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

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5,835 Holiday homes

Kissimmee holiday home let

Kissimmee house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £73 / night

£476 / week

1 / 26

Holiday villa in Kissimmee

Kissimmee villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

from £136 / night

£952 / week

1 / 29

Home rental in Kissimmee with indoor pool

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from £109 / night

£761 / week

1 / 29

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.

from £161 / night

£859 - £939 / week

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Holiday home in Kissimmee

Kissimmee house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 6

from £136 / night

£1,359 / week

1 / 13

Townhouse rental in Kissimmee

Kissimmee townhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £108 / night

£755 / week

1 / 14

Holiday home with swimming pool in Oak Island Cove

Kissimmee house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

“Great location for a brilliant price!” Just returned from this villa on Sunday and we had a great time. The location is really good (20 minutes to Disney and 30 minutes to Universal) and the villa is about a 20-30 minute walk from shops, restaurants, etc, so while the location is quiet, you can still get out in the evening for a bite to eat in the area. The villa itself is looking a bit dated but I think this is reflected in the price, which is way below anything I priced up for villas of a similar size. Although the villa has everything you need for a great family holiday, we did have a few niggles, which I will feedback to the owner directly, but nothing which spoilt our stay in Orlando. Communication with the owner (Paul) before we left was very good, and instructions for accessing the villa were very clear (though we struggled to follow the maps and got lost en-route from the airport!!). The pool is brilliant, the Jacuzzi is huge but just be aware that it gets very warm in the garage where the games room is located and some of the bedrooms didn't appear to have air conditioning and the fans didn't really circulate the air in the rooms. Having said that, we were always so tired from busy days, we never had any trouble falling asleep!!

from £123 / night

£859 / week

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Holiday villa with golf nearby in Cumbrian Lakes

Kissimmee villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

“Great place for a Florida trip” As a frequent Florida visitor and previous house owner this is a wonderful house to stay. The house are ideal for families with a separate Master bedroom and the other four bedrooms two and two with bathrooms. The house are well maintained and tasteful decorated. Best part are the pool area facing a small lake with sun from dusk till dawn. Close to Disney and most Orlando attractions within a hour’s drive. Owners are quick to reply Will for sure recommend to friends and family and will return

from £109 / night

£762 / week

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Holiday home in Kissimmee

Kissimmee house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £145 / night

£906 / week

1 / 11

Holiday villa rental

Kissimmee villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £91 / night

£635 / week

1 / 73

Holiday condo in Kissimmee

Kissimmee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from £107 / night

£517 / week

1 / 23

Holiday villa with swimming pool in Kissimmee

Kissimmee villa

  • 12 bedrooms
  • 12 bathrooms
  • sleeps 28

from £271 / night

£1,896 / week

1 / 45

Holiday apartment with shared pool in Kissimmee

Kissimmee apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £89 / night

£635 - £1,812 / week

1 / 8

Holiday townhouse in Kissimmee

Kissimmee townhouse

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

from £200 / night

£1,314 / week

1 / 21

Kissimmee holiday apartment rental

Kissimmee apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £77 / night

£539 / week

1 / 58

Holiday villa rental

Kissimmee villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

from £161 / night

£1,123 / week

1 / 25

Holiday villa in Kissimmee

Kissimmee villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

from £127 / night

£761 - £2,537 / week

1 / 47

Holiday apartment in Kissimmee

Kissimmee apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £99 / night

£633 / week

1 / 70

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.

from £137 / night

£958 / week

1 / 41

Kissimmee holiday home rental

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

from £109 / night

£761 / week

1 / 24

Holiday apartment in Kissimmee

Kissimmee apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £86 / night

£599 / week

1 / 13

Holiday apartment with shared pool in Kissimmee

Kissimmee apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £65 / night

£453 / week

1 / 5

Holiday condo in Kissimmee

Kissimmee condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £91 / night

£635 / week

1 / 25

Holiday townhouse in Kissimmee

Kissimmee townhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £163 / night

£1,135 / week

1 / 56

Kissimmee holiday villa rental

Kissimmee villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £272 / night

£1,903 - £2,125 / week

1 / 15

Kissimmee holiday villa rental

Kissimmee villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 11

“Amazing Stay” Could not recommend this place enough, leaving a review on behalf of my father in law Philip Kirk who booked. 10/10 -close to the parks, easy drive and lovely location. Made some amazing memories here with our family, plenty of room, clean , comfortable, outside facilities where fabulous too. We hope to come back in 2022 with my side of the family! x

from £135 / night

£861 - £1,178 / week

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Kissimmee holiday villa rental

Kissimmee villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

from £291 / night

£2,036 / week

1 / 82

Holiday home rental

Kissimmee house

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 14

from £192 / night

£1,345 / week

1 / 37

Kissimmee holiday villa rental

Kissimmee villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £96 / night

£662 / week

1 / 40

Holiday apartment in Kissimmee

Kissimmee apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

from £77 / night

£540 / week

1 / 13

Holiday home letting

Kissimmee house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

from £188 / night

£1,314 / week

1 / 4

Home rental in Kissimmee with swimming pool

Kissimmee house

  • 12 bedrooms
  • 12 bathrooms
  • sleeps 30

from £326 / night

£2,277 / week

1 / 46

Holiday home with swimming pool in Kissimmee

Kissimmee house

  • 12 bedrooms
  • 12 bathrooms
  • sleeps 30

from £271 / night

£1,896 / week

1 / 59

Holiday home with swimming pool in Kissimmee

Kissimmee house

  • 12 bedrooms
  • 12 bathrooms
  • sleeps 29

from £271 / night

£1,896 / week

1 / 50

Holiday villa with swimming pool in Kissimmee

Kissimmee villa

  • 10 bedrooms
  • 8 bathrooms
  • sleeps 25

from £452 / night

£3,165 / week

1 / 7

Holiday home with swimming pool in Kissimmee

Kissimmee house

  • 12 bedrooms
  • 12 bathrooms
  • sleeps 29

from £543 / night

£3,799 / week

1 / 60

Kissimmee holiday villa rental

Kissimmee villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £75 / night

£520 / week

1 / 14

Home rental in Kissimmee with swimming pool

Kissimmee house

  • 9 bedrooms
  • 5 bathrooms
  • sleeps 27

from £122 / night

£850 / week

1 / 89

Holiday home with swimming pool in Kissimmee

Kissimmee house

  • 9 bedrooms
  • 5 bathrooms
  • sleeps 26

from £132 / night

£921 / week

1 / 100

Holiday home in Kissimmee

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £82 / night

£572 - £1,016 / week

1 / 20

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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

Exquisite Villa, Private Pool/Spa, Game Room
Lovely Home in Beautiful Bella Vida

We have just returned from a two week stay in this lovely home. The villa is in a great location, off Oren Brown Road, just behind the large Walmart. On arrival the wifi wasn’t working but the management company had already noted this and had it sorted within 48 hours. We also had a problem with the downstairs air con, again the management company sorted this within a few hours. The home has four en-suite bedrooms which is perfect for large families and the living/dining/kitchen area is very spacious and airy. The kitchen is well stocked with cutlery, crockery, pots, pans and utensils and it even has a kettle and teapot! The sofas and recliner chair are very comfy. The dining table is large but only had 5 chairs (not 6 as shown in the pictures), but we improvised by using the desk chair! The pool was south facing, getting the sun all day. We paid extra for pool heat which was worth it as the water temperature was just right. Unfortunately, we didn’t get to eat alfresco as there were only 3 out of the 6 patio chairs usable (2 were broken and 1 was missing)! All in all we had a lovely stay and thanks to Claire and Shaun from the management company for being so prompt in answering any of our questions and issues. I have given the villa 4 stars because some of the furniture is a little tired and would need updated, other than that, it is a lovely home. Would we return……yes, if updated.see more
Stunning Sunset Villa includes Wi-Fi, Game room, Pool, Lake View, A/C
As we remember and why we go time & time again!

Having now stayed in the hosts property 3 times, its always reassuring to know that somethings never change. Its a lovely, quiet location, off the main strips of the 192 and I-Drive. This suits us perfectly. With a 20 minute drive you can be at a Disney - Universal park, or on I-Drive. Equally you will find ample shopping opportunities at Vineland, Florida Mall and Premium Outlets, which really is easy to navigate to. The villa is clean, its got a welcoming feel about it, still after all the times we have stayed here. The views over the lakes, and the 2 alligators popping up to say hi is great. A new cooker and huge American fridge/freezer are a great addition. Bedrooms are great for the kids, singles or double option. With the covered seating area, it gives you an opportunity to "hide" from the sun a little whilst the kids enjoy the brilliant pool area. We didn't go away to have a B-B-Q, so no big deal it wasn't there, neither did we want a noisy, tourist surrounding, just peace, quiet and the most amazing sun sets after a long day at the parks or shopping. If your looking for somewhere that offers a little bit of living in the states, this is great. We have already looked at returning in 2024, and the villa is already booked as far as we are concerned. One last thing. The management team, Derek is very helpful, an ex Brit and is more than happy to return calls when we needed any help or had any questions. Thanks Maureen, it was a great vacation, hub for our wedding holiday and we look forward to returning.see more
WINNER! TRIP ADVISOR CERTIFICATE OF EXCELLENCE, WINDSOR HILLS 3B/ 3B TOWN HOME
Wonderful Townhouse!

We have stayed at Windsor Hills many times and can honestly say this was one of the best kept properties we have experienced. Not only is the townhouse well-positioned for access to the clubhouse facilities and resort pool, it is spacious, clean and well-maintained. The hosts are delightful and very responsive. We have no hesitation in recommending this townhouse and would return in the future.see more
BRUSONS RETREAT, 5 Bed Villa, South Facing Pool & Terrace.
Beautiful Property

We had an amazing two weeks at this property. The whole villa was immaculate upon arrival, the pool was simply perfect and the location was ideal. Can’t wait to re-book. … see more
Villa Journey - 3 miles from Disney, 2 Masters and a Private Pool & Spa!
Great Holiday

Fantastic time in Orlando the Villa was everything we could have hoped for well worth the 2 year wait from original booking to finally getting over to the USA due to Covid etc... The location is fantastic when they said 15 minutes from Disney they are not wrong and a variety of excellent restaurants and supermarkets all within 5 minutes drive. Pool & hot tub are a real bonus and we're enjoyed by all during our trip. Thanks to the owners for all their help during the booking.see more
Spacious 4-bed lakeside pool villa near Disney
Good sized villa

Enjoyed the villa really quiet area, plenty of space for the 6 of us (5 Adults and 1 child) & good sized pool, the Wi-Fi & washer & dryer came in really handy, quick email response from owners when it was required, Walmart was only 5 mins down the road & both Disney & universal was about 25 mins drive away, would not hesitate to stay here again when we return to Orlando.see more

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