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Upscale Kissimmee Retreat 8BR w/ Pool & Resort Access – 7 Min to Disney

Holiday home in Kissimmee with private pool and kitchen

Photo gallery for Upscale Kissimmee Retreat 8BR w/ Pool & Resort Access – 7 Min to Disney

Communal Pool, Children's Play Area
Private pool + relaxing spa
Fully equipped modern kitchen
Large dining area for groups
Bright open‑concept living space

Reviews

10 out of 10, Loved by Guests
8 bedrooms6 bathroomsSleeps 164001 sq ft

Popular amenities

  • Pool
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi

Rooms & beds

8 bedrooms (sleeps 16)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Bedroom 3

1 King Bed

Bedroom 4

1 Queen Bed

Bedroom 5

1 Queen Bed

Bedroom 6

2 Single Beds

Bedroom 7

2 Single Beds

Bedroom 8

1 King Bed

6 bathrooms

Bathroom 1

Bathtub · Toilet · Shower only

Bathroom 2

Toilet · Shower only

Bathroom 3

Toilet · Shower only

Bathroom 4

Toilet · Shower only

Bathroom 5

Bathtub or shower · Toilet

Bathroom 6

Toilet · Shower only

Spaces

Deck or patio
Porch or lanai
Kitchen
Separate dining area
Garden

About this property

Upscale Kissimmee Retreat 8BR w/ Pool & Resort Access – 7 Min to Disney

Enjoy a stylish stay at this spacious 8‑bed, 6‑bath Kissimmee retreat just minutes from Disney. Relax in the private pool, cook in the fully equipped kitchen, or challenge friends in the game room. Access the community fitness center, then explore Orlando’s top attractions, including Universal Studios and world‑class golf. Your sunny Florida getaway awaits.

Permit: 5073857 | 4,001 Sq Ft | Free WiFi | Nearby Golf Courses

Take a break from the daily grind and escape with friends and family to this beautiful, spacious Orlando area abode.

Bedroom 1: King Bed | Bedroom 2: Queen Bed | Bedroom 3: King Bed | Bedroom 4: Queen Bed | Bedroom 5: Queen Bed | Bedroom 6: 2 Twin Beds | Bedroom 7: 2 Twin Beds | Bedroom 8: King Bed | Additional Sleeping: 2 Pack 'n Plays

COMMUNITY AMENITIES: Outdoor pool, fitness center, game room, clubhouse, arcade, lazy river

OUTDOOR LIVING: Screened lanai w/ heated private pool & spa (heated for an additional fee), gas grill, furnished patio

INDOOR LIVING: 4 Smart TVs w/ cable, 6 LED TVs w/ cable, dining table, pool table, air hockey table

KITCHEN: Fully equipped w/ stainless steel appliances, microwave, coffee maker, cooking basics, dishware/flatware, island (4 stools)

GENERAL: Free WiFi, washer/dryer, linens/towels, central heating & air conditioning, iron/board, keyless entry, starter set of cleaning essentials and toiletries

FAQ: Pool heat fee (paid pre-trip), step-free entry, stairs required to access upper floor, 2 exterior security cameras (facing out)

PARKING: Garage (2 vehicles), driveway (2 vehicles), additional street parking (first-come, first-served)

THE LOCATION

WALT DISNEY WORLD (~7 Miles): EPCOT, Magic Kingdom, Hollywood Studios, Animal Kingdom, Art of Animation Resort, Disney Springs, golf courses, shopping, dining

UNIVERSAL STUDIOS (~20 Miles): Islands of Adventure, Volcano Bay, The Wizarding World of Harry Potter

ORLANDO HIGHLIGHTS: Old Town (10.6 miles), SeaWorld Orlando (16.8 miles), ICON Park (19.5 miles), Downtown Orlando (29.0 miles), The Holy Land Experience (23.0 miles), Orlando Science Center (30.5 miles), Orlando Museum of Art (30.7 miles), LEGOLAND (32.8 miles)

GOLFING: Highlands Reserve Golf Club (4.3 miles), ChampionsGate Golf Club (4.8 miles), Orange Lake Golf (5.1 miles), Mystic Dunes Golf Club (6.6 miles)

AIRPORT: Orlando International Airport (27.9 miles)

HOUSE RULES

- No smoking

- No pets allowed

- No events, parties, or large gatherings

- Must be at least 25 years old to book

- Additional fees and taxes may apply

- Photo ID required prior to check-in

- NOTE: Although the property features step-free entry, stairs are required to access the bedrooms on the top floor and may be difficult for guests with limited mobility

- NOTE: Your safety matters. This property features 2 exterior security cameras: 1 camera is a Ring doorbell camera located on the front porch facing the front entry, and 1 camera is on the side of the house facing the side of the property. The cameras are outward facing and do not look into interior spaces. The cameras actively record video and sound when activated by motion

- NOTE: The pool can be heated for an additional $30 per day and is charged for your entire stay. If you'd like the pool to be heated, please add a request to your Permit: 5073857 | 4,001 Sq Ft | Free WiFi | Near Disney & Top Golf Courses

Escape to this spacious 8‑bedroom, 6‑bath Kissimmee retreat, perfect for large families and groups seeking comfort, convenience, and resort‑style amenities. Located just 7 miles from Walt Disney World, this upscale home offers everything you need for a relaxing Orlando getaway.

Sleeping Arrangements
- Bedroom 1: King
- Bedroom 2: Queen
- Bedroom 3: King
- Bedroom 4: Queen
- Bedroom 5: Queen
- Bedroom 6: 2 Twins
- Bedroom 7: 2 Twins
- Bedroom 8: King
- Additional: 2 Pack ’n Plays
-Additional: Crib

Community Amenities
Outdoor pool • Fitness center • Game room • Clubhouse • Arcade • Lazy river

Outdoor Living
Screened lanai • Private heated pool & spa (fee applies) • Gas grill • Furnished patio

Indoor Living
4 Smart TVs + 6 LED TVs (cable) • Dining table • Pool table • Air hockey • Open living spaces

Fully Equipped Kitchen
Stainless steel appliances • Microwave • Coffee maker • Cooking basics • Dishware/flatware • Island w/ 4 stools

General
Free WiFi • Washer/dryer • Linens/towels • Central A/C & heat • Iron/board • Keyless entry • Starter toiletries & cleaning essentials

FAQ
- Pool heat available for $30/day (entire stay)
- Step‑free entry; stairs required for upper‑floor bedrooms
- 2 exterior security cameras (front door + side of home; outward‑facing only)

Parking
Garage: 2 vehicles • Driveway: 2 vehicles

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⭐ Location Highlights

Walt Disney World (~7 miles)
Magic Kingdom • EPCOT • Hollywood Studios • Animal Kingdom • Disney Springs • Golf • Dining • Shopping

Universal Studios (~20 miles)
Islands of Adventure • Volcano Bay • Wizarding World of Harry Potter

Orlando Attractions
Old Town (10.6 mi) • SeaWorld (16.8 mi) • ICON Park (19.5 mi) • Downtown Orlando (29 mi) • LEGOLAND (32.8 mi)

Nearby Golf
Highlands Reserve (4.3 mi) • ChampionsGate (4.8 mi) • Orange Lake (5.1 mi) • Mystic Dunes (6.6 mi)

Airport
Orlando International Airport (27.9 mi)

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⭐ House Rules
- No smoking
- No pets
- No parties or large gatherings
- Must be 25+ to book
- Photo ID required before check‑in
- Additional taxes/fees may apply

Notes:
- Stairs required for upper‑floor bedrooms
- Cameras record motion at entry points only
- Pool heat optional ($30/day)
- Grill available; propane may be refilled by guest if needed

We are located in the beautiful Windsor at Westside - a gated, resort-style vacation rental community in the heart of Kissimmee, Florida. Guests have use of the on-site facilities which includes access to the 10,000 sq. ft. clubhouse, fitness center, video arcade, children's water play area, resort-style swimming pool, water slide, lazy river and Tiki Bar! Experience your luxury vacation getaway here with us!

Add dates for prices

Amenities

Pool
Hot tub
Kitchen
Washing machine
Dryer
Free WiFi

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House Rules

Check in after 4:00 PM
Minimum age to rent: 24
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Check-out instructions

The host requires you to complete the following before checking out:
Load the dishwasher
Gather used towels
Remove personal items, remove leftover food and drinks and take out the rubbish
Turn off the lights and lock the doors
Please place all remotes by their respective televisions
Please sign out of any accounts used on smart devices
Turn off propane if grill was used
Failure to complete these may result in a negative review from the host.
Guests are required to sign the Rental Agreement

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock

We should mention

A car is recommended for transport to and from this property

About the area

Kissimmee

Located in Kissimmee, this holiday home is near theme parks. ChampionsGate Golf Club and Mystic Dunes Golf Club are worth checking out if an activity is on the agenda, while those wishing to experience the area's popular attractions can visit Walt Disney World® Resort and Disney's Animal Kingdom® Theme Park. Old Town and Disney's Hollywood Studios® are not to be missed. Spend some time exploring the area's activities, including golfing.
Map
Kissimmee, FL

What's nearby

  • Northeast Regional Park - 4 min drive - 3.1 km
  • Lake Davenport - 4 min drive - 3.1 km
  • Highland Reserve Golf Club - 6 min drive - 4.0 km
  • Four Corners FC - 6 min drive - 5.4 km
  • ChampionsGate Golf Club - 8 min drive - 8.1 km

Getting around

  • Kissimmee Station - 33 min drive
  • Kissimmee, FL (ISM-Kissimmee Gateway) - 32 min drive

Restaurants

  • ‪McDonald's - ‬7 min drive
  • ‪7-Eleven - ‬4 min drive
  • ‪Dutch Bros Coffee - ‬7 min drive
  • ‪Chick-Fil-A - ‬10 min drive
  • ‪Twistee Treat Berry Town - ‬7 min drive

Frequently asked questions

Does Upscale Kissimmee Retreat 8BR w/ Pool & Resort Access – 7 Min to Disney have a pool?

Yes, this property has a pool. Pool types include heated pools.

Is Upscale Kissimmee Retreat 8BR w/ Pool & Resort Access – 7 Min to Disney pet-friendly?

No, pets are not allowed at this property.

What time is check-in at Upscale Kissimmee Retreat 8BR w/ Pool & Resort Access – 7 Min to Disney?

Check-in begins at 4:00 PM.

What time is check-out at Upscale Kissimmee Retreat 8BR w/ Pool & Resort Access – 7 Min to Disney?

Checkout is at 10:00 AM.

Where is Upscale Kissimmee Retreat 8BR w/ Pool & Resort Access – 7 Min to Disney located?

Situated in Kissimmee, this holiday home is 2.8 mi (4.5 km) from Lake Davenport and within 6 miles (10 km) of Northeast Regional Park and Four Corners FC. Highland Reserve Golf Club and Surfari Water Park are also within 6 miles (10 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 20 out of 22 reviews
Rating 8 - Good. 2 out of 22 reviews
Rating 6 - Okay. 0 out of 22 reviews
Rating 4 - Poor. 0 out of 22 reviews
Rating 2 - Terrible. 0 out of 22 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

9.6/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Theresa J.

Liked: Cleanliness, check-in, communication, location, listing accuracy

10/10 AWESOME

My stay was awesome. The host was great even allowed me to check in early I would definitely stay here again
Stayed 2 nights in May 2024

10/10 Excellent

Susan P., Amityville

Liked: Cleanliness, check-in, communication, location, listing accuracy

New Years Family Trip

We had a great time in this beautiful home. Owners are so accommodating. It was perfect for our family of 12
Stayed 4 nights in Dec 2022

10/10 Excellent

cynthia w.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family Time

Very relaxing. Really enjoyed the quietness and that we were not too far from stores. Kids loved the pool 10:am -10:00pm. Lovely place
Stayed 7 nights in Jul 2024

10/10 Excellent

Tamont W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Friend and family meet up

Overall the house was great and has alot of space and has stuff you can cook with and the location was great the host for the house was on point with everything and very nice
Stayed 4 nights in Nov 2023

8/10 Good

Phia L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Grad bash

Our group enjpyed our stay in the home. All of the rooms were spacious and accommodated everyone in our party without concern. The living area
Stayed 2 nights in Aug 2024

10/10 Excellent

Betsy O.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Last minute booking

Because of a mistake our family had to find a last minute home to stay in to finish our vacation.Jean and Shanelle were gracious hosts and their home was beautiful and well maintained. When we made dinner and breakfast the pans and cooking utensils were top quality and the beds and accomodations were comfy and up to date. Thank uou
Stayed 1 night in Mar 2025
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Cheryl G.

A Must Stay

I have stayed at other short term vacay rental properties and this one stands out by far. If you're ever in Orlando and need an upscale rental property, this is it. This is my second time staying here. It is spotless, organized, and a simply elegant upscale home away from home. The owners and property manager(s) are extremely professional and accommodating and respond promptly to your requests, even a last minute change to extend your stay. You can travel with practically the bare necessities as the things you may need are there. Thank you for entrusting us with your impeccable property, we treated it with the care with which you obviously maintain it. Best wishes.

10/10 Excellent

Alan M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
House was excellent. Host was always available for any queries we had and replied immediately. House is in an excellent location for Disney parks.
Stayed 28 nights in Jul 2025

10/10 Excellent

Patrick G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Stay!

Everything was as expected and the owners / hosts were supper communicative and helpful!
Stayed 5 nights in Nov 2022

10/10 Excellent

Lynn W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect house

Room to spread out and fun for everyone.
Stayed 6 nights in Oct 2022

10/10 Excellent

Coneatra M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Very spacious home

Beautiful home location convenient to shopping and restaurants
Stayed 3 nights in Oct 2022
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Cheryl

A must!

From the moment that you open the front door, you felt at home. All the things you'd need for a vacation were there (except for a chef). Beautifully decorated, spotless, spacious and did I mention, clean! I must add that the team behind the home were very gracious. An awesome experience. I definitely recommend this place.

10/10 Excellent

Gabriela D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Halloween Horror Nights Weekend

We had a great time with our friends and family, the house fit 12 adults comfortably. The pool was a good size for our group and communication with the owners was an easy and smooth process.
Stayed 3 nights in Sep 2022

10/10 Excellent

Yolanda W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

It was nice

Good
Stayed 3 nights in Aug 2022

10/10 Excellent

Mary P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Disney in July

The home was so spacious! The 12 of us were never on top of each other. The house was clean and neat. The owners are very responsive. It was so convenient having a washer and drier, and more than enough beach towels to use for the pool. The only downside is beyond the owner’s control unfortunately. The homes are close together and if your neighbors are loud and rowdy or don’t observe the 10:00 quiet time, you need to call either the roving night patrol or the Sheriff. We needed to do both. , you need to call either the roving night patrol or the
Stayed 7 nights in Jul 2022

10/10 Excellent

Garrye C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

like staying at this area would want to stay here every time we come here

just love the place and area.
Stayed 5 nights in Jul 2022

8/10 Good

cykenia r.

Liked: Cleanliness, check-in, communication, listing accuracy

Great house

The house was awesome and the property manager was outstanding she made sure we had everything we needed to make our stay memorable. The only thing we had an issue with was inconsiderate neighbors they consistently played loud music during late night and had no regards for anyone. Overall I would still give the house we were in, peoperty manager, and house owners 5 stars. Thank you for a great stay.
Stayed 10 nights in Jun 2022

10/10 Excellent

Corliss R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful Experience

Every year we choose somewhere to vacation as a family . And this year we choose Florida the beautiful sunshine state! This property was the perfect place for our family to stay!!!! The owners were great with communicating with us each day to make sure our needs were meet. This property is everything that's advertise and more; spacious , comfy and clean. We enjoyed having a pool and jacuzzi on site. ( This was a great hit with the kids). We will definitely stay here again in the near future.
Stayed 3 nights in Jun 2022

10/10 Excellent

Lynn T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

very lovely house

We had a great time, the house was spectacular, the amenities were a bonus for the children. nice quick getaway for the 4 days we were there, just wish we could of stayed longer. Maybe next time !
Stayed 4 nights in Apr 2022
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Leslie

Fantastic Home

We had a wonderful time. The home was lovely. Plenty of rooms, space and very accommodating. We enjoyed the pool and hot tub. Would definitely stay again!
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Bryan

Awesome Property

Very nice, modern, spacious property enough for the whole family!!! Very clean, Upscale, and family friendly. The kids and adults loved it!!!Pool and Pool Table/Air Hockey were big hits.

10/10 Excellent

Maria Q.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 2 nights in May 2024

About the host

Hosted by JEAN & SHANELLE

Host profile image

Languages:

English, French
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