Vacation Rentals & House Rentals in Kissimmee

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Cozy One Bedroom Villa in Gorgeous Resort & Spa

Kissimmee villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Fax machine, Shared outdoor pool (heated)

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Price per night from

$180

Four Bedroom home near Disney/Orlando

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Fax machine, Shared outdoor pool (heated)

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Price per night from

$121

Beautiful 2 BR, 2BA Orlando Florida!

Kissimmee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Fax machine, Shared outdoor pool (heated)

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Price per night from

$492

One of Disney's premier locations

Kissimmee villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Fax machine, Shared outdoor pool (heated)

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Price per night from

$562

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Price per night from

$430

A Bit of Disney World Paradise Aka Villas at Seven Dwarfs Lane!

Kissimmee villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Fax machine, Shared outdoor pool (heated)

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Price per night from

$132

LUXURY 3BR 3BA WINDSOR HILLS POOL TOWNHOME 2 mi to DISNEY - Sleeps 8

Kissimmee villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Fax machine, Shared outdoor pool (heated)

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Price per night from

$161

“Beautiful spacious home in a quiet Gated Community.” We were in Florida for the National Pop Warner Football finals. I was able to rent this home on short notice (one week) and was pleasantly surprised it was beautifully maintained and well stocked. Sri was very accommodating and easy to reach. We had several children with us of various ages and they were all kept occupied in the game room. Pool never really got warm but we did read the literature and wasn't expecting bath water but the pool and spa at the clubhouse was comfortable. Had a great time and would definitely rent again great value for your money. Also is very close to all the attractions just a short drive to any park you plan to visit.

1 of 2 match: Fax machine, Shared outdoor pool (heated)

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$430

“Great place, good value!” This was our first time renting a house from an owner. We had a great experience. The owner Mary was very helpful and she even called us right after we checked-in to make sure that everything met our standards and we had what we needed. The unit is very clean, quiet and had everything we needed for our stay. The resort is in a great location and has easy access to expressway I-4 and 417. It takes less than 10 minutes to get to Disney and the Espn World Sport Center. We also enjoyed walking around Old Town in the evenings. We really enjoyed our stay in this unit. Thank you Mary for letting us stay there.

Responds fast! avg. 3 hours 41 minutes

1 of 2 match: Fax machine, Shared outdoor pool (heated)

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$109

“nice place well kept” This condo is in a good location. You can walk to Old Town to the car shows every friday and saturday nights. The wi-fi is excellent. There is plenty of room. We ride our bicycles up and down 192 on the very wide sidewalks. Many good restaurants within walking distance. The owner keeps you informed of the things you need to know in a timely fashion

Responds fast! avg. 3 hours 41 minutes

1 of 2 match: Fax machine, Shared outdoor pool (heated)

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Price per night from

$101

Regal Oaks at Old Towne

Kissimmee villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Fax machine, Shared outdoor pool (heated)

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$127

Vacation Villa near Disney with Wireless Internet.

Kissimmee apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Fax machine, Shared outdoor pool (heated)

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Price per night from

$115

Venetian Bay Village 3 Bedroom Townhouse

Kissimmee villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“MAGICAL EXPERIENCE.” Our stay at the Venetian Bay Townhouse was a wonderful experience everyone should experience. It feels like Home away from home. It was secure the amenities were great. And the check-in process was seamless. Everything from the workout facility to the swimming pool was amazing. This should be apart of everyone's Florida experience.

1 of 2 match: Fax machine, Shared outdoor pool (heated)

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$92

FLAGSTONE VILLA

Kissimmee villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

1 of 2 match: Fax machine, Shared outdoor pool (heated)

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Price per night from

$362

No Resort Fees + No Cleaning Fees + Disney Is Right Next Door!

Kissimmee house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

1 of 2 match: Fax machine, Shared outdoor pool (heated)

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Price per night from

$144

“Large enough for the whole family” We had a great stay and were really pleased with the size of the house. It allowed members of our extended family to have privacy but of course the family room, kitchen, and media/game room were the most popular areas. The kids and grand kids enjoyed the pool. The weather was unseasonably cold but we paid to heat the pool and everyone seemed surprised and pleased that is was so comfortably warm. Sri is very easy to work with and responded super fast to email communication. This is definitely the way to go when you have a large family. Very reasonably priced for the space and accommodations.

1 of 2 match: Fax machine, Shared outdoor pool (heated)

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Price per night from

$430

“Wonderful holiday” We had a lovely holiday staying at Emerald magic, the villa was just right for our family of 12 , our 5 grandsons loved the south facing swimming pool which was always lovely and warm while we enjoyed relaxing on the 6 sunbeds. The games room had loads of things to keep them happy and occupied while the adults relaxed. The barbecue with free gas was great at mealtimes, although it was out of gas when we arrived it was very quickly replaced with one phone call as were any other problems which occurred, excellent service. Plenty of pool towels, saving packing our own and the double buggy was so handy at the parks. The location to disney parks could not be better, only about 10 minutes drive and the complex is lovely with a really friendly lady at reception. Also Thank you for the special touch of the rose on the bed which made celebrating our ruby wedding anniversary a special occasion.

1 of 2 match: Fax machine, Shared outdoor pool (heated)

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Price per night from

$430

❤️ Super Cozy Home Minutes to Disney

Kissimmee house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Birthday Trip!” I do believe this might have been the funnest trip I've ever taken in my life. Having every single thing just minutes away from you was such a delight and such a pleasure to not have to drive around constantly in the car. This community is gated and seems like a really fun place to actually buy a vacation home. Actually, while we were there we looked into it and might be doing the same thing that this particular person is offering on TripAdvisor as well! First of all, the house was just absolutely amazing... Bigger than my own home even. It was just me, my son and my husband and our house was absolutely humongous. We actually had thought we would have another family with us but it fell through. Everything was clean and perfect. There were many things like dishwasher, laptop, printer, hair dryer, straightener, toiletries, food! When we arrived, we already had some basic needs that were furnished To Us by the owners. It was such a treat to see that they really cared about us to furnish those things! There was a perfect screened in porch out the back over looking a little bit of a water marsh where we got to watch the birds everyday. The wildlife in our particular yard was extremely delightful. From frogs to lizards two birds two cranes we had an amazing time when we were relaxing at home. To my delight, there were also three swimming pools in the complex. One of the pools were in the middle of the community which was right down the street from our home, then there were two others inside the clubhouse which were also fantastic. We really enjoyed the hot tub and sitting underneath the shelter when it started to rain. Since I knew it would be very hot and we would be extremely exhausted, I asked for a maid service halfway through our vacation and I'm so happy I did. It was nice to come home after dinner to a 100% clean house with clean towels and everything perfect. I recommend that you get the service as the cleaning lady does an excellent job! The next time we booked our Walt Disney World vacation I will be using this home again without a doubt. Even though we stayed 7 days, we still did not get to see everything that we wanted to. Next time we come down we are doing 10 to 12 days for sure and cannot wait to come back to Vista Del Lago. I was really surprised on how many friends we made while we were there!! If you are looking for a family home that could easily sleep 7 people, please do yourself a favor and book this, you will be so glad that you did!!

1 of 2 match: Fax machine, Shared outdoor pool (heated)

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Price per night from

$253

Legacy Dunes Condo, Kissimmee, Orlando

Kissimmee apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Fax machine, Shared outdoor pool (heated)

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Price per night from

$103

Amazing Disney Oasis Condo with Sauna and Gym

Kissimmee villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

1 of 2 match: Fax machine, Shared outdoor pool (heated)

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Price per night from

$125

Disney themed villa/private pool/tub.

Kissimmee villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

“Amazing vacation” The house was perfect. Everything was great. House looks just like the pictures. George was a great host. Very nice and made it feel like a second home. Cant wait to go back.

Responds fast! avg. 3 hours 15 minutes

1 of 2 match: Fax machine, Shared outdoor pool (heated)

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Price per night from

$193

You Gotta See This

Kissimmee villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Fax machine, Shared outdoor pool (heated)

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Price per night from

$91

4 Bed/3 bath Condo with only 2 miles to Disney

Kissimmee apartment

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Fax machine, Shared outdoor pool (heated)

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Price per night from

$132

From $110/nt,Near Disney,Seaworld,Convention Center,4br/3ba townhome with hottub

Kissimmee apartment

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 27 minutes

1 of 2 match: Fax machine, Shared outdoor pool (heated)

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Price per night from

$132

Legacy Vacation Club Orlando - 1BR Efficiency Unit - Sleeps 4

Kissimmee apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Fax machine, Shared outdoor pool (heated)

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Price per night from

$98

5 Miles from Disney, Amazing Rental Home in Kissimmee

Kissimmee apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Disney vacation” The condo was great. Close to almost everything. Clean, fully stocked, Joanne was awesome.we can't wait to come back again next year.

Responds fast! avg. 2 hours 49 minutes

1 of 2 match: Fax machine, Shared outdoor pool (heated)

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Price per night from

$98

From $110/nt,4br/3ba townhome with lake view,Near Disney,Seaworld

Kissimmee apartment

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 27 minutes

1 of 2 match: Fax machine, Shared outdoor pool (heated)

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Price per night from

$132

Caitlins Disney Condo - Spacious and convenient

Kissimmee apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Clean, quiet, comfortable, and roomy!” We have a large family, with 5 kids. We brought my mother with us on vacation, giving us a whopping 8 people to accommodate, for a week and this condo gave us plenty of space and beds for everyone to sleep comfortably! The gated community is great! Clean and quiet with plenty of parking.

Responds fast! avg. 3 hours 4 minutes

1 of 2 match: Fax machine, Shared outdoor pool (heated)

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Price per night from

$137

From $100/NT,1.5 Mile to Disney ,1808 sq ft 4br/3ba townhome with lake view

Kissimmee apartment

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Great location” We had great times in Oakwater, all was perfect! The house is fully equipped, all is clean, new and works perfect!It is an ideal location, close to everything. Near the home are so many great restaurants such as: Bonefish, Longhorn, Golden Corral, Ihop, Bahama Breeze, Buffalo Wild Wings, Flippers Pizza*, Red Lobster and lots more! The super target is within 2 min as well as the Publix.It is also located in very quiet area. There are great sports facilities, tennis court, and the pool area itself is fantastic. We enjoyed it very much and the pool s huge and warm !!! We loved it and will definitely recommend to our friends and family!

Responds fast! avg. 1 hour 27 minutes

1 of 2 match: Fax machine, Shared outdoor pool (heated)

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Price per night from

$121

Donald Duck's Condo Unit 305

Kissimmee apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“A vacation to be remembered” The service was very friendly and courteous. Checking in was speedy but thorough. The condo was clean, comfortable and adequately furnished. The condo is conveniently located near Disney,Orlando, retail shopping and the beaches. The resort and condo itself was the best part of the entire vacation. What I liked least about the area is the cheap little tourist stores.

1 of 2 match: Fax machine, Shared outdoor pool (heated)

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Price per night from

$178

Donald Duck's Condo

Kissimmee apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Chrismas holidays at Donald Ducks condo” Windsor Hill was exacly what we wanted ,a clean and safe place to stay with lots to do for the teenagers.The pool area his fantastic. The condo was greate for 6 adults ,beds were super comfortable.All the aminities were there in good working order, the free long distance calling was practical at new year. I have only one comment to make we could of used a few more plate and utensel in the kitchen we were always doing the dishes.We will be back.

1 of 2 match: Fax machine, Shared outdoor pool (heated)

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Price per night from

$178

2 miles to Disney,1650 sqft 4BR/3BA big Condo from $80/nt

Kissimmee apartment

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Excellent location and all the comforts of home.” Condo was within walking distance of a Winn Dixie grocery store, Fridays, Cracker Barrel, and Outback. The community pool and hot tub were excellent. The condo was equipped with everything we needed. The only negatives were the fact that we were a little disappointed that the ice maker didn't work and definitely dismayed by the fact that the smoke alarms were disconnected. We also had some periodic problems with the cable TV and wi-fi. Those are the things that caused a very good rating instead of an excellent rating. But other than those we would highly recommend the place and definitely stay again, especially if the smoke alarms are fixed.

Responds fast! avg. 1 hour 27 minutes

1 of 2 match: Fax machine, Shared outdoor pool (heated)

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Price per night from

$127

5br/3ba townhome with hot tub,Near Disney,Seaworld,Convention center

Kissimmee apartment

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

“Vacation rental” The overall experience was nice. The hot was only hot for one day and wouldn't get hot again there after. The cookware needs to be updated but overall we had a great time. I wouldn't definitely rent this rental again.

Responds fast! avg. 1 hour 27 minutes

1 of 2 match: Fax machine, Shared outdoor pool (heated)

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Price per night from

$149

1.5 M to Disney,From $100/nt,3BR 1600 sqft Townhome

Kissimmee apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

“Spacious family friendly condo close to Disney.” Perfect location to visit Disney. Very spacious with a full kitchen . A great family friendly condo.

Responds fast! avg. 1 hour 27 minutes

1 of 2 match: Fax machine, Shared outdoor pool (heated)

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Price per night from

$115

“Good price for family of 10” With 5 bedrooms, fits 10 comfortably. Owner is very helpful and location is 20mins from the parks. Walmart and restaurants are very close.

Responds fast! avg. 1 hour 27 minutes

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Price per night from

$149

Gorgeous apartment just minutes to Disney parks, Orlando Florida.

Kissimmee hotel apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Wonderful Place to stay” I stayed at the Island Club for a period of 3 months and was very happy with my stay. It was quiet, and comfortable. I liked the layout of my condo which was on one floor. My family of 5 had plenty of room to enjoy. I also liked how there was a patio in back. It made it feel more like a home. We stayed on the top floor where there was vaulted ceilings and lots of windows in the front room. This made it feel more spacious and rich. The amenities were additionally nice as well. There were 2 different pools and jacuzzis, tennis court, clubhouse and work out room to enjoy. I also liked how you could park right up against your condo building. The location was very convieinent as well. It is close to all major attractions. 15 minutes from Disney - 25 from Universal and close to shopping, and restaurants. I would stay here again in a heart beat!

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Price per night from

$125

Tropical Lakefront Villa, Gated, Pet-Friendly, less than 10 mins to Disney!

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Excellent location!” The house was very clean and well maintained. It was a short and easy drive to the Disney parks and Universal. We enjoyed relaxing in the pool after a long day of walking in the heat. It was a perfect size for my husband and I,our two grown sons and their fiancés. A great alternative to staying on Disney property because it was like being in our own home. Laree is fantastic to work with!

1 of 2 match: Fax machine, Shared outdoor pool (heated)

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Price per night from

$178

THE HAVEN IN EMERALD ISLAND RESORT

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 25 minutes

1 of 2 match: Fax machine, Shared outdoor pool (heated)

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Price per night from

$172

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