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Villas in Kissimmee and Apartments - Holiday Lettings - Holiday Rentals Kissimmee

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12,943 Holiday homes

Holiday condo with golf nearby in Kissimmee

Kissimmee condo

3 bedrooms / 2 bathrooms / sleeps 6

“Awesome condo” Do to problems at work I was not able to vacation with my two friends but they told me that the condo was awesome in every way, great location, great amenities, convenient to Disney World which was their main reason for going, and beautifully decorated. They loved it!

66

Responds fast! avg. 2 hours 4 minutes

Travellers’ Choice award

from £63 / night

£264 - £422 / week

Kissimmee holiday villa rental

Kissimmee villa

4 bedrooms / 3 bathrooms / sleeps 8

“The house is in an amazing location, in a quiet enough location to relax but not too far away from disney or universal” Great place to stop, in a quiet enough area to get some much needed RNR but also only 20 minutes away from the disney and universal parks,

29

from £85 / night

£636 - £882 / week

Holiday villa with swimming pool in Kissimmee

Kissimmee villa

3 bedrooms / 2 bathrooms / sleeps 6

“The best villa we've ever had!” We have been visiting Florida since 2000 and this is definitely the cleanest, most comfortable villa we have ever stayed in. There was nothing else that we could have asked for - it really was a home away from home! The area was lovely and quiet, the local neighbours were friendly and it was the perfect distance from the main attractions. There are not many places you can sunbathe and watch an alligator sunbathing at the same time! Would definitely reccommend and hope to return soon! Thank you for taking such good care of your property!

38

Travellers’ Choice award

from £103 / night

£567 - £630 / week

Kissimmee holiday villa rental

Kissimmee villa

4 bedrooms / 3 bathrooms / sleeps 8

“Very Nice Property” Property well situated, clean and modern, Nice size pool,all of group pleased with choice Be prepared to pick the bins up every morning as the wildlife enjoy going through them in the nights.

28

Responds fast! avg. 2 hours 33 minutes

from £115 / night

£802 - £916 / week

Holiday villa with swimming pool in Bellavida Resort

Kissimmee villa

4 bedrooms / 4 bathrooms / sleeps 8

43

Responds fast! avg. 2 hours 58 minutes

Travellers’ Choice award

from £132 / night

£745 - £859 / week

Holiday home rental

Kissimmee house

5 bedrooms / 4 bathrooms / sleeps 13

18

Responds fast! avg. 3 hours 2 minutes

from £115 / night

£773 - £1,082 / week

Holiday villa in Kissimmee

Kissimmee villa

5 bedrooms / 5 bathrooms / sleeps 10

1

from £303 / night

£2,119 / week

Kissimmee holiday villa rental

Kissimmee villa

4 bedrooms / 3 bathrooms / sleeps 8

“We will not be going anywhere else!” This was our second stay at the beautiful villa. Local to all the best restaurants, Wall-Mart and Target for food shops. With only a 15 minute drive we were in the theme parks, International Drive and only 45 minutes from Lego Land. The views from the pool across the lakes are so relaxing, a peaceful location and private. With plenty of room for the whole family, all the rooms are kitted out to a high standard, themed for the kids as well! We will not be looking for anywhere else when we return, only here!

21

Responds fast! avg. 3 hours 35 minutes

from £166 / night

£911 / week

Kissimmee holiday villa rental

Kissimmee villa

4 bedrooms / 3 bathrooms / sleeps 9

21

from £121 / night

£802 - £916 / week

Holiday villa in Seasons Resort

Kissimmee villa

5 bedrooms / 4 bathrooms / sleeps 10

“Perfect home away from home” This is is in an amazing location. All Disney has to offer is within a 20 minute drive as well as Walmart, Aldi’s and many restaurants are right around the corner. This is a small development that is very well lit and has sidewalks for evening strolls. There is a small children’s playground in the development. The villa exceeded our expectations. It was immaculately clean & very comfortable. There is plenty of room for the whole family to enjoy the wall mounted TV in the living room on the 3 couches. The bedrooms are comfortable. The outstanding attraction for this home is the huge south facing pool & spa. We were here for 5 weeks & had the pool heated. The water temperature was so comfortable even When going for a swim before bed. Peter was excellent to rent from. He responded quickly to any questions & was very helpful. His management company was quick to respond to a minor issue and was very friendly. Overall this is the best villa we have rented in the Orlando area over the past 3 years and is an exceptional value for the price. We would highly recommend this villa & will book again. Thanks, Peter for sharing your Florida home with us.

41

Travellers’ Choice award

from £81 / night

£458 - £802 / week

Holiday villa in Kissimmee

Kissimmee villa

4 bedrooms / 2 bathrooms / sleeps 6

13

from £92 / night

£665 / week

Holiday villa in Westside

Kissimmee villa

4 bedrooms / 4 bathrooms / sleeps 9

“Highly recommended - Great place with all you need” Took the family to Disney for a few days in March and found Lee's place on VRBO - first time we use this service. This home is amazing, the whole family loved the pool, hot tub, games room, and overall comfort. Nice quiet neighborhood, tons of restaurants very close by. We went to Magic Kingdom and Animal Kingdom, and both were about 15 minutes away. Special thanks to Lee who was extremely kind and helpful, walking me through the VRBO process as well as providing advice on how to make the best of our Disney visits. Will definitely reach out again next time we plan a Disney trip.

53

from £113 / night

£781 - £1,007 / week

Holiday townhouse in Kissimmee

Kissimmee townhouse

4 bedrooms / 3 bathrooms / sleeps 8

21

from £115 / night

£687 / week

Kissimmee holiday villa rental

Kissimmee villa

4 bedrooms / 3 bathrooms / sleeps 8

“Fantastic first visit to florida” When we arrived the first walk around the villa was greeted with "oh my god it's amazing! " Great size and space In really good condition Great pool and outdoor area with all day sun - great sunset and great bbq Great location on a lake with varied wildlife and not too close to neighbours. Great games room - used every day by kids. Pretty much everything in the villa you'd need Not too far from all major attractions and conveniences

41

Responds fast! avg. 1 hour 17 minutes

Travellers’ Choice award

from £126 / night

£859 - £1,174 / week

Holiday home rental

Kissimmee house

4 bedrooms / 3 bathrooms / sleeps 8

23

Responds fast! avg. 3 hours 52 minutes

Travellers’ Choice award

from £83 / night

£577 / week

Kissimmee holiday villa rental

Kissimmee villa

4 bedrooms / 2 bathrooms / sleeps 8

8

from £159 / night

£1,110 - £1,343 / week

Kissimmee holiday villa rental

Kissimmee villa

3 bedrooms / 2 bathrooms / sleeps 6

9

Responds fast! avg. 2 hours 19 minutes

from £126 / night

£745 - £1,088 / week

Holiday villa rental

Kissimmee villa

4 bedrooms / 2 bathrooms / sleeps 8

9

from £109 / night

£762 / week

Holiday villa in Kissimmee City

Kissimmee villa

3 bedrooms / 2 bathrooms / sleeps 6

“Very comfortable home from home with the sun” We had a great time at Christine’s villa. The villa is extremely well located in a very quiet, residential area just outside Kissimmee. The villa is very easy to find from the airport, and is just off the US 192 and close to the freeways. Very central to Disney, and a not too distant drive to Universal, close to all the shopping malls and within a short distance to many restaurants, Black Angus almost on the doorstep. The villa itself was very well equipped, everything necessary for a great stay was there, all the amenities from cooking to internet, really made you feel at home, with the added benefit of the pool and sun. We would certainly recommend the villa to our family and friends and are planning another visit next year. Christine was very helpful, good communication, with clear concise details of getting to and accessing the villa. Thanks again we really did have a memorable holiday, and great stay.

36

from £60 / night

£375 - £795 / week

Kissimmee holiday townhouse rental

Kissimmee townhouse

3 bedrooms / 3 bathrooms / sleeps 6

4

from £81 / night

£504 / week

Kissimmee holiday villa rental

Kissimmee villa

3 bedrooms / 2 bathrooms / sleeps 6

“Our stay” Loved it, very clean and had everything we needed. Would definitley recommend, 10 mins from disney 2 mins from shops/ restaurants whilst still being in a very quiet street.

40

Responds fast! avg. 2 hours 48 minutes

Travellers’ Choice award

from £103 / night

£659 - £722 / week

Kissimmee holiday villa accommodation

Kissimmee villa

4 bedrooms / 2 bathrooms / sleeps 8

13

Responds fast! avg. 1 hour 16 minutes

Travellers’ Choice award

from £105 / night

£729 - £904 / week

Bungalow rental in Kissimmee

Kissimmee bungalow

4 bedrooms / 2 bathrooms / sleeps 8

25

Responds fast! avg. 1 hour 39 minutes

Travellers’ Choice award

from £108 / night

£710 - £735 / week

Holiday villa with shared pool, golf nearby in Orange Lake Resort

Kissimmee villa

2 bedrooms / 2 bathrooms / sleeps 8

3

from £196 / night

£1,374 / week

Villa rental in Kissimmee with golf nearby

Kissimmee villa

6 bedrooms / 4 bathrooms / sleeps 14

13

from £165 / night

£1,082 - £1,712 / week

Emerald Isle Kissimmee holiday villa rental

Kissimmee villa

5 bedrooms / 4 bathrooms / sleeps 12

37

Responds fast! avg. 2 hours 15 minutes

from £149 / night

£991 - £1,203 / week

Holiday villa in Doral Woods

Kissimmee villa

4 bedrooms / 3 bathrooms / sleeps 8

29

Responds fast! avg. 1 hour 25 minutes

Travellers’ Choice award

from £114 / night

£796 - £1,094 / week

Holiday villa in Kissimmee

Kissimmee villa

4 bedrooms / 4 bathrooms / sleeps 8

“Fantastic Top Quality Home” Immaculate house with plenty of room, the rooms had everything we needed. This property has gone beyond a standard rental as has everything you need from toys for pool, beach towels, baby accessories to waterproof ponchos for wet days! Nothing had not already been thought of. Definitely will be booking again and highly recommend to anyone. It was easy to find in a secluded cul de sac location not far from all main routes.

58

Travellers’ Choice award

from £165 / night

£1,149 - £1,273 / week

Villa accommodation in Kissimmee

Kissimmee villa

3 bedrooms / 2 bathrooms / sleeps 6

6

Responds fast! avg. 2 hours 19 minutes

from £81 / night

£561 / week

Villa rental in Kissimmee with swimming pool

Kissimmee villa

3 bedrooms / 2 bathrooms / sleeps 6

“An excellent holiday with fantastic accommodation.” Our family stayed here whilst holidaying in Orlando this year, and the accommodation was absolutely superb. The location is not too far from all the Disney/Universal and Seaworld attractions and also easy access to routes to the east coast (Kennedy space center). All amenities at the villa were spot on, with the pool being both big enough for adults and safe enough for children, with the added bonus that there are water toys for the children located in the garage, and the pool itself is secluded. The property itself is in a beautiful estate, which we walked around as it was scenic and all the residents were so cheerful and helpful, (with the added bonus of a state trooper living right across the street). The local eateries are clean and cheap, with great service. We thoroughly recommend this villa and will definately be staying here again. Thank you for making our holiday that extra special, we look forward to coming next year.

71

Responds fast! avg. 1 hour 30 minutes

Travellers’ Choice award

from £149 / night

£710 - £733 / week

Kissimmee holiday villa let

Kissimmee villa

3 bedrooms / 2 bathrooms / sleeps 6

38

Responds fast! avg. 1 hour 42 minutes

Travellers’ Choice award

from £92 / night

£573 - £722 / week

Doral Woods holiday villa rental

Kissimmee villa

4 bedrooms / 2 bathrooms / sleeps 8

“Perfect for couples and families” I stayed here for 9 days with my husband and 5 month old daughter and we had lovely time! My husband and I had previously been to Florida and stayed in a property in Doral Woods so we knew we wanted to be in the same location this time around. The area is quiet and beautiful, you get to wake up every morning to hear the birds and the other wildlife surrounding you, rather than traffic and people. But only 20-25 minute drive to the parks and tourist attractions, it is literally the perfect location. The property itself was well presented with plenty of clean linen and a cute little cot in the garage for our little one. We paid for pool heat on our second day because the pool was a little colder than we would have liked but we suspected that may be the case being as it was just on the cusp of fall. But the pool was a decent size, and our daughter loved it, especially at night when we turned the lights on in the pool and she could see the water sparkling. There was an information pack in the TV room which we found really useful and would recommend reading ASAP as it gives info re garbage disposal, garbage collection etc which is v important to read (especially if you are from the UK where we don't really have garbage disposals and our trash collection works a bit differently). I would highly recommend this property to other families, and to couples who want to stay in Florida but don't want the noise of being in the city. This villa was also faaaaar cheaper than staying in a hotel in the centre, even when we added car hire into the equation. Thanks very much to Walter & Linda, we had a lovely first family holiday and will definitely be checking your availability when we return in a couple of years.

33

Responds fast! avg. 2 hours 34 minutes

Travellers’ Choice award

from £109 / night

£745 / week

Holiday villa rental

Kissimmee villa

4 bedrooms / 3 bathrooms / sleeps 8

“Family trip” This was a wonderful trip and the house was magnificent. My family felt very at home and the pool was wonderful after a long hot day at the park.

45

Responds fast! avg. 51 minutes

from £118 / night

£825 / week

Holiday villa in Kissimmee

Kissimmee villa

5 bedrooms / 5 bathrooms / sleeps 10

22

Responds fast! avg. 2 hours 32 minutes

Travellers’ Choice award

from £207 / night

£1,443 / week

Holiday villa in Kissimmee

Kissimmee villa

5 bedrooms / 4 bathrooms / sleeps 12

24

from £130 / night

£907 - £1,053 / week

Kissimmee holiday home rental

Kissimmee house

5 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 1 hour 39 minutes

from £210 / night

£1,470 / week

Holiday villa rental

Kissimmee villa

3 bedrooms / 2 bathrooms / sleeps 6

16

Responds fast! avg. 1 hour 29 minutes

from £103 / night

£687 / week

Kissimmee holiday villa rental

Kissimmee villa

5 bedrooms / 3 bathrooms / sleeps 10

27

from £115 / night

£802 - £905 / week

Holiday townhouse in Kissimmee

Kissimmee townhouse

4 bedrooms / 3 bathrooms / sleeps 10

10

from £121 / night

£739 - £1,088 / week

Holiday townhouse in Kissimmee

Kissimmee townhouse

4 bedrooms / 3 bathrooms / sleeps 10

10

Responds fast! avg. 25 minutes

from £103 / night

£679 / week

Viewing 40 of 12,943
rentals in Kissimmee

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Kissimmee holidays

Just south of Disney World in north-central Florida, Kissimmee is a fun, family-style resort town with an unbeatable range of recreation and entertainment options. While most people come here to visit the Magic Kingdom, there are dozens of other ways to enjoy a holiday in this upbeat city. From go-kart racing and miniature golf to water parks and adventure sports, Kissimmee offers family-oriented activities to suit any taste. With its favourably warm and balmy climate, it's no surprise that Kissimmee is a popular destination for many American families throughout the year.

Fun in the sun is the name of the game, yet Kissimmee, FL, also offers great nightlife options, appropriate for the whole family. Every Saturday night in Old Town Kissimmee, there is a classic car cruise through the city streets, accompanied by a live band. Kissimmee is also famous for its dinner theatres, where you can see a Broadway-style performance or a trick horse show while dining. When it comes to food, the dining options are myriad. There are Spanish, Italian, and Japanese restaurants in Kissimmee, in addition to a huge selection of classic American joints, perfect for the kids.

Amongst Kissimmee's greatest attractions:

-Walt Disney World: The world's most popular theme park is Kissimmee's most famous attraction, drawing huge crowds every day of the year.

-Universal Studios Florida: Universal Studios' theme park is dedicated to blockbuster movies, like Harry Potter and Jurassic Park, with plenty of rides, restaurants, and live shows.

-Gatorland: Named after Florida's most famous reptile, Gatorland is a giant animal theme park with lots of wildlife, especially alligators.

-The Holy Land Experience: This theme park recreates the world at the time that Jesus lived, including shows and events with Bible themes.

-Titanic The Experience: This theme park recreates the experience of being on the Titanic.

-Aquatica: SeaWorld's large aquatic park offers amusement rides, an aquarium, and live animal shows.

-Lake Tohopekaliga: One of the Kissimmee Chain of Lakes, the giant Lake Toho is the place to head for fishing and water sports in Kissimmee.

As many seasoned Kissimmee visitors know, renting a house can be the most comfortable option when travelling with a family. Accommodating the whole crew, a big rental home or condo gives you lots of private space, while still providing easy access to the regional theme parks. Within the town of Kissimmee, there are plenty of holiday rentals near Disney World, including luxurious villas or large houses with multiple bedrooms, modern entertainment systems, and private pools.

Top Destination reviews

Paradise Found Kissimee Rental
Amazing villa close to all parks

We have just spent two weeks in this beautiful villa. There was 6 adults and an 11 year old. The villa is very spacious and has everything you need. The view from the pool is amazing so nice waking up to that view everything we will definitely miss that. The villa is close to all the parks and plenty of restaurants and supermarkets in the area. The host was very accommodating too nothing too much trouble thank you very much . We will definitely be back.see more
Lovely Mango Keys Home includes WiFi and Hot Tub
Great location and features

Can't fault this condo, pictures tell the tale well, probably a bit more space than what you imagine. Four of us and no issues with hot water for showers. Iron and kettle were dead when we arrived but replaced immediately. WiFi perfect. Only negative was the hot tub was not heated which was a let down, we did report it but nothing done, was looking forward to some relief for my back and legs after long days out and about.see more
Amazing Disney Condo, Pool & Hot tub Onsite
Clean, comfortable & convenient

We’ve just spent over a week in this accommodation and it has been perfect. It’s convenient for the parks and shopping areas but on a quiet gated estate for those days of relaxation. It is situated on the third floor but that didn’t bother us, even after a full day on our feet. Everything you could need is available from towels to ice packs and tin opener to hairdryer. The 3 bedrooms are spacious and the sofa is very comfortable. The well equipped kitchen is perfect if you wish to cook and the dishwasher, washing machine and tumble dryer are also very handy. I would definitely recommend this apartment and would look to book again for our next visit to Florida.see more
Family-Friendly Large Villa with a Pool, Jacuzzi,
Village in blooming alAmanda loop

Stayed in this lovely villa for one month over christmas and new year.Had an amazing time villa was very big plenty of room every think you would need for your stay It is ten minutes away from Disney parks and five from walmart.The pool was brilliant and the hot tub was so nice at the end of a long day in the parks.If you have Eny questions Paul gets right back to you.So thank Paul you're home was lovely and hope we can come back again in the future.see more
Stunning Lakeview Luxury Villa with WiFi and Hot Tub
Great Facilities

Just back from another stay at this superb villa. Location is ideal for parks and shops and is situated on a very peaceful sub-division. South facing pool has sun all day and looks out over a lake with an abundance of wildlife. All TV's recently updated, wifi excellent and there is a new washer and dryer also. Highly recommend .see more
villanirvana
Amazing Villa,Great Location, Value for money

o we have just got back from the villa last night. It was an amazing experience.the villa was beautiful and clean.My dad is disabled and the villa catered for everything.The little touches the owners had put in the villa to help us manage with dad was just amazing. So we had a hoist into the pool,a very spacious wet room, extra wheelchair,ramps everywhere, lovely high bed to transfer dad easily,large doorways for wheelchairs.The location is just so perfect.we walked to the creek which is just behind the villa with a lovely hike trail. The villa is literally 15 minutes from all of the parks. You have so many supermarkets and eating places close by.On the complex is a lovely swimming pool you can use as well. What we thought was super nice was the owner called us on our first day to make sure everything was ok and I thought that was a really nice touch. The villa was huge beautifully decorated, lovely and clean.The owner had thought of everything you can possibly need.Hairdryers etc.it really felt like a family home. We will defiantly be returning to this villa next year as we were super impressed by everythingsee more

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