Lakeside Dream on Windward Cay

Lakeside Dream is a luxury south facing very secluded lakeside villa with heated pool and large deck area on Windward Cay. The villa is on a large plot set back from the lake which is very private. It is a perfect short-term holiday home for an average sized family with older children, or for couples of any age.

Often referred to as a ‘hidden jewel in Kissimmee’s crown’, Windward Cay is a popular and well established community in a tranquil, pleasant and peaceful location set amongst pine trees and lakes in the heart of a conservation area.

Windward Cay is conveniently located in Central Kissimmee just to the south of the action packed Highway 192 with its vast range of shopping outlets, restaurants, pubs, leisure amenities and entertainment, with Disney’s Main Entrance around a 15 minute drive to the West. There is a huge Walmart Superstore only a few minutes walk to the East.

Windward Cay is also in easy reach of ‘Sea World’, ‘Aquatica’, ‘Universal Studios’, 'Islands of Adventure', 'the Wizarding World of Harry Potter', and 'Gator Land'.
  • Walt Disney World - The Magic Kingdom10 miles
  • Seaworld, Orlando11 miles
  • Universal Studios, Orlando15 miles
  • Orlando International Airport. (MCO)21 miles
  • Legoland Florida38 miles
  • Sanford International Airport. (SFB)51 miles
  • Kennedy Space Center67 miles
  • Busch Gardens, Tampa71 miles
Rates Quoted in  Please wait...

Owner's preferred payment currency is GBP (£)

Rental Tariffs

All prices below are quoted in GBP (£). Dates are specified in day/month/year. Any converted rates are not guaranteed to be accurate.
Label (e.g. High Season) Start Date End Date Price Per Night Price Per Week Price Per Month
High Season 11/02/2022 05/04/2022


Peak Season 06/04/2022 27/04/2022


Low Season 28/04/2022 10/06/2022


High Season 11/06/2022 31/08/2022


Low Season 01/09/2022 15/12/2022


Peak Season 16/12/2022 06/01/2023


Low Season 07/01/2023 08/02/2023


High Season 09/02/2023 26/03/2023


Peak Season 27/03/2023 23/04/2023


Low Season 24/04/2023 11/06/2023


High Season 12/06/2023 27/08/2023


Low Season 28/08/2023 15/12/2023


Peak Season 16/12/2023 06/01/2024



All prices below are quoted in GBP (£). Dates are specified in day/month/year. Any converted rates are not guaranteed to be accurate.
Label (e.g. High Season) Start Date End Date Price Per Night Price Per Week Price Per Month Service Charge
Refundable Security Deposit


Additional Information

7 nights minimum stay in Low and High Seasons;
14 nights minimum stay in Peak Season;
£75 cleaning charge for bookings of 10 nights or less;
Monthly rates available on request for January, February and March;
Sales Tax (7.5%) and Tourist Tax (6%) included;
20% non refundable deposit payable on booking;
Balance to be paid 8 weeks before date of arrival;
Payment by BACS transfer or cheque;
Electric pool heating available (recommended November - April) 29C/84F:
£150 for 1 week; £280 for 2 weeks, £360 for 3 weeks.
Refundable £200 security deposit to be paid with balance.
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Review added by Property Owner
Steve & Audrey Butcher
We count ourselves fortunate to have been able to stay for a second time in this superb villa. It would have been the third time had it not been for lack of availability previously. This time we stayed for five weeks and loved every minute of it. It’s hard to believe how close you are to the sights yet you can sit out on the pool deck, overlooking the lake and trees, and not hear, or even see a thing apart from the wildlife. Truly amazing and relaxing.

There have been some changes to the villa. We thought it would be hard to improve on things, however, David and Jan have done just that. Extremely well appointed with everything you need for a short or a longer stay. The pool was perfect and kept in order with the weekly maintenance visits and the grounds around the villa and the the neighbouring house were well maintained. The house is very secure with it’s own alarm system and monitoring, however, we were never concerned about this aspect of our stay given the very quiet and friendly neighbourhood.

Prior to our visit David was happy to help and answer any questions and was very flexible in helping us make our arrangements. Once we were there he called from the UK to check all was OK and in order. There is a management company available locally if need be and, whilst we had no reason to call on them, we had no doubt that any problems would have been addressed very quickly.

The information pack we received just before we left the UK was incredibly detailed and far exceeded anything we have had before on any of our other rentals.

The only issue we now have is that it’s becoming so difficult to rebook given it’s popularity! So if your dates are available don't hang around because you can guarantee they won't be there for long – because we will book them!

We are missing it already!

July 2019

Paul Humphries
Stayed at lakeside dream for 12 nights for our honeymoon, the villa was easy to find and gain access to all communication was excellent (even after setting off the alarm) super villa clean x tidy plenty of towels ,bedding etc!lovely pool for relaxing around, good access to all theme parks around 20-30 mins depending on traffic , we had a lovely time and will return in the future!

Great Villa
Everything you read about this Villa is true.
David was so helpful and nothing was a problem replying to any questions we had.
We had a late flight back to the Uk David said no problem we could check out later in the afternoon with no extra costs.
Location was great just a short drive off the 192 very close to everything.
Thank you David.
Call you next year
Glenn & Steph

Amazing in every way
Everything about this villa was amazing including the owners.

Location, facilities, cleanliness, all amazing.

Very easy to book and nothing too much trouble.

We hope to return as we had a great holiday there and didn't want to leave!

Highly recommended.

Everything about this villa is amazing including the owner David who made our booking so very easy and nothing was too much trouble.

The location, setting, facilities and condition of the villa was fantastic.

We had a great holiday here and we didn't want to leave. If we can find a vacancy space in the future we will definitely return. I'm not surprised how quickly this place gets booked up.

Highly recommended.

Thanks for sharing your beautiful villa with us.

Review added by Property Owner
Spotless and Spot On
Kate S
My husband and I stayed at Lakeside Dream in July for 10 days using the villa as a base to explore the surrounding areas and visit the many theme parks that Orlando has to offer.

We had found Lakeside Dream through research on the Holiday Rentals site, taking the other reviews into account and we were not disappointed! The villa is perfectly positioned with easy access to both local shops and restaurants as well as being only a short drive from Disney land etc. Having stayed in villas previously in Orlando, the best element was the fantastic lakeside location which meant the villa was not as over looked as previous villas I have stayed in and offers a fantastic view of the peaceful lake after a day of queuing for rides! Spending the early evening watching the wildlife, in particular our own local peacock whilst cooling off in the pool was a great way to unwind. The pool area was very clean and clearly well looked after and whilst the pool is not huge it is perfect for that all important dip after a long day, the only small comment would be the lack of shade when the sun is at its highest in the outside area…it does get very hot!

The villa itself is incredibly well stocked and has plenty of room for a large family, we effectively only used half the villa as there was just the two of us. The kitchen amenities meant the villa was a real home from home, with everything you could possibly need for your stay and there were plenty of towels and extra bedding if required. The villa was comfortable and spotless. Most importantly the villa has a fantastic air conditioning unit which was very well received at times! The instructions left around the villa were very clear and easily understood as well as a great welcome pack with all the info you could need for your stay.

The owner of the villa David made himself available to contact should we require anything and was always incredibly quick to respond to any questions we had via email.

All in all we had a great stay in Orlando and would most definitely book the Lakeside Dream again for a future trip and would recommend to friends and family. Thank you David for a great stay.

Review added by Property Owner
Absolutely superb!
Steve & Audrey Butcher
We booked this villa after a lot of research and boy we were not dissapointed.

Right from our initial contact with the owner, David, we knew we had made the right choice. The information he gave us before our arrival was excellent and he left nothing to chance.

When we arrived we were bowled over by how clean and how well presented the villa was. The pictures do not do it justice, it is even better in real life. David called us on our first morning to see how we had settled and due to the information we had been given and the welcome folder we had absoutely no questions. We had one very small problem when the kettle packed in a few days later. No worries, one call to the management company and they appeared with a new one. He even left us a christmas tree to put up!

Location was great and it was very peaceful with the outlook over the lake. The pool and the surrounds were very well maintained as was the whole villa.

We have stayed in a number of villas in Florida and this without doubt was the best. If we return to Kissimmee then we will definitely be staying here again

Dream Villa
Mark Kerrigan
My wife and I stayed at this villa for the first time in September 2017. We already knew the location as we had stayed in Windward Cay villas for the five years previous to staying here, and so we knew the location was spot on. We checked the photos before we booked and the villa looked good, but on arrival we were taken aback because the photos didn't do it justice as this villa is ‘wow’ factor. You have the sun all day if you want it, the pool is great for what you need and the lakeside location of the villa is peaceful and tranquil, with the wildlife a pleasure to observe.
The owner, David, is very friendly and caring as we were there when Hurricane Irma hit Florida. He was always ringing to see how we were, and trying to make sure we were safe. He continued to give us up to date information on the path of the storm and this was very much appreciated. He repeatedly said ‘it's only a villa it’s insured, just make sure you are both safe’, which was a very nice and genuine touch.
We have been coming to Kissimmee since 1989 and so we have seen many villas in our time but none to match this little gem of a place. On that note, we have booked four more trips there, the last one as far ahead as 2020 just to make sure availability is there for us. We would book further in advance but bookings aren't available yet.
This is a fantastic villa and all that visit there will go back again that's a promise. I would like to thank the owners for a fantastic stay in their home as Hurricane Irma did nothing to spoil our holiday. Thanks again. Mark and Mandy

Is smoking allowed in your villa?

NO, smoking is not permitted anywhere inside the villa or on the pool deck, only outside.

Are pets allowed?

NO, pets are NOT allowed at any time.

About Lakeside Dream on Windward Cay

This spacious fully air conditioned villa has a prime, south-facing lakeside position on the charming and tranquil Windward Cay estate, an attractive and exclusive location in a conservation area, which is well hidden from the busy surrounds of Kissimmee. Surrounded by pine trees and ranch land, this estate is a very well-kept Kissimmee secret.

“Lakeside Dream” accommodates 6 comfortably with plenty of living space for everyone and a really lovely pool/deck area that you can enjoy for hours on end without being overlooked by anyone.

The villa is perfect for couples of any age and especially those lucky enough to be retired! You can enjoy the wonderful Florida sunshine in peaceful surroundings without being disturbed by neighbours.

The villa is within easy walking distance of several restaurants and shops, including a large Wal-Mart supermarket, which should provide you with absolutely everything you need.

Due to its proximity to the lake and the very large pool deck area, this villa is NOT suitable for young children aged 5 or under / or for children of any age that cannot swim unaided.


Living Room
As you walk in through the front door you enter into the living room, which is very spacious, warm and welcoming. Here you will find two very comfortable sofas and a single fully reclining chair in which you can sit back and watch cable TV or a DVD on the 55" wide screen full HDMI TV. Alternatively, you can just relax or curl up with a book, or enjoy a quiet conversation after a busy day.

The air conditioning system (providing cold air in the summer and warm air in the winter) is controlled from a thermostat in the living room, and there is also a ceiling fan for those very hot days in July and August.
Kitchen and Dining Area
The villa has a modern, fully equipped kitchen which has every major appliance, including a microwave, a very large upright fridge-freezer, a dishwasher, electric kettle, coffee maker, toaster and a waste disposal unit.

One of the two inter connected house telephone handsets is located in the kitchen adjacent to the dining area.

The dining area, which is adjacent to the living room on one side and the open-plan kitchen on the other, is furnished with a table and 6 chairs. The lighting above the table has a dimmer control and there is a standard lamp to provide alternative lighting.

A sliding patio door leads to the pool deck where there is a large round table and 6 chairs for dining al fresco.
Master Bedroom
The Master Bedroom is located at the rear of the villa and looks out across the lake through a double French window that provides direct access to the pool area.

The Master bedroom has a queen bed with bedside cabinets, table lamps, a dressing table with a large mirror, chest of drawers and a large walk in closet, which houses a floor mounted safe to store your valuables.

The second telephone handset is located in the Master Bedroom.

There is also has a ceiling fan to complement the air conditioning system during the hot summer nights.

Although close enough to the rest of the house to be aware of the others in your party, it is annexed sufficiently for you to be able to retreat in total privacy.

There is an en-suite shower room and toilet for your private use and there is also a single-door access to the pool deck from the shower room area. It is ideal for a late night swim when other family members are fast asleep elsewhere in the villa! This bedroom comes equipped with cable TV and DVD/VCR.
Bedroom 2
Bedroom 2 is a double room located at the front of the house. It also has a queen bed with bedside cabinets, table lamps, a dressing table with a large mirror and a chest of drawers.

It also has cable TV and DVD/VCR.
Bedroom 3
Bedroom 3 is also located at the front of the house.

Bedroom 3 has two twin beds with bedside cabinets, table lamps, a dressing table with a large mirror, a chest of drawers, and cable TV.

South Facing Pool Deck
The pool has a very large screened deck which includes a dining lanai/porch area with shade umbrella, table and chairs as eating out in the open air by the pool side is a well established Florida tradition. There are 4 full length sun loungers available and also a clothes drying rack.

There is an electric pool heater which is an optional extra and is usually required from November to April. It maintains the water temperature at 30C/86F during the cooler winter days. Both the pool and the deck area can be lit at night.

The view from the pool is particularly stunning as the rear of the villa faces south and is only 10 metres from the edge of a beautiful tranquil lake. Pine trees beyond combine to make this a particularly pleasing outlook.

The lake is full of fish and turtles and it attracts all kinds of other wildlife, including numerous species of birds; especially, during the migrating season.

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Owners Terms & Conditions


As owners, we offer our Florida house at 4704 Alexis Drive, Kissimmee FL34746, hereafter known as ‘Lakeside Dream’, for rental and will indicate if it is available for the dates you hereafter known as the ‘lead guest’ have requested. Bookings are only confirmed once we have received a non-refundable 20% deposit and also the completed booking form, which must be signed and dated by the lead guest.

One of us will then sign and date the booking form, which will then become the ‘Contract’ between us as owners, and you as the lead guest. A copy of the ‘Contract’ will be sent to the lead guest in pdf format by email.


If a booking is made within 8 weeks of arrival at ‘Lakeside Dream’, the lead guest must pay the full rental price plus the £200 refundable security deposit at the time of booking, and complete/sign the booking form immediately.

One of us will then sign the booking form and return it to the lead guest by email in pdf format as the ‘Contract’ between us as owners and the lead guest.


Any outstanding balance plus the £200 security deposit is due for payment 8 weeks before the start date of the booking. It is the responsibility of the lead guest to ensure that the final payment is made by the due date.

If payment of the balance is not made by the due date, we reserve the right to cancel the booking and retain the original 20% deposit without any prior notice.


By you the lead guest:

A booking may be cancelled at any time provided that it is done by the lead guest and is communicated to us by telephone as soon as possible, and confirmed immediately in writing by email or letter. In this event, the following percentages of the entire cost of the booking will be charged:

- More than 90 days prior to the start of the booking: 20% deposit;

- 57 to 89 days prior to the start of the booking: 50% of the rental cost;

- Less than 56 days prior to the start of the booking: 100% of the rental cost.

By us as owners:

If for any reason we have to cancel your booking of ‘Lakeside Dream’, we will make every effort to find suitable alternative accommodation for you, which may in rare instances incur an increased booking fee payable by you.

Should you reject this alternative arrangement, we will at your request and in full and final settlement, refund all amounts paid to date.


Accommodation provided at ‘Lakeside Dream’ is only for the use of those guests named and numbered on the ‘Contract’, and no one else is permitted to stay overnight, unless agreed by us in writing beforehand. Any subletting, sharing, over occupation or assignment is strictly prohibited.

Failure to adhere to this pre condition will render the booking void and our managers will have the right to evict your party from ‘Lakeside Dream’ immediately, and to notify law enforcement authorities if necessary to assist in the process.


As the lead guest, you are responsible for ensuring that you have holiday / travel insurance to cover cancellation prior to your booking or other loss or accident that may occur during the period of your booking.

All those guests named and numbered on the ‘Contract’ should also have adequate Travel Insurance, and have a 24-hour emergency telephone number for the company that provided the insurance.


As owners, we will not be accountable for any disruption of, delay to, or cancellation of your travel arrangements and/or holiday due to any of the following occurrences: hostilities, threat of hostilities, riots, civil commotion, terrorist activities, political unrest, industrial unrest/strikes, natural disasters, closure of airports, change of airline schedules, adverse weather conditions, unavoidable circumstances at ‘Lakeside Dream’, which result in us having to change your accommodation at short notice, or any other circumstances beyond our control.


Use of the accommodation and all amenities at ‘Lakeside Dream’ including the pool are offered on the condition that they are used entirely at the guest(s) own risk. We cannot accept responsibility for accidents, injuries, illness, death or loss or damage to guest(s) property or belongings, including motor vehicles, howsoever caused.

All baggage, money and personal possessions remain at all times and in all circumstances at the guest(s) risk, and all items of value should be covered by the guest(s) insurance.


As owners, we will not accept responsibility for:

- inconvenience caused by disturbance of any kind and at any time from neighbouring property, land, tenants/guests or animals;

- failure of local services for any length of time, such as electricity or water supply;

- unavailability of any general amenities including telephone, internet or television;

- unavailability of the swimming pool if it has to be drained and re-filled for any reason, or closed due to health and/or safety concerns;

- road works or condition of the roads on the Windward Cay development or its approaches;

- injury to a guest or damage that may be as a result of using any electrical items, such as the washing machine, dishwasher, iron, televisions, kettle, coffee maker etc, which is entirely at the discretion of the user.


All doors and windows must be closed and locked, and the alarm system activated whenever the house is left empty. The alarm system is linked directly to ADT and also to the emergency services, including the police and sheriff. If the alarm is inadvertently set off, the charges to reset it can be very steep, so great care must be taken to follow all the instructions precisely, including what to do in the event of a false alarm, or a bill in excess of $100 could be levied on the lead guest in the event of a house visit from the emergency services.

Valuables (jewellery/passports/cash etc) should be placed in the safe whenever they are not required. The safe combination must not be changed under any circumstances.


Smoking and/or vaping is strictly prohibited inside the house at all times. Costs required to deodorize the house or for additional cleaning will be deducted from the security deposit, and any damage from cigarette burns will be charged at full replacement cost.

12. POOL

The lead guest is responsible for ensuring that there are no children aged 5 or under in their party, or children of any age that cannot swim.

Children are not allowed to use the pool at any time without adult supervision.

We will not be liable for any injury howsoever caused resulting from use by guests or their visitors of the swimming pool.


Any pool heating requirements should be indicated at the time of original booking and paid for as part of the final balance. The thermostat will be set to 84F and, under normal circumstances and proper use, the heat pump will be able to raise the water temperature to this level.

When the air temperature is cold, however, the heat pump cannot raise the water temperature more than 10-15 degrees above the air temperature and it may take longer than usual to reach this temperature. Furthermore, on rare occasions cold weather may make it impossible for the heat pump to raise the water temperature to the thermostat setting.

When the pool heating is in use (normally November to April), the blue pool blanket must always be put on at night, or during the day if the pool is not in use.


Under no circumstances is the portable charcoal BBQ ever to be lit within the screened pool deck area. It should only be used outside in the open on the adjacent grass area, and a minimum of 3 metres distance from the exit door to the screened pool deck area.

The BBQ must be put back in the garage once it has cooled, and cleaned thoroughly and hygienically before departure. Failure to clean the BBQ will result in a cleaning charge, which will be deducted from the security deposit.

In using the BBQ the lead guest must accept full responsibility for the consequences of its use; in particular for any personal injury howsoever caused, or for any damage that might be caused to the house or its surrounds by fire or hot embers.


Animals and pets are never allowed at ‘Lakeside Dream’.


Swimming, fishing or throwing stones of any size into the lake is strictly prohibited. Feeding the wildlife is strongly discouraged; in particular, squirrels and feral cats although it is OK to feed the ducks and the turtles.

Please note that it is illegal to feed alligators in Florida and the fines are HUGE if you are caught.


As lead guest you are responsible for ensuring that all members of your party take good care of the house throughout the duration of the rental period. If anything is damaged or broken during your stay, it should either be replaced before you leave or, if that is not practical (for example a carpet stain), the Management Company should be informed immediately so that it can be rectified before the next guests arrive.

The security deposit will be used to pay for any damage/breakages as they are the legal responsibility of the guests; moreover, we retain the right to charge for damage/breakages if not replaced or paid for at the time of occupancy.

We will refund the security deposit once the house has been checked by the management company less any charges levied for things such as excess cleaning costs, replacements or repairs for damage/breakages.


Guests may arrive at the house any time after 17.00 hours on their arrival date.


Guests must leave the house by 10.00 hours on the morning of their departure, unless otherwise agreed with us in advance.

The house must be left clean and tidy at the end of the rental period, and this includes all equipment and kitchen utensils. Linen should be removed from beds.

The lead guest is responsible for ensuring that all doors and windows are closed and locked, and the blinds drawn. The air conditioning should be set to 82F on a permanent hold and the alarm set when the house is left for the last time.


We fully expect you will be very happy with the accommodation and amenities provided at ‘Lakeside Dream’. Any complaints regarding the condition of the house on arrival must be made to our management company ‘Key Vacation Homes’ within 24 hours of arrival, and conveyed to us by email to us at: so that we can assist if necessary.

We will not be responsible for any matter that is not brought to our attention during your stay at ‘Lakeside Dream’.

If any problem was not resolved locally, the lead guest should register a complaint in writing to us within 7 days of leaving the house.
Property summary
Property typeVilla Property number1817 Bedrooms3 Bathrooms2 Sleeps6 Rating
Located in
Windward Cay, Kissimmee, Orlando
Property brochure
Owner's details
Owner's name
David Morgan
Contact number
Member Since
At a glance
  • Beautiful secluded south facing lakeside location
  • Haven of nature in a conservation area
  • Private heated pool
  • Very large pool deck
  • Fully monitored alarm system
  • Free secure high speed wireless internet
  • Cable TV with DVD/VCR in the living area and bedrooms, 200+ channels, live Premier League Football
  • Monthly rates available January, February and March

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