Vacation Rentals & House Rentals in Kissimmee

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25,127 house rentals

(6) Very Good 

23

From $80/nt,Close to Disney,Seaworld,Convention Center,4br Townhome with Hot Tub

Central Florida / Kissimmee

Kissimmee townhouse

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Nearest beach 97 mi
  • Swimming pool
  • Child Friendly
“Great Family Friendly Home” We had a blast. It felt safe and secure. It was clean and spacious. I have a large family of 9 and everyone had plenty of space. Quiet but friendly neighbors. Amenities were awesome. Hot tub was so relaxing. We had a great
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Price per night from

$80

Responds fast!
avg. 2 hours 29 minutes

Price per night from

$80

(25) Excellent 

15

Luxury 4 Bedroom Villa w/pool, 2 Miles from Disney

Central Florida / Kissimmee

Kissimmee house

4 8 4 nights min

  • 4 bedrooms
  • sleeps 8
  • 4 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Beautiful Home, It was so relaxing and comfortable!!” Our family had a wonderful time on our Vacation. The location was very convenient. The pool and hot tub was great. The house was amazing, and my children loved it, I like the entrance to the pool a
…see more

Price per night from

$102

Price per night from

$102

(33) Very Good 

27

1.5 M to Disney,From $70/nt,3BR 1600 sqft Townhome

Central Florida / Kissimmee

Kissimmee apartment

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 97 mi
  • Swimming pool
  • Child Friendly
“Spacious family friendly condo close to Disney.” Perfect location to visit Disney. Very spacious with a full kitchen . A great family friendly condo.
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Price per night from

$70

Responds fast!
avg. 2 hours 29 minutes

Price per night from

$70

(22) Very Good 

29

Inexpensive Disney Luxury Home, Pet-Friendly, 1 mile from Parks-2

Central Florida / Kissimmee

Kissimmee apartment

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Pet friendly gated community” We enjoyed or stay at Manny's townhouse. The neighborhood was quiet, clean, and the neighbors were very friendly. I love that the pool was very close to where we stayed and all the activities we had planned was close by.
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Price per night from

$95

Price per night from

$95

(7) Very Good 

40

Lakefront, gated 4Br/3Ba, 6mile to Disney, Private Jacuzzi, Free WiFi/Cable TV

Central Florida / Kissimmee

Kissimmee villa

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 72 mi
  • Swimming pool
“Very pleased” We were very pleased with the house and the attention given by the owner, I emailed a concern and 1 hour later it was resolved. House is good for parents with kids.
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Price per night from

$67

Responds fast!
avg. 1 hour 33 minutes

Price per night from

$67

(35) Very Good 

17

Luxurious 3 Bedroom Townhome-1.5 miles from Disney

Central Florida / Kissimmee

Kissimmee villa

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Great Experience” The villa did not disappoint and was a great place for my family and I to stay during our world wind visit to Disney. I would recommend this place to anyone who is going to Orlando with a large group :-)
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Price per night from

$79

Responds fast!
avg. 2 hours 43 minutes

Price per night from

$79

(29) Very Good 

49

Pat and Ron's Holiday Home, Relaxing Retreat

Central Florida / Kissimmee

Kissimmee villa

3 6 4 nights min

  • 3 bedrooms
  • sleeps 6
  • 4 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Great accommodations for the price!” My best friend, her daughter, and I stayed in Pat and Ron's Holiday Home in June. Overall, for the price you can't really beat it. The house was clean and inviting and in a great location. The neighborhood appears
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Price per night from

$88

Price per night from

$88

(7) Very Good 

16

The Charming Mickey's Tree House,

Central Florida / Kissimmee

Kissimmee villa

4 9 min stay varies

  • 4 bedrooms
  • sleeps 9
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Awesome vacation!!” My husband and I took our 3 year old daughter and had a wonderful time. The house had everything we needed and more. We felt right at home from the time we got there until the time we went home. The pool and hot tub were perfect
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Price per night from

$100

Price per night from

$100

(4) Excellent 

41

Dec 10-22 Special --Windsor Hills Luxury pool house/Wifi/1.5 mile to Disney

Central Florida / Kissimmee

Kissimmee house

6 13 min stay varies

  • 6 bedrooms
  • sleeps 13
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$165

Responds fast!
avg. 1 hour 51 minutes

Price per night from

$165

49

NEW! 4/3 Private Town Home at Storey Lake Resort-Near Disney Theme Parks

Central Florida / Kissimmee

Kissimmee townhouse

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$149

Responds fast!
avg. 38 minutes

Price per night from

$149

(16) Very Good 

35

Spacious 4-bed lakeside pool villa near Disney

Central Florida / Kissimmee

Kissimmee villa

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 97 mi
  • Swimming pool
“Peaceful location with stunning views” We had a wonderful holiday in this lovely villa. It is spacious and well appointed everything was beautifully clean. The estate is quiet and peaceful considering how close it is to the 192 and all it has to offer
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Price per night from

$109

Responds fast!
avg. 2 hours 53 minutes

Price per night from

$109

(16) Excellent 

28

** SEPT & OCT SPECIAL ($1000 for Week) (TAXES INCLUDED IN PRICE) **********

Central Florida / Kissimmee

Kissimmee house

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Awesome Stay!” Can't say enough great things about this property. It was everything as described and pictured. The location was perfect being only about 20 minutes from the Disney parks. The pool, which is beautiful, was a welcome addition after s
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Price per night from

$129

Price per night from

$129

(15) Very Good 

26

Kissimmee Townhouse 4 bedrooms

Central Florida / Kissimmee

Kissimmee townhouse

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Great Place” This vacation home is absolutely beautiful and convenient to everything. Still here and having a great time.
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Price per night from

$120

Price per night from

$120

(2) Excellent 

37

2636TW- Veranda Palms

Central Florida / Kissimmee

Kissimmee house

6 13 min stay varies

  • 6 bedrooms
  • sleeps 13
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$218

Price per night from

$218

(20) Excellent 

25

From $80/nt,4br/3ba townhome with hot tub/lake view,Near Disney,Seaworld

Central Florida / Kissimmee

Kissimmee apartment

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$80

Responds fast!
avg. 2 hours 29 minutes

Price per night from

$80

(5) Excellent 

23

Disney World 2 Miles

Central Florida / Kissimmee

Kissimmee condo

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • Nearest beach 142 mi
  • Child Friendly
  • Air conditioning

Price per night from

$88

Responds fast!
avg. 3 hours 30 minutes

Price per night from

$88

(3) Very Good 

43

Close2theMagic 3br/3ba Townhouse Windsor Hills

Central Florida / Kissimmee

Kissimmee house

3 7 2 nights min

  • 3 bedrooms
  • sleeps 7
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Vacation comfort at its Best!” This was a family vacation to bring my 5 yr old granddaughter to Disney for her first time. It was spectacular! The condo was so close to Disney that we could be there in a few minutes. The heated splash pool was so a
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Price per night from

$119

Price per night from

$119

(26) Very Good 

26

3 Bedroom Vacation Home in Kissimmee Pet-Friendly

Central Florida / Kissimmee

Kissimmee house

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Vacation 2017” The house is really beautiful, clean and well maintained. We had a wonderful time and really felt at home. The owner Philip was very friendly and helpful. Thanks to Al for setting up the internet for us. Hoping to come back again next y
…see more

Price per night from

$80

Price per night from

$80

16

Reunion-Kissimmee-3 Bedroom Condo-R106

Central Florida / Kissimmee

Kissimmee house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$129

Price per night from

$129

(17) Excellent 

53

'Casa Linda' Beautiful Lakeside Home with Gym and Hot Tub

Central Florida / Kissimmee

Kissimmee house

3 8 4 nights min

  • 3 bedrooms
  • sleeps 8
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 121 mi
  • Swimming pool
“Amazing” Beautiful :) This was definitely a great place to stay My daughter and I had a nice relaxing vacation while staying here Definitely would recommend this to anyone looking for a nice place to stay Thank you :)
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Price per night from

$90

Price per night from

$90

(19) Very Good 

21

Furnished apartment - weekly & monthly Orlando rental.

Central Florida / Kissimmee

Kissimmee hotel apartment

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 64 mi
  • Swimming pool
  • Child Friendly
“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
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Price per night from

$89

Price per night from

$89

(2) Very Good 

49

☀ One Time Offer ☀ perfect for families! Spacious pool villa with spa near parks

Kissimmee / Paradise Palms

Kissimmee townhouse

6 14 min stay varies

  • 6 bedrooms
  • sleeps 14
  • min stay varies
  • Nearest beach 97 mi
  • Swimming pool
  • Child Friendly

Price per night from

$114

Price per night from

$114

(20) Very Good 

73

Luxury Lakeside House with private solar heated pool & spa

Central Florida / Kissimmee

Kissimmee villa

5 13 3 nights min

  • 5 bedrooms
  • sleeps 13
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“Wonderful vacation home” I rented this house for 6 days for our family’s Disney vacation. The house was wonderful. Great location, very clean. Everything we needed was provided. Would definitely book again.
…see more

Price per night from

$95

Price per night from

$95

(12) Very Good 

21

100 Aker Woods

Central Florida / Kissimmee

Kissimmee house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“AMAZING!!!” This house was Wonderful! Exactly as described! Loyalty USA was GREAT to work with!!! Very pleased all around!!!!
…see more

Price per night from

$129

Price per night from

$129

(27) Excellent 

24

Dec 1-15 Special.~ Windsor Hills 3BD/3BA w/FREE Pool Ht & Welcome Package

Central Florida / Kissimmee

Kissimmee house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 97 mi
  • Swimming pool
  • Child Friendly
“A Magical Stay” What's not to love about this home! First and foremost Brandie herself is a genuine person who really cares about the people who stay at her home. From the initial contact of a personal phone call, to her follow ups on every little qu
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Price per night from

$115

Responds fast!
avg. 2 hours 32 minutes

Price per night from

$115

(13) Very Good 

24

New Opening 5Br/3Ba Hot Tub/Lake View,Close Disney,Seaworld,Convention Center

Central Florida / Kissimmee

Kissimmee townhouse

5 12 min stay varies

  • 5 bedrooms
  • sleeps 12
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“Ok” Overall it was fine..checkout was at 11 and at 10 cleaners knocked on door and then preceded to sit in driveway waiting for us to leave. There was no dish soap or soap in bathrooms which would have been nice.
…see more

Price per night from

$90

Responds fast!
avg. 2 hours 29 minutes

Price per night from

$90

24

Enjoy Beautiful Cypress Palms in Florida!

Central Florida / Kissimmee

Kissimmee apartment

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$89

Price per night from

$89

(14) Excellent 

35

Terra Verde 5 Bedroom with Conservation View

Central Florida / Kissimmee

Kissimmee villa

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 56 mi
  • Swimming pool
“Very nice” The home was just as promised. It was clean and well kept. The location was a straight shot to disney. We didn't have to go on the toll road. Terra verde was great also. I liked the idea of a safe and secure place to stay in a home away fro
…see more

Price per night from

$179

Responds fast!
avg. 1 hour 39 minutes

Price per night from

$179

26

RVH_042R Contemporary Luxury

Central Florida / Kissimmee

Kissimmee house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly

Price per night from

$86

Price per night from

$86

(24) Excellent 

41

Sunny Oaks

Central Florida / Kissimmee

Kissimmee house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“This has been our second stay in the same house and it's been aw” Sunny Oaks is a beautiful and spacious house. We loved it so much the first time (Aug. 2011) that we rented it again this summer (Aug. 2013). The kids loved the pool and the adults love
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Price per night from

$129

Price per night from

$129

(6) Very Good 

22

Dolce Vita

Kissimmee / Bellavida Resort

Kissimmee townhouse

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$79

Price per night from

$79

27

4678CLD. 4 Bed Pool Home In Cumbrian Lakes With Games Room

Central Florida / Kissimmee

Kissimmee house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$150

Price per night from

$150

39

Disney Area 5 Bedroom Home at Veranda Palms

Central Florida / Kissimmee

Kissimmee house

5 14 min stay varies

  • 5 bedrooms
  • sleeps 14
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$194

Price per night from

$194

(8) Very Good 

Certificate of Excellence

25

Large 3-Bedroom Resort Villa Near Disney

Central Florida / Kissimmee

Kissimmee villa

3 10 2 nights min

  • 3 bedrooms
  • sleeps 10
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 81 mi
  • Swimming pool
“Beautiful Resort” The unit was absolutely spacious. Chris was very helpful in booking the unit. He told me that the unit number was assigned by the resort and it would be look identical to the pictures. The unit that was assigned to us was exactly as
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Certificate of Excellence

Price per night from

$155

Price per night from

$155

(36) Very Good 

33

7 Bedroom Home and only 10 minutes to Disney, Newly Renovated, Forest View,

Central Florida / Kissimmee

Kissimmee villa

7 17 3 nights min

  • 7 bedrooms
  • sleeps 17
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 97 mi
  • Swimming pool
“Best time ever” This was our second time staying in that dame house, we loved it and plan on staying there more in the future. The house was more then enough on space. Everything very clean and comfortable. The pool was a amazing time on a hit day. E
…see more

Price per night from

$158

Responds fast!
avg. 1 hour 45 minutes

Price per night from

$158

31

DISNEY AREA 5 BEDROOM PRIVATE POOL VILLA

Central Florida / Kissimmee

Kissimmee villa

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$100

Responds fast!
avg. 2 hours 34 minutes

Price per night from

$100

(8) Excellent 

12

FLORIDA Kissimmee VILLA 3 bed 2 bath private pool

Central Florida / Kissimmee

Kissimmee villa

3 4 14 nights min

  • 3 bedrooms
  • sleeps 4
  • 14 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Great home” Thanks to Kelly, her parents,and her brother Chris for a wonderful stay in their home. The home was in a perfect area for what we wanted to do. I would rent this home again. Other than one event where some young men were in the woods behi
…see more

Price per night from

$127

Price per night from

$127

(3) Very Good 

47

Kissimmee Windsor at Westside's "The Second Star to the Right" vacation home

Central Florida / Kissimmee

Kissimmee villa

7 18 min stay varies

  • 7 bedrooms
  • sleeps 18
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$239

Price per night from

$239

About Kissimmee

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 vacation 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 favorably 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 theaters, 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.

Among 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 traveling 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 vacation rentals near Disney World, including luxurious villas or large houses with multiple bedrooms, modern entertainment systems, and private pools.