La Siesta Resort

What La Siesta Resort does

La Siesta Resort & Villas is a privately held boutique resort located at 80241 Overseas Highway in Islamorada, Florida, within the Florida Keys. It operates as one of three properties in the Islamorada Resort Collection alongside Amara Cay Resort and Three Waters Resort & Marina, with guests receiving cross-property access to five beaches and pools, twelve restaurants, and a Rum Runner water taxi service. The property offers four accommodation tiers — Beachfront Cottages, Coastal Villas, Ocean Suites, and Tropical Garden Suites — including four premium Coastal Villas (notably the Marbella) with dedicated butler service and private dock slips, complemented by amenities such as the SIDECAR poolside bar, Siesta Mercato retail shop, full-service marina, watersports (kayaks, paddleboards, bikes, fishing charters, jet skis), and destination wedding/event venues.

The resort runs on the third-party Synxis property management and booking platform, which powers centralized reservations across the three collection properties via the islamoradaresortcollection.com website and a single 1-888-313-6200 phone line. Revenue is generated across five streams: accommodation (rooms, cottages, villas, suites), food and beverage, marina services, bookable experiences, and retail. Go-to-market is direct-to-consumer with promotional pricing tiers (up to 40% off standard rooms, up to 30% off advance purchase, regional resident and AAA discounts, villa packages with F&B credits), supported by a multi-channel social presence (Instagram, Facebook, YouTube, TikTok), email marketing, and a Travel Professionals referral program.

Customer segmentation is horizontal across couples and individual travelers, families and groups, wedding couples, special-event organizers, and boaters/watersports enthusiasts. No AI/ML capabilities, no venture or private equity backing, and no publicly disclosed financial metrics (revenue, headcount beyond a 7-employee figure likely limited to corporate staff, ownership structure) are present in the source material, and the resort received the 2025 TripAdvisor Travelers' Choice Award based on guest review performance.

Name

La Siesta Resort

Legal name

La Siesta Resort & Villas

Website

https://lasiestaresort.com

Company type

Private

Operating status

Operating

Headcount range

1–10 employees

Short description

La Siesta Resort & Villas is a privately held boutique beachfront resort in Islamorada, Florida Keys, offering cottages, villas, and suites as part of the three-property Islamorada Resort Collection. It serves leisure couples, families, wedding groups, and boaters through direct-to-consumer bookings, on-site dining, marina, and watersports amenities.

Ownership category

akta.pro rank

Product category

Beach Resort Hospitality

NAICS

Hotels (except Casino Hotels) and Motels (72111), Traveler Accommodation (7211)

SIC

Hotels & Motels (7011), Hotels, Rooming Houses, Camps & Other Lodging Places (7000)

akta.pro industry

PRIMARYTHAGACAA

Beachfront & Island Luxury Resorts

Travel & Hospitality/Lodging & Accommodation/Luxury Hotels & Resorts

SECONDARYTHAGACAM

Luxury Villas & Residences Resorts

Travel & Hospitality/Lodging & Accommodation/Luxury Hotels & Resorts

SECONDARYTHAGAAAK

Marina & Waterfront Full-Service Hotels

Travel & Hospitality/Lodging & Accommodation/Hotels (Full-Service)

SECONDARYTHAMAEAE

Luxury Beachfront & Waterfront Villas

Travel & Hospitality/Vacation Rentals & Short-Term Stays/Luxury Villas & Premium Rentals

Keywords

• Beachfront resort accommodations
• Marina dock services
• Destination wedding venues
• Watersports recreational activities
• Island hospitality services

Headquarters

HQ city

Islamorada

HQ country

United States

HQ region

North America

Offices1 record

Markets served

GTM type

B2C

Offering type

Services

Cost components

Personnel, Operations, Marketing or Sales, Infrastructure, Supply Chain

Revenue model

1. Accommodation Revenue: Room, cottage, villa, and suite rentals across multiple accommodation types including Beachfront Cottages, Coastal Villas, Ocean Suites, and Tropical Garden Suites. Includes villa Butler Service.
2. Food and Beverage: On-site dining through SIDECAR poolside bar, In-Room Dining, Siesta Mercato, and access to 12 culinary destinations across the three-resort collection. Includes $100-$200 food and beverage credits offered in promotional packages.
3. Marina Services: Dock slips for boats and jet skis, marina access connecting to Three Waters Resort & Marina for fuel, ice, and provisions. Water taxi service.
4. Experiences and Activities: Watersports equipment (kayaks, paddleboards, bikes included), fishing charters, poolside cabana rentals, bookable experiences, wedding and event venues. Some experiences require additional fees beyond accommodation.
5. Retail and Shopping: Siesta Mercato retail shop offering souvenirs and goods. Salt and Sea store with 10% discount offered to resort guests.

Pricing tiers

Go-to-market motion1 record

Distribution channels3 records

Marketing channels4 records

Core offering

La Siesta Resort & Villas operates a Florida Keys beachfront resort in Islamorada offering tropical island-style accommodations (Beachfront Cottages, Coastal Villas, Ocean Suites, Tropical Garden Suites), on-site dining (SIDECAR poolside bar, In-Room Dining, Siesta Mercato retail), marina and water taxi services, watersports activities, and destination wedding/event venues. Guests also gain access to amenities across the three-resort Islamorada Resort Collection, including five pools and beaches and twelve restaurants.

Product overview

La Siesta Resort & Villas is a Florida Keys resort offering a portfolio of island-style accommodations and experiences. The property features multiple accommodation tiers: Beachfront Cottages, Beachfront Casitas, Ocean Suites, and Tropical Garden Suites as core room products, plus four premium Coastal Villas (including the Marbella villa) with dedicated butler service and private dock slips. Dining offerings include SIDECAR poolside bar, in-room dining, and Siesta Mercato retail shop. The resort provides water transportation via the Rum Runner Water Taxi, full-service marina facilities, and recreational activities including kayaks, paddleboards, bikes, fishing charters, and jet skis. Event services encompass beachfront wedding venues and special event planning. Guests receive access to all restaurants, amenities, and experiences across the three sister resorts in the Islamorada Resort Collection (La Siesta, Amara Cay, and Three Waters), which collectively offer five beaches and pools and twelve culinary destinations.

Differentiator

Problem solved

Functional benefit

Products and services

• Beachfront Cottages

Segments5 records

Ideal customer profiles4 records

Technology focussed No

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Feature1 record

Partnerships

Two partnerships are on record, tiered core.

• Amara Cay ResortcoreOthersSister resort property within the Islamorada Resort Collection. La Siesta guests have access to amenities, restaurants, and experiences at Amara Cay as part of the collection benefits.
• Three Waters Resort & MarinacoreOthersSister resort and marina property within the Islamorada Resort Collection. Connected via Rum Runner water taxi service. La Siesta guests access Three Waters' fuel, ice, marina services, and additional dining options.

Scale indicators5 records

Recent moves5 records

Expansion highlights4 records

Direct peers

• The Moorings Village: Boutique luxury resort in Islamorada featuring private villas, beach access, and concierge service. Comparable because of shared Islamorada micro-market, villa-based product, and similar luxury positioning.
• Pier House Resort & Spa: Key West beachfront resort with suites, spa, marina proximity, and wedding venues. Comparable Keys-based full-service resort serving couples, families, and event business with similar amenity mix.
• Three Waters Resort & Marina: Sister property and marina hub in the Islamorada Resort Collection; offers comparable accommodations, marina services, and dining. Comparable because of shared customer overlap and direct cross-property integration via the Rum Runner water taxi.
• Playa Largo Resort & Spa: Key Largo oceanfront resort with bungalows, villas, marina/dock access, multiple dining outlets, and event venues. Comparable Keys luxury resort with similar marina-adjacent amenity set and event-driven demand.
• Hawks Cay Resort: Full-service Florida Keys resort in Marathon offering villas, marina, multiple dining outlets, and watersports. Comparable as a similar Keys-based resort operating comparable accommodation tiers and marina amenities for leisure travelers and boaters.
• Amara Cay Resort: Sister property within the Islamorada Resort Collection operating the same direct-to-consumer booking model and sharing guests, amenities, and dining venues. Directly comparable because it shares location, customer base, and operational structure.
• Tranquility Bay Resort: Marathon, FL beachfront resort offering beach houses, suites, marina access, and watersports. Comparable because of overlapping product (villa-style accommodations, marina, included watersports) and overlapping Keys leisure and family traveler demand.
• Cheeca Lodge & Spa: Long-established Islamorada luxury resort with cottages, suites, spa, and oceanfront F&B. Comparable because it targets the same Islamorada leisure traveler, weddings/events segment, and price-tier as La Siesta.
• Baker's Cay Resort: Curio Collection resort in Key Largo offering beachfront accommodations, marina, multiple dining venues, and event space. Comparable Florida Keys luxury positioning with overlapping amenities and target segments.

Broad incumbents

• The Ritz-Carlton Key Biscayne: Established luxury beachfront resort in South Florida offering comparable premium accommodations, multiple dining outlets, spa, and event venues. Comparable as a Florida beachfront luxury resort competing for the same Florida leisure and event demand at a higher brand tier.

Market position

Strengths5 records

Weaknesses5 records

Competitive moat4 records

Key risks5 records

Key highlights6 records

Customer concentration

• YouTubeyoutube.com/@islamoradaresortcollection
• Facebookfacebook.com/LaSiestaResortandMarina
• Instagraminstagram.com/lasiestaresortmarina
• TikToktiktok.com/@lasiestaresortandvillas
• LinkedInlinkedin.com/company/la-siesta-resort

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 La Siesta Resort