Kissimmee Vacation Rentals

(272 rentals)
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South facing heated pool and spa

6 BR | 4 BA | Sleeps 12 | Quick View

6

Distance to park: 3 miles to Disney World

$263

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

Situated in the Window Hills resort community about 2 miles from Disney, this 6-bedroom, 4-bath vacation rental home specializes in providing fantastic Florida vacations! With 2,812 square feet and accommodations for 14, guests can enjoy not only the private pool and spa in the enclosed lanai but also ...

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Property Type

Kissimmee House

"Girls Trip 2020"
Reviewed July 24, 2020

My friends and I absolutely loved this home ...it was perfect for the 8 of us. I WOULD DEFINITELY RENT AGAIN!!

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FROZEN Retreat with Private Pool & Baby Gear near Disney World

4 BR | 3 BA | Sleeps 10 | Quick View

Distance to park: 5 miles to Disney World

$143

avg/night

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Key Amenities

  • Air Conditioning

About this property

This Frozen themed townhome sleeps 10 with 4 bedrooms, a well appointed kitchen and private heated pool.Enjoy the convenience of a fitness center, tennis courts, sand volleyball, basketball, game room, movie theater, huge pool, hot tub and tiki bar for hours of endless entertainment within the gated ...

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Property Type

Kissimmee Apartment

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Luxury Villa with own private pool on gated Resort. Free gas BBQ. Near Disney

$120

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

A stunning, larger than average 4 Bed 3 Bathroom villa that had a major refurbishment in 2017There are 2 sitting rooms both with lots of comfortable seating. Both rooms have large screen TVs, ideal for when the adults want to watch the latest sports programme whilst the kids enjoy the latest Disney ...

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Property Type

Kissimmee Villa

"My Stay"
Reviewed July 20, 2021

This was a very beautiful home, well maintained and lots of space. You would really love staying here. Convenient to many useful places, especially Walmart my favorite place. I would not hestitate to ask ...

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Champions Estate

8 BR | 5 BA | Sleeps 16 | Quick View

$370

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Located in one of the most sought-after resorts in the Orlando area, welcome to Champions Estate. The newly built 8 bedroom, 5 bath pool home is the perfect destination for your family getaway. The home was designed to fit every need that you could have when visiting the area. This villa accommodates ...

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Property Type

Kissimmee Villa

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Resort living while visiting the theme parks and next door to Margaritaville

$155

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Our beautiful FOUR-BEDROOM, THREE-BATHROOM, luxury home is located at the gated community of Emerald Island Resort, surrounded by lush Florida vegetation, is the one of the latest full-facility resort in the Disney area. The winding, palm-lined road that leads to the impressive entry to the resort gives ...

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Property Type

Kissimmee House

"Wonderful Home"
Reviewed August 3, 2021

Home was great. Have stayed in emerald Island multiple times and this home was one of our favorites.

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Sunny Luxury Legends Villa only 6 miles to Disney

$333

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

This beautiful home has everything you need to create your dream stay in Reunion Resort - 6 Miles to Disney!Legends Villa includes a large pool with a spillover spa, luxurious decor that creates an elegant ambiance, over 5,000 sq.ft of spacious living areas & large inviting bedrooms, a cinema, ...

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Property Type

Kissimmee Villa

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Perfect Paradise

7 BR | 4.5 BA | Sleeps 16 | Quick View

$333

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool
  • Rentals by Owner

About this property

LOCATED IN GUARD GATED RESORT COMMUNITY of Emerald Island 3 MILES TO DISNEY 4 KING MASTER BEDROOMS (7 TOTAL BEDROOMS) 4 FULL BATHROOMS plus a half bath downstairs HUGE PATIO AREA so you always have sun on the pool PLUSH PORCH FURNITURE SPA AIR-CONDITIONED MOVIE THEATRE ROOM/GAME ROOM (POOL ...

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Property Type

Kissimmee Villa

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TWO MASTER SUITES - Peaceful view

$113

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Cozy 4/3 single story home on the lake. Beautiful views, birds, ducks, turtles, catch and release only, please. Two en suite queen bedrooms, 1 queen beds and 2 twin beds, , WiFi, Free US, Canada and US Territory phone calls. Recently upgraded, large refrigerator, new range, dishwasher, etc. Tile floors, ...

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Property Type

Kissimmee House

"Nice rental"
Reviewed June 28, 2021

Diane does and excellent job of having the home prepared for guests. This home did not have pool towels as the other, but I had brought my own for the beach. The rain kept us at bay most all week, but ...

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Gigantic Pool 6 BR 4 BA, Two Themed Bedrooms, Games room

6 BR | 4 BA | Sleeps 13 | Quick View

2

Distance to park: 3 miles to Disney World Animal Kingdom

$235

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool
  • Rentals by Owner

About this property

Welcome to BigPoolVilla!Our 6 bed (3 en-suite masters) 4 full bathrooms (with a spectacular pool) is where you want to be - as close to Disney as it gets, only at 2 miles from Disney in the prestigious Rolling Hills at Formosa Gardens Estate on a QUIET street.The Pool is Gigantic it's in the top ...

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Property Type

Kissimmee Villa

"Awesome"
Reviewed May 7, 2021

This house was located just a short driving distance from Walt Disney World. It was very easy to get to the parks. This was the first time we have ever rented a vacation home and we were not disappointed! ...

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CLOSE TO DISNEY BUT NOT EXPENSIVE

$73

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

Nice 3/2 condo. Granite counters, new cupboards, tile floors except for bedrooms. patio with table & chairs. Pool, hot tub, workout area, playground, grills, Close to the Attractions, and less than 10 minutes from 24 hour Walmart, fast food, fine dining, shopping. You can be at Disney Springs or ...

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Property Type

Kissimmee Condo

"EXCELLENT PROPERTY"
Reviewed January 4, 2020

CONDO IS VERY ROOMY AND VERY COMFORTABLE. UP-TO-DATE APPLIANCES AND LARGE SCREEN TV. VERY REASONABLE PRICES,WILL DEFINITELY RECOMMEND TO FRIENDS AND FAMILY

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Champions Breeze | 5 Bed Townhome in Champions Gate

$164

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Enjoy these amenities and more at The Retreat, only 12 miles to the gates of Disney World® and 6 miles from Reunion

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Property Type

Kissimmee Townhome

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Hidden Treasure

3 BR | 2 BA | Sleeps 6 | Quick View

1

$121

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool

About this property

No booking fees! Four night minimum please. Welcome to this beautifully furnished gorgeous 3 - bedroom and 2-bathroom Villa. This stunning home features a very private and totally fenced heated glistening swimming pool with plenty of seating, 55" LED TV, 40” LED TV and a LED TV for the kids ...

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Property Type

Kissimmee House

"Will Return!"
Reviewed January 21, 2021

I really enjoyed Cathy’s home. The layout was perfect as on one side of the home was the master bedroom and the kids close enough on the other side that offered nice privacy and quiet. Having no backyard ...

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Fairway Joy | 5 Bedroom Pool Home with Extended Pool Deck and Conservation Views

$263

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

This luxurious and comfortable home is located in Reunion Resort and has 3,203 square feet of living space, complete with a pool and balcony. The location of this property allows you to enjoy the resort’s many amenities and attractions that central Florida has to offer.This vacation home is ...

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Property Type

Kissimmee Villa

"WOW! YOUR HOUSE IS JUST WHAT I,VE BEEN LOOKING FOR WOW!"
Reviewed May 22, 2021

I LOVE THE WAY YOUR HOUSE LOOKS FROM THE OUTSIDE ITS BEAUTIFUL AND IT SEEMS VERY SPACEOUS ALSO AND I LOVE THE WAY YOUR HOUSE LOOKS VERY CLEAN AND VERY SPACEOUS ,I SURE HOPE MY FAMILY WILL ENJOY THEIR STAY.THANK ...

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West Reunion Estate | Games Room, Theater and South Facing Pool!

$332

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

Situated within the West-side of the exclusive Reunion Resort and Just 6 miles from the gates of Disney World!Pull up to your home away from home, and prepare to indulge in luxury. This home has been furnished with no expense spared. This beautiful home boasts a rare combination of characteristics ...

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Property Type

Kissimmee House

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Family Vacation Home, Only 4 Miles to Disney, 8 BR, 4.5 Bath, Pool & Game Room

8 BR | 4.5 BA | Sleeps 16 | Quick View

7

Distance to park: 3 miles to Disney's Animal Kingdom

$262

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool
  • Rentals by Owner

About this property

Mickey's Mansion is happy to present our newly updated, themed twin bedroom sure to please Star Wars fans of all ages. It gives the feel of being in a spaceship looking out into outer space surrounded by stars and planets while being watched over by R2D2 and BB8. Drift off to sleep knowing the force will ...

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Property Type

Kissimmee House

"Family Vacation"
Reviewed September 21, 2021

I brought my family to Florida for a vacation. My 95 year old grandmother enjoyed the trip as well as everyone else. The house was just as it was stated on the site. The Wilson’s were very tentative to ...

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Milazzo Florida Villa - 3 Miles from Disney / Orlando - Indian Creek / Kissimmee

4 BR | 3 BA | Sleeps 8 | Quick View

Distance to park: 2 miles to Disney's Animal Kingdom

$160

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

4 Bedroom /3 Bath / Pool & Spa Vacation HomeCONTACT US AND REQUEST A DETAILED QUOTE !! No Booking Fees - Book Direct with the HomeownerCheck our Reviews on VRBO - Property #284051

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Property Type

Kissimmee House

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Luxury Villa with own private pool on gated Resort. Close to Disney

$115

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool

About this property

This is a beautiful professionally decorated and furnished 3 Bed, 2 Bath Villa located at Lake Berkley Resort. Have your vacation here in comfort and relaxation with air conditioning throughout.The spacious sitting room has a Queen sofa sleeper bed so the villa can easily accommodate 8 persons. This ...

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Property Type

Kissimmee Villa

"Kissimmee Villa"
Reviewed August 20, 2021

The house was great!! Very clean. Would definitely stay again. We had a great time. The girls loved the pool!! The owners were easy to get in touch with and very helpful! The house was close to shopping ...

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3BR 1st Floor Condo Near Disney, Steps from Pool, Loaded with Amenities

$85

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Rentals by Owner

About this property

Built in 2002, Windsor Palms Resort is a gated community approximately five miles from Disney. This luxury complex has a 7500 square foot clubhouse, basket ball courts, volleyball courts, children's play area, large swimming pool, splash pad, hot tub, picnic and barbecue area, outdoor bar, convenience ...

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Property Type

Kissimmee Condo

"Disney trip"
Reviewed January 5, 2020

Our stay was wonderful! Clean, close to Disney, beautiful pool! Loved it!! Check-in was easy and quick. Everyone was very polite and helpful.

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4 Bed Beaufitful Town House

4 BR | 2.5 BA | Sleeps 8 | Quick View

$101

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Rentals by Owner

About this property

Bedroom 1 queen bedBedroom 2 King bedBedroom 3 double bedBedroom 4 2 single bedsUse of clubhouse, pool, gym, pool table, cinema room wi-fi

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Property Type

Kissimmee Townhome

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MAKING HAPPY MEMORIES

4 BR | 2 BA | Sleeps 6 | Quick View

3

$125

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

LARGEST POOL IN THE COMMUNITY! HUGE POOL AND DECK. ENJOY BREAKFAST AND MEALS IN THE SUNSHINE . TERRIFIC SOUTH FACING POOL AND BACKS TO CONSERVATION SO YOU ARE NOT OVERLOOKED. SPLIT PLAN BEDROOMS, KING AND 2TWINS IN BACK BY THE POOL, AND QUEEN AND 2TWINS IN FRONT. EAT-IN KITCHEN, BREAKFAST BAR, Q-LED ...

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Property Type

Kissimmee House

"Loving Memories"
Reviewed July 19, 2021

My family and I enjoyed everything this home had to offer. The pool was great for endless fun. The deck was great for my my morning breakfast and coffee just so peacefully and beautiful. The bedrooms ...

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Stunning 4 Bed villa with own large South facing pool. Gated Resort near Disney

$123

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

Welcome to our four bedroom executive villa with south facing pool in award winning gated Lake Berkley Resort. The villa has a mix of tiled flooring and laminate flooring.Extremely spacious villa with large sitting room, leather sofas and large screen TV.Fully equipped kitchen, everything is provided, ...

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Property Type

Kissimmee House

"Awesome Vacation Home"
Reviewed April 17, 2021

We really enjoyed our stay while in FL. Any issues that came up, Aimee was more than happy to assist. We would rent again and we have recommended others.Thanks again

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The Floridian : Ultra Luxuary 5BR Pool Home, 2 Master Suites, Sleeps 12!

$286

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool

About this property

Enjoy our three-thousand square foot, custom luxury pool home, less than four miles from Disney World. We offer two master suites with king-size beds (one with Jacuzzi), two queen-bedrooms, one twin-bedroom, and queen size pullout-couch, all on one floor. This is not your typical Rolling Hills house. ...

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Property Type

Kissimmee House

"Vacation"
Reviewed August 3, 2021

The house was beautiful and very clean and spacious, the pool was a little to hot, had to contact owner to lower the temperature in the jacuzzi and pool also the pool speaker did not work, owner stated ...

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Indian Creek Disney Retreat

4 BR | 3 BA | Sleeps 8 | Quick View

13

$139

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool
  • Rentals by Owner

About this property

Indian Creek Disney Retreat is a beautiful 1800SF, well maintained home in the Indian Creek subdivision which is literally on Disney's doorstep and your home away from home. Indian Creek is not a gated community but has a lot of community amenities.COVID-19 Precaution Implementations: We have installed ...

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Property Type

Kissimmee Villa

"Vacation Stay"
Reviewed August 9, 2021

I absolutely love renting this house when I get the chance! This house never fails me. It is right next to all the main attractions and plenty of places to eat! My family was never bored and we were constantly ...

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Florida Family Vacation Rental Home In Disney Area!!!

$120

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

Welcome to family comfort and convenience minutes from Disney & other area attractions!Close to shopping, dining, golf and other recreational activities, this 4 bedroom, 2 bathroom, air conditioned, pool home is single storey, with fenced & locked rear yard for extra privacy & security ...

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Property Type

Kissimmee Bungalow

"Perfect Disney Vacation House"
Reviewed October 25, 2019

The house was well equipped and stocked with plenty of towels and blankets. Seemed to be updated . LVT flooring throughout. Very clean and comfortable. Pool was a little cold..I recommend adding pool heat ...

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Stunning 5 Bed Villa with own pool. Gated Resort very close to Disney.

$155

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

This fantastic 5 bedroom, 4 bath Vacation Villa offers all of the conveniences of home and everything you need for a fun family vacation including a Private Screened-In Pool, Outdoor Spa, Games Room, Fully Equipped Kitchen, Free Wireless High-Speed Internet, Full Size Washer/Dryer, Coffee Maker and Microwave. ...

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Property Type

Kissimmee Villa

"Great Stay"
Reviewed July 13, 2021

8523 Sunrise Key was a Great stay my family and I really enjoyed everything about the Villa and the process was very quick and easy And Stephen and Joann were very helpful I totally recommend

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Refinished/Painted S. Facing Pool/Spa, Updated Decor, Near Disney, Sleeps 8

4 BR | 3 BA | Sleeps 8 | Quick View

12

Distance to park: 4 miles to Disney

$139

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool

About this property

Magical Dreams come true in our elegant private 4 bedroom villa, 3 bathroom, all located on one floor, Quiet upgraded comforts of home and luxuries of an exceptionally rated vacation resort/hotel. Newly resurfaced and freshly painted pool and spa is sure to impress. There will be no waiting in line ...

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Property Type

Kissimmee House

"Perfect Rental….."
Reviewed July 7, 2021

Staying here was perfect…. Nice big house , lots of room , everything you need is just about there and an excellent location . The pool and hot tub are exactly what you need after a long day running around ...

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❤EIR Fun House Pool/Arcade/Theatre/GameRoom 15min/4mi to Disney

$503

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

Relax

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Property Type

Kissimmee Villa

"Great House"
Reviewed April 20, 2021

This is a clean home that is very well equipped for a nice stay and my family and I really enjoyed it!

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The perfect Disney vacation home rental property! Only Weekly/Monthly Rentals

3 BR | 2 BA | Sleeps 8 | Quick View

3

Distance to park: 12 miles to All Disney Theme Park

$100

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool

About this property

If you will be visiting Orlando Florida for all of the great attractions including Walt Disney World, Universal Studios, Sea World theme parks, and all of the other major attractions? You can stay in our beautifully decorated 3 bedroom private villa, which boasts it's own private pool for less than it ...

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Property Type

Kissimmee Villa

"2021 vacation"
Reviewed July 7, 2021

A well kept nice home. Everything as shown in the pictures. Excellent communication from owner and the property manager.

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Beautiful lakeside villa with private pool.

$74

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Beautiful south facing lakeside villa with solar and electric heated pool. Great location for all the theme parks, Disney 20 mins, Seaworld 15mins, Universal 30 mins and Cocoa Beach/Kennedy Space Centre 45 mins. Local English management contact and fully inspected/licensed by the Florida Hotels Board. ...

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Property Type

Kissimmee Villa

"Peaceful, Beautiful, Spacious surroundings."
Reviewed September 22, 2021

We are more than pleased with the spacious, clean home in a peaceful and safe neighborhood. The home could not be in a better neighborhood. It is very close to anything kids and adults would want during ...

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One mile from Disney, Celabration, family condo, gated, Free WI-FI

3 BR | 2 BA | Sleeps 6 | Quick View

2

Distance to park: 1 miles to Disney Animal Kingdom

$93

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Rentals by Owner

About this property

Come and enjoy your vacation in this comfortable condo, right by Disney. Yes Enjoy Three large screen TV's, DVD and free Wi-FI.Yes Beautiful/alluring condo, 1 mile from Disney world and minutes from other attractions, Such as sea world and Universal studio. In Celebration area Florida. Walking distance ...

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Property Type

Kissimmee Condo

"Recommended"
Reviewed August 27, 2021

This is a beautiful property to stay in. Very clean and neat. I truly recommend it to anyone who wants to be near the main attractions. Everything is very close. You have gift shops, souvenirs shops, target ...

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Windsor Hills resort Private Pool Home (FREE WATER PARK USE DURING STAY!)

6 BR | 3.5 BA | Sleeps 14 | Quick View

1

Distance to park: 2 miles to Disney World

$300

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

COVID 19 INFO UPDATED ON OUR WEBSITE, CANCEL FOR ANY REASON TRAVEL PROTECTION COVERAGE OFFERED, FLEXIBLE CHANGES up to 31 days prior to arrival. **Due to the number of inquiries we receive, you are welcome to send an inquiry through this page but please allow a day for us to respond, for faster reply, ...

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Property Type

Kissimmee House

"Perfect"
Reviewed July 17, 2021

The owner was excellent with communication and the my family loved the house. My room was beautiful and the garden tub was magical definitely will rent from David again

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Modern Serenity Vacation Home | Private and Screened Pool | Home Theater |

$291

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

THIS HOME IS LOCATED IN THE RETREAT AT CHAMPIONS GATE, WHICH IS 6 MILES FROM REUNION RESORTThis home has everything you need for your next vacation. This brand new home with 8 beds and 5 baths can accommodate up to 16 guests with a spacious living area, fully equipped kitchen, private and screened ...

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Property Type

Kissimmee House

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Affordable Disney Villa - just 5 minutes to Disney

$141

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Our property maintains a gap of 3 days between each booking for health safety measures during this crisis and we also follow stated mandated cleaning procedures and guidelines after each guest checks out.This Disney Villa is a fully furnished home and is one of the best kept turnkey properties you ...

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Property Type

Kissimmee Villa

"Perfection vacation getaway"
Reviewed March 24, 2020

I rented this house for my 1 week vacation to Disney and Universal Studios and was truly impressed by all it offered. To start the location was perfect, as it was close to both theme parks (being minutes ...

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Luxury Windsor Hills 3/2 Condo

3 BR | 2 BA | Sleeps 6 | Quick View

5

Distance to park: 2 miles to Disney

$95

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

Windsor Hills is one of the greatest gated community located within the heart of Orlando’s premier tourist attractions. Windsor Hills boasts the closest proximity to Central Florida's theme parks. Windsor Hills has all the amenities of a Five Star Hotel or Resort.Our 3 bed/2 bath (1 king, 1 ...

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Property Type

Kissimmee Apartment

"Excellent resort facilities"
Reviewed March 24, 2020

Resort was excellent with all the Disney attractions. Plus all the restaurants nearby and the Walmart store just one half mile away. The pool area was very large and accommodated all the guests. Very well ...

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Any Closer to Disney and You'll Need a Park Pass! Southfacing Pool

$187

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly

About this property

Less than 2 miles and only 5 minutes to Disney! Located in the new and most upscale location, the Emerald Island Resort, just 3 traffic signals from Disney off of Hwy 192 in Kissimmee. We feature concierge & shuttle service, so you are never "on your own" unless you want to be! Tennis and ...

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Property Type

Kissimmee Villa

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Casa Bonita -- near Disney!

4 BR | 3 BA | Sleeps 8 | Quick View

33

Distance to park: 4 miles to Walt Disney World

$132

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool
  • Rentals by Owner

About this property

Florida License DWE5916118 (A five day minimum stay is required to reserve this property)'Casa Bonita' which means 'Beautiful Home' is a beautifully furnished four bedroom, three bathroom home with a 26 ft x 14 ft swimming pool and covered lanai and is just a 3.5 mile drive to Walt Disney ...

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Property Type

Kissimmee House

"2021 stay!"
Reviewed August 27, 2021

Internet went out often and the TV service and phones were internet based. Also you couldn't control the temp in the house. 78 in the house was too hot for us and it kept resetting to it shortly after we ...

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My Disney Townhouse

4 BR | 3.5 BA | Sleeps 10 | Quick View

4

Distance to park: 5 miles to Animal Kingdom

$103

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Rentals by Owner

About this property

Enjoy Orlando, Florida, home to Disney World, Sea World, Universal Studios, and Islands of Adventure, in style. Our home is within minutes of all the Orlando attractions, golf courses, shopping, and exciting night life. Our richly appointed vacation Townhouse will give you luxurious living and a vacation ...

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Property Type

Kissimmee Townhome

"Mydisneytownhouse"
Reviewed April 14, 2021

The Emerald Isle resort was easily accessible. The checkin/checkout process was fast and convenient. The best pet was our unit. The owner/host Emery was fabulous. Answered questions quickly, gave us ...

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Goofy’s Getaway

5 BR | 5 BA | Sleeps 10 | Quick View

1

$251

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

Goofy’s Getaway is a stunning five bedroom vacation home located at Windsor Hills Resort in sunny Central Florida. Here, you and your family can enjoy the very best in luxurious and stylish living combined with the convenience of being located just minutes from Walt Disney World Resort and many ...

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Property Type

Kissimmee Villa

"Outstanding rental"
Reviewed April 29, 2021

We rented this home as our first vacation home rental. I can definitely say we will return. Ray and Eileen have an amazing home that they offered to us for 10 days. Nothing was wrong and if it was I am ...

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Villa own pool and close to Disney. Only $90 per night

$90

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool
  • Rentals by Owner

About this property

Welcome to VIPvilla Johanna and Stephen thank you for visiting our website of hand-picked 5 Star quality villas. We manage the bookings for 50 private villa owners on this website and we can personally assure you that you will be delighted with any of the villas offered to you. We have many repeat ...

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Property Type

Kissimmee Villa

"Awesome vacation home."
Reviewed September 23, 2021

We had a great time in this lovely home. Very clean, updated, and had all the likings to home that we needed. Truly enjoyed the pool. Will definitely be using again.

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Four Bedroom Family Vacation Home Close to Disney!

4 BR | 2.5 BA | Sleeps 8 | Quick View

4

Distance to park: 4 miles to Disney World

$200

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool

About this property

Great vacation home just three miles from the gates of Disney! Flat screen TV's in living room and all 4 bedrooms. Free wireless hi-speed internet and cable TV. HD TV in living room and all bedrooms. King bedroom has a flat screen 50" TV and 2 additional bedrooms have a built in DVD player in the ...

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Property Type

Kissimmee House

"Perfections"
Reviewed June 30, 2021

This lovely vacation home proved to be the perfect place for making and sharing vacation memories! The pool was wonderful on those days when we stayed home and a welcome respite after our return from the ...

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Classic Condo | 3 Bed 3 Bath for 6 in Reunion Resort

$142

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

This condo is located in the neighborhood Villas South in Reunion Resort near the many world-class entertainments and theme parks Orlando is notorious for. It has everything you need for an Orlando vacation, including a fully equipped kitchen with stainless steel appliances and a beautiful granite countertop. ...

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Property Type

Kissimmee Condo

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LUXURIOUS 14B 11BA PRIVATE POOL/PATIO Solterra Resort-7013- Property 4831

$612

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Be sure to visit our website to check availability on all our homes!Visit us at lostinthemagic . comSolterra Resort - Davenport, Florida is a paradise located only 15 minutes from the area's main attraction... Walt Disney World. This luxury resort sits nestled just outside of Orlando, Florida ...

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Property Type

Kissimmee House

"Toya review"
Reviewed July 2, 2021

The location was amazing. The house was super spacious, super clean. The pool was amazing. Everything was great Just awesome

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KENNEDY-1 LAKESIDE POOL AND SPA AHHHH!

$122

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool
  • Rentals by Owner

About this property

CHEERY AND BRIGHT. Just what a vacation home should be. 4 bedrooms, 2 bathrooms, great views and just minutes from all the fun. Fully furnished , just bring personal items or things you cannot live without. Located in Eagle Pointe, a well sought-after vacation home community. Just minutes from what ...

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Property Type

Kissimmee House

"Great if going to the Parks!"
Reviewed August 16, 2021

If you want to be about 15 minutes from the parks this is it. The house is very well decorated. We enjoyed using the pool and the view of the lake.

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Coral Heights Luxury Vacation Villa - 6 Bed, South Facing Pool & Lake Views!

6 BR | 3 BA | Sleeps 12 | Quick View

1

Distance to park: 15 miles to Disney World Orlando

$234

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool

About this property

Superb Large South-Facing Villa with 6 Bedrooms & 3 Bathrooms, Large Swimming Pool & Jacuzzi that overlooks a beautiful fishing lake!Thank you taking the time to look at our beautiful 6 bedroom fully air conditioned villa. Our Villa is situated in the beautiful area of Crescent Lakes which ...

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Property Type

Kissimmee Villa

"Fabulous Villa!"
Reviewed February 24, 2021

We booked just after December for a family vacation in this beautiful Villa. We definitely made the right choice! The Villa itself is gorgeous, tons of space inside and the owners have gone the extra mile ...

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Stunning Lakeview Vacation Villa, Gated Community, Just a Few Miles to Disney

5 BR | 4 BA | Sleeps 10 | Quick View

LAST MINUTE DEAL 10/25 - 10/30: 15% Off Regular Rate - Just 158.00 per night

$193

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool
  • Rentals by Owner

About this property

Sunset Vista Shores is a vacation home located in the gated Sunset Lakes community, just a few miles from Walt Disney World and convenient to Universal and Sea World. This lakeside retreat offers stunning water and sunset views. With the lake on one side of the home and acres of natural conservation ...

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Property Type

Kissimmee House

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DEAL
Enchanted Emerald Oasis (At the gates of Disney World)!

7 BR | 4.5 BA | Sleeps 16 | Quick View

1

Distance to park: 3 miles to Disney World Resort

$277

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

Welcome to the Enchanted Emerald Oasis! The perfect vacation rental home for you, your family and friends! Located in the upscale Emerald Island Resort, just outside of the gates of Disney World theme parks, minutes to Universal Studios Orlando, Sea World and so much more in the Orlando area! Also, ...

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Property Type

Kissimmee Villa

"Can’t wait to go back!"
Reviewed January 18, 2020

Awesome property that was simply perfect for our extended family trip to Disney. Over half of our group flew in from Ireland and the remainder of us are Irish living here in the states. Comfortable, clean, ...

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4-Bed Pool Home on 5 Star Resort near Disney

$130

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

Gorgeous 4 Bedroom/2 Bath Orlando Vacation Home located in the very popular Lake Berkley Resort. A great choice for your next Florida vacation, your family will enjoy the comforts home and the amenities of a 5 Star Resort! Beautifully landscaped, this Gated resort is ideally located just 10-20 minutes ...

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Property Type

Kissimmee Villa

"Family Trip "
Reviewed August 1, 2021

Love the place did not want to leave. So much room for everyone to have there own space, neighborhood was vey nice and quite DEFINITELY WOULD STAY AGAIN!!!

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HERITAGE-1 HUGE POOL AND SPA

4 BR | 2 BA | Sleeps 7 | Quick View

1

$125

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool
  • Rentals by Owner

About this property

WELL CARED FOR HOME IN LOVELY COMMUNITY. HOME BACKS TO CONSERVATION SO YOU ARE NOT OVERLOOKED AND IS A FEW STEPS FROM RETENTION POND WITH POND VIEWS FROM THE POOL DECK. SHADED PATIO WITH TABLE AND CHAIRS .KING, KING AND 4 TWIN BEDS WITH THEMED TWIN BEDROOMS - LITTLE MERMAID AND DORY. TV IN ALL ...

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Property Type

Kissimmee House

"Amazing time"
Reviewed June 14, 2020

This is one of the most beautiful homes I've ever stayed in. Plenty of space with private pool cant get any better. Very good location and neighborhood. Will be going back very soon.

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Family Fun | Games Room & No Rear Neighbors

$269

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

This expansive 3,909sq. ft home can also sleep 18 comfortably, set within a luxury resort. With 9 bedrooms and 5 bathrooms, this is a perfect home for a large family or group vacation. Your family will love relaxing in the Florida sun by the pool!The living area has an open floor plan, you will find ...

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Property Type

Kissimmee Villa

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The perfect Disney vacation home rental property! ATTENTION-ONLY WEEKLY RENTALS

3 BR | 2 BA | Sleeps 8 | Quick View

8

Distance to park: 12 miles to All Disney Theme Park

$112

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool

About this property

If you will be visiting Orlando Florida for all of the great attractions including Walt Disney World, Universal Studios, Sea World theme parks, and all of the other major attractions? You can stay in our beautifully decorated 3 bedroom private villa, which boasts it's own private pool for less than it ...

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Property Type

Kissimmee Villa

"Vacation"
Reviewed August 4, 2021

our stay her was nice. It had all our basic needs and a nice private pool. We plan to return to this home on our next trip. The only thing we haven't received our deposit yet. But I'm sure it will be soon.

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Kissimmee Vacation Rentals


Kissimmee Weather

 | 

7222°  489°
JANUARY
7323°  499°
FEBRUARY
7725°  5312°
MARCH
8228°  5814°
APRIL
8731°  6418°
MAY
9032°  7021°
JUNE
9233°  7222°
JULY
9233°  7222°
AUGUST
9032°  7122°
SEPTEMBER
8429°  6518°
OCTOBER
7926°  5714°
NOVEMBER
7323°  5010°
DECEMBER

Find your ideal Kissimmee vacation rental today
 
Aiming to take an incredible vacation to this year? Ditch the traditional hotel and opt for one of our Kissimmee vacation rentals instead. We have plenty of condos available in Kissimmee on FloridaRentals.com. Whether you’re looking for luxury Kissimmee villa rentals or kid-friendly mansions with an arcade, you can find it on our site.
 
Kissimmee, Florida travel advice
 
A short drive south of Orlando finds you in sunny, friendly Kissimmee. Here you’ll be near all the theme parks, but you’ll be away from the bustling crowds. Rentals will cost less than a stay in Orlando, so you’ll have extra cash to spend on park tickets and meals. This area also offers activities for those who love outdoor exploration, with exotic plants and animals in the local nature preserves.
 
Top attractions
 
The Florida theme parks are the major draw for visitors to the area. Walt Disney World, Universal Studios, SeaWorld, and the Wizarding World of Harry Potter draw millions of families every year. 
 
The fun doesn’t stop as kids and adults alike can mingle with their favorite characters, feel the chills and thrills of amusement rides, and cool off in the area’s water parks. If the theme parks don’t meet your need for speed, spend an afternoon at Fun Spot America. With two unique go-kart tracks and 18 rides you’ll be dizzy with delight. 
 
The Museum of Military History offers exhibits that highlight the bravery and humanity of the men and women who have served in the armed forces. Genuine artifacts, military relics, photographs and memorable accounts by former soldiers are on display here.
 
For some Florida history, stop in to Osceola County Pioneer Village and Museum. This museum features many exhibits depicting life in the 19th century. The Pioneer Village has a general store, blacksmith shop, one room schoolhouse, and nature preserve.
 
Family-friendly activities
 
Strap on your hiking boots and take off on the Shingle Creek Regional Trail. The trail offers a beautiful, natural environment for cyclists, pedestrians, canoeists/kayakers, bird watchers and other nature lovers.  A wide variety of habitats on the trail include Lake Tohopekaliga waterfront and islands, a pristine cypress swamp, an orange grove and wild grasslands.
 
For a more cuddly experience, Green Meadows Petting Farm has over 50 acres of animals to greet and family rides. If you’re visiting during spring training, stop in to see the Houston Astros practice as Osceola County Stadium. 
 
Of course, the options for fun aren’t limited to the parks. For golfers, Central Florida is a veritable paradise. With dozens of award-winning courses within a few square miles, you should definitely pack your clubs when visiting. If your family prefers mini-golf you have plenty of options, too. 
 
Kissimmee Lakefront Park features a playground and splash park for kids, BBQ grills for a cookout, and fishing piers. For more along these lines, nearby St. Cloud Lakefront Park and Beach offers a family picnic area and volleyball court. Located along the breathtaking Lake Tohopekaliga, these parks are great options to spend a relaxing afternoon.
 
Spend your evenings in Old Town Kissimmee, where every Saturday night there is a classic car cruise through the city streets, accompanied by a live band. In Old Town you’ll also find everything from high end retailers to souvenir shops. There is live music playing almost every night, and restaurants offering pizza, Tex-Mex, or anything in between. 
 
Annual events
 
Osceola Heritage Park has a variety of world-class shows and sporting events. You'll find the Silver Spurs Rodeo here, too. It's a real crowd pleaser, offering a taste of the Wild West and reflective of the area's ranching heritage. You can watch bull riding, bronco bucking, barrel racing, steer wrestling, team roping, and even those funny rodeo clowns.
 
Kissimmee vacation home rentals on FloridaRentals.com
 
Booking one of our vacation homes in Kissimmee on FloridaRentals.com can save you 15% over our competitors. Plus, we have a wide array of inventory appealing to any group size or traveler tastes. Book today!


FAQ

How many vacation rentals are there in/around Kissimmee?

There are 272 Kissimmee vacation rentals available on FloridaRentals.com. From house rentals to cottage rentals to beach condos and beyond, find a unique vacation rental for you to enjoy a memorable vacation in Florida.

How much does it cost to rent a vacation rental in Kissimmee?

There are vacation rentals available in Kissimmee for as low as $68 per night with an average price per night of $186.

Can I rent a house in Kissimmee?

Yes, you can find house rentals in Kissimmee close to Lakefront Park, Monument of States, and Old Town. Don't forget to stop in to Shingle Creek Park or the nearby theme parks!

Do any vacation rentals in Kissimmee have a pool?

Yes, there are 219 vacation rentals in Kissimmee with a pool on FloridaRentals.com. Search using our filters and book one for your next vacation!

What are the best vacation rentals in Kissimmee?

Visitors give great reviews to these top-rated Kissimmee vacation rentals available on FloridaRentals.com:
Indian Creek Retreat: Well maintained home in the Indian Creek subdivision which is literally on Disney's doorstep and your home away from home.
Casa Bonita: 'Casa Bonita' which means 'Beautiful Home' is a beautifully furnished four bedroom, three bathroom home with a 26 ft x 14 ft swimming pool.
Mickey's Villa: This beautiful 5-Bed 4-Bath home located in the very popular community of Indian Creek is one of only three homes in the development with a Mickey Pool.