Orlando Florida Holiday Accommodation Rental Homes – Apartments - Pool Homes Villas, Condos, Beach Homes, Townhomes Resorts with Suites, Villas and Apartments

Call us 023 9204 3686
International: +44 23 9204 3686
- Information

Kissimmee, Orlando, Florida

The Kissimmee area has a number of established and popular communities offering Holiday Rental 'home-away-from-home' self-catering accommodation including Condos, Apartments, Townhouses and Homes with screened-in private swimming pool. Many of the locations offer on-site leisure amenities. The Kissimmee area is on Disney World Orlando's doorstep and the Maingate Entrance is situated on the famous Highway 192 strip, with its multiple of shopping, restaurants, fast food outlets, pubs and entertainment activities. To view all properties in the Kissimmee area search for 'Kissimmee' or drill down to one of the Kissimmee communities.




kissimmee Overview


Kissimmee is a very popular Orlando holiday area, situated next door to Walt Disney World Resort Orlando Florida, offering a vast choice of self-catering accommodation. Kissimmee is packed with a diverse tourism of attractions, shops, restaurants and night time entertainment - including the Old Town Shopping, Dining and Entertainment Attraction - plus a multitude of leisure amenities. Major attractions include Walt Disney World Resort theme parks The Magic Kingdom at Disney World, Epcot Center, Hollywood Studios Florida and Animal Kingdom. Evening entertainment includes Medieval Times and Capone's dinner shows. NB: The Disney Maingate Area in Kissimmee is located near to the Interstate 4 East/West Junction and is the start of the drive to the actual Disney Theme Park Entrances for the parking lots and ticket gates and is around 2 miles in distance. The Lake Buena Vista Resort Area including Downtown Disney with its shopping, dining and cutting edge entertainment in one fun-filled location is adjacent to Kissimmee and is easily accessed off Highway 192.


kissimmee Amenities


Kissimmee has an endless 'things-to-do' list! Relaxing, invigorating, stimulating, breathtaking - there's plenty of things to do in Kissimmee with attractions and activities in every direction. Look to the sky and soar high above Central Florida in a hot air balloon. Fly around the water on a thrilling airboat ride that introduces you to Florida nature and maybe even a real live alligator. Or just play it cool with water park adventures for more family fun. Shopping malls, fast food outlets, great restaurants, championship golf courses, festivals, dancing and nightlife. Kissimmee is truly a gateway to fun.

  • Water Sports
  • Action Packed!
  • Kid Friendly!
  • Near Disney
  • Fun Galore!
  • Homes with Pool

kissimmee Rental Types and Size


  • 1 Bed - Apartment - Sleeps 4 -
  • 2 Bed - Apartment - Sleeps 6 -
  • 3 Bed - Apartment - Sleeps 8 -
  • 3 Bed - Townhouse - Sleeps 8 -
  • 3 Bed - Townhouse with Private Pool - Sleeps 8 -
  • 3 Bed - Home with Private Pool - Sleeps 8 -
  • 4 Bed - Home with Private Pool - Sleeps 10 -
  • 5 Bed - Home with Private Pool - Sleeps 12 -
  • 6 Bed - Home with Private Pool - Sleeps 14 -
  • 7 Bed - Home with Private Pool - Sleeps 16 -

View all our kissimmee Rental Properties


Where is kissimmee



Kissimmee, Orlando, Florida, USA



kissimmee Quick FAQs


Are the properties bookable online ?
Yes, all properties can be booked online, securely using Paypal. Please note that some properties have 'instant' confirmation and others are 'on request'.
Can I make a booking by telephone ?
Yes, just call us on our Freephone Telephone no: 0800 180 4889 and we will be pleased to help you.
How do I book a Holiday Rental ?
All properties can be booked, or requested, online. Payments are secure using Paypal (NB: You do not have to be registered to use Paypal) or by telephone. We accept most major credit and debit cards – there is a small fee of 2.9% to cover the cost of processing bank fees. The deposit to make a definite booking is 20% or full payment if the arrival date is within 8 weeks. If the availability status of a property shows as 'On Request' you may process your online booking without a payment and we will verify availability prior to your payment being made
Who are Deal-A-Trip Holiday Rentals ?
Deal-A-Trip Holiday Rentals is operated by Destination America who have offered Holiday Rental Accommodation in Florida for over 25 years – with Orlando the main destination. See our website at www.destinationamerica.co.uk
Are the properties vetted and checked ?
All properties are thoroughly checked over by us direct or through the local property management agents to establish that all information is accurate. All properties are Owner Verified
Can I rely on the availability of a property ?
Yes. Most property calendars are 'live' and maintained bang up to date. Each property shows as one of these: Up to date (Live), On Request or the date of the last update
What is included in the Rental Rate ?
The rental of the property, taxes and local fees. Optional Extras may be offered during the booking process. The property is checked and prepared prior to your arrival and cleaned after the departure of each guest by the management company with linens and towels changed - this is included in the rates. There is nothing else to pay with regard to the property rental unless otherwise stated
What is in each property as standard ?
Properties are air-conditioned throughout, fully equipped and furnished for 'home-away-from-home' living up to the maximum number of persons allowed for; main TV with cable in the lounge, usually one in the Master Bedroom and often in each bedroom. The kitchen with come complete with utensils and crockery, fridge, freezer, electric stove, microwave oven, toaster, coffee-maker and most will have a dishwasher. There will be a change of linen and towels. The laundry area will have washer, dryer, iron and ironing board, hoover. Some properties will have infant/baby equipment included. Many properties will have many additional features and amenities available. Exceptions will be clearly stated
What should we take with us that may not be in the property ?
All properties are fully equipped for 'home-away-from-home' living with everything – including the kitchen sink! The one item we do recommend taking is 'beach or pool' towels – they will not be in the property. Also take into account that as for all self-catering rentals only the most basic of personal or kitchen items will be in the property – so an early trip to the supermarket is called for. Each Bathroom should have a hair dryer
Is smoking permitted in the property ?
The majority of rental properties now have a non-smoking policy, there are few exceptions
What are the Check-in and Check-Out Times ?
Check-in is from 4pm on / Check-out is by 10am


kissimmee Customer Reviews


Dereck

Dereck

(England)

Windsor Palms Kissimmee 6 Bed 3.5 Bath Resort Holiday Home with West facing swimming pool and spa
We have settled in well thanks. What a beautiful villa.Reviewed on 15-06-2023

Hi Kym We have settled in well thanks. What a beautiful villa. In typical Brit fashion the boys spent time around the pool yesterday and ended up looking like lobsters! The parcel arrived fine and Carolyn and Rachel are wearing their lovely robes while they are having their hair and makeup done right now. We are looking forward to a fantastic day. The weather is lovely (but a bit too warm for a suit!), and all plans have come together. Thanks again for all your help and contribution to making our holiday perfect. Warm wishes Dereck

Comment(Top Tip):- Thanks again for all your help and contribution to making our holiday perfect.

Check-in Date: 03-06-2023

Rating:

Donna

Donna

(West Lothian, Scotland)

Windsor at Westside Resort Kissimmee Orlando 6 Bed 4 Bath Rental Home with pool and spa, games room
The Villa was absolutely perfect, stunning and more than enough room for all of us, it was beautifulReviewed on 29-09-2022

The Villa was absolutely perfect Kym, stunning and more than enough room for all of us, it was really beautiful, thanks for arranging it for us ☺️ Donna x

Comment(Top Tip):- We always book with Kym who takes care of our Villa bookings for us.

Check-in Date: 08-09-2022

Rating:

Alyssa

Alyssa

(USA)

Storey Lake Resort Kissimmee Orlando 5 Bed 4 Bath Townhouse enclosed patio with pool and lakeview
Wonderful place, great community area.Reviewed on 17-02-2022

"Wonderful place, great community area with walking trails, pool and lazy river, clubhouse bar. The house had plenty of space for 5 adults. Beds comfortable, basic kitchen and shower, pool needs supplied. Everything was clean. Location was only about 10 mins from Disney springs. Many restaurants nearby (ate at a bahama breeze and Smokey bones) plenty of shopping nearby a Walmart and supermarkets. Plenty of parking available too. We all said we would most definitely stay here again".

Comment(Top Tip):- We all said we would definitely stay here again.

Check-in Date: 17-11-2021

Rating:

Robert

Robert

(USA)

Storey Lake Resort Kissimmee Orlando 5 Bed 4 Bath Townhouse enclosed patio with pool and lakeview
The house is a thousand times better than expected.Reviewed on 17-02-2022

"First I'd like to thank you for your awesome customer service. The house is a thousand times better than expected, very very clean, spacious, well decorated, great location and a very well located and specious swimming pool. My family and I had a great stay and we will definitely return. one more time thanks for all your service and my quick answers to all my questions."

Comment(Top Tip):- We will definitely return to this property.

Check-in Date: 04-01-2021

Rating:

John

John

(USA)

Storey Lake Resort Kissimmee Orlando 5 Bed 4 Bath Townhouse enclosed patio with pool and lakeview
Our stay was absolutely amazing.Reviewed on 17-02-2022

"Our stay was absolutely amazing. So easy to communicate with the local Management Company and they always gave very detailed information and instructions. The townhome itself was in very good condition and had everything we needed. I would absolutely recommend this & hope to stay again soon! "

Comment(Top Tip):- I would absolutely recommend this property and hope to stay again soon.

Check-in Date: 05-03-2021

Rating:

Erica

Erica

(USA)

Storey Lake Resort Kissimmee Orlando 5 Bed 4 Bath Townhouse enclosed patio with private pool
The home was fabulous, spacious, clean, beautifully decorated. The beds are so relaxing ...Reviewed on 24-11-2021

"The home was fabulous, spacious, clean, beautifully decorated. It accommodated me plus 7 other women. The beds are so relaxing after a long day of being out. There are plenty stores near amusement parks it the perfect area to be in. It was quiet no loudness very peaceful. A safe environment I loved it. " Erica P.. from , 05/27/2021

Comment(Top Tip):-

Check-in Date: 27-05-2021

Rating:

John

John

(USA)

Storey Lake Resort Kissimmee Orlando 5 Bed 4 Bath Townhouse enclosed patio with private pool
Great place to stay. Lots of space. Decent beds. Resort was fun.Reviewed on 24-11-2021

"Great place to stay. Lots of space. Decent beds. Resort was fun. Almost a perfectly stocked kitchen. Bring kitchen towels and oven mitts. Bath and swim towels were provided. Management was quick to reply and take care of concerns. Family friendly. Close to shopping and destinations. " 11/11/2021

Comment(Top Tip):-

Check-in Date: 11-11-2021

Rating:

John

John

(England)

Windsor at Westside Resort Kissimmee Orlando 4 Bed 3 Bath Townhouse enclosed patio with private pool
This house is right across from the main clubhouse pool so we went almost every day. Reviewed on 07-02-2020

Best rental process EVER. Checking in an out was a breeze. This house is right across from the main clubhouse pool so we went almost every day. The house was spacious, clean, and very comfortable. We felt at home!

Comment(Top Tip):-

Check-in Date: 13-05-2019

Rating:

Robert

Robert

(England)

Windsor at Westside Resort Kissimmee Orlando 4 Bed 3 Bath Townhouse enclosed patio with private pool
Home was beautiful and comfortable. Lots of room for a family of 8.Reviewed on 07-02-2020

Home was beautiful and comfortable. Lots of room for a family of 8.

Comment(Top Tip):-

Check-in Date: 19-12-2019

Rating:

Gail

Gail

(Maryland, USA)

Windsor Hills Resort Kissimmee Orlando Florida 3 Bed 2 Bath Holiday Rental Apartment Ground Floor
Large and comfortable, beautifully furnishedReviewed on 26-01-2015

My husband, two adult children and I stayed in this unit for five nights. The unit was large enough to provide comfortable and private accommodations for all of us. It is beautifully furnished, very well maintained and exceedingly affordable. It is an easy drive to Universal and other attractions.

Comment(Top Tip):- It is an easy drive to Universal and other attractions.

Check-in Date: 20-12-2013

Rating:

Becky

Becky

(Wisconsin)

Windsor Hills Resort Kissimmee Orlando Florida 3 Bed 2 Bath Holiday Rental Apartment Ground Floor
Amazing!Reviewed on 26-01-2015

We stayed at this property for 10 days. It was exactly as described in the pictures. The resort is beautiful. We have stayed in other condos and rental before and this place was amazing!

Comment(Top Tip):- Lots of space.

Check-in Date: 15-08-2013

Rating:

Martine

Martine

(Athens, Greece)

Windsor Hills Resort Kissimmee Orlando Florida 3 Bed 2 Bath Holiday Rental Apartment Ground Floor
Great PropertyReviewed on 26-01-2015

The house was excellent, exactly like the pictures! The property itself and the amenities were really nice and well kept. I would definitely stay here again and recommend it to friends and family.

Comment(Top Tip):- Excellent house.

Check-in Date: 01-08-2014

Rating:

Greg Robertson

Greg Robertson

(Savannah, Georgia)

Windsor Hills Resort Kissimmee Orlando Florida 3 Bed 2 Bath Holiday Rental Apartment Ground Floor
Wonderful Stay!Reviewed on 26-01-2015

Fabulous place to stay. Well appointed and spacious. Great to ave a private bathroom for each bedroom. Excellent location to all attractions yet removed from the busy touristy areas. Beautiful townhome in a beautiful resort. Would certainly stay again....

Comment(Top Tip):- Excellent location

Check-in Date: 01-09-2014

Rating:

Holiday Rental Location Information - More Suggestions

Villas, Homes, Homes with Pool, Townhouses, Apartments & Condos