://holidayisle.net

Company type

Private

Founded year

1985

Operating status

Operating

Headcount range

11–50 employees

Short description

Holiday Isle Properties is a privately held, owner-operated vacation rental management company founded in 1985 in Destin, Florida, managing beachfront condos, homes, and townhomes across Destin, Okaloosa Island, and Miramar Beach via a direct-to-consumer website and phone booking channel.

Ownership category

akta.pro rank

Product category

Vacation Rental Services

NAICS

Other Traveler Accommodation (72119)

SIC

Hotels, Rooming Houses, Camps & Other Lodging Places (7000)

akta.pro primary industry

Beachfront & Lakefront Homes (THAMAAAF)

akta.pro secondary industries

Luxury Beachfront & Waterfront Villas (THAMAEAE), Resort-Style Extended-Stay Properties (THAGAEAL)

Keywords

• Vacation rental management
• Beachfront rental properties
• Short-term condo rentals
• Destin vacation rentals
• Property management services

Headquarters

HQ city

Destin

HQ country

United States

HQ region

North America

Offices1 record

Markets served

GTM type

B2C

Offering type

Services

Cost components

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

Revenue model

1. Vacation Rental Bookings: Short-term vacation rental income from condominiums, beach homes, and townhomes in Destin, Florida. Properties range from 1-bedroom condos to 6-bedroom beach homes. Revenue is generated through nightly and weekly rental rates with seasonal pricing variations.

Go-to-market motion1 record

Distribution channels3 records

Marketing channels7 records

Core offering

Holiday Isle Properties is a vacation rental management company that books and manages short-term rentals of beachfront condominiums, beach homes, townhomes, and villas across Destin, Okaloosa Island, and Miramar Beach, Florida. Its portfolio ranges from one-bedroom condos to six-bedroom homes accommodating up to 16 guests, with select units including daily beach chair and umbrella service. The company sells and books these rentals directly to consumers via its website and toll-free phone line, supported by a Best Price Guarantee that avoids third-party booking fees.

Product overview

Holiday Isle Properties operates as a vacation rental management company offering a portfolio of beachfront properties across Destin, Okaloosa Island, and Miramar Beach, Florida. The core offering consists of individual vacation rental units managed across multiple property types: beachfront condos (at resorts such as SeaCrest, Alerio, Oceania, Mainsail, Silver Beach, Jade East, and Shoreline Towers), standalone beach homes (including luxury properties), townhomes, and villas. The company supplements its core rentals with specialized offerings including pet-friendly units, boat dock access, snowbird extended stays, and The 100 Collection™ premium tier. Guests access properties through a direct online booking engine on the company website, with amenities such as beach chair service, private pools, hot tubs, and smart TV systems included at select properties. The company was established in 1985.

Differentiator

Problem solved

Functional benefit

Products and services

• Destin Vacation Rentals

Quantifiable outcome

• Save 5%-20% by booking direct vs. third-party vacation rental sites

Segments4 records

Ideal customer profiles4 records

Technology focussed No

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Feature3 records

Scale indicators3 records

Recent moves6 records

Expansion highlights5 records

Broad incumbents

• Vacasa: One of the largest U.S. vacation rental management companies, operating in Destin and across Florida. Offers a directly comparable product (full-service vacation rental management) but at national scale with proprietary dynamic-pricing technology and unified brand.
• Evolve Vacation Rental: National vacation rental management company with a lightweight, tech-forward model for homeowner-managed properties. Competes for the same owner sign-ups in coastal Florida markets and benefits from broader marketing reach.
• Airbnb: Largest global short-term rental marketplace and the dominant demand source for Florida Gulf Coast vacation rentals. While not a direct management competitor, its algorithm and brand shape Holiday Isle's direct-booking strategy.
• VRBO: Major U.S. vacation rental marketplace (Expedia Group brand) with strong family-travel positioning that overlaps with Holiday Isle's primary family/group customer segment. A primary channel alternative for guests searching the same Destin inventory.

Direct peers

• Five Star Beach Properties: Destin-area vacation rental management company offering beachfront condos and homes in the same Emerald Coast market. Closely comparable product mix (condos, beach homes, luxury tier) and direct booking model to Holiday Isle.
• Southern Vacation Rentals: Regional vacation rental manager serving the Alabama and Florida Gulf Coast (including nearby beaches). Comparable product mix of condos and beach homes with a similar family/group traveler target customer.
• Panhandle Getaways: Boutique Florida Panhandle vacation rental company offering beachfront homes and condos in Destin and 30A-adjacent markets. Similar small-scale, locally owned management model targeting family beach vacations.
• Coastal Living Vacations: Locally owned vacation rental company on the Florida Panhandle offering Gulf-front homes and condos. Comparable product type (beachfront whole-home rentals) and similar target customer in overlapping geography.
• Newman-Dailey Resort Properties: Long-established Destin-based vacation rental and real estate management company. Directly competes with Holiday Isle Properties on condo and beach home rentals across the same Destin/Okaloosa Island geography with a similar local-expert value proposition.
• ResortQuest by Wyndham (now Vacasa): Legacy Wyndham-branded vacation rental manager operating throughout Destin and the Emerald Coast. Directly comparable managed inventory and target customer; now operated under the Vacasa umbrella, increasing scaled competition in Holiday Isle's core geography.

Market position

Strengths5 records

Weaknesses5 records

Competitive moat3 records

Key risks6 records

Key highlights6 records

Customer concentration

• Xx.com/destinrental
• YouTubeyoutube.com/user/HolidayIsleRentals
• Facebookfacebook.com/HolidayIsleProperties

Revenue estimate

Valuation estimate

Number of profiles

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 Holiday Isle Properties