The perfect start to our honeymoon. It was so nice to relax in total luxury while being driven to our hotel.Amanda S. · Honeymoon transfer
Private chauffeur service · Key West, Florida
Arrive with the island spirit
The exact Cadillac Escalade shown. Its owner as your chauffeur. Private airport, hotel, celebration, executive, and long-distance transportation—personally handled.
5passengers
4standard bags
24/7advance requests
EYW& Signature access
Actually in Key West.Real vehicle · real local service
Boutique, not anonymous
Your ride should feel as considered as your stay
Island Spirit Luxury Rides is a personal, owner-operated transportation service, and the owner is your chauffeur. It is built around one exceptionally maintained Cadillac Escalade 600. No crowded shuttle. No guessing which vehicle will arrive. Just calm, private service and a chauffeur who is happy to talk, share local recommendations, or let you enjoy a quiet ride.
Chilled refreshmentsBottled water, soda, and Diet Coke
Device chargingUSB-C, Lightning cables, and charging ports
Flight-aware pickupWhen a valid flight number is supplied
Luggage assistanceDoor to door, terminal to destination
Quiet ride availableConversation or calm privacy—your choice
Celebration conciergeArranged in advance around your occasion
Private transportation, your way
From first arrival to final farewell
Every service is built around the same promise: one private Escalade, direct communication, and timing that respects your plans.
01
Arrivals, handled
Airport & Private Aviation
Flight-aware transfers at EYW plus authorized planeside pickup and drop-off at Signature Flight Support.
Explore service →
02
Door to door
Hotel & Resort Transfers
Private transportation between Key West hotels, resorts, marinas, restaurants, and island destinations.
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03
A polished arrival
Weddings & Special Occasions
Personal transportation for weddings, anniversaries, birthdays, proposals, and romantic evenings.
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04
Quietly professional
Executive & Corporate
Discreet transportation for executives, client meetings, retreats, private dinners, and corporate events.
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05
Your time, your itinerary
Hourly Private Chauffeur
Keep the Escalade and chauffeur available for dinners, shopping, nightlife, meetings, or a custom island itinerary.
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06
Beyond the island
Florida Keys & Long Distance
Private one-way transfers from Key West to Marathon, Islamorada, Key Largo, Miami, Fort Lauderdale, and more.
Explore service →Authorized planeside service
From aircraft steps to island time
Authorized pickup and drop-off at Signature Flight Support creates a seamless private aviation arrival. The first 60 minutes are $180 total, including the 20% chauffeur gratuity/service charge.
Private aviation arrivals and departures60 minutes of service includedDirect resort, residence, marina, or yacht transfer
Planeside detailsClear starting rates
Private from Key West, one way
Every published fare already includes the exact Escalade, its owner-chauffeur, and the 20% chauffeur gratuity/service charge.
Key West local transferOne way$180 total
Little Palm Island Resort ferry terminalOne way$300 total
MarathonOne way$360 total
Hawks CayOne way$420 total
IslamoradaOne way$480 total
Key LargoOne way$540 total
Parking, excess waiting, approved additional stops, and concierge purchases are separate when applicable. Return transportation is quoted separately.
See all rates
Rooted in Key West
Local knowledge comes with the ride
Historic lanes, resort entrances, airport timing, dinner reservations, and the road north through the Keys all move more smoothly with someone who knows the island.
Old TownNew TownBahama VillageTruman AnnexCasa MarinaThe MeadowsMidtownStock IslandBig Pine KeyKey Colony BeachLayton
Explore the service area →Guest notes
The feeling after a seamless ride
Personal service is measured in the small things: being ready, keeping the vehicle pristine, and making every guest feel looked after.
Seamless service from the airport to our resort. The vehicle was spotless and the driver was a true professional.Brian T. · Airport transfer
Always on time, the car is always immaculate, and the Island Spirit hospitality is genuine.Chris P. · Private transfer
Ready when you are
Tell us where you need to be—we’ll handle the ride
Submit a reservation request for personal review, or get a quick answer by phone or WhatsApp.