Vacation Rentals & House Rentals in Kissimmee

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Howell's Nest at Windsor Hills

Kissimmee apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private fishing lake or river, Shared outdoor pool (heated)

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Price per night from

$171

Cozy One Bedroom Villa in Gorgeous Resort & Spa

Kissimmee villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private fishing lake or river, 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: Private fishing lake or river, 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: Private fishing lake or river, Shared outdoor pool (heated)

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Price per night from

$492

Entire New Home! Gorgeous Decor, , Sleeps 10,TWO King Bedroom Suites, Pool!

Kissimmee condo

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Responds fast! avg. 1 hour 24 minutes

1 of 2 match: Private fishing lake or river, Shared outdoor pool (heated)

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Price per night from

$200

One of Disney's premier locations

Kissimmee villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private fishing lake or river, Shared outdoor pool (heated)

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Price per night from

$561

1 of 2 match: Private fishing lake or river, Shared outdoor pool (heated)

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Price per night from

$144

1 of 2 match: Private fishing lake or river, Shared outdoor pool (heated)

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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: Private fishing lake or river, 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: Private fishing lake or river, Shared outdoor pool (heated)

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Price per night from

$161

Luxury 4 bd near Disney - pet friendly - free WIFI

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

1 of 2 match: Private fishing lake or river, Shared outdoor pool (heated)

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Price per night from

$245

“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: Private fishing lake or river, Shared outdoor pool (heated)

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Price per night from

$430

Luxurious 3 Bedroom with Pool and Jacuzzi, near Disney

Kissimmee hotel apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Clean and secure.” Close to everything that we had planned. Loved the security. Nice pool and grounds. Quiet area ,well maintained.

1 of 2 match: Private fishing lake or river, Shared outdoor pool (heated)

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Price per night from

$98

“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: Private fishing lake or river, Shared outdoor pool (heated)

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Price per night from

$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: Private fishing lake or river, 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: Private fishing lake or river, Shared outdoor pool (heated)

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Price per night from

$126

Cozy resort townhome 4Br/3Ba, 5 miles from Disney

Kissimmee hotel apartment

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Great location” This condo was conveniently located and in a very nice, safe location. The owners were very kind and responsive.

1 of 2 match: Private fishing lake or river, Shared outdoor pool (heated)

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Price per night from

$102

Vacation Villa near Disney with Wireless Internet.

Kissimmee apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Private fishing lake or river, 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: Private fishing lake or river, Shared outdoor pool (heated)

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Price per night from

$92

FLAGSTONE VILLA

Kissimmee villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

1 of 2 match: Private fishing lake or river, Shared outdoor pool (heated)

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Price per night from

$361

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

Kissimmee house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

1 of 2 match: Private fishing lake or river, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$144

Dis Oasis Villa at Windsor Palms Resort - Close to Disney!

Kissimmee villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 13

“Wonderful house for a large family group” The beds were comfortable, the house was immaculate and our needs were taken care of instantly by the owner. Close to shopping, restaurants and Disney World parks.

1 of 2 match: Private fishing lake or river, Shared outdoor pool (heated)

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Price per night from

$400

“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: Private fishing lake or river, 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: Private fishing lake or river, Shared outdoor pool (heated)

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Price per night from

$430

Home away from Home. Great for large or multi-generational families!

Kissimmee villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 14

“Love, Love, Love!” Beautiful home in convenient area (to Universal, Disney & more). Homeowners are wonderful, available & extremely easy to deal with. We will definitely be back!

1 of 2 match: Private fishing lake or river, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$252

❤️ 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: Private fishing lake or river, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$252

Legacy Dunes Condo, Kissimmee, Orlando

Kissimmee apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private fishing lake or river, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$102

**2BR/2Bath Condo Near Disney–gated resort, free Wifi & parking

Kissimmee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Private fishing lake or river, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$115

Villas at Seven Dwarfs 25

Kissimmee villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“very nice” Very nice unit, we were 2 but will sleep 6, lots of amenities in private secure location right on 192 direct to Magic Kingdom. Bar, grille, heated pool , lake, picnic area, volleyball, basketball good value, easy to stay.

1 of 2 match: Private fishing lake or river, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$114

Villas at Seven Dwarfs 24

Kissimmee villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Private fishing lake or river, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$114

Amazing Disney Oasis Condo with Sauna and Gym

Kissimmee villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

1 of 2 match: Private fishing lake or river, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$125

Awesome 4 Bedroom Gated Condo with only minutes to the Disney area

Kissimmee apartment

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Excellent stay” Great location, Close to outlet stores and wall mart. Lots of things to do around there, Will stay there again, with owners permission. THANK YOU Esmeralda Vicent.

1 of 2 match: Private fishing lake or river, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$137

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: Private fishing lake or river, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$193

You Gotta See This

Kissimmee villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private fishing lake or river, Shared outdoor pool (heated)

1 of 2 filters match

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: Private fishing lake or river, Shared outdoor pool (heated)

1 of 2 filters match

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: Private fishing lake or river, Shared outdoor pool (heated)

1 of 2 filters match

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: Private fishing lake or river, Shared outdoor pool (heated)

1 of 2 filters match

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: Private fishing lake or river, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$98

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