Kissimmee Vacation Rentals

(374 rentals)
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4 BR | 2.5 BA | Sleeps 8 | Quick View

Distance to park: 3 miles to Disneys Animal Kingdom

$177

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

Our Home Features are 4 bedrooms consisting of 1 Master suit with en-suite bathroom located on the main level. 1 Queen and 2 twin rooms,1 twin room is themed Winnie the Poo,on the upper level, these bedrooms share the upper bathroom all bedrooms are equipped with TV and DVD player. There is a further ...

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Property Type

Kissimmee Villa

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9 BR | 6 BA | Sleeps 19 | Quick View

2

Distance to park: 8 miles to Disney

$528

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

9 Bedrooms 6 Bathrooms Family Room with large HD Cable TV Large Upstairs Loft HD Cable TV and play area All bedrooms with Flat Screen TVs Fully Equipped Chefs Gourmet Kitchen with Granite Counters and Stainless Steel Appliances Formal Dining Room seating 8 plus breakfast bar and outdoor dining Private ...

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Property Type

Kissimmee House

"Great family and friends vacation rental!!"

Had a great time In central Florida while staying at this rental property. April was a great host, quick at replying on any question, issue, or concern. The Windsor facilities were nice and clean staff ...

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5 BR | 5 BA | Sleeps 12 | Quick View

6
last minute deal
LAST MINUTE DEAL 11/26 - 12/4: Last minute price reduction. Book your Magical stay now.

$360

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

About this property

☆☆ HIGHLIGHTS ☆☆️ 3 Fun Kids Bedrooms: Pirate room, Choo-Choo Train room & Enchanted Fortress Room 2 Master Suites Total 8 beds; 3 Kings, 1 Queen + 4 Twins 5 Full Bathrooms: all essential toiletries provided Full Kitchen w/ Island with seating for 4 ️ Coffee bar ️ ...

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Property Type

Kissimmee House

"Nice home, spacious and clea"

The clubhouse was nice as well. Very good experience. Close to restaurants and close to the attractions.

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

Private Pool, Spa and Premium Resort Amenities Included! Fantasia @ – Sleeps 14Welcome to your Magical Place!!Beautifully designer decorated 6 bedroom, 4 bathroom home inside the premium Storey Lake Resort Community. Private pool AND Spa with more than enough space for up to 14 to stay ...

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Property Type

Kissimmee Villa

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6 BR | 5.5 BA | Sleeps 18 | Quick View

1

Distance to park: 4 miles to Animal Kingdom

$361

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

Pack your bags for an unforgettable trip to the happiest place on Earth at 'Minnie's Maingate Manor'! Minnie’s Maingate Manor is a 6-bedroom, 5.5-bathroom vacation rental home with themed bedrooms, sleeping accommodations for 16, and a private screened-in pool and spa. This Florida ...

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Property Type

Kissimmee House

"Amazing"

Such an amazing home! You want for nothing. My grandkids were in awe of the dress up clothes.They loved the games room. It was very clean. The pool was warm and they had so many beach towels and pool toys. ...

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

Private Pool, Spa and Premium Resort Amenities Included! Blissful haven @You have found your bliss!Comfortably sleeping up to 12, this professionally redecorated (February 2022) 5-bedroom, 4 bathroom, gated resort community home has all you could possibly want:Private Pool and Spa / (Hot ...

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Property Type

Kissimmee Villa

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9 BR | 8 BA | Sleeps 18 | Quick View

1

Distance to park: 3 miles to Disney Animal Kingdom

$533

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

We’ve fallen in love with our new vacation villa, and we think you will too. Located just minutes from Disney (Animal kingdom is a 6 minute drive!) plus Margaritaville with its Water Park and many restaurants, Hartley House is the perfect home for your next family vacation. You’ll be so close ...

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Property Type

Kissimmee Villa

"Hartley House family gathering"

We have just returned from a great family holiday in Florida we took all our family away for our fiftieth wedding anniversary ,three years late .We stayed at Hartley House ,we have never stayed in a american ...

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5 BR | 4.5 BA | Sleeps 10 | Quick View

1

Distance to park: 8 miles to Disney

$244

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

5 Bedrooms 4.5 Bathrooms Family Room with large HD Cable TV Upstairs TV Den / Loft with HD Cable TV All bedrooms with Flat Screen TVs Fully Equipped Chefs Gourmet Kitchen with Granite Counters and Stainless Steel Appliances Formal Dining Room seating 8 plus breakfast bar and outdoor dining Private ...

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Property Type

Kissimmee Townhome

"Great house for a family."

This house was in an ideal location and was clean. The kitchen was great with a large island for eating.

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

Property Reference RVH_1029RExperience luxury and elegance at Bear's Den Delight, a nine-bedroom custom-built retreat located in the highly sought-after Bear's Den neighborhood of Reunion Resort. This spacious and peaceful end lot boasts an extended patio and yard, perfect for a large family ...

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Property Type

Kissimmee House

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6 BR | 5.5 BA | Sleeps 13 | Quick View

Distance to park: 8 miles to Disney

$351

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

6 Bedrooms 5 1/2 Bathrooms Designer furnishings throughout Family Room with large HD Cable TV Upstairs Loft / TV Den with HD Cable TV Cinema / Home Movie Theater Room Air Conditioned Monopoly themed Games Room with Pool, Foosball, TV, All bedrooms with Flat Screen TVs Fully Equipped Chefs Gourmet ...

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

This Disney Villa is a fully furnished home and is one of the best kept turnkey properties you will find in Indian Creek ! Has an airy open floor plan, lots of light. Enjoy the crystal clear South facing pool and the covered lanai on your sunny and warm Florida holidays.This luxurious private home ...

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Property Type

Kissimmee Villa

"Awesome place to stay!"

We are currently on vacation at this home. We have rented this many times through the years. Kim the owner will do anything to ensure you have the best vacation. House is clean, the pool is beautiful ...

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9 BR | 6 BA | Sleeps 18 | Quick View

Distance to park: 8 miles to Disney

$417

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

9 Bedrooms 6 Bathrooms Family Room with large HD Cable TV Adjacent billiard room Upstairs Loft with HD Cable TV All bedrooms with Flat Screen TVs Fully Equipped Chefs Gourmet Kitchen with Granite Counters and Stainless Steel Appliances Formal Dining Room seating 10 plus breakfast bar seating 5 ...

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Property Type

Kissimmee House

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4 BR | 3 BA | Sleeps 8 | Quick View

Distance to park: 3 miles to Disney Parks

$141

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

This home is thoughtfully furnished. Recently upgraded with a Tempur-Pedic contour supreme king size mattress, LED TV in every bedroom, Frozen themed and Mickey themed twin rooms. This four bedroom luxury home is specifically set up for vacationing guests. The house, just three miles from Disney, is located ...

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

About this property

Recently renovated luxury property now available for your next Orlando adventure. Two themed kids bedrooms each sleep 4 kids (or adults), five oversized bedrooms each with king size beds. All bedrooms feature en-suite bathrooms. Two bedrooms downstairs, 5 bedrooms upstairs (including the two themed bedrooms). ...

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Property Type

Kissimmee House

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$308

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

Golf Course Views, Grand 6 Bedroom Home in Reunion Welcome to WellerDen at Reunion Resort! Just 12 Miles from Walt Disney World Resort.This Two story home has 6 bedrooms, 5.5 bathrooms South East facing pool and much more to enjoy your Florida vacation in the Resort community of Reunion Resort and ...

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Property Type

Kissimmee Villa

"Not Bad"

The villa was not bad just a little hick up with the pool not clean and the wifi did not connect to the tv in theatre room. The house was clean and the area was nice. We going back in August

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

South Facing Private Pool, Spa and Premium Resort Amenities Included! We welcome primary bookers/travelers aged 25 and over and their young families aged 0-110! in this truly amazing family home.WELCOME To “Rebel Flamingo” at Solara Resort by Shine Villas!Sleeps Up to 16 Adults ...

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Property Type

Kissimmee Villa

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool
  • Rentals by owner

About this property

Hello, Our vacation home is located in a gated community with a large swimming pool, playground for the children, shuffle board, pool table and a workout room. It’s a duplex with its own separate driveway. There are three bedrooms and two full baths. The kitchen was just fully remodeled in 2022 ...

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Property Type

Kissimmee Villa

"Quiet relaxing rental"

We have been staying at Randy’s rental for the past 10 years and it has become our winter home away from home. Randy has continued to upgrade his villa over the years and it has become more comfortable ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

Property Reference RVH_1021RBalconies, patios, and lanais are not accessible. During 2023 there may be construction occurring on the exterior of the building by the home owners association.Welcome to Seven Eagles Joy. This 3 bed, 3 bath townhome is located in the heart of Reunion Resort - Seven ...

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Property Type

Kissimmee Townhome

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

About this property

12 Min Drive to Disney World20 Min Drive to SeaWorld26 Min Drive to Universal StudiosLocated in the gated Storey Lakes resort, this modern 8 bedroom, 5 bathroom home is the perfect place for large groups looking to stay near all the action of central Florida. Aside from an amazing location, ...

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Property Type

Kissimmee Villa

"Excellent stay in the magical mansion!"

Great place, very clean and comfortable. Kids had a blast in the game room and cars room. The movie theater was perfect! Loved the modern and contemporary style of the home with tons of space for everyone ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool
  • Private pool
  • Rentals by owner

About this property

Get ready to experience the vacation of a lifetime at Big Top Family Vacation Villa, situated in the heart of Solara Resort. This stunning villa boasts 9 spacious bedrooms and 6.5 luxurious bathrooms, providing ample space for up to 22 guests. Perfectly located just 8 miles away from Walt Disney World ...

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Property Type

Kissimmee Villa

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

About this property

A fabulous home-base for your trip to Orlando! Just Minutes to Theme Parks.Home Features:* 3 Bedrooms* 1 King, 1 Queen, 2 Full, 1 Twin (Sleeps 7-8) * All New Mattresses * TV's in every bedroom * USBs & Outlets convenient for charging* 3 Bathrooms* All En-Suite * ...

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Property Type

Kissimmee Townhome

"Loved it."

Beautiful House, and a wonderful experience from start to finish! Cant wait to go back! The home was spacious and beautifully decorated and Lisa was a Pleasure to work with, and very helpful.

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

About this property

* LOCATED 3 miles from the Disney World Theme Parks*KEY-LESS entry with personalized access code is provided to each guest for enhanced security. Home Security Alarm with 24/7 monitoring for added security.* FREE Welcome starter items provided, including 1 roll of Paper Towels, Toilet Paper in ...

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Property Type

Kissimmee Villa

"Family vacation"

We had the best time at My Disney Castle. Our kids spent most of their days in the house’s pool and hot tub. We paid for pool heat and it was so worth it. The pool and hot tub were so warm! It was great. ...

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$224

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly

About this property

This 7 bedroom/4½ bathroom private house features a huge 10' x 40' covered lanai, with ceiling fans, extra patio furniture and a large flatscreen TV (accessed only by Netflix/Hulu, etc). Nice pool area in general. Interior furnishings are nice (certainly not spectacular). This is ...

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Property Type

Kissimmee House

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14 BR | 14 BA | Sleeps 38 | Quick View

$1081

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool
  • Private pool

About this property

Looking for the ultimate getaway for your next celebration or gathering? Look no further than our luxurious safari-themed bowling villa near Disney World! With ample space for large families and groups, our villa is perfect for all of life’s unforgettable moments, from weddings to family reunions ...

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Property Type

Kissimmee Villa

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4 BR | 2 BA | Sleeps 10 | Quick View

$165

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

About this property

The heart and soul of any Disney vacation is the centerpiece in this Mickey Mouse themed villa.Leading from the living/dining room is the upgraded and fully-equipped kitchen, which includes a ceramic top range, side by side refrigerator/freezer, dishwasher, garbage disposal, and microwave. Along with ...

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Property Type

Kissimmee Villa

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

Private Pool, Premium Resort Amenities Included Star Hideaway at Storey Lake by Shine Villas Gorgeous and designer decorated 4 bedroom, 3 bathroom townhome with private splash pool sleeping up to 8.Newly Decorated October 2021 Located in one of Orlando's newest and finest resort communities: ...

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Property Type

Kissimmee Townhome

"Nice"

We definitely enjoyed our stay here. It was clean and comfortable. We were able to enjoy the small private pool and also the lazy river at the resort. The resort has 2 club houses, each with a lazy ...

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3 BR | 2 BA | Sleeps 9 | Quick View

Distance to park: 10 miles to Disney World

$135

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Designed to seamlessly merge comfort and convenience, this two-story vacation home is an ideal retreat for remote workers and business travelers in search of a welcoming home away from home. With access to resort amenities including a well-equipped gym, refreshing pool, and more, this cozy townhome offers ...

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Property Type

Kissimmee Apartment

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

Property Reference #RVH_1009RWelcome to Radiant View! This gorgeous 5 bedroom, 5 bath pool home is located in Reunion Resort in the Homestead neighborhood of the exclusive Reunion Resort. A truly beautiful place with world-class amenities such as infinity pools, a full-service spa, scenic walking ...

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Property Type

Kissimmee House

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4 BR | 3 BA | Sleeps 8 | Quick View

26

$143

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • 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.In the 1st section of Indian Creek you will ...

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Property Type

Kissimmee Villa

"great vacation home"

I loved this home and Lisa was very nice and helpful. The house was very clean and well kept. We would definitely recommend this home. Very family friendly with a great pool and hot tub. We will use again ...

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

Fireworks from Balcony, No Resort Fees! Catch the Disney and Epcot Fireworks at Night from your top floor private balcony, Resort Living by Day!Sleeps up to 8 when using the bunk room trundle and the pull out sofa bed.Master Suite has a King Bed with fabulous en-suite, large walk in shower, ...

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Property Type

Kissimmee Condo

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2 BR | 2 BA | Sleeps 6 | Quick View

$142

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen

About this property

Be sure to visit our website to check availability on all our homes! Save our page for future vacations to the Orlando area!Visit us at lostinthemagic . comStorey Lake - Kissimmee is a brand new vacation community located just 4 miles from the magical world of Disney and just minutes to Universal, ...

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Property Type

Kissimmee Condo

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

Private Pool, Spa and Premium Resort Amenities Included! Summer Solstice @Welcome to The Summer Solstice, your haven home at . Sleeps up to 14. With your own private pool and spa (can be heated – see details and optional costs below), you never need to leave your Oasis inside this luxury ...

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Property Type

Kissimmee Villa

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

Located in popular Sonoma Resort, our home is the perfect place to stay for a care and stress-free holiday away. Whether you are looking to spend long days lounging by the pool, exploring the parks or stretching your legs on one of the surrounding golf courses, this is the perfect location. Guests benefit ...

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Property Type

Kissimmee Villa

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

Property Reference RVH_1018RMajor Excitement is situated in the Liberty Bluff neighborhood of Reunion Resort, this luxurious 6-bedroom, 6 bath home offers a private pool and much more!With an open-planned floor plan, the living area is bright and spacious with an "L-Shaped" sofa before ...

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Property Type

Kissimmee House

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7 BR | 6.5 BA | Sleeps 14 | Quick View

$349

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

Private Pool, Spa and Premium Resort Amenities Included! Wow – Sea Shore at Solara by Shine Villas!!7 Bedrooms and 6.5 Bathrooms – Sleeps 14 in comfort. This home is exquisitely designed and has all you could want from your vacation home away from home. Private Pool with Spa, Media ...

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Property Type

Kissimmee Villa

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

This 33 person capacity home is located at the Veranda Palms Resort, and is perfect for family holidays. The home includes a private outdoor swimming pool, spill-over hot tub, poolside dining option and BBQ grill! You'll love soaking up the Florida sunshine in one of the poolside lounge chairs. Kids ...

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Property Type

Kissimmee House

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6 BR | 5 BA | Sleeps 13 | Quick View

Distance to park: 4 miles to Disney

$268

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

6 Bedrooms 5 Bathrooms Family Room with large HD Cable TV Second upstairs TV Loft All bedrooms with Flat Screen TVs Fully Equipped Chefs Gourmet Kitchen with Granite Counters and Stainless Steel Appliances Formal Dining Room seating 8 plus breakfast bar seating 4 and outdoor dining Private screened ...

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

Magnificent Views over Water, Private Pool, Spa - First Class Home! Water Kingdom @! Sleeps up to 28! Resort Living In The Tropics! * South Facing Pool * * Water/Lake and Conservation View * * Hot Tub Heat Included at no extra cost * Walking Distance and access to the brand Second ‘Pirate’ ...

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Property Type

Kissimmee Villa

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

Jurassic Water View at . 9Beds HotTub. Resort Living, South Facing Pool Incredible Views and Hot Tub Heat Included Jurassic Water View @! Sleeps up to 24!Resort Living In The Tropics!South Facing Pool Water/Lake and Conservation View*Incredible Pool Deck Views and Interior Themeing ...

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Property Type

Kissimmee Villa

"Great experience"

This was a beautiful and clean house. The resort was great for the kids. The rental agent was very responsive even at midnight when my wife and I were planning this trip. Great service and experience!

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7 BR | 5.5 BA | Sleeps 14 | Quick View

2

Distance to park: 6 miles to Disney

$351

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

7 Bedrooms 5.5 Bathrooms Family Room with large HD Cable TV All bedrooms with Flat Screen TVs Amazing Star Wars themed games room Fully Equipped Chefs Gourmet Kitchen with Granite Counters and Stainless Steel Appliances Formal Dining Room seating 8 plus breakfast bar seating 4 and outdoor dining Private ...

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Property Type

Kissimmee House

"Family Vacation"

My family had a great time! The location is convenient. The house was very clean, organized and well equipped (although the water pressure in the shower is very low). The only issue we had was no cellular ...

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$126

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

Close to the Attractions but away from the crowds. 4 bedroom/3 bath single story home on "lake". Ducks, Sandhill Cranes, sometimes a falcon, turtles. King, king, and 4 twin beds, TV in all bedrooms, WiFi, FREE US, Canada and US Territory phone calls. Fully furnished. Not suitable for ...

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Property Type

Kissimmee House

"Fabulous!"

We were so pleased we chose this home for our holiday. It is by far the best property we have stayed in over many years of coming to Florida.The area is perfect……lovely and peaceful on the lake ...

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7 BR | 4.5 BA | Sleeps 14 | Quick View

9

Distance to park: 3 miles to Disney World Parks

$244

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

Huge Orlando vacation rental home has 7 bedrooms and 4.5 bathrooms. Great for a large Family with up to 14 guests! There are two King Master Suites, one on each floor. The master bathroom on the first floor has a walk-in shower and separate garden tub. Bedroom 3 & 4 King beds and Bedroom 5 One Queen ...

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Property Type

Kissimmee House

"Excellent"

Great place. So much room to spread out. Great decor. Large kitchen. We cooked breakfast, lunch and dinner daily. Bunk room huge hit w the kids.Thanks for everything. We’ll be rebooking

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4 BR | 3 BA | Sleeps 8 | Quick View

1

Distance to park: 8 miles to Disney

$227

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

THIS AMAZING HOME IS VERY AFFORDABLE AND INCLUDES FREE USE OF ALL THE AMAZING STOREY LAKE FACILTIES. CLOSE TO DISNEY.4 Bedrooms 3 Bathrooms Family Room with large HD Cable TVAll bedrooms with Flat Screen TVs Fully Equipped Chefs Gourmet Kitchen with Granite Counters and Stainless Steel Appliances Formal ...

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Property Type

Kissimmee Townhome

"Great Stay"

We stayed at Reunion Resort. The condo was in good condition and the owner was very responsive to our needs. We had a great stay and would have stayed longer if unit had been available for an extended stay.

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7 BR | 5.5 BA | Sleeps 18 | Quick View

3

Distance to park: 4 miles to Disney

$351

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

7 Bedrooms (Sleeps 18) 51/2 Bathrooms Family Room with large HD Cable TV Huge second floor TV loft with HD Cable TV All bedrooms with Flat Screen TVs Fully Equipped Chefs Gourmet Kitchen with Granite Counters and Stainless Steel Appliances Formal Dining Room seating 8 plus breakfast bar and outdoor ...

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Property Type

Kissimmee House

"Beautiful House"

Beautiful house. Opted for the heated pool which was the perfect temperature. Also opted for the grill which we used to do Hamburger and hotdogs one night. Had some minor problems. You should know that ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

Imagine a vacation like no other spent in a 9 bedroom, 10 bath custom luxury lakefront pool villa. The Formosa Grand is located in the exclusive gated community of Formosa Gardens Estates and one of the closest communities to Disney (less than 10 minutes!!) No expense was spared in the gorgeous estate ...

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Property Type

Kissimmee Villa

"West Family Reunion"

We had a great time at the mansion. Only a few things I would change. The hot tub price should have been included in the rental agreement.

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

About this property

A beautiful vacation condo located in a prestigious gated and guarded community, for you to relax and spend time with your family and friends. With the prime location in Kissimmee near Disney World, major parks and restaurants, shops and so much more, this 3BD/2BA condo unit is designed for your best ...

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Property Type

Kissimmee Condo

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

Come stay in our luxury family villa that features 5 bedrooms, 3 bathrooms, full kitchen and private pool and spa. Sleeps 12 guests.Full air con and hi speed WiFi throughout the villa.Strictly no smoking and no petsOur home is very well located in Lake Berkley Resort with short walking distance ...

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Property Type

Kissimmee Villa

"Very convenient and lovely Villa"

Villa easy to book and no issues on arrival all ready and as described. Villa location brilliant for all the Disney Parks within 15 mins drive at most. 3 supermarkets near by would recommend the Target ...

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7 BR | 5.5 BA | Sleeps 14 | Quick View

2

Distance to park: 5 miles to Disney World

$244

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool
  • Private pool
  • Rentals by owner

About this property

Excellent Private Detached Family Vacation home/Villa located in prestigious man gated Vacation Resort of EMERALD ISLAND RESORTS. SPECIAL DISCOUNTS !!! ! 25% OFF FOR WEEKLY AND 30% OFF FOR MONTHLY BOOKINGS. SPECIAL RATES FROM JANUARY TO MARCH monthly bookings. Weekly $1706 Monthly $5900.00 ...

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Property Type

Kissimmee House

"Amazing 7 Bed rooms Villa Near Disney"

Our stay with Family and friens were superb. Cost is just a fraction of what otherwise with any Hotels. VEry large House with 7 Bedrooms and 6 Wash rooms. Own private pool and lanai . Bbq grill was provided ...

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4 BR | 3 BA | Sleeps 8 | Quick View

$181

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Be sure to visit our website to check availability on all our homes! Save our page for future vacations to the Orlando area!Visit us at lostinthemagic . comThe Retreat at Champions Gate - Kissimmee, Florida is a new upscale gated resort community located just 12 miles from Walt Disney World. ...

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Property Type

Kissimmee House

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$375

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen

About this property

Be sure to visit our website to check availability on all our homes! Save our page for future vacations to the Orlando area!Visit us at lostinthemagic . comWindsor at Westside - Kissimmee, Florida is an upscale gated community located just 10 minutes from Walt Disney World. This luxury home sits ...

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Property Type

Kissimmee House

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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

Soak up the Sun on Your Next Trip to Kissimmee Vacation Rentals


There’s nothing quite like a vacation to sunny Florida, a unique and inviting state with a huge variety of distinctive cities and natural areas to explore. One popular vacation destination in Florida is Kissimmee, a charming city with plenty to see and do just south of the Orlando metropolitan area. 

Kissimmee has a lot more to offer visitors than just excellent weather year-round. With a huge variety of scenic nature, shopping opportunities, and outdoor activities, Kissimmee itself has lots to offer every member of the family, not to mention its extremely close proximity to some of Orlando’s biggest amusement parks. 

You could stay in a busy hotel during your trip to Kissimmee, but then you wouldn’t be able to get a truly immersive experience of local city life. Kissimmee vacation rentals allow you to enjoy Kissimmee from inside its authentic residential neighborhoods. Additionally, having your own home to live in rather than a jam-packed hotel will provide some much-needed peace and quiet during your vacation. It will also offer plenty of space for the whole family to spread out.  

Top Tips for Traveling to Kissimmee Rentals


Like most other Florida cities, Kissimmee enjoys sunshine and clear skies throughout the majority of the year. However, the tropical climate of the state means that bouts of rain can occur throughout the seasons, particularly during the summer months, peaking in August. 

In addition to a higher likelihood of rain, the summer season in Kissimmee tends to be the most humid time of year. That’s why most vacationers choose mid to late spring or early autumn to make their trip to the city. At those times of the year, vacationers can enjoy great weather and lots of outdoor activities. 

Though the Kissimmee Gateway Airport is located centrally within the city, most vacationers taking commercial flights will fly into Orlando International Airport. It is located roughly 17 miles northeast of the city center, about halfway between Kissimmee and Orlando. Vacationers coming in from elsewhere in Florida can access Kissimmee by road using U.S. Route 192 and U.S. Route 441.

Things to Do Nearby Kissimmee House Rentals


Some of the most popular natural areas around Kissimmee are the swamps, which are located in major local bodies of water like Lake Tohopekaliga (known around town as Lake Toho). At Boggy Creek Airboat Adventures, you can experience the swamps from the water and get the thrill of a lifetime on an airboat driven by a local wetlands expert. Get up-close views of gator ponds, discover precious gemstones, and then grab a delicious lunch with the family at Boggy Bottom BBQ! 

Looking to explore a piece of history during your trip to Kissimmee? Medieval Times Dinner & Tournament allows visitors to step into the 11th century for an evening of authentic feasting, jousting, and sword fighting in true medieval style! Enjoy a delicious four-course meal, incredible performances, and a truly unforgettable experience for the entire family.
 
Any vacation to Kissimmee isn’t complete without a trip or two to Old Town, a popular outdoor attraction with opportunities for shopping, dining, and family fun. Old Town is made up of an 18-acre stretch of classic city attractions, including the Old Town Ferris Wheel, the Great Magic Hall, and Mortem Manor, a year-round haunted house that is open for visitors to explore.

Kissimmee Annual Events


Kissimmee is a vibrant area with lots of annual festivals and events to enjoy in and around the city throughout the year. Kissimmee locals and visitors alike flock to the Ford Cuban Sandwich Festival each May near downtown Kissimmee, which celebrates the colorful history of Cuban cuisine in the area. Watch as local dining professionals attempt to build the world’s biggest Cuban sandwich during the event!
 
The Ford Taste of Latino Festival is another local opportunity to celebrate and experience the best in authentic Latin cuisines in Kissimmee. The event features a contest to find the Top Latino Chef as well as plenty of live music and dance performances to enjoy as you taste a variety of Latin dishes. 

Not sure if you’ll be in town for any of Kissimmee’s larger annual events? You can enjoy Show Car Saturday Nights every Saturday night in the city on Margaritaville Boulevard. Check out the city’s best classic cars from a variety of eras and enjoy the plethora of delicious eateries and exciting shops located along the boulevard.

Wining and Dining in Kissimmee  


Between your outdoor activities and trips to local amusement parks while in Kissimmee, you’re sure to need some satisfying food and refreshing drinks to complete your perfect day. Luckily, Kissimmee is home to some of the best restaurants that Florida has to offer, combining authentic local flavors with worldly cuisine. 

To start your day off right with a delicious and hearty breakfast, look no further than Woodsby’s Countryside Café. This spot has authentic, cozy diner vibes to spare, not to mention a stacked menu of classic breakfast favorites, coffee bar items, and unique dishes you won’t want to miss out on. 

Tarantino’s Italian Restaurant is a great choice for a vacation date night or simply a nice dinner out with the family. A hearty Italian meal is a great way to finish a fun day of activities, and you’re sure to get that and more at Tarantino’s. If you bring the family along, you can take advantage of the takeout dinner special, which feeds four and includes a massive entrée, salad, and garlic bread.


FAQ

How many vacation rentals are there in/around Kissimmee?

There are 374 Kissimmee vacation rentals available on FloridaRentals.com. From house rentals to villa rentals 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 $64 per night with an average price per night of $236.

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 302 vacation rentals in Kissimmee with a pool on FloridaRentals.com. Search using our filters and book one for your next vacation!