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

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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


Gerry

Gerry

(Scotland)

Storey Lake Resort Kissimmee Orlando 4 Bed 3 Bath Townhouse enclosed patio with private pool
We had a fantastic time, it was excellent and our favourite location to date.Reviewed on 19-07-2017

Hi Kym Just thought I'd drop you a line to say thanks to you and david for all your help organising our holiday. We had a fantastic time and glad you convinced us to hang off for storey, it was excellent and our favourite location to date. Thanks again. Ps think we might need at least 3 villas in storey next year as family and friends who visited loved it too and have been asking for your details. Do you do any buy 2 get one free deals? Haha Regards Gerry Archibald

Comment(Top Tip):- Kym & David can always be reached on the Company chatline 7 days a week to answer any questions and help you with your booking.

Check-in Date: 29-06-2017

Rating:

Agnes & John

Agnes & John

(Motherwell, Scotland)

Windsor at Westside Resort Kissimmee Orlando 8 Bed 6 Bath Home with private swimming pool and spa
This was our first time using Destination America U.K. and we were all delighted with the Villa.Reviewed on 05-07-2017

Dear Kym, We just wanted to extend our thanks for the arrangements you made on our behalf to secure our holiday accommodation. This was our first time using Destination America U.K. and we were all delighted with the villa, it's location and facilities were ideal. Additionally, the back up support you provided was fantastic!! this helped make our holiday trouble free. Your attention to detail was most re-assuring and made our holiday just perfect. Without hesitation we would use your company again to support further holiday considerations. You gave us great support, very helpful information, very prompt replies to enquiries made, all of this made our holiday very enjoyable!!! Very well done Kym. Many thanks Agnes & John

Comment(Top Tip):- We were all delighted with the Villa, it's location and facilities were ideal.

Check-in Date: 07-06-2017

Rating:

Tina

Tina

(Worcestershire, UK)

Calabria at Westside Kissimmee Orlando 4 Bed 3 Bath Holiday Rental Home with swimming pool (AOA)
It's beautiful. Quite possibly the best one we have stayed in throughout our 15years of coming here.Reviewed on 17-06-2017

Hi Kym Just to let you know we finally arrived at the villa and I have to say it's beautiful. Quite possibly the best one we have stayed in throughout our 15years of coming here. The owners have some personal touches inside such as photos and memorabilia which is clearly very dear to them. It doesn't feel like a hire from a business. Very much feels like we are loaning from a friend. Again beautiful. Thanks very much! You know we will be getting in touch again to sort next year's visit! Tina

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

Check-in Date: 16-06-2017

Rating:

Helen & Jim

Helen & Jim

(Scotland)

Windsor Hills Resort Kissimmee Orlando 5 Bed 5 Bath Rental Home with swimming pool, spa, games room
The villa was the right choice as our niece and nephew are never out of the pool. Reviewed on 05-04-2017

Having a good time here in sunny Orlando. The villa was the right choice as our niece and nephew are never out of the pool. Mind you the adults are just as bad. Off to Hollywood studios today. Thanks again for everything you do for us Kym. Helen

Comment(Top Tip):- We booked this property early with Kym to secure the best one for us.

Check-in Date: 30-03-2017

Rating:

Sidraima

Sidraima

(USA)

Cumbrian Lakes Kissimmee Orlando Florida 5 Bed 3 Bath Holiday Rental Home with swimming pool and spa
Perfect!Reviewed on 27-08-2016

It was a nice clean house, perfect situated and easy to get to... very close to 192 rd... and close to some parks... Beautiful front view..

Comment(Top Tip):- Close to Parks and 192

Check-in Date: 28-07-2016

Rating:

Michel

Michel

(Spain)

Windsor Palms Resort Kissimmee Orlando Florida 3 Bed 2 Bath Ground floor Holiday Rental Apartment
PerfectReviewed on 23-08-2016

The house is exactly as published on the site offers all the comfort and items to stay, well located, clean. When we had questions, we were served quickly.

Comment(Top Tip):- Well located for the Parks.

Check-in Date: 22-03-2016

Rating:

Bob Robinson

Bob Robinson

(Renfrewshire, Scotland)

Windsor Hills Resort Kissimmee Orlando 3 Bed 3 Bath RentalTownhouse with swimming pool, 50 Inch TV
Townhouse is fabulous !Reviewed on 17-08-2016

Hi Kym Yes, everything else is great. Flights were good. Villa is fabulous. Thanks. Bob

Comment(Top Tip):- I have booked my Orlando accommodation with Kym for the last few years - normally quite close to the date of travel & Kym always takes care of us.

Check-in Date: 13-08-2016

Rating:

Ryan & family

Ryan & family

(East Ayrshire)

Paradise Palms Resort Orlando 4 Bed 3 Bath Townhome with enclosed patio decking with private pool
Just to let you know we arrived and everything is great!!! Love the place!!!! Reviewed on 22-05-2016

Hi Kym Just to let you know we arrived and everything is great!!! Love the place!!!! Thanks for everything! Ryan

Comment(Top Tip):- We booked this property early with Kym at Deal A Trip in Peebles, Scotland

Check-in Date: 21-05-2016

Rating:

Anon

Anon

(New York)

Windsor Palms Resort Orlando 4 Bed 3 Bath Holiday Rental Home with private swimming pool and spa
Great Place to StayReviewed on 26-01-2015

The accomodations were great. The gated community was definitely 5 star in everyway. It is also very economical when you share with couples. We had no complaints. If you are going to Orlando on a vacation, this is the place to stay. It is located close next to the Convention Center and close to restaurants, shops, etc. You are also close to all attractions. I believe there is a shuttle for the attractions, but you have to check with guest services. The next time we are in the Orlando area, we will be booking this property.

Comment(Top Tip):- The gated community was definitely 5 star in everyway.

Check-in Date: 04-07-2009

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:

Peter

Peter

(UK)

Eagle Pointe Kissimmee Orlando 3 Bed 2 Bath single storey Holiday Rental Home with swimming pool
“Well presented, roomy with all the facilities you could ask for and in a great convenient location.Reviewed on 31-05-2014

We stayed for 5 nights following a Caribbean cruise . The villa is extremely well presented and the layout is well thought out too, There is an abundant choice of crockery, cutlery, glassware and more importantly plastic glasses, plates, bowls if you wish to eat and drink in the pool area. The main room has a formal dining area and two large comfy sofas with large flat screen TV, with cable, DVD and Video players. Nothing better than enjoying your favourite beverage around the pool which when illuminated in the evening is great and the whole area is screened to prevent the local bugs attacking! This area is also completely screened by fencing so it is extremely private and something not all villas have and was appreciated as personally I like to relax without being watched by neighbours! All in all, this villa has everything you could possible need for a relaxing stay.

Comment(Top Tip):- “Well presented, roomy with all the facilities you could ask for and in a great convenient location.”

Check-in Date: 03-02-2014

Rating:

Harker Family

Harker Family

(UK)

Eagle Pointe Kissimmee Orlando 3 Bed 2 Bath single storey Holiday Rental Home with swimming pool
Absolutely perfectReviewed on 31-05-2014

Stayed here many times over the years and never disappoints. Everything you need for a comfortable, yet luxurious holiday as a family. Very high level of cleanliness throughout villa and well equipped. Pool is amazing (especially with the pool heat on for a late night dip after a long day at the Disney parks.) Paula (the owner) was very helpful throughout the booking process and was able to organise us discounted disney tickets and car hire. Can't recommend enough!

Comment(Top Tip):- Book early, avoid dosapointment

Check-in Date: 15-03-2014

Rating:

O` Neil

O` Neil

(Ireland)

Eagle Pointe Kissimmee Orlando 3 Bed 2 Bath single storey Holiday Rental Home with swimming pool
Home from HomeReviewed on 31-05-2014

Fantastic, well kept villa, right in the middle of kissimmee but secluded enough so your out of the hustle and bustle. Great amenities close by with a 24 hour wall Mart 5 mins drive away. Great private pool with the option to have it heated! Excellent communication from the owner. With a management company always on hand to rectify any problems (which we never had). Pool is cleaned on e weekly. Plenty I kitchen utensils so your not busy washing up all the time. Great household appliances, dishwasher, washing machine, tumble dryer. Also a new addition for 2013 is the games room great for family fun in the evenings. I would definitely recommend and I myself will be back I stay again!

Comment(Top Tip):- Would I recommend this vacation rental to my best friend? Yes.

Check-in Date: 08-07-2013

Rating:

Dalaski

Dalaski

(UK)

Eagle Pointe Kissimmee Orlando 3 Bed 2 Bath single storey Holiday Rental Home with swimming pool
Chill out timeReviewed on 31-05-2014

This is the fourth time we have stayed here, we love it. Our only challenged each time we go is not getting lost lol. This time we did not go to any of the theme parks as we had no children with us, we visited historic districts, went on an airboat ride and visited other places such as Cocoa Village and Savannah. Shopping as always was good, but we take few clothes with us. Would recommend this house, it's near the parks shopping malls and supermarkets. Plenty of places to eat.

Comment(Top Tip):- The property was "as advertised". I recommend the location. The property was a good value for the price paid. The property provided wifi/internet access. My security deposit was returned on time.

Check-in Date: 26-01-2014

Rating:

Levitt family

Levitt family

(USA)

Terra Verde Resort Kissimmee 3 Bed 2 Bath Townhouse, enclosed patio deck with hot tub and lakeview
We loved staying here!Reviewed on 20-05-2014

We loved staying here! The property is centrally located to all of the parks, with shopping nearby so we could keep the fridge stocked. Baby ducks came to visit from the lake while we were in the hot tub - such fun! We had one rainy day during our stay, and we felt right at home hanging out on the comfy couches and reading. The property management and desk staff were very helpful and friendly. I'll definitely come back. Thanks for the great stay!

Comment(Top Tip):-

Check-in Date: 13-07-2013

Rating:

Wenique Brooks

Wenique Brooks

(USA)

Terra Verde Resort Kissimmee 3 Bed 2 Bath Townhouse, enclosed patio deck with hot tub and lakeview
This was the perfect getaway over the summer. Reviewed on 20-05-2014

This was the perfect getaway over the summer. My boyfriend and I went to the beach, the parks, and stayed at the resort one day and went swimming at the pool. I was so relaxed in this quiet community! I am looking forward to booking next year!

Comment(Top Tip):- Perfect Getaway location.

Check-in Date: 17-10-2013

Rating:

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