Kissimmee Vacation Rentals

(323 rentals)
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Key Amenities

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

About this property

PLEASE EMAIL AND ASK FOR RATES. DIFFERENT TIMES OF THE YEAR HAVE DIFFERENT RATES AN MINIMUM STAYS - THANKS.Free WiFi, 3 miles to Disney, Huge pool and spa, Game room (pool table, air hockey, big screen tv, leather sectional, Wii), Internet access (wireless), Completely, private back yard, BBQ Grill, ...

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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

Enjoy a magical vacation just 3 miles from all the Disney parks at the Pineapple Vacation Villa situated in the elegant Windsor Palms Resort. -Our holiday home offers all of the latest features in vacation rentals. With four bedrooms including two master-en-suites with private bathrooms plus two twin ...

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Property Type

Kissimmee Villa

"Home away home."

We enjoyed 10 nights here late July. Karen is amazing to work with. Communication is number 1. Very safe and quiet within a gated community. This was just the kind of place we were looking for, cozy, ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • 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 Villa

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Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Welcome to our stunning 4 Bed 3 bath villa on 5 Star gated Emerald Island Resort.Emerald Island is one of the closest Resorts to Disney, so close you can nip home at lunchtime for a bite to eat and a drink and then return back to Disney....saving you $s compared to dining at Disney.The villa ...

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Property Type

Kissimmee Villa

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6 BR | 6 BA | Sleeps 12 | Quick View

Owner special: 10-35% off Listed Nightly Rates. **Price listed includes already discounted rates.**

$425

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

The Retreat at Champions Gate - Kissimmee, Florida is a new upscale gated resort community located just 12 miles from Walt Disney World. This luxury home sits nestled just outside of Orlando, Florida and will quickly become one of the most desired locations in the Orlando area. During your stay, you will ...

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Property Type

Kissimmee House

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9 BR | 6 BA | Sleeps 18 | Quick View

4
Owner special: 10-35% off Listed Nightly Rates. **Price listed includes already discounted rates.**

$673

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Solara Resort - Kissimmee, Florida is an upscale community currently under development just 7 miles from Walt Disney World. This gated resort community sits nestled just outside of Orlando, Florida. During your stay, you will enjoy this well-appointed home that has been designed and decorated to provide ...

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Property Type

Kissimmee House

"What an enjoyable week-end"

My family had a relaxing and enjoyable weekend at this house. We had more than enough food, the rooms were great and the kitchen had two large refrigerators and two dish washers. We were so glad for that, ...

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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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5 BR | 4 BA | Sleeps 12 | Quick View

5

Distance to park: 6 miles to Disney Animal Kingdom

$205

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

***FREE WIRELESS INTERNET JUST BRING YOUR MOBILE DEVICES**Sleeps a maximum 12 guests, with a maximum of 8 guests over the age of 14 years old.As you enter our lovely home, you will be impressed with the soaring 17ft high ceilings in the spacious hallway & living room. The living room is a ...

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Property Type

Kissimmee House

"Lovely home"

Lovely home will definitely recommend to others wish the pool and jacuzzi was heated though. Bring tissue and your own dish liquid and own laundry detergent if staying full week

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Key Amenities

  • Air conditioning
  • 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

"Fantastic villa for your holiday"

The perfect villa for your family holiday , perfect location, excellent condition, with every thing you need for a great holiday, great communication very friendly and helpful, would not hesitate to book ...

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Key Amenities

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

About this property

Large 6 Bedroom Executive Vacation Home With 2 Themed Kids Rooms, Sleeps 14 Disney Dream Vacation Villa is located in the #1 rated upscale five-stars Windsor Hills Resort at the doorstep of Disney world.This property was newly thoroughly renovated. Web photos here won't be able to show all the beautiful ...

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Property Type

Kissimmee House

"Family Vacation"

My family stayed at this property from July 1-9 the house was clean upon arrival and the check in process went smooth. The owner was great to work with and handled any problems or concerns that we had during ...

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4 BR | 3 BA | Sleeps 8 | Quick View

5
Owner special: Get 10% discount for November and December bookings if you book before September 30th.

Distance to park: 4 miles to Disney World

$144

avg/night

View Details

Key Amenities

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

About this property

Enjoy Orlando, Florida, home to Disney World, Sea World, Universal Studios, and Islands of Adventure, in style. Conveniently located on the Exclusive Emerald Island Resort. The house is spacious where family can enjoy being together and also have some alone time. Our home is within minutes of all the ...

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Property Type

Kissimmee House

"Family Vacation"

The house and location was perfect. Everyone enjoyed the stay at the house; very spacious for us. The swimming pool was the absolute best. We would definitely stay here again.

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Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Stay near all the excitement and thrills of Orlando’s theme parks, just 10 minutes from Walt Disney World Resort®, 15-20 minutes from Universal Studios Florida® and SeaWorld® Orlando. Florida’s famous beached are a short 45 minute drive.At Eagle Pointe, you will enjoy a welcoming ...

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Property Type

Kissimmee Villa

"Perfect villa close to attractions"

Superb villa close to Disney, Universal and Seaworld an all the other Attractions Kissimmee has to offer. The villa is near the 192 and that is my favorite spot. A lot of attractions and nice stores are ...

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5 BR | 4 BA | Sleeps 12 | Quick View

2

Distance to park: 5 miles to Disney's Animal Kingdom

$380

avg/night

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Key Amenities

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

About this property

Imagine coming home at the end of an exhilarating day at the theme parks...You grab a refreshing drink from the fridge, flake out on the sofa in the outdoor living area right by the pool and reminisce about all the amazing things you did that day.The kids are splashing around in the pool, you ...

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Property Type

Kissimmee House

"Family Birthday Vacation"

Everything was great! The house was very spacious. The back area a bit small but still great! We had a blast!

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

This fabulous 4 Bed Villa is located in secure gated Lake Berkley ResortThis fabulous 4 Bed Villa is located in a peaceful corner of Lake Berkley Resort with beautiful views to the Conservation Area and one on the lakes at Lake Berkley.The villa is fully equipped with everything you will need ...

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Property Type

Kissimmee Villa

"Perfect"

Our villa was in the perfect location close to all amenities. The service was 1st class with great comunication.

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4 BR | 3.5 BA | Sleeps 12 | Quick View

1

Distance to park: 10 miles to Disney world

$215

avg/night

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Key Amenities

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

About this property

Welcome to Be My Guest Vacation Home! Enjoy your vacation at this welcoming house with a fully equipped kitchen, 4 bedrooms, and 3.5 bathrooms. The home has an open floor plan and offers the community pool right next to the townhouse. Everything here was designed for you to have the best experience and ...

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Property Type

Kissimmee Townhome

"Awesome place!!"

Stayed here for the weekend with my family & absolutely loved it! House is right next to the pool and was super easy to access. I could see the pool from the living room window.Home was spotless & ...

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3 BR | 2 BA | Sleeps 6 | Quick View

Owner special: 10-35% off Listed Nightly Rates. **Price listed includes already discounted rates.**

$153

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen

About this property

Reunion Resort -Kissimmee, Florida is only 15 minutes to the area's main attraction... Walt Disney World. This gated luxury resort sits nestled just outside of Orlando, Florida and has quickly become one of the most desired resorts in the Orlando area. This home will provide you and your family with an ...

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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

Welcome to Magic Disney Memory, our luxurious vacation home located right in the middle of all the Central Florida magic. Our home is just 2 miles from Walt Disney World property in the 24 hour guard-gated resort community of Windsor Hills. This is the premier vacation home destination in the Orlando ...

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Property Type

Kissimmee Villa

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15 BR | 15 BA | Sleeps 30 | Quick View

Owner special: Save on Nightly Rate! Rates have been updated

$901

avg/night

View Details

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 . comVeranda Palms Resort-Kissimmee, Florida is an upscale gated community located just 5 miles from Walt Disney World. This resort sits nestled ...

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Property Type

Kissimmee Villa

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3 BR | 2.5 BA | Sleeps 6 | Quick View

Distance to park: 4 miles to Disney World

$160

avg/night

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Key Amenities

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

About this property

Touches of Disney around every corner make this town home a fun spot to stay during your Florida adventure! Enjoy Orlando, Florida, home to Disney World and a lot of other AMAZING attractions! This property is located on the Exclusive Emerald Island Resort and is inviting and convenient for any planned ...

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Property Type

Kissimmee Townhome

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6 BR | 4 BA | Sleeps 12 | Quick View

8

Distance to park: 3 miles to Disney World

$362

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • 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

"Perfect for our family"

Located a couple miles from Animal Kingdom and close to other Disney World attractions, the home was perfect for 3 generations of our family. It is spacious and well appointed. The kids loved the private ...

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Key Amenities

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

About this property

KEY FEATURES 7 Spacious, themed bedrooms; 4 kings, 2 queens, 2 doubles + 2 sofa beds 4.5 Large bathrooms; 3 full ensuites, 1 shared full, 1 half Modern kitchen; dining area and kitchen island seating Two separate lounge areas; each with a Smart TV and comfortable seating High-speed WiFi throughout ...

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Property Type

Kissimmee House

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7 BR | 7 BA | Sleeps 14 | Quick View

Owner special: 10-35% off Listed Nightly Rates. **Price listed includes already discounted rates.**

$445

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Reunion Resort -Kissimmee, Florida is only 15 minutes to the area's main attraction... Walt Disney World. This gated luxury resort sits nestled just outside of Orlando, Florida and has quickly become one of the most desired resorts in the Orlando area. This home will provide you and your family with an ...

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Conservation View, Games Room & Outdoor Spa!Ideal for your next family vacation, this striking 4-bedroom, 3 bath Disney area vacation home is conveniently located just 10 minutes to the Walt Disney World Resort®, 15-20 minutes from Universal Studios Florida® and SeaWorld Orlando®. ...

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Property Type

Kissimmee Villa

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Stay in our Massive, single family home located in the Amazing Encore Resort! Large 4,800 square foot home in a fantastic location House sleeps up to 26 people in our 16 total beds 10 Minutes to Disney 10 Bathrooms Cable TV at the home Fast WiFi - ideal for working remotely Beautiful Pool ...

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Property Type

Kissimmee House

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4 BR | 3 BA | Sleeps 8 | Quick View

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

$170

avg/night

View Details

Key Amenities

  • Air conditioning
  • 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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$123

avg/night

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Key Amenities

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

About this property

Come relax in this 4 bedroom, 3 bathroom home. Sit on the screened in pool deck and just watch the wildlife , eat meals, have a cup of coffee and just relax. You are on vacation. Two king beds, queen and 2 twin beds .

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Property Type

Kissimmee House

"Disney Bound 2021"

The location was perfect with easy access. The house was very nice with a great view overlooking the pond. Had everything we needed. About 15 to 20 minutes away from Disney. Ms. Diane is a great host. Will ...

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Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Beautiful south facing lakeside villa with electrically heated pool option. 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

"Family Disney vacation"

We stayed here for almost 2 weeks, has everything you need, they are very quick to respond back to you if you have any issues or questions, the on site management we’re quick to get back to you also! ...

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Key Amenities

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

About this property

This luxurious home will not disappoint with its 8 bedrooms and 6 bathrooms. Two masters - one on the main floor and the second master is located on the upper floor - both with en-suites.This home has a two car garage, with a South facing pool & spa overlooking the conservation area. The oversized ...

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Property Type

Kissimmee House

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5 BR | 5 BA | Sleeps 10 | Quick View

1
Owner special: 10-35% off Listed Nightly Rates. **Price listed includes already discounted rates.**

$296

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Reunion Resort -Kissimmee, Florida is only 15 minutes to the area's main attraction... Walt Disney World. This gated luxury resort sits nestled just outside of Orlando, Florida and has quickly become one of the most desired resorts in the Orlando area. This home will provide you and your family with an ...

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Property Type

Kissimmee House

"Open space, perfect for entertaining and gathering."

Property is very nice and well maintained. Space is very accommodating for large families. Well enjoyed!

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6 BR | 5.5 BA | Sleeps 18 | Quick View

Distance to park: 4 miles to Animal Kingdom

$394

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 escape is perfect ...

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Property Type

Kissimmee House

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8 BR | 7 BA | Sleeps 16 | Quick View

3
Owner special: 10-35% off Listed Nightly Rates. **Price listed includes already discounted rates.**

$373

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen

About this property

PLEASE NOTE: Encore Resort amenities are not included in the rental of this homeEncore Club at Reunion-Kissimmee, Florida is only 15 minutes to the area's main attraction... Walt Disney World. This gated luxury resort sits nestled just outside of Orlando, Florida, and has quickly become one of the ...

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Property Type

Kissimmee House

"Excited!!"

I didn't go yet but I'm going next summer with my best friend and our families. More excited to go now that I have heard great new about it!!

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • 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 "

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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5 BR | 5 BA | Sleeps 10 | Quick View

Owner special: 10-35% off Listed Nightly Rates. **Price listed includes already discounted rates.**

$380

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

The Retreat at Champions Gate - Kissimmee, Florida is a new upscale gated resort community located just 12 miles from Walt Disney World. This luxury home sits nestled just outside of Orlando, Florida and will quickly become one of the most desired locations in the Orlando area. During your stay, you will ...

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Property Type

Kissimmee House

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5 BR | 6 BA | Sleeps 13 | Quick View

Distance to park: 10 miles to Disney World

$371

avg/night

View Details

Key Amenities

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

About this property

We are a Superhost on Airbnb! Huge resort home with 12 foot ceilings, 5 master suites, and private pool10 miles to Disney World Private heated pool 3,800 sq ft private luxury home 5 Master Suites Indoor game room Hardwood and tile - no rugs Professionally cleaned GB InternetOf all ...

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Property Type

Kissimmee House

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8 BR | 6 BA | Sleeps 20 | Quick View

4

Distance to park: 11 miles to Disney Theme Parks & Water Parks

$421

avg/night

View Details

Key Amenities

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

About this property

You can Book the property by clicking on the link which you can find under " OWNER INFO "Enjoy the comforts in this spacious home located in the community of Windsor At Westside that has a water park with a lazy river, tiki bar, and spa. You will love your stay in this 8-bed x 6-bath home ...

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Property Type

Kissimmee House

"House Rental Stay"

Exceeded my expectations. The place was well kept will definitely recommend the house to people I know.

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4 BR | 3 BA | Sleeps 8 | Quick View

19

$145

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.COVID-19 Precaution Implementations: We have installed ...

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Property Type

Kissimmee Villa

"Our Retreat"

We had an enjoyable stay. The property was clean and we were emailed about all of the eaters and amusement parks. The owner was very nice to us. I will stay there again.

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8 BR | 6 BA | Sleeps 20 | Quick View

3

Distance to park: 3 miles to Disney World Animal Kingdom

$391

avg/night

View Details

Key Amenities

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

About this property

You and your family can have the vacation of a lifetime in this exquisite home in a quiet neighborhood that has all the extras you could imagine and one of the largest pools in the entire area. It's in the best location - super close to all attractions as well as restaurants, shopping, golf courses, mini-golf, ...

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Property Type

Kissimmee House

"Wonderful, Beautiful, Clean, and Convenient to the Parks!"

My children and grandchildren stayed at this beautiful home for our Disney World trip. This home was so beautiful and clean and set the tone of our trip. Seeing the excitement on my 5-year-old granddaughter's ...

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4 BR | 2.5 BA | Sleeps 11 | Quick View

Distance to park: 14 miles to Disney

$307

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Enjoy Orlando, Florida, home to Disney World, Sea World, Universal Studios, and Islands of Adventure, in style. Conveniently located on Crescent Lakes. The house is spacious where family can enjoy being together and also have some alone time. Our home is within 11 miles approximately of all the Orlando ...

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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

Booking is available from the website in Owner info.Modern architecture, state-of-the-art furnishings, and hip-to-the-minute décor make this 5 bedroom, 5 bath getaway in Storey Lake a bonafide safe haven for luxury and comfort. This home is brimming with amenities, from an action-packed game ...

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Property Type

Kissimmee House

"Comfortable vacation home"

Great location and very nice property. Close to Disney Parks and restaurants. I recommend pay the extra fee for the pool heater because the pool was cold even in March. My young daughters enjoy the resorts ...

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7 BR | 4.5 BA | Sleeps 14 | Quick View

3

Distance to park: 4 miles to Animal Kingdom

$271

avg/night

View Details

Key Amenities

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

About this property

Conveniently located on the Exclusive Emerald Island Resort. With 7 Bedrooms and 4.5 bathrooms, Berni’s Home from Home can easily accommodate two families travelling together or will give one family plenty of space.Enjoy relaxing by your very own private extended south facing pool or spend some ...

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Property Type

Kissimmee Villa

"Very well maintained home"

This home was lovely and very well kept. Would rent again if the occasion arose that we needed a home this big again.

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Key Amenities

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

About this property

Welcome to Mickey’s condo! This is not your regular, company managed Airbnb. This is a family owned, loved place. We poured so much effort in each detail of this apartment. We hope you feel the love and enjoy this place we call our home. The place has 2 bedrooms and 2 bathrooms. The living room ...

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Property Type

Kissimmee Condo

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7 BR | 7.5 BA | Sleeps 14 | Quick View

$763

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Situated a short drive away from Disney, this impressive 7-bedroom, 7.5-bathroom mansion has enough space to sleep up to 14 guests. Inside you are spoiled with a home theater, themed game room, spacious living spaces, themed children’s bedrooms. Outside you have a private infinity pool with a spillover ...

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Property Type

Kissimmee House

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6 BR | 5.5 BA | Sleeps 18 | Quick View

54

Distance to park: 4 miles to Animal Kingdom

$287

avg/night

View Details

Key Amenities

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

About this property

We have a SPECIAL SALE for check-ins starting on Sep 24, Oct 30 and Nov 26, 2022. The regular price is $209/night and the sale price is $129/night.Some of the best features of this house from Guest Reviews • Beautiful Vinyl Plank Flooring in all bedrooms, halls and on the steps • Less ...

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Property Type

Kissimmee House

"Fantastic Disney Vacation Rental Home"

We throughly enjoyed our stay in your lovely home! The location was perfect, as it allowed us to get to and from the parks in minimal time. We loved having the 4 master bedrooms with their own private bathrooms! ...

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6 BR | 5 BA | Sleeps 12 | Quick View

Owner special: 10-35% off Listed Nightly Rates. **Price listed includes already discounted rates.**

$288

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

PLEASE NOTE: PHOTOS ARE OF MODEL HOME IN STOREY LAKE. ACTUAL PHOTOS WILL ARRIVE IN MID JULY.Storey Lake - Kissimmee is a brand new vacation community located just 4 miles from the magical world of Disney and just minutes to Universal, Sea World, and the many water parks in the area. Central Florida ...

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Property Type

Kissimmee House

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Key Amenities

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

About this property

Palm Tree Villa Florida, is tucked away in the much sought after location of Doral Woods. This large 4 Bedroom, 3 Bathroom villa, is ideal for making the perfect vacation.This is our own holiday home, so the furnishings are to a high standard, as you can see from the pictures and video. Fully Air ...

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Property Type

Kissimmee Villa

"Great home to stay for a vacation. The home met our expectations, clean and family ready."

Located in Doral Woods, only a few miles from Disney and the other attractions.Fully updated and rooms adequately furnished and beautifully decorated.Large family and living room and large TV.The ...

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

If cozy decor, epic themed bedrooms, and multiple entertainment quarters are at the top of your vacation checklist, look no further than this adorable villa—located just minutes from Disney World in the amazing new Solara Resort! The kids will marvel at the wizard-themed bedroom, featuring life-sized ...

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • 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

"Perfect for our family."

Great house. Pool had best heat we have had in Florida rental and we have been going for years.Needed a few more pool towels,only had 3. We went out and purchased a few more. Very happy with our stay.

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9 BR | 8 BA | Sleeps 18 | Quick View

1

Distance to park: 3 miles to Disney Animal Kingdom

$991

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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Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Beautiful Lagoon Style Pool with water view! Stay close to the excitement and discover amazing things to do in Orlando! Just 10 minutes away, visit the world's most visited attraction, the Walt Disney World® Resort. Literally, ride the movies at Universal Studios Florida® or take your family on ...

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Property Type

Kissimmee Villa

"Excellent place to stay"

Great location for the Disney parks, Walmart and restaurants on the 192 Our 7 year old grand-daughter loved the pool. There is an alarm which sounds when the patio doors to the pool are opened which means ...

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9 BR | 5 BA | Sleeps 18 | Quick View

Owner special: 10-35% off Listed Nightly Rates. **Price listed includes already discounted rates.**

$657

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Storey Lake - Kissimmee is a brand new vacation community located just 4 miles from the magical world of Disney and just minutes to Universal, Sea World, and the many water parks in the area. Central Florida is also home to some of the nation's top-rated golf courses and many are within a 10-minute drive ...

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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 323 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 $23 per night with an average price per night of $232.

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