Jeeves Florida Rentals
Jeeves Florida Rentals is a Kissimmee-based vacation rental management company managing 250+ privately owned villas across six Orlando-area resort communities, serving families, groups, and corporate travelers visiting the Orlando theme park market.
- Company typePrivate
- Founded2009
- HeadquartersDavenport, United States
- Headcount101–250
- GTM typeB2B and B2C
- OfferingServices
What Jeeves Florida Rentals does
Jeeves Florida Rentals, operating under the legal entity Jeeves Property Management and branded as Jeeves by Casago, is a privately held vacation rental management company headquartered in Kissimmee, Florida. The company manages a portfolio of 250+ privately-owned villas across six premier Orlando-area resort communities, including Reunion Resort, Encore Resort, The Bear's Den, ChampionsGate, Solterra Resort, and Solara Resort. Its inventory is organized into four pricing tiers ranging from $79/night townhomes to $1,750/night luxury elite custom mansions, targeting families, groups, and corporate travelers visiting Orlando's theme park corridor.
The company's core technology stack is built on the Streamline VRS property management and booking platform, layered with Lynbrook third-party guest identity verification and the Casago corporate technology infrastructure inherited from its parent company. Distribution is primarily direct-to-consumer via the jeevesfloridarentals.com website with real-time availability and pricing, supplemented by a phone-based call center handling value deals and custom quotes, plus a 24/7 on-call operations manager for guest and owner support.
The business model operates three revenue streams: (1) short-term vacation rental transaction fees on nightly bookings ranging from $79-$1,750/night depending on property tier; (2) ancillary concierge and add-on services including attraction tickets, private chef, transportation, pool heating, housekeeping, grocery delivery, and spa services; and (3) recurring managed services revenue from full-service property management contracts with 200+ vacation property owners. Go-to-market combines a self-serve consumer booking experience with a sales-led property acquisition motion targeting homeowners, supported by preferred partnerships with the six resort communities that provide differentiated inventory access and exclusive amenity positioning.
Jeeves Florida Rentals firmographics
Firmographics- Name
- Jeeves Florida Rentals
- Legal name
- Jeeves Property Management
- Website
- https://jeevesfloridarentals.com
- Company type
- Private
- Founded year
- 2009
- Operating status
- Operating
- Headcount range
- 101–250 employees
- Short description
- Jeeves Florida Rentals is a Kissimmee-based vacation rental management company managing 250+ privately owned villas across six Orlando-area resort communities, serving families, groups, and corporate travelers visiting the Orlando theme park market.
- Ownership category
- akta.pro rank
Jeeves Florida Rentals industry classification
Industry- Product category
- Vacation Rental Management
- NAICS
- Real Estate Property Managers (53131), Residential Property Managers (531311)
- SIC
- Real Estate Agents & Managers (For Others) (6531), Hotels, Rooming Houses, Camps & Other Lodging Places (7000)
- akta.pro primary industry
- Vacation & Short-Term Rental Management (BPAJAFAI)
- akta.pro secondary industries
- Resort & Branded Residence Vacation Rental Management (BPAJAIAE), Luxury & Estate Rentals (THAGANAF)
Keywords
Where Jeeves Florida Rentals is headquartered
LocationHeadquarters
- HQ city
- Davenport
- HQ country
- United States
- HQ region
- North America
Offices1 record
Markets served
Jeeves Florida Rentals business model
Business model- GTM type
- B2B and B2C
- Offering type
- Services
- Cost components
- Personnel, Operations, Marketing or Sales, Technology or R&D
Revenue model
- Short-term Vacation Rental Revenue: Nightly rental fees charged to guests for vacation home stays. Properties range from budget-friendly townhomes ($79/night) to luxury elite estates ($1750/night). Revenue varies by property type, size, season, and length of stay.
- Concierge and Add-on Services: Additional revenue from ancillary services including attraction tickets, transportation, private chef, pool heating, housekeeping, grocery delivery, spa services, and event rentals.
- Property Management Services for Owners: Revenue from managing vacation rental properties for homeowners, including marketing, maintenance, guest services, and booking management.
Pricing tiers
| Model | Billing | Price |
|---|---|---|
| Unit Pricing | Pay-as-you-go | Townhomes - 3 bedroom properties in resort communities |
| Unit Pricing | Pay-as-you-go | Condos - 2-3 bedroom units in resort communities |
| Unit Pricing | Pay-as-you-go | Premier Homes - 4-8 bedroom luxury villas |
| Unit Pricing | Pay-as-you-go | Elite Custom Homes - Luxury 5-11 bedroom mansions |
| Unit Pricing | Multi-year contract | Extended Stay Discount |
| Unit Pricing | Pay-as-you-go | New Home Promotion |
Go-to-market motion3 records
Distribution channels4 records
Marketing channels8 records
Jeeves Florida Rentals product offering
Product offeringCore offering
Jeeves Florida Rentals manages and rents out luxury vacation homes across premier Orlando-area resort communities, offering tiered properties (Elite, Premier, Condos, Townhomes) plus concierge add-ons. It also provides full-service property management for vacation home owners.
Product overview
Jeeves Florida Rentals is a luxury vacation rental management company offering a portfolio of hand-picked private residences across premier Orlando resort communities. The core offering is organized into four property tiers — Elite Custom Homes (top-tier custom mansions with premium amenities), Premier Homes (enhanced vacation villas), Condos, and Townhomes — located within five resort destinations: Reunion Resort, Encore Resort, The Bear's Den at Reunion, ChampionsGate Resort, Solterra Resort, and Solara Resort. Each resort provides shared amenities such as water parks, golf courses, pools, restaurants, and fitness facilities. Jeeves layers a concierge services platform on top of its rentals, offering theme park tickets, transportation, private chefs, housekeeping, pool heating, childcare, grocery delivery, character visits, spa services, and more. The company also markets promotional offers including Value Deals, an Extended Stay Offer (15% off 14+ nights), an Encore Special Offer (waterpark access included), and a New Home Promo (10% off new inventory). Together, the property tiers, resort destinations, and concierge services form a unified luxury vacation rental platform.
Differentiator
Problem solved
Functional benefit
Products and services
- Elite Custom Homes The highest-tier vacation home collection featuring custom mansions with private pools, home theaters, themed bedrooms, game rooms, bowling alleys, and arcades. Properties span 5-11 bedrooms, accommodate up to 30 guests, and start at approximately $380/night. For luxury travelers and large groups.
- Premier Homes Mid-to-upper-tier vacation homes with enhanced amenities, themed bedrooms, game rooms, theaters, and private pools. Typically 5-8 bedrooms, starting at approximately $153/night.
- Condos Vacation condominiums within resort communities, typically 2-3 bedrooms with balconies, golf course views, and access to resort amenities. Starting at approximately $85/night.
- Townhomes Vacation townhomes offering 3 bedrooms with private patios, game rooms, and pool access. Starting at approximately $79/night.
- Concierge Services A suite of supplementary guest services including theme park and attraction tickets, travel insurance, transportation booking, BBQ rental, pool and spa heating, private chef, housekeeping, childcare, grocery welcome packs, character visits, stroller rentals, photography, helicopter tours, pet sitting, food delivery, spa services, event rentals, party bus, and golf bookings.
- Property Management Services for Owners Full-service management of vacation rental properties for homeowners, including marketing, maintenance, guest services, and booking management, with 24/7 owner support. Over 250 villas managed for 200+ property owners.
- Value Deals Budget-friendly vacation rental deals available exclusively through the Jeeves call center, not listed online. Includes private pool homes and properties near theme parks at discounted rates.
Quantifiable outcome
- 250+ villas under management
- +2 more outcomes
Companies that use Jeeves Florida Rentals
Customer profileNamed customers7 records
Segments4 records
Ideal customer profiles2 records
Jeeves Florida Rentals technology and API
TechnologyTechnology focussed No
API detail
- Has API
- No
- API docs
- API detail
Core technology
AI maturity
App detail
Integration10 records
Feature3 records
Jeeves Florida Rentals partnerships and signals
Strategic signalPartnerships
13 partnerships are on record, tiered flagship, core and minor.
- Reunion ResortflagshipPreferred Resort Partner providing exclusive access to Reunion Resort's 2,300-acre AAA Four-Diamond community. Jeeves guests receive access to 10 community pools, three championship golf courses, sports courts, six on-site restaurants, and water park. Reunion Resort spans 17 exclusive neighborhoods including Bear's Den.
- Encore ResortcorePreferred Resort Partner located just 7 miles from Disney World. Features 10-acre water park, 4-13 bedroom private pool homes, complimentary shuttle service to theme parks. Dining options include Finns Restaurant, Bis Grill, and Shark Lounge.
- Bear's Den ResortcoreExclusive gated enclave along 18th fairway of Jack Nicklaus Tradition Course. Offers 4-8 bedroom estate homes with private pools, gourmet kitchens, and golf course views. Full access to Reunion Resort amenities included.
- ChampionsGate ResortcorePremier vacation rental resort 15 minutes from Disney World. Features Oasis Club with lazy river, zero-entry pool, water slides, two Greg Norman championship golf courses, fitness center, and movie theater. Properties range from 3-bedroom condos to 8-bedroom homes.
- Solterra ResortcoreGated community minutes from Walt Disney World. Features resort-style pool with lazy river and water slide, on-site restaurant (Cafe Sol Bar & Grill), fitness center, tennis/volleyball courts, and soccer field. Properties are 5-10 bedroom homes with private pools.
- Solara ResortminorNewest family resort destination near Walt Disney World. Features sports courts, fitness center, resort swimming pool, and Flow Rider for adventurous guests.
- Enterprise Rent-A-CarminorCar rental partner providing preferential rates and inventory for Jeeves guests. Booking available through dedicated Enterprise link.
- Alamo Rent A CarminorCar rental partner providing preferential rates and inventory for Jeeves guests.
- National Car RentalminorCar rental partner providing preferential rates and inventory for Jeeves guests.
- Mears TransportationminorTrusted Orlando taxi company providing transportation to/from Orlando International Airport, Disney, Universal Studios, and other Central Florida destinations.
- Lenox TransportminorPremium luxury black car service for airport and theme park transportation in Central Florida.
- Kissimmee Guest ServicesminorCertified attraction ticket sellers at Jeeves main office, providing theme park tickets and additional services for Orlando visitors.
- CasagoflagshipParent company providing the Jeeves by Casago brand platform and technology infrastructure for booking and property management operations.
Scale indicators5 records
Recent moves6 records
Expansion highlights5 records
Jeeves Florida Rentals competitors and assessment
Company assessmentBroad incumbents
- Marriott Homes & Villas: Hospitality major operating branded luxury vacation rental inventory. Overlaps with Jeeves on luxury guest segment and premium villa positioning, though delivered as part of a much larger hotel portfolio.
- Vrbo: Tripadvisor-owned vacation rental marketplace with D2C booking and managed inventory programs. Competes with Jeeves for guest bookings and offers an alternative distribution channel for managed properties.
- Airbnb (Luxe): World's largest vacation rental marketplace, with the Airbnb Luxe tier offering professionally managed luxury villas. Competes for direct bookings of luxury Orlando villas and sets the platform-level standard.
Direct peers
- Vacasa: Largest US full-service vacation rental management company, managing tens of thousands of homes with direct booking and owner-management services. Directly comparable to Jeeves on business model, including managed inventory and D2C booking channels, with greater national scale.
- Sonder: Tech-enabled short-term rental operator and manager with properties in multiple markets; matches Jeeves on managed-inventory + booking model with similar reliance on technology platforms.
- Global Resort Homes: Orlando-based vacation rental manager operating in many of the same resort communities (Reunion, ChampionsGate, Solara, Solterra). Direct intra-market competitor for owners and guests.
- Blue Fox Property Management: Florida-focused vacation rental property manager serving similar homeowner clients in the Orlando/Disney market with comparable full-service management and direct-to-guest booking.
- Magical Vacation Homes: Orlando-focused vacation rental manager offering tiered property collections near Disney. Directly competes for the same family/group guest segment and for property owners in Jeeves' catchment.
- Evolve Vacation Rental Network: National light-management vacation rental operator with an owner-acquisition-led model and D2C booking site. Directly competes with Jeeves for owner signups and guest bookings in Orlando.
- Casiola: Orlando-based vacation rental manager with luxury home offerings near Disney. Operates an asset-light management model very similar to Jeeves for both guests and property owners.
Market position
Strengths5 records
Weaknesses5 records
Competitive moat5 records
Key risks5 records
Key highlights6 records
Customer concentration
Jeeves Florida Rentals social profiles
Digital presenceJeeves Florida Rentals compliance and trust
Trust signalCompliance1 record
Jeeves Florida Rentals financial estimates
Financial estimateRevenue estimate
Valuation estimate
Jeeves Florida Rentals leadership team
Management profileNumber of profiles
Jeeves Florida Rentals funding detail
Funding detailFunding overview
Funding rounds
Investors
Funding detail is available on the Subscription and Enterprise plan.Contact sales →
Jeeves Florida Rentals M&A and investment
M&A and investmentM&A
Investments
M&A and investment is available on the Subscription and Enterprise plan.Contact sales →
Frequently asked questions about Jeeves Florida Rentals
What does Jeeves Florida Rentals do?
Jeeves Florida Rentals manages and rents out luxury vacation homes across premier Orlando-area resort communities, offering tiered properties (Elite, Premier, Condos, Townhomes) plus concierge add-ons. It also provides full-service property management for vacation home owners.
Is Jeeves Florida Rentals a public or private company?
Jeeves Florida Rentals is a private company. It is classified as corporate owned and is currently operating.
When was Jeeves Florida Rentals founded?
Jeeves Florida Rentals was founded in 2009. It employs 101 to 250 people.
Where is Jeeves Florida Rentals based?
Jeeves Florida Rentals is headquartered in Davenport, United States, in the North America region.
How does Jeeves Florida Rentals make money?
Three revenue lines are on record. Short-term Vacation Rental Revenue is the primary driver. The others are concierge and Add-on Services and property Management Services for Owners.
Who are Jeeves Florida Rentals's main competitors?
Broad incumbents on record are Marriott Homes & Villas, Vrbo and Airbnb (Luxe). Direct peers are Vacasa, Sonder, Global Resort Homes, Blue Fox Property Management, Magical Vacation Homes, Evolve Vacation Rental Network and Casiola.
Does Jeeves Florida Rentals have an API?
No public API is recorded for Jeeves Florida Rentals.
What industry is Jeeves Florida Rentals in?
Jeeves Florida Rentals's product category is Vacation Rental Management. Its primary akta.pro industry code is BPAJAFAI, Vacation & Short-Term Rental Management, with a secondary code of BPAJAIAE, Resort & Branded Residence Vacation Rental Management. Its NAICS code is 53131 and its SIC code is 6531.