Keys Holiday Rentals, Inc

What Keys Holiday Rentals, Inc does

Keys Holiday Rentals, Inc. is a privately held vacation rental management company operating in the Upper Florida Keys, headquartered in Islamorada, Florida. The company curates and manages a portfolio of 45+ properties, including single-family homes, condos, and townhomes across Islamorada, Key Largo, and Tavernier, offered on 7-night weekly and 28-night monthly minimum-stay terms. Many properties feature waterfront access, private docks, boat lifts, pools, and pet-friendly accommodations, targeting vacationing families, watersports enthusiasts, and seasonal snowbird travelers.

The business operates a two-sided model: it markets, books, and manages vacation properties on behalf of homeowners (earning management fees), while also serving as the direct booking channel for guests (earning a transaction fee on rental revenue). All reservations are processed through the StreamlineVRS property management platform, which provides a guest portal, owner portal, and availability calendar integration. The company emphasizes a 'Book Direct and Save' positioning to capture bookings outside of third-party OTAs and markets through its own website, email newsletter, and Instagram presence.

Keys Holiday Rentals was founded in 2007 and operates with a micro team of 1-10 employees. It does not publicly disclose revenue, has no recorded funding rounds, no disclosed institutional investors, and no parent company. Ancillary offerings include local-area concierge guides covering dining, activities, and groceries, and a recommended travel insurance partnership with TripPreserver. The company positions itself on 40+ years of local property management experience and strong community relationships in the Florida Keys.

Name

Keys Holiday Rentals, Inc

Legal name

Keys Holiday Rentals

Website

https://keysholidayrentals.com

Company type

Private

Founded year

2007

Operating status

Operating

Headcount range

1–10 employees

Short description

Keys Holiday Rentals is a privately held vacation rental management company in the Upper Florida Keys that curates and manages 45+ waterfront, pool, and dock-equipped homes and condos for weekly and monthly stays, serving vacationers and property owners.

Ownership category

akta.pro rank

Product category

Vacation Rental Services

NAICS

Rental and Leasing Services (532)

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), Large Group & Event-Friendly Homes (THAMAAAM)

Keywords

• Vacation rental management
• Short-term rental properties
• Property management services
• Florida Keys accommodations
• Weekly monthly rentals

Headquarters

HQ city

Islamorada

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, Supply Chain

Revenue model

1. Vacation Rental Revenue: Keys Holiday Rentals generates revenue by managing and renting vacation properties on behalf of property owners in Islamorada and the Florida Keys. The company offers 7-night weekly rentals and 28-night monthly rentals, with published rates plus 12.5% state/local taxes. Revenue is collected from guests at the time of booking.
2. Property Management Services: The company provides property management services for property owners, including marketing, maintenance, guest services, and rental income optimization. The property management section emphasizes 'over 40 years of property management and unsurpassed community relationships.' Revenue from this stream comes from management fees charged to property owners.

Pricing tiers

Go-to-market motion1 record

Distribution channels3 records

Marketing channels5 records

Core offering

Keys Holiday Rentals manages and markets a curated collection of 45+ vacation rental properties (homes, condos, townhomes) in the upper Florida Keys for 7-night weekly and 28-night monthly stays, generating rental income from guests. The company also provides property management services to homeowners, handling marketing, reservation management, guest coordination, and maintenance, earning management fees on that stream.

Product overview

Keys Holiday Rentals operates a vacation rental marketplace platform offering a curated collection of properties throughout Islamorada and the Florida Keys. The core product is the vacation rental marketplace, which connects property owners with travelers seeking short-term accommodations. Properties span multiple categories including single-family homes, condominiums, and townhomes, with specialized options for private pools, boat docks, waterfront access, and pet-friendly stays. Rental terms include weekly (7-night minimum) and monthly (28-night minimum) options. The company also provides ancillary services including concierge services for local area guidance (dining, activities, groceries) and property management services for homeowners seeking to list their properties. The platform emphasizes direct booking through its 'Book Direct and Save' program. Notable properties include Sandglass 4 (luxury 5-bedroom home), Twice The Charm (4-bedroom with private pool), Villa Riolo (oceanfront), multiple units at The Palms and Ocean Harbour condo complexes, and Martin Family Fish Camp (Keys-style cottages).

Differentiator

Problem solved

Functional benefit

Products and services

• Vacation Rentals Curated collection of 45+ vacation rental properties throughout Islamorada and the upper Florida Keys, including homes, condos, and townhomes available for weekly (7-night minimum) and monthly (28-night minimum) stays. Properties include amenities such as private pools, boat docks, waterfront access, and pet-friendly options.
• Property Management Services Full-service property management for homeowners in the Florida Keys, including rental marketing, reservation management, guest coordination, maintenance coordination, and rental income optimization. Backed by 40+ years of property management experience and community relationships.
• Concierge Services Local concierge support for guests, including local area guides, dining recommendations, activities, and grocery store information to help plan the Florida Keys experience.
• Book Direct and Save Direct booking incentive program allowing guests to book directly with Keys Holiday Rentals to save on booking fees, bypassing third-party platforms.

Named customers6 records

Segments4 records

Ideal customer profiles4 records

Technology focussed No

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Integration2 records

Scale indicators3 records

Recent moves4 records

Expansion highlights4 records

Direct peers

• Vacasa: Vacasa is the largest US vacation rental management company, offering full-service property management and direct booking for homeowners in destinations including Florida. It is a direct competitor to Keys Holiday Rentals' management-and-rental model in coastal Florida markets.
• Evolve Vacation Rental Network: Evolve is a national vacation rental management company using a lighter-touch professional management model for homeowners. It directly competes for Keys-area homeowner contracts and competes for traveler bookings via direct-book channels.

Broad incumbents

• Vrbo (Expedia Group): Vrbo is a leading vacation rental OTA specializing in whole-home family travel. It is a primary competitor for Keys Holiday Rentals' 'Book Direct and Save' positioning, especially with multi-generational family travel to Florida.
• Airbnb: Airbnb is the dominant OTA for vacation rentals globally and in the Florida Keys. It competes directly for guest bookings while also enabling hosts to self-manage, putting pressure on professional managers like Keys Holiday Rentals.
• Tripadvisor / FlipKey: Tripadvisor's FlipKey vacation rental marketplace aggregates Keys listings alongside reviews. Functions as an OTA competitor and a marketing channel alternative to Keys Holiday Rentals' direct-booking site.
• Marriott Homes & Villas: Marriott's vacation rental platform offers professionally managed whole-home rentals through a major hotel loyalty ecosystem. It competes for upscale Keys travelers and brings brand-driven distribution advantages.

Regional players

• Rentals United Florida Keys: A Florida-focused regional vacation rental platform aggregating Keys inventory and offering channel management tools. Competes with Keys Holiday Rentals for traveler demand and, indirectly, for homeowner supply in the same geography.
• Florida Keys Vacation Rentals (Coldwell Banker Schmitt): A Florida Keys-focused vacation rental program operated by a brokerage, managing Keys homes and condos. Directly comparable in geography, target customer, and service offering to Keys Holiday Rentals.
• American Dream Vacations (Florida Keys): A local Florida Keys vacation rental management company offering direct booking of homes and condos. Directly competes with Keys Holiday Rentals for both homeowners and guests in the same upper Keys sub-market.

Emerging players

• Sonder: Sonder operates tech-enabled short-stay apartments and vacation-style accommodations in select destinations. While not currently a major Keys operator, it represents the emerging tech-enabled managed-stay model that could compete for premium Keys inventory over time.

Market position

Strengths5 records

Weaknesses5 records

Competitive moat3 records

Key risks6 records

Key highlights6 records

Customer concentration

• LinkedInlinkedin.com/company/keys-holiday-rentals-inc

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 Keys Holiday Rentals, Inc