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Expiry: [12 months from booking date]
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guaranteed best price
no services fees added, the price advertised is the price you pay with no hidden fees. great!
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Free Cancellation
Cancel within 48 hours of booking to get a full refund. More details. -
Earn Villa Miles With This Booking
Happy days! You get credit to spend on your next 5 Star Villa Holiday. Expires 12 months from booking date.
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Free Accidental Damage Insurance, Worth
Your covered! If you accidentally break something, you will be covered up to . Please note excess fees may apply.
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Guaranteed Best Price
No services fees added, the price advertised is the price you pay with no hidden fees. Great!
-
Free Cancellation
Cancel within 48 hours of booking to get a full refund. More details. -
Earn Villa Miles With This Booking
Happy days! You get credit to spend on your next 5 Star Villa Holiday. Expires 12 months from booking date.
-
Free Accidental Damage Insurance, Worth
Your covered! If you accidentally break something, you will be covered up to . Please note excess fees may apply.
Dear Guest
Let us give you peace of mind.
When you reserve a villa on 5 Star Villa Holidays and are unable to travel due to Covid 19 travel restrictions.*
5 Star Villa Holidays will allow you to move your reservation to a date in the future at no charge.
Enhanced cleaning
All 5 Star Villas meet our 6 step enhanced cleaning guidelines.
Surfaces sanitised All high touch surfaces sanitised e.g Remote controls, door handles etc
Linens All linens washed on a high heat setting.
Extensive clean Following our cleaning checklist, available on request.
Wear gloves and mask To prevent cross contamination.
Approved cleaning products Disinfectants with 70% alcohol or more.
Local guidelines followed Any additional or safety measures complied with.
Reserve online with confidence knowing 5 Star Villa Holidays has you covered.
All the best,
John Paul Donnelly
P.S Go on then, reserve your 5 Star Villa Holiday knowing you are covered.
*Covid-19 travel restrictions is when laws state you are unable to travel to a certain country.
Request Your Free Travel Consultation
Arrange your free consultation at a time that is convenient for you 
-
Guaranteed Best Price
No services fees added, the price advertised is the price you pay with no hidden fees. Great!
-
Free Cancellation
Cancel within 48 hours of booking to get a full refund. More details.
-
Earn Villa Miles With This Booking
Happy days! You get credit to spend on your next 5 Star Villa Holiday. Expires 12 months from booking date.
-
Free Accidental Damage Insurance, Worth
Your covered! If you accidentally break something, you will be covered up to . Please note excess fees may apply.
Book Soon!
2 villas booked in
in the past 7 days
2 villas booked in
in the past 7 days
Your Family will love the 1st Class Amenities at Your Private Villa on Windsor Island Resort, Orlando Villa 5044
18 Guests
7 Bedrooms
6 Bathrooms
5 Star Villa Holidays is proud to present Orlando Villa 5044
Windsor Island is Kissimmee’s newest and most luxurious resort community. This stunning vacation rental community features all the popular resort amenities of its sister communities - Windsor Hills Resort and Windsor Palms Resort, AND so much more! An extraordinary 5,000 sq.ft. clubhouse is the centerpiece, as well as a huge resort-style pool, complete with cabanas, a water slide, and lazy river – perfect for families to enjoy for hours! When it’s time for a drink or a bite to eat, the tiki bar serves both your favorite libation, along with a tempting menu for poolside dining. With all the latest in cardio and strength building equipment, the fitness center will keep you in shape while on vacation. For some friendly competition, there are sand volleyball courts and a multi-purpose sports courts. In addition, a sundry shop is located in the clubhouse, along with a video arcade. Windsor at Westside is a gated community, with an attendant, to ensure the safety for all our visiting guests.Windsor at Westside Resort is strategically located in the Kissimmee area, with easy access to the theme parks, dining and shopping. For those who are visiting Disney, the location provides quick access to all the Disney parks, via just one exit up Toll Road 429 to the Western Way Blvd. Disney entrance. Access to this “secret” west Disney entrance is just 8 minutes away and avoids the heavy traffic that can occur with the main Disney entrance.There is no better way to vacation than a rental home, and Windsor at Westside is sure to impress!
FEATURES
Meals
Chef optional- Self Catering
Housekeeping
- Housekeeping optional
Themes
- Adventure
- Away From It All
- Family
- Luxury
- Sports and Activities
- Tourist Attractions
Location
- Resort
General
- Air Conditioning
- Clothes Dryer
- Essentials
- Free Wifi
- Hair Dryer
- Heating
- Iron and Board
- Laptop Friendly Workspace
- Linens Provided
- Living Room
- Self Check in
- Towels Provided
- Washing Machine
Kitchen
- Coffee Maker
- Dishes and Utensils
- Dishwasher
- Fully Equipped Kitchen
- Kettle
- Microwave
- Oven
- Refrigerator
- Stove
- Toaster
Dining
- Dining Area
Entertainment
- Air Hockey Table
- Arcades
- Games Room
- Pool Table
- Satellite or Cable TV
- TV in every bedroom
- Video Games
Outside
- Covered Lanai
- Deck/Patio
- Outdoor Dining Area
- Sun Loungers
Pool & Spa
- Heated Pool optional
- Hot tub
- Jacuzzi/Spa
- Private Pool
Outside Services
- Airport Transfer - On Request, Additional Cost
- Car Hire - On Request, Additional Cost
- Experiences & Tours - On Request, Additional Cost
- Free Parking
- Private Chef - On Request, Additional Cost
- Security 24/7
Resort
- Bar
- Business Centre
- Children's Playground
- Children's Pool
- Cinema
- Club House
- Communal Pool
- Fitness Centre
- Games Room
- Lagoon style Pool
- Pool Table
- Restaurant
- Spa centre
- Spa/Jacuzzi
- Tennis Courts
- Tiki Bar
- Volley Ball Courts
Home Truths
- Family/Children Friendly
- Long term renters welcome
- Parking
- Parties/Events not allowed
- Wheelchair Accessible
- Nosmoking
- Nopets
- Check in: 16:00
- Check out: 10:00
- Size: 550
square meters
Sleeping Arrangements
- Bedroom 1: 1 King bed
- Bedroom 2: 1 King bed
- Bedroom 3: 1 King bed
- Bedroom 4: 1 Queen bed
- Bedroom 5: 1 Queen bed
- Bedroom 6: 1 Bunk bed
- Bedroom 7: 1 Bunk bed
EVERY 5 STAR VILLA HOLIDAY INCLUDES
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Towels -
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Bed Linen -
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Free WiFi -
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Professional Clean -
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24/7 Client Support -
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Free Accidental Damage Insurance -
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No Hidden Fees
Orlando Unlocked
AVAILABILITY
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Reviews
Jakensi, Billings, United States, Nov, 2021
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(5.0)
Great house, everything we expected!
Manu Saini
Hi Jakensi! Thank you for staying with us and for leaving us a review. We are so glad to hear that you enjoyed your stay and we hope to see you again in the future! Thanks Manu.
Josh, Pittsburgh, United States, Nov, 2021
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(5.0)
Very nice place! Multiple families can stay! Clean, spacious and within 30 minutes to a lot! When t...he construction for the extra activities throughout the resort is finished, we will definitely be back! Read More
Manu Saini
Thanks very much for your review. Looking forward to reserving another 5 Star Villa Holiday for you and your family.Thanks Manu
Tankya, Kansas City, United States, Nov, 2021
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(5.0)
Omg everything was just like the picture! Didn’t know I had to pay extra for the heat for the spa /p...ool area but I’m happy I did . Didn’t even want to leave lol very clean& location is not too far from everything Read More
Manu Saini
Hi Tankya! Thank you for staying with us and for leaving us a review. We are so glad to hear that you enjoyed your stay and we hope to see you again in the future! Thanks Manu.
Shamell, Cleveland, United States, Nov, 2021
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(5.0)
The house is exactly how the pictures show. It is new and clean. My family really felt at home and c...omfortable in this house. The rooms were beautiful and comfy. Read More
Manu Saini
Hi, thanks for your review, it's always nice to hear our guests experience. Looking forward to helping you reserve another 5 Star Villa Holiday. Thanks Manu
Dominique, Provo, United States, Nov, 2021
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(5.0)
My family and I really enjoyed the place. It looks like the picture and the size was great! The reso...rt is not complete so if you are looking for the resort activities, it’s not currently finished. There was a lot of construction happening around the property because of other houses being built but overall I really liked it! The kids loved the game room and the pool! I highly recommend! Read More
Manu Saini
Hi, thanks for your review, it's always nice to hear our guests experience. Looking forward to helping you reserve another 5 Star Villa Holiday. Thanks Manu
Rushelle, Wichita, United States, Nov, 2021
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(5.0)
awesome house exactly like the pics. wish it was a lil more clean. will definitely book again.
Manu Saini
Thanks very much for your review. Looking forward to reserving another 5 Star Villa Holiday for you and your family.Thanks Manu
Latorial, Aurora, United States, Nov, 2021
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(5.0)
The house was exactly what the picture was. The kids loved the game. When ever I had a question abou...t something it was a quick response. Read More
Manu Saini
Thank you for your review, I really appreciate your feedback. I am always here to help you reserve again in the future. Thanks Manu
Corrine, Toledo, United States, Nov, 2021
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(5.0)
House is amazing, lots of spaces and get for the kids with the game room and the 2 themed rooms upst...airs. Just be sure to bring your own supplies. But everything else is great. Read More
Manu Saini
Thanks very much for your review. Looking forward to reserving another 5 Star Villa Holiday for you and your family.Thanks Manu
Marisol, Buffalo, United States, Nov, 2021
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(5.0)
What a great house. We had a great time it was very clean. We are definitely coming back next year. ...My family and I had a great time. Read More
Manu Saini
Thank you for your review, I really appreciate your feedback. I am always here to help you reserve again in the future. Thanks Manu
Jessica, Laredo, United States, Nov, 2021
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(5.0)
The house was even better than the pictures we really enjoyed our trip will be booking again soon! A...ndy was a great host Read More
Manu Saini
Thanks very much for your review. Looking forward to reserving another 5 Star Villa Holiday for you and your family.Thanks Manu
LOCATION
$0
/per night
5.0 (13 Reviews)
GUEST
0 X NIGHTS
$0 per night
Helena Doyle
P.S5 Star Villa Holidays is a referral based business. Please refer your friends and family. Because they are referred by you, they will get preferential service
Book Soon!
2 villas booked in
in the past 7 days
2 villas booked in
in the past 7 days
CONFIRM & PAY 
Orlando Villa 5044
-
Guaranteed Best Price
No services fees added, the price advertised is the price you pay with no hidden fees. Great!
-
Free Cancellation
Cancel within 48 hours of booking to get a full refund. More details. -
Earn Villa Miles With This Booking
Happy days! You get credit to spend on your next 5 Star Villa Holiday. Expires 12 months from booking date.
-
Free Accidental Damage Insurance, Worth
Your covered! If you accidentally break something, you will be covered up to . Please note excess fees may apply.
CONFIRM & PAY
-
Guaranteed Best Price
No services fees added, the price advertised is the price you pay with no hidden fees. Great!
-
Free Cancellation
Cancel within 48 hours of booking to get a full refund. More details. -
Earn Villa Miles With This Booking
Happy days! You get credit to spend on your next 5 Star Villa Holiday. Expires 12 months from booking date.
-
Free Accidental Damage Insurance, Worth
Your covered! If you accidentally break something, you will be covered up to . Please note excess fees may apply.
-
PAY LESS UPFRONT
PAY PART OF YOUR RESERVATION NOW AND YOUR BALANCE LATER WITH NO EXTRA FEES.
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Pay part of your total now.
Confirm your reservation by paying part of the total price now.
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Pay your balance before check in
On your second payment date the balance will be charged to your original payment method.
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Balance payment is automatic.
No need to worry, you will receive a reminder 3 days before your next payment.
EVERY 5 STAR VILLA HOLIDAY INCLUDES:
-
![]()
Towels -
![]()
Bed Linen -
![]()
Free WiFi -
![]()
Professional Clean -
![]()
24/7 Client Support -
![]()
Free Accidental Damage Insurance -
![]()
No Hidden Fees
What Our Clients Are Saying
Verified by
EXCELLENT SERVICE!!!! I stayed in a Villa in
Protaras that I rented from them. Joe was extremely nice and helpful. I
strongly recommend this company. My next trip will surely include
renting...
- Amanda Maalouf, Lebanon
We've used 5 star several times and they have
been great. The test of any agency is when something goes wrong. This
happen to us, nothing to do with 5 star, but we explained...
- Sid Gleeson, UK
We loved staying at the house. Will stay again
and highly recommend to anyone! More than enough room and so close to
everything...
- Laura Meeks, USA
5 star is now my number one pick for my
vacations. They are very professional and always priced reasonably.
- Oneika, USA
Great communication, very helpful and the villa
was totally amazing even better than the photographs. I would highly
recommend...
- Jessica Parkes, UK
A Gift From 5 Star Villa Holidays
Please accept this FREE copy of “No More Stressful Travel Days! Here is a Proven Way to Travel in Style and Comfort with our Top 5 Secrets.” as my gift to you
Meet Your Expert Travel Consultants
John Paul Donnelly
Founder & CEO
John Paul's deep love for travel inspired him to turn his passion into a business and 5 Star Villa Holidays was founded in 2011. He is one of eight children and loves spending quality time with his larger-than-life family. In his spare time he loves immersing himself in different sporting activities around the world; skiing, surfing and football. He is always seeking new adventures and his philosophy is simple; love the journey of life.
Helena Doyle
Marketing Manager
Currently travelling the world and working remotely, it's no surprise that Helena is the author of 5 Star Villa Holidays' collection of travel guides. She loves exploring new countries and experiencing new cultures. If you need some holiday tips, look no further! In her spare time she loves going to the gym, compiling her 'Living the Dream' travel blog and enjoying fine wines!
Joe Donnelly
Sales Director
Living in Ireland, Joe is a family man with 2 beautiful daughters and a mischievous dog called Bruno. He is a very skilled chef who loves hosting dinner parties for family and friends. He is passionate about sport and boating. Joe is a keen golfer and loves nothing more than playing 18 holes on the best golf courses Europe has to offer. Joe has worked in the travel industry since 2005 and prides himself and his team as trustworthy travel experts.
Suzanne Pilcher
Creative Director
Born and raised by the beach in sunny Australia, Suzanne carries a deep-seeded affinity with the ocean and loves nothing more than exploring beautiful seaside destinations around the globe. As our travelling Creative, she is currently doing her best to experience and capture all that this incredible world has to offer, while living on a steady diet of coffee and art gallery visits.
Wilter Franceschi
Developer
Wilter's desire to see and experience the world took him from his home country of Brazil all the way to Vancouver, Canada, where he now lives and works for 5 Star Villa Holidays. He is an avid lover of the great outdoors and volunteers for the Canadian boat race committee. Wilter is a man of many talents, with a persevering passion for technology, programming (of course!) and science, as well as being a talented musician who likes to unwind by playing the bass and piano in his spare time.
Request Your Free Travel Consultation
Let us do the research, saving you time. Arrange your free consultation at a time that is convenient for you. Tell our travel experts your itinerary and requirements. They will email you a short list of luxury villas for your perfect holiday.
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