Anna Maria Vacations

What Anna Maria Vacations does

Anna Maria Vacations, legally organized as AMI Sunshine Vacations LLC, is a locally owned and operated vacation rental management company headquartered at 3018 Avenue C in Holmes Beach, Florida. Founded in 2004, the company manages approximately 168 short-term rental properties spanning homes, condos, duplexes, and townhouses across Anna Maria Island's three communities: Anna Maria, Holmes Beach, and Bradenton Beach. The company serves individual leisure travelers — primarily families, couples, extended-stay guests, and pet owners — seeking direct-booked beach accommodations on the Florida Gulf Coast, with select discount programs extending marketing reach to Siesta Key and Lido Key.

The business operates a direct-to-consumer model with reservations handled through the company's proprietary booking platform built on the TrackHS property management system, which integrates reservation management, guest login, owner portal access, and property listings. The platform is complemented by phone-based reservations, third-party guest screening through SafelyStay, and on-island 24/7 guest services with in-house maintenance. Revenue is generated through booking fees and property management economics on the rental portfolio, supplemented by ancillary streams including Travel Protect Insurance commissions (partnered with Generali Global Assistance), supplemental pet fees, non-refundable damage waivers, and curated Exclusive Experiences (dolphin tours, sunset cruises, parasailing, sandbar tours, watersports). Pricing follows a tiered transaction-based model with property-specific rates, staged payment schedules (25% at reservation, 25% at 90 days, 50% at 60 days prior to arrival), and a multi-channel marketing approach spanning the company's website, Facebook, Instagram, email, and a Guest Storytellers referral program.

Name

Anna Maria Vacations

Legal name

AMI Sunshine Vacations LLC

Website

https://annamaria.com

Company type

Private

Founded year

2004

Operating status

Operating

Headcount range

1–10 employees

Short description

Anna Maria Vacations is a locally owned, Holmes Beach-based vacation rental management company operating 168 properties across Anna Maria Island, Florida. It serves individual leisure travelers via direct online booking on its TrackHS-powered platform, with on-island guest services and ancillary insurance and experience offerings.

Ownership category

akta.pro rank

Product category

Vacation Rental Services

NAICS

Residential Property Managers (531311), Real Estate Property Managers (53131), Accommodation (721), Other Traveler Accommodation (72119)

SIC

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

akta.pro primary industry

Full-Service Vacation Rental Property Management (BPAJAIAA)

akta.pro secondary industries

Vacation & Short-Term Rental Management (BPAJAFAI), Full-Service Vacation Rental Property Management (THAMAKAA), Beachfront & Lakefront Homes (THAMAAAF)

Keywords

• Vacation rental management
• Beachfront property rentals
• Short-term rental services
• Property management services
• Island vacation accommodations

Headquarters

HQ city

Holmes Beach

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, Others

Revenue model

1. Vacation Rental Bookings: The company earns revenue through booking fees and rental income from managing a portfolio of vacation rental properties on Anna Maria Island. Revenue is generated from property owners who list their homes, with the company handling reservations, guest services, and property maintenance. The payment structure requires 25% at reservation, 25% at 90 days prior, and 50% at 60 days prior to arrival.
2. Travel Insurance Partnerships: Partnership with Generali Global Assistance to offer Travel Protect Insurance plans to guests during checkout or via phone, generating referral or commission revenue
3. Pet Fees: Supplemental pet cleaning fee of $250 per reservation for dog-friendly properties, plus taxes
4. Damage Waiver and Incidentals: Non-refundable damage waiver included in reservations covers accidental damage; charges may apply for intentional damage, theft, excess cleaning, or pet damage

Pricing tiers

Go-to-market motion1 record

Distribution channels3 records

Marketing channels6 records

Core offering

Anna Maria Vacations manages and rents a portfolio of 168+ vacation rental properties on Anna Maria Island, Florida, including beachfront homes, waterfront villas, pool retreats, pet-friendly rentals, and beach condos. The company provides direct booking services, on-island guest support, professional cleaning, and property maintenance, while also offering property management services for homeowners and curated local experiences.

Product overview

Anna Maria Vacations operates a vacation rental platform offering short-term rental properties on Anna Maria Island, Florida. The core offering consists of vacation rental properties across multiple sub-categories including beachfront rentals, waterfront/canal-front rentals, pet-friendly homes, pool homes, and beach condos. The company also offers 168+ properties available for booking. Add-on services include Travel Protect Insurance (partnered with Generali Global Assistance), curated Exclusive Experiences (dolphin tours, sunset cruises, watersports), and various promotional discounts. Property Management Services are offered for homeowners. The portfolio spans three island communities: Anna Maria (North End), Holmes Beach (Central), and Bradenton Beach (South End).

Differentiator

Problem solved

Functional benefit

Products and services

• Vacation Rental Properties Short-term vacation rental properties on Anna Maria Island, including beachfront homes, waterfront rentals, pool retreats, pet-friendly rentals, and beach condos. Available for booking through the company's website and phone reservations, serving families, couples, and groups seeking beach vacations.
• Property Management Services Full-service vacation rental property management for homeowners on Anna Maria Island, including listing creation, guest reservations, 24/7 guest services, professional cleaning, linen service, and in-house maintenance. Targeted at property owners seeking professional rental management.
• Travel Protect Insurance Travel insurance offered in partnership with Generali Global Assistance, covering trip cancellation, trip interruption, flight delays, lost baggage, and medical emergencies. Available as an add-on at checkout or via phone reservations.
• Exclusive Experiences Curated local activities and tours available to guests, including dolphin tours, Egmont Key tours, sunset cruises, parasailing, sandbar tours, watersports rentals, and boat rentals, designed to enhance the island vacation experience.

Quantifiable outcome

• 168 vacation rental properties available
• +2 more outcomes

Named customers3 records

Segments5 records

Ideal customer profiles2 records

Technology focussed No

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Feature2 records

Partnerships

Six partnerships are on record, tiered core and supporting.

• Generali Global AssistancecoreStrategic or Co-development PartnerPartnership with Generali Global Assistance to offer Travel Protect Insurance plans to guests. The insurance covers trip cancellation, trip interruption, flight delays, lost luggage, and medical emergencies during stays. Offered during online checkout or by phone through the Reservations team.
• SafelyStay, Inc.supportingTechnology or IntegrationThird-party guest screening and background verification service used to verify guest identity and check criminal databases as part of the reservation process. Failure to complete screening may result in reservation cancellation.
• ABC Baby RentalssupportingGTM or Marketing PartnerRecommended partner for baby equipment rentals including highchairs and cribs, with delivery available to vacation properties.
• Fun and More RentalssupportingGTM or Marketing PartnerRecommended partner for beach equipment rentals including chairs and umbrellas, referenced in FAQ section for guest convenience services.
• Island Mail & PrintsupportingGTM or Marketing PartnerRecommended partner for secure package receiving, as the company does not recommend sending mail or packages directly to rental properties.
• Manatee County Emergency ManagementsupportingStrategic or Co-development PartnerCoordination with Manatee County for hurricane evacuation protocols, mandatory evacuation orders, and emergency communication during tropical weather events.

Scale indicators3 records

Recent moves3 records

Expansion highlights6 records

Emerging players

• AvantStay: Tech-forward short-term rental manager focused on premium U.S. leisure destinations, combining professional property management with a tech-enabled guest booking experience. Comparable business model at the property-management layer and increasingly overlapping beach destinations.

Broad incumbents

• Vrbo: Major vacation rental platform (part of Expedia Group) with deep presence in U.S. family beach destinations including the Florida Gulf Coast. Competes as both a distribution channel and increasingly as a managed-listing competitor to local managers like Anna Maria Vacations.
• Airbnb: Global online travel platform and the dominant third-party channel for short-term vacation rentals. A broad incumbent that competes indirectly by aggregating Anna Maria Island inventory and capturing booking flow that Anna Maria Vacations explicitly tries to disintermediate via direct bookings.

Direct peers

• Vacasa: Largest full-service vacation rental management company in North America, operating professional property management for owners across beach, mountain, and urban destinations. Directly comparable business model to Anna Maria Vacations — local-market full-service management, owner-portal PMS, and direct guest booking — but at vastly greater scale.
• TurnKey Vacation Rentals: Technology-enabled full-service vacation rental manager operating in top U.S. leisure destinations. Comparable end-to-end model — professional cleaning, in-house maintenance, local field teams, direct booking — and overlapping coastal/leisure customer base.
• Evolve: National full-service vacation rental manager that combines a homeowner-facing property management offering with a guest booking platform. Highly comparable to Anna Maria Vacations in core service model (full-service management plus direct booking) and in emphasizing owner and guest experience.
• iTrip Vacations: Franchise-based short-term rental property management company with strong presence in U.S. beach and ski destinations, including the Florida Gulf Coast. Comparable full-service vacation rental management model and similar local-market direct-booking emphasis.

Market position

Strengths4 records

Weaknesses4 records

Competitive moat3 records

Key risks6 records

Key highlights7 records

Customer concentration

• Facebookfacebook.com/amivacations
• Instagraminstagram.com/annamariavacations
• Xx.com/AMIvacations
• LinkedInlinkedin.com/company/anna-maria-vacations

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 Anna Maria Vacations