Pineapple Hospitality Company

What Pineapple Hospitality Company does

Pineapple Hospitality Company is a privately held US boutique hotel operator founded in 2011, doing business as Staypineapple and headquartered in Kirkland, Washington. It owns and operates 10 individually branded boutique hotels across seven major US metros: New York City, Chicago, San Francisco, Boston, Seattle (four properties: The Maxwell Hotel, Hotel FIVE, Watertown Hotel, and University Inn), and Portland (Hotel Rose), with San Diego also referenced in its operating geographies. The company targets leisure travelers as its primary segment, with secondary segments spanning business travelers, pet owners (anchored by the Pineapple Pup Package and Pet Wellness Program), military and veterans (15% discount tier), and groups/events (weddings, corporate meetings). Brand identity centers on a colorful, design-forward aesthetic under the 'Where Stays Become Stories' tagline, with signature amenities including The Naked Experience bedding, complimentary Pineapple Bikes, and food and beverage via Bottle + Kitchen at Hotel Rose in Portland.

The underlying technology stack is built around Sabre's SynXis platform, which serves as both the responsive booking engine on staypineapple.com and the property management system across all properties; the booking engine is coded to WCAG 2.0 AA accessibility standards, audited by Accessible360, and secured via Cloudflare and SSL. The company does not disclose proprietary AI, ML, or data assets, and there are no APIs, apps, or SDK integrations documented. Revenue mechanics span five streams: hotel room bookings (primary, via direct website, phone reservations at 1-866-866-7977, and third-party OTAs), food and beverage (Bottle + Kitchen restaurant and Pineapple Hour bar program), merchandise and retail through Shop Pineapple, digital and physical gift cards, and group/event bookings handled by a dedicated sales team. Pricing is dynamic by hotel, room type, and date, with CORE loyalty membership offering the lowest guaranteed rates and targeted promotional pricing (military, pet, extended-stay). Distribution is direct-to-consumer-led with OTA marketplace supplementation; there are no enterprise contracts, channel partnerships with travel management companies, or corporate anchor accounts disclosed. The company is independently owned with no parent, subsidiaries, M&A history, or external funding rounds in the source data.

Name

Pineapple Hospitality Company

Legal name

Pineapple Hospitality Company

Website

https://staypineapple.com

Company type

Private

Founded year

2011

Operating status

Operating

Headcount range

251–500 employees

Short description

Pineapple Hospitality Company, operating as Staypineapple, is a privately held US boutique hotel operator running 10 individually branded properties across 7 major US cities, serving primarily leisure travelers, pet owners, and small group/event customers with direct-to-consumer booking via Sabre SynXis.

Ownership category

akta.pro rank

Product category

Boutique Hotels

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 primary industry

Boutique Resorts (Small-Scale Resorts) (THAGADAJ)

Keywords

• Boutique hotel accommodations
• Hospitality services
• Pet-friendly hotels
• Hotel loyalty programs
• Hotel room bookings

Headquarters

HQ city

Bellevue

HQ country

United States

HQ region

North America

Offices7 records

Markets served

GTM type

B2C

Offering type

Services

Cost components

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

Revenue model

1. Hotel Room Bookings: Primary revenue from guest room reservations across 10 boutique hotels in major US cities. Bookings available through direct website, phone reservations, and third-party OTAs.
2. Food & Beverage: On-site restaurant and bar operations including Bottle + Kitchen at Hotel Rose, providing breakfast and dinner service plus lounge/bar revenue
3. Merchandise & Retail: Staypineapple branded merchandise sold through Shop Pineapple (shop.staypineapple.com) including apparel and goods
4. Gift Cards: Digital and physical gift card sales for hotel stays
5. Group & Event Bookings: Revenue from group room blocks, weddings, parties, celebrations, and corporate meetings

Pricing tiers

Go-to-market motion2 records

Distribution channels4 records

Marketing channels6 records

Core offering

Pineapple Hospitality Company operates the Staypineapple boutique hotel brand, managing 10 individually branded properties across 7 major US cities (New York, Chicago, San Francisco, Boston, Seattle, Portland, and San Diego). The company's core offering is overnight hotel accommodations enhanced by signature amenities such as The Naked Experience bedding, complimentary cruiser bicycles, pet-friendly packages, and on-site food and beverage venues including Bottle + Kitchen at Hotel Rose in Portland.

Product overview

Staypineapple is a boutique hotel brand operating 10 properties across major U.S. cities including New York, Chicago, San Francisco, Boston, Seattle (4 hotels), and Portland. The company offers a portfolio of individually branded boutique hotels under names like An Artful Hotel, An Iconic Hotel, The Maxwell Hotel, Hotel FIVE, Hotel Rose, and others, each featuring distinctive design and upscale amenities. The product portfolio centers on overnight accommodations but extends to value-added services including The CORE loyalty program offering exclusive rates, The Naked Experience bedding, complimentary yellow cruiser bicycles, and pet-friendly packages (Pineapple Pup Package). Staypineapple also operates food and beverage offerings such as Bottle + Kitchen at Hotel Rose. Technology infrastructure includes a Sabre SynXis-powered booking engine for reservations. The company differentiates through sustainability initiatives including Green Key certification, Coulée Coffee compostable brewing systems, and PATH Water refill stations.

Differentiator

Problem solved

Functional benefit

Brands

• Pineapple Pup Package: Pet-friendly package offering discounted pet fees and exclusive amenities including collapsible water bowl, dog waste bag dispenser, treats, dog bed, and access to Pet Wellness Program.
• The CORE
• The Naked Experience
• Bottle + Kitchen
• Pineapple Hour

Products and services

• An Artful Hotel (Midtown New York) Boutique hotel in Midtown Manhattan with vibrant colors and upscale amenities, catering to leisure and business travelers visiting NYC.
• An Iconic Hotel (The Loop Chicago) Boutique hotel in Chicago's The Loop district, housed in a converted 19th-century office building featuring original vintage doors and historic architectural touches, serving business and leisure travelers.
• An Elegant Hotel (Union Square San Francisco) Boutique hotel in San Francisco's Union Square, providing upscale accommodations near Moscone Center and major shopping destinations for business and leisure guests.
• A Delightful Hotel (South End Boston) Boutique hotel in Boston's historic South End neighborhood offering comfortable accommodations for visitors to one of America's oldest cities.
• The Maxwell Hotel (Seattle Center) Boutique hotel steps from the Space Needle and Seattle Center attractions, featuring colorful interiors and modern conveniences for leisure and family travelers.
• Hotel FIVE (Downtown Seattle) Boutique hotel in downtown Seattle with fun, funky décor positioned as a jumping-off point for city exploration by leisure travelers.
• Watertown Hotel (University District Seattle) Boutique hotel in Seattle's University District near UW campus, featuring open concept industrial design with concrete and wood accents.
• University Inn (University District Seattle) Boutique hotel in Seattle's University District near the University of Washington, featuring 1960s-style mid-century modern décor.
• Hotel Rose (Downtown Portland) Boutique hotel in downtown Portland with colorful style, located across from Tom McCall Waterfront Park and near the Moda Center, hosting the on-site Bottle + Kitchen restaurant.
• Bottle + Kitchen (Restaurant at Hotel Rose) On-site restaurant and bar at Hotel Rose in Portland offering locally sourced food, craft cocktails, wine, and beer, with Pineapple Hour happy hour service.
• Group Room Blocks and Event Hosting Sales-managed group booking and event hosting service for weddings, corporate meetings, celebrations, and parties across Staypineapple properties, handled by a dedicated group sales team.
• Pineapple Pup Package (Pet-Friendly Add-On) Bookable add-on pet package including 50% off regular pet fees, dog bed, treats, collapsible water bowl, waste bag dispenser, and access to the Pet Wellness Program with Zoundz sound therapy and VEG ER vet access.
• Staypineapple Branded Merchandise Direct e-commerce store at shop.staypineapple.com selling Staypineapple branded apparel and goods to consumers and guests.
• Staypineapple Gift Cards Digital and physical gift cards redeemable for hotel stays at Staypineapple properties, sold directly through the brand website.

Quantifiable outcome

• All 10 hotels achieved Booking.com Traveler Review Awards with 8.0+ ratings in 2026
• +4 more outcomes

Named customers3 records

Segments5 records

Ideal customer profiles5 records

Technology focussed No

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Integration1 record

Feature2 records

Partnerships

Six partnerships are on record, tiered core and minor.

• Coulée Coffee Co.coreStrategic or Co-development Partner · 1 April 2026Starting April 2026, Staypineapple partnered with Coulée Coffee Co. to replace plastic-heavy coffee pods with the world's first automated, compostable single-serve pour-over system (SWIRL Brewing System). Includes 100% compostable EcoPour Filters and plastic-free stainless steel brew path. Supports sustainability initiatives across all hotels.
• Sabre (SynXis)coreTechnology or IntegrationSabre's SynXis Responsive Booking Engine (RBE) powers Staypineapple's digital room reservation transactions. Engine coded to WCAG 2.0 AA standards as of June 30, 2018. SynXis also serves as the property management system.
• ZoundzminorGTM or Marketing PartnerScience-backed sound therapy app for pets offered as part of Staypineapple's Pet Wellness Program. Free 14-day trial included with Pineapple Pup Package.
• VEG ER for PetsminorGTM or Marketing Partner24/7 emergency vet care service available near almost every Staypineapple hotel, offered as part of Pet Wellness Program.
• wear blue: run to rememberminorGTM or Marketing PartnerNational nonprofit that honors U.S. military service and sacrifice through community running events. Staypineapple is a proud supporter of the organization.
• Toby & LinusminorGTM or Marketing PartnerPet apparel brand that provided matching sweater sets as prizes for Staypineapple's 8th Annual Dash, The Pineapple Pup Costume Contest.

Scale indicators4 records

Recent moves5 records

Expansion highlights5 records

Broad incumbents

• Hotel Indigo (IHG): IHG's boutique-style soft brand with hundreds of properties globally — competes with Staypineapple for boutique-minded leisure and business travelers but operates at much larger scale with chain loyalty distribution advantages.
• Autograph Collection (Marriott): Marriott's soft-brand collection of independent boutique hotels — competes directly for boutique travelers but leverages Marriott Bonvoy's massive loyalty base and global distribution, presenting scale pressure on independent operators like Staypineapple.

Direct peers

• Ace Hotel: Independent design-forward boutique hotel group with properties in major US cities (NYC, LA, Portland, Seattle, Chicago, Pittsburgh) — shares Staypineapple's emphasis on distinctive design, urban locations, cultural cachet, and Instagram-friendly branding.
• citizenM: Design-led compact lifestyle hotel brand with locations in major US cities (NYC, Washington, Boston, LA, Seattle) — comparable to Staypineapple in urban boutique positioning, tech-enabled booking, and millennial traveler focus.
• The Standard Hotels: Lifestyle boutique hotel brand with properties in major US gateway cities (NYC, Miami, LA) — comparable to Staypineapple in design-forward positioning, urban locations, and appeal to lifestyle-conscious leisure travelers.
• 21c Museum Hotels: Boutique hotel brand combining contemporary art museums with lodging in multiple US cities — comparable to Staypineapple as a multi-city independent boutique operator with design-led positioning and curated guest experiences.
• Moxy Hotels: Marriott's lifestyle boutique brand targeting design-conscious urban travelers in major US cities — directly overlaps Staypineapple's boutique/lifestyle positioning, urban footprint, and millennial/Gen X leisure and business traveler segments.
• Kimpton Hotels & Restaurants: Iconic US boutique hotel brand, now part of IHG, with urban properties emphasizing design, pet-friendliness, and lifestyle amenities — directly comparable to Staypineapple in target customer, brand positioning, and per-property scale.
• Joie de Vivre Hotels: Independent boutique hotel collection (now part of Hyatt's Inclusive Collection) with urban and destination properties emphasizing distinctive local character — comparable to Staypineapple in independent boutique positioning and lifestyle-driven brand ethos.
• Dream Hotels: Boutique lifestyle hotel brand operating in major US cities (NYC, Miami, Hollywood, Nashville) — comparable to Staypineapple in boutique urban positioning, design-led experiences, and leisure/business dual-segment focus.

Market position

Strengths5 records

Weaknesses5 records

Competitive moat4 records

Key risks6 records

Key highlights7 records

Customer concentration

• Xx.com/staypineapple
• Facebookfacebook.com/staypineapple
• LinkedInlinkedin.com/company/pineapple-hospitality-company
• Instagraminstagram.com/staypineapple
• TikToktiktok.com/@staypineapplehotels

Compliance3 records

Revenue estimate

Valuation estimate

Number of profiles

Profiles2 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 Pineapple Hospitality Company