From $600 per vehicle: a private, one-way ride from Port of Miami to Windsor Hills Resort in a chauffeured SUV or van.
Pricing is by vehicle, not by seat: a solo traveler and a full car pay the same flat one-way rate.
Walk off, clear the terminal, and the private vehicle is already outside. The driver knows which terminal the ship uses and times the pickup to the real disembarkation, with the curbside greeting included in the fare and the Meet & Greet at the terminal available for $40 if you want it. Bags in, and the car heads out of the port.
Windsor Hills Resort sits in the Davenport and Clermont area, west of the Disney exits off I-4, in the stretch of Central Florida where golf resorts and rental villas spread out and the theme parks stay only minutes away. It is a vacation-home community built for families who want space to unpack, cook, and settle in between park days rather than a single hotel room. When your group is coming straight off a cruise with a week of luggage, that room to breathe is the whole point.
The surrounding area gives you plenty of reasons to slow down between park visits. ChampionsGate and Reunion Resort sit within simple reach, both known for their golf, and the Clermont chain of lakes and Lake Louisa State Park are close enough for a quieter afternoon on the water or under the trees. You get the parks when you want them and the calm when you don’t, without the crowds pressing in on every side.
On arrival, the practical side of the stay is handled at the property itself. Windsor Hills Resort covers the details that matter after a long travel day, including on-site amenities, luggage holds if your room is not ready, and early check-in when it can be arranged. Your ride ends right at the door, so the last leg of a long cruise-to-villa trip is simply stepping out of the vehicle and walking in, bags and all, with the rest of your vacation still ahead of you.
This is a long, direct run, and it is built to feel simple from the first minute. Your chauffeur is staged at the curb of your ship’s own terminal before your group clears the disembarkation hall, so the waiting is theirs, not yours. Bags go straight into the vehicle with full luggage help at the port end, you climb in, and the trip is one continuous drive reserved for your group alone. There is no transfer, no second stop, and no scramble on the sidewalk with your cases.
From the pier it runs up Florida’s Turnpike, a single road for most of the way, ending at the door of Windsor Hills Resort. Plan on roughly 235 to 246 minutes terminal to door depending on how the traffic sits that morning. On a ride this long, having your own vehicle changes the day: you set the departure, the pace, and how many quick stops you make, and your chauffeur handles the rest of the drive while you settle in.
From the Port of Miami, plan on about 3 hours 53 minutes and 234.3 miles to reach Windsor Hills Resort in Kissimmee via Florida’s Turnpike. Prices are per vehicle, not per seat: $600 for the Black SUV, $850 for the Van, $1050 for the Van XL. Pickup is at your cruise terminal curb at PortMiami.
| Road distance | 234.3 miles |
|---|---|
| Black SUV, 1-5 | $600 |
| Drop-off address | 2600 N Old Lake Wilson Rd, Kissimmee |
| Drive time | 3 hours 53 minutes |
| Van, 6-9 | $850 |
| Main roads | Florida’s Turnpike |
| Van XL, 10-14 | $1050 |
| Back from Windsor Hills Resort | $600 / $850 / $1050 |
The return covers the same 234.3 miles: pickup at the main entrance of the resort (2600 N Old Lake Wilson Rd), drop-off at your cruise terminal at PortMiami after about 3 hours 53 minutes. From Windsor Hills Resort the Black SUV costs $600, the Van $850 and the Van XL $1050. Open the booking box with the points swapped and choose the date and time. Book the return
The 234.3 miles from the Port of Miami to Windsor Hills Resort take about 3 hours 53 minutes without heavy traffic via Florida’s Turnpike. At busy hours, allow extra time. Each vehicle has a fixed fare, no traffic or surge charges: $600 for the Black SUV, $850 for the Van and $1050 for the Van XL.
Book the time you expect to walk out of the terminal with your bags, not the docking time. The waiting rules for slow disembarkation days are on the FAQ page linked below. The drive to Windsor Hills Resort then takes about 3 hours 53 minutes.
At the curb outside your own cruise terminal (the terminals are listed below). Before the pickup you get the driver’s name, car and plate; when you are outside with your bags, message us and the car pulls up for the ride to Windsor Hills Resort.
The Black SUV holds up to 5 passengers, with passengers plus big suitcases up to 10; on this route it costs $600. Six to nine travelers with their cases take the Van ($850), ten to fourteen the Van XL ($1050). All three go door to door to Windsor Hills Resort.
Yes. The return from Windsor Hills Resort to the Port of Miami costs $600 in the Black SUV, $850 in the Van and $1050 in the Van XL. Allow about 3 hours 53 minutes for the drive, plus a margin, before your boarding time; the return section above has the booking link.
Every policy in full: FAQ
As a solo cruiser I lined up a private transfer from the terminal to Windsor Hills Resort for the morning I got off, and it was the best call of the trip. I’ve already saved them for my next cruise out of PortMiami.
Los dos salimos en crucero desde PortMiami y tener un auto privado esperándonos en la terminal para el viaje hasta Windsor Hills Resort hizo la mañana fácil. Llegar a Windsor Hills Resort sin vueltas significó que pudimos hacer el check-in y por fin darnos una ducha tras la semana en el mar. Para llegar del barco a Windsor Hills Resort sin estrés, fue dinero bien gastado. Hizo el desembarque facilísimo.
Primeira vez de cruzeiro por conta própria saindo do PortMiami, e ter um carro privativo pronto no meio-fio para a viagem até Windsor Hills Resort não podia ter saído melhor. Havia uma placa com o meu nome no meio-fio, então achei o motorista sem dar voltas.
As a solo cruiser I lined up a private transfer from the port to Windsor Hills Resort for the morning I got off, and it was the best call of the trip. I was dropped right at the front door of Windsor Hills Resort, not down the block.
Descemos do navio cansados mas felizes e um motorista já esperando para nos levar até Windsor Hills Resort foi a decisão certa. O trajeto do terminal até Windsor Hills Resort foi tranquilo e estável, e pudemos só nos acomodar. Para sair do navio e chegar a Windsor Hills Resort sem complicação, foi dinheiro bem gasto.