Kissimmee Vacation Rentals

(259 rentals)
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Kissimmee Villa
6 BR | 8 BA | Sleeps 12 | Quick View
Sleeps 12, 6 bedrooms, 8 bathrooms

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

$266

avg/night

$266
avg per night
View Details

Key Amenities

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

About this property

Safe & Comfortable Haven for Hurricane Milton Evacuees Welcome to your elegant vacation retreat in Emerald Island Resort, Orlando, FL! This spacious 6-bedroom, 5-bathroom home has been recently upgraded and is located just 3 miles from Walt Disney World and only minutes from top attractions like Universal ...

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Property Type

Kissimmee Villa

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Kissimmee Villa
9 BR | 5 BA | Sleeps 28 | Quick View
Sleeps 28, 9 bedrooms, 5 bathrooms

$356

avg/night

$356
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

Water Kingdom @! Sleeps up to 28! Resort Living In The Tropics! * South Facing Pool * * Water/Lake and Conservation View Walking Distance and access to the brand Second ‘Pirate’ Water Park at Storey Lake Resort* - Find Your Amazing here! Access available IN ADDITION to the ...

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Property Type

Kissimmee Villa

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Kissimmee House
5 BR | 4 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 4 bathrooms
8 reviews

$224

avg/night

$224
avg per night
View Details

Key Amenities

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

About this property

*** For smaller groups we offer the opportunity to rent the main house. This area has 4 Bedrooms and 3 Bathrooms Please contact us and ask for a quote *** Our beautiful 3000sq 5 Bed, 4 Bathroom home is located on a generous corner plot. With a south facing Pool and stunning views over the second ...

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Property Type

Kissimmee House

Featured review

"A Memorable Vacation"

We are delighted with the care and wonderful hospitality that Jackie and Vicky provided to us during our stay. Their attention to any needs were met promptly and respectfully. We are so fortunate of their ...

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Kissimmee Villa
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms
27 reviews

$145

avg/night

$145
avg per 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

Featured review

"House rental on Santee Dr"

The house was very clean and well furnished. The location is perfect. I dealt with the homeowner Lisa who was professional and returned my text quickly. The pool and hot tub were also very clean. Quiet ...

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Kissimmee House
3 BR | 2 BA | Sleeps 10 | Quick View
Sleeps 10, 3 bedrooms, 2 bathrooms
19 reviews

$190

avg/night

$190
avg per night
View Details

Key Amenities

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

About this property

Sunset Lakes is ideally situated, just 4 miles from Disney World and a short drive from other popular attractions like Universal Studios, Sea World, and more. The proximity to Orlando and other destinations makes it a prime choice for travelers. The gated community offers various amenities such as a community ...

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Property Type

Kissimmee House

Featured review

"Vacation retreat/$15 Uber to Disney/ HGTV looking retreat"

We are completing our stay in the morning at this beautiful vacation retreat! We brought the family all seven of us ranging from age in two years old to 60 years old. The pool and patio is incredibly maintained, ...

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Kissimmee Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
2 reviews

Distance to park: 2 miles to Disney

$133

avg/night

$133
avg per night
View Details

Key Amenities

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

About this property

Our exquisite, tastefully decorated and perfectly maintained 2-bedroom and 2 full bath condo is perfect for your family and friends up to 6 people. We are on the top floor, and you will hear no noise from above! There are two double beds in the Master Bedroom with a walk-in closet and ensuite. The ...

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Property Type

Kissimmee Condo

Featured review

"Fabulous Host and Fantastic Accomodations!"

We stayed at this gorgeous condo resort for a week with my family and had a most comfortable and peaceful stay. The bedrooms were perfect for our family and I loved the separate full master bedroom ensuite. ...

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Kissimmee House
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms
9 reviews

Distance to park: 4 miles to Disney World

$158

avg/night

$158
avg per night
View Details

Key Amenities

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

About this property

Welcome to La Casita on the Island (The Little House on the Island) "Our house, our casita" If you want a place to relax and enjoy the beautiful weather of Florida, I invite you to see the "encanto" (charm) that you can experience during your stay at La Casita on the Island. Enjoy ...

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Property Type

Kissimmee House

Featured review

"Great Villa"

Had a fantastic stay in the villa. Would definitely stay again and highly recommend. It was extremely clean and in a great location near shops, resturaunts and 192 and Disney. Would highly recommend and ...

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Kissimmee House
5 BR | 4 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 4 bathrooms
1 review

$160

avg/night

$160
avg per night
View Details

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

Featured review

"Great stay"

Home was just right. Pool , lawn was beautiful the yard well kept garbage was collected on time We enjoy every moment of our stay .We are looking forward to return again in the new year.

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Kissimmee House
4 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 4 bedrooms, 3 bathrooms
15 reviews

$132

avg/night

$132
avg per 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

Featured review

"Great Location for your stay."

The home was very comfortable and dealing with the owner was a breeze. Check in was very easy and the location is ideal for Disney and Universal visitors. Nice lake view and several chairs for outdoor seating. ...

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Kissimmee Villa
9 BR | 7.5 BA | Sleeps 22 | Quick View
Sleeps 22, 9 bedrooms, 7.5 bathrooms

$355

avg/night

$355
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

Moana Castle at Solara Resort by Shine Villas! Your children will thank you for years to come after they arrive and run around exploring this home excitedly. It has absolutely everything. 9 Bedrooms, 7 bathrooms, sleeps up to 22. This home is exquisitely designed and has all you could want from ...

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Property Type

Kissimmee Villa

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Kissimmee Townhome
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms
1 review

$189

avg/night

$189
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

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: Storey Lake. Less than 10 minutes ...

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Property Type

Kissimmee Townhome

Featured review

"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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Kissimmee Villa
6 BR | 5 BA | Sleeps 12 | Quick View
Sleeps 12, 6 bedrooms, 5 bathrooms
1 review

$263

avg/night

$263
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

Stars Align @ – Sleeps 12 Welcome to your Cosmic Place!! You have found your vacation home here – Congratulations! Beautifully designer decorated 6 bedroom, 6 bathroom home inside the premium Storey Lake Resort Community. Play Planet Pinball in the games area, hideaway in one of ...

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Property Type

Kissimmee Villa

Featured review

"Excellent"

This home was well taken care of. The moment we arrived the house was clean and even more beautiful than the pictures. The cleaning crew did an amazing job. The owner was so polite and made us feel welcomed. ...

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Kissimmee Condo
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
3 reviews

Distance to park: 1 miles to Disney Animal Kingdom

$97

avg/night

$97
avg per night
View Details

Key Amenities

  • Air conditioning
  • 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 ...

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Property Type

Kissimmee Condo

Featured review

"Great location, clean and comfortable."

We had everything we needed. Excellent communication. Perfect location. Close to the parks as well as restaurants, etc! We will be back.Thanks

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Kissimmee House
7 BR | 6.5 BA | Sleeps 16 | Quick View
Sleeps 16, 7 bedrooms, 6.5 bathrooms
1 review

$491

avg/night

$491
avg per night
View Details

Key Amenities

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

About this property

This gorgeous home was completely redesigned in 2023! Experience unforgettable moments with your family at Solara Resort. The kids will delight in our thoughtfully designed themed bedrooms, while others can unwind on the inviting custom patio or enjoy a refreshing swim in the private heated pool. Is ...

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Property Type

Kissimmee House

Featured review

"AMAZING customer service"

I was skeptical of booking online with a company I wasn't familiar with, however they ended up being so responsive to any concerns or questions I had, including when me and my kids were in the house. It ...

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Kissimmee House
8 BR | 6 BA | Sleeps 16 | Quick View
Sleeps 16, 8 bedrooms, 6 bathrooms
2 reviews

$260

avg/night

$260
avg per night
View Details

Key Amenities

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

About this property

Enjoy a whimsical getaway when you book a stay at this sleek, refreshing, 8-bedroom, 6-bathroom vacation rental home. Take a dip in the private pool, fix up something tasty in the fully equipped kitchen, play a game of pool in the game room, or head to the community fitness center for a quick workout. ...

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Property Type

Kissimmee House

Featured review

"Kissimmee Home/Windsor"

My family & I enjoyed our stay at this lovely home during the summer time. This house gave us an enjoyable experience that we will all remember. We didnt have any problems with the house and we hope to ...

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Kissimmee Villa
7 BR | 6 BA | Sleeps 14 | Quick View
Sleeps 14, 7 bedrooms, 6 bathrooms
3 reviews

$338

avg/night

$338
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Introducing 101 Happy Memories Florida Villa, your gateway to unforgettable vacations in the heart of Formosa Gardens, just minutes from the enchantment of Disney World! Step into luxury with our private heated pool and spa, perfect for unwinding after a day of adventure. Thrill-seekers will love our ...

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Property Type

Kissimmee Villa

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Kissimmee Townhome
3 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 3 bathrooms
4 reviews

$217

avg/night

$217
avg per night
View Details

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

Featured review

"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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Kissimmee House
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms
16 reviews

Distance to park: 4 miles to Disney

$162

avg/night

$162
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • 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

Featured review

"Perfect rental for all of our needs!"

This was a Christmas vacation never to be forgotten! We had the time of our lives! My children, grandchildren and I enjoyed the comforts and privacy of a home where we could take in all the theme parks ...

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Kissimmee Villa
6 BR | 4 BA | Sleeps 14 | Quick View
Sleeps 14, 6 bedrooms, 4 bathrooms

$288

avg/night

$288
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

Fantasia @ – Sleeps 14 Welcome 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 in comfort. Storey Lake, Located in ...

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Property Type

Kissimmee Villa

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Kissimmee Villa
5 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 3 bathrooms
13 reviews

$160

avg/night

$160
avg per night
View Details

Key Amenities

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

About this property

Welcome to this beautiful luxury villa on the gated 5 Star Resort of Lake Berkley. This villa has 5 bedrooms, 2 of which are on the ground floor and 3 are on the first floor. It can sleep up to 10 comfortably. This is a perfect location for fishing on 3 well stocked lakes. Fish all day long whilst ...

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Property Type

Kissimmee Villa

Featured review

""

Booked to stay in our favourite place Lake Berkley through VIP Villas again for our Florida holiday. Stayed here many times. Cannot fault Stephen and Joanna, always there to help and promptly sort out ...

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Kissimmee House
9 BR | 5 BA | Sleeps 22 | Quick View
Sleeps 22, 9 bedrooms, 5 bathrooms
1 review

$274

avg/night

$274
avg per night
View Details

Key Amenities

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

About this property

Brand new, very spacious, modern 9-Bed 5-Bath pool home in an exclusive, private gated golf resort. You'll love the feeling of luxury and space throughout the house, the 2 King en-suite master bedrooms, 4 kids themed bedrooms, 3 additional King bedrooms, the games room, the private pool and spa, ...

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Property Type

Kissimmee House

Featured review

"Florida Holiday"

Hi there! We enjoyed our stay quite a bit. However, there were a few things that could have improved our stay. The one lounger was damaged and the one chair was damaged. There was not a bottle opener ...

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Kissimmee Apartment
1 BR | 1 BA | Sleeps 3 | Quick View
Sleeps 3, 1 bedroom, 1 bathroom

$88

avg/night

$88
avg per night
View Details

Key Amenities

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

About this property

A newly constructed one-bedroom, one-bathroom luxury apartment situated in the charming area of Kissimmee, conveniently located from theme parks, attractions, restaurants, and shopping. This upscale apartment is equipped with all the amenities to ensure comfort, security, and an exceptional experience ...

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Property Type

Kissimmee Apartment

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Kissimmee House
9 BR | 6 BA | Sleeps 23 | Quick View
Sleeps 23, 9 bedrooms, 6 bathrooms

$667

avg/night

$667
avg per night
View Details

Key Amenities

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

About this property

Embark on the ultimate Disney vacation at Jurassic Encanto! With elegantly designed thematic rooms, this spacious home provides ample room for larger groups and multiple families. Compete in the epic game room or take in the lake views while relaxing by the luxurious private pool and spa amidst world-class ...

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Property Type

Kissimmee House

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Kissimmee Villa
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms
16 reviews

$145

avg/night

$145
avg per night
View Details

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

Featured review

"Excellent villa"

We have been so pleased with this villa. Very clean, has everything we need and more. Very close to Disney and easy to get to Univerdal Studios and SeaWorld as well as easy commute from the airport. Would ...

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Kissimmee House
6 BR | 5 BA | Sleeps 14 | Quick View
Sleeps 14, 6 bedrooms, 5 bathrooms

Inquire for rates

Inquire for rates

View Details

Key Amenities

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

About this property

Brand new 6 bedroom resort home located in Champions Gate.This home is brand new and has been finished to a very high standard by an interior designer.From the minute you walk in this home does not dissapoint with modern furnishings and fittings throughout the home.The home features 6 bedrooms , 5 bathrooms, ...

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Property Type

Kissimmee House

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Kissimmee Villa
7 BR | 7 BA | Sleeps 18 | Quick View
Sleeps 18, 7 bedrooms, 7 bathrooms
1 review

$303

avg/night

$303
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

Just Wow - Monterey Bay at Solara by Shine Villas! 7 Bedrooms and 7 Bathroom - Sleep up to 18 when using the trundle beds. This home is exquisitely designed and has all you could want from your vacation home away from home. Private Pool with Spa, Media Loft Area, Air-Conditioned Avengers ...

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Property Type

Kissimmee Villa

Featured review

"Very beautiful home"

It’s a very beautiful home and real spacious and clean I will love to book again very professional and the host was very sweet and kind

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Kissimmee Condo
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms
1 review

$131

avg/night

$131
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool

About this property

This wonderful resort home is a three-bedroom, 2-bath town gem that sleeps 8. A short hop to Orlando’s world class theme parks this incredible location is just 6 miles to Disney, 25 minutes from Orlando Airport, West Lucaya Village Resort is an upscale gated resort community that is perfectly ...

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Property Type

Kissimmee Condo

Featured review

"My New Home Away from Home!"

I almost didn't want to write this review so that I can keep this home to myself, My family of 5 plus an infant stayed in this condo for 10 days and It was amazing, it looked just like the pictures, everything ...

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Kissimmee Villa
3 BR | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2.5 bathrooms

$152

avg/night

$152
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen

About this property

Surfstyle at Margaritaville by Shine Villas This 3 bedroom getaway is the Surfstyle Margaritaville Cottage home of your family dreams. Sitting outside overlooking the lake is what where you will find yourself drawn. Your decision is whether this will be with a coffee or a Margarita in hand! Margaritaville ...

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Property Type

Kissimmee Villa

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Kissimmee House
6 BR | 5.5 BA | Sleeps 13 | Quick View
Sleeps 13, 6 bedrooms, 5.5 bathrooms

$361

avg/night

$361
avg per night
View Details

Key Amenities

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

About this property

Newly renovated and professionally decorated with upscale furnishings, this luxury family vacation home is an ideal get-away to relax with family and friends following visits to busy theme parks and area attractions. As a large private manor, located on a quiet cul-de-sac, Emerald Escape is a modern ...

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Property Type

Kissimmee House

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Kissimmee Townhome
4 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 3 bathrooms

$191

avg/night

$191
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

Plush Pelican - Sleeps 10 at Storey Lake by Shine Villas! Gorgeous, beautifully appointed and high end designer decorated 4 bedroom, 3 bathroom townhome with private splash pool sleeping up to 10. Located in one of Orlando's newest resort communities: Storey Lake. Less than 10 minutes ...

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Property Type

Kissimmee Townhome

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Kissimmee Townhome
4 BR | 3 BA | Sleeps 11 | Quick View
Sleeps 11, 4 bedrooms, 3 bathrooms
1 review

$175

avg/night

$175
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

Happy Haven at Storey Lake Resort by Shine Villas – Sleeps up to 12 Welcome to your Holiday Home! Beautifully decorated 4 bedroom, 3 bathroom home inside the premium Storey Lake Community. Private Splash pool and space for up to 12 to stay. Storey Lake, Located in ...

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Property Type

Kissimmee Townhome

Featured review

"Beautiful house and location"

The house is in a resort complex and even we did not use they much for the weather cold. I want to say it is a very nice place for family vacation. House was clean and in excellent location. I would stay ...

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Kissimmee House
5 BR | 4 BA | Sleeps 12 | Quick View
Sleeps 12, 5 bedrooms, 4 bathrooms
2 reviews
last minute deal
LAST MINUTE DEAL 11/13 - 12/17: Discounts for November/December Dates!! Message for personalized quote :)

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

$334

avg/night

$334
avg per night
Offer for: Nov 13 - Dec 17:
Discounts for November/December Dates!! Message for personalized quote :)

View Details

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 parks... You grab a refreshing drink, relax in the poolside living area and reminisce about all you did that day. Memories made, job done! Serendipity offers all the comforts you dreamed of putting on your wish List: ★ Pool & ...

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Property Type

Kissimmee House

Featured review

"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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DEAL
Kissimmee House
4 BR | 3 BA | Sleeps 9 | Quick View
Sleeps 9, 4 bedrooms, 3 bathrooms
5 reviews

Distance to park: 3 miles to Disney

$187

avg/night

$187
avg per night
View Details

Key Amenities

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

About this property

The Magic Emerald Island Villa invites you to experience an elegant escape near Disney World and Universal Studios. Our 4-bedroom, 3-bathroom villa accommodates up to 9 guests in comfort and style: • The main master bedroom features a king-size bed, a private en suite bathroom with a garden tub, ...

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Property Type

Kissimmee House

Featured review

"5*+ Magic Emerald Island Villa"

Excellent villa wonderful host. From the very first enquiry about renting Yelena’s Magic Emerald Island villa she was fantastic, guiding me through the booking and rental period until we left. Yelena ...

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Kissimmee House
7 BR | 4 BA | Sleeps 14 | Quick View
Sleeps 14, 7 bedrooms, 4 bathrooms

$224

avg/night

$224
avg per 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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Kissimmee Villa
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms

$187

avg/night

$187
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Star Oasis at Citrus Ridge by Shine Villas 091 Welcome to this wonderful 4-bedroom home by Shine Villas at Citrus Ridge in Kissimmee, magnificently located close to Parks and all that Orlando has to offer. Sleeps up to 10 with space and rear views to die for, watching local birds and wildlife in the ...

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Property Type

Kissimmee Villa

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Kissimmee Villa
4 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 2 bathrooms
7 reviews

Distance to park: 7 miles to Walt Disney World

$207

avg/night

$207
avg per night
View Details

Key Amenities

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

About this property

Welcome to our Florida villa, the Lake House at Sunset Lakes. The Lake House at Sunset Lakes is an upscale rental villa in the greater Orlando Florida area, minutes away from Disney’s Magic Kingdom and theme parks, your choice of fine golf courses and many other attractions. This four bedroom house ...

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Property Type

Kissimmee Villa

Featured review

"Lake house villa"

Lovely villa,spotlessly clean & well equipped,management company are very helpful & quick to respond,Jane the owner was also very helpful & quick to respond to any enquiries we had,great location & the ...

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Kissimmee House
4 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 2 bathrooms

$121

avg/night

$121
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Whether you are looking for a place to relax and unwind, or a place to call home while you are making memories and enjoying fun-filled days at Orlando's many attractions, you will want to bring your entire family to Indiana J's Attraction! This spacious, newly refurbished and decorated home ...

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Property Type

Kissimmee House

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Kissimmee Townhome
3 BR | 2.5 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2.5 bathrooms

$79

avg/night

$79
avg per night
View Details

Key Amenities

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

About this property

One of the closest possible communities to Walt Disney World (less than 3 miles away), Emerald Island is a quiet oasis in which to spend your vacation. Emerald Island is an exclusive gated community less than a mile from the world famous US Highway 192 where you will find shops, restaurants, and entertainment. ...

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Property Type

Kissimmee Townhome

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Kissimmee Villa
9 BR | 10 BA | Sleeps 26 | Quick View
Sleeps 26, 9 bedrooms, 10 bathrooms
15 reviews

$958

avg/night

$958
avg per night
View Details

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

Featured review

"Great Experience"

Had a great exerience. Owner was very pleasant to deal with throughout. I would definitely recommend this property to others.

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Kissimmee House
8 BR | 6 BA | Sleeps 22 | Quick View
Sleeps 22, 8 bedrooms, 6 bathrooms

$525

avg/night

$525
avg per night
View Details

Key Amenities

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

About this property

Experience the popular "Queen of Hearts" villa in the Windsor at Westside Resort! This home boasts a private heated pool & hot tub, fire pit and outdoor TV. The themed bedrooms are loaded with amazing details. All guests have free access to resort amenities. Your host Vacation Alchemy provides ...

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Property Type

Kissimmee House

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Kissimmee House
5 BR | 5 BA | Sleeps 12 | Quick View
Sleeps 12, 5 bedrooms, 5 bathrooms
2 reviews

$433

avg/night

$433
avg per night
View Details

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

Featured review

"Great place, nice price!"

The themed kids' rooms and game room are topping on this rental a club house with so much going on for everyone, including pickup/drop off service to and from the club house. Heated pool and gas grill. ...

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Kissimmee Villa
7 BR | 6.5 BA | Sleeps 14 | Quick View
Sleeps 14, 7 bedrooms, 6.5 bathrooms

$372

avg/night

$372
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

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 Loft Area, Air-Conditioned ‘Starcade’ ...

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Property Type

Kissimmee Villa

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Kissimmee Townhome
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms

$186

avg/night

$186
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

Magic Lily Gorgeous and designer decorated 4 bedroom, 3 bathroom townhome with private splash pool sleeping up to 8. Brand New July 2021 Located in one of Orlando's newest and finest resort communities: Storey Lake. Less than 10 minutes from Walt Disney ...

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Property Type

Kissimmee Townhome

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Kissimmee House
9 BR | 8 BA | Sleeps 18 | Quick View
Sleeps 18, 9 bedrooms, 8 bathrooms
11 reviews

Distance to park: 3 miles to Disney Animal Kingdom

$671

avg/night

$671
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Mickey's Oyster is a luxurious oasis designed to make your Disney World vacation unforgettable. Nestled in a prestigious, gated community just minutes away from the magic, this freshly remodeled and renovated home offers an enchanting escape with all the comforts of a five-star resort. Luxurious ...

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Property Type

Kissimmee House

Featured review

"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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Kissimmee Villa
7 BR | 6 BA | Sleeps 18 | Quick View
Sleeps 18, 7 bedrooms, 6 bathrooms
2 reviews

$338

avg/night

$338
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

Treat Retreat @ – Sleeps 16 Welcome to your awesome vacation spot by Shine Villas at Storey Lake. Beautifully decorated superior location, 7 bedroom, 6 bathroom home inside the premium Storey Lake Resort Community with full resort access included in the advertised rate. No resort fees ...

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Property Type

Kissimmee Villa

Featured review

"Wonderful home"

We loved our stay. Large, clean, gated community. Pool was beautiful and hot tub was a hit during the cold front. Some negatives…. Not well stocked and about a 45 minute drive to Disney parks, due ...

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Kissimmee Villa
Studio | 4.5 BA | Sleeps 14 | Quick View
Sleeps 14, 0 bedrooms, 4.5 bathrooms

$331

avg/night

$331
avg per night
View Details

Key Amenities

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

About this property

7 bedroom 4.5 bath waterfront home located in the highly desired Emerald Island resort close to Disney and Universal Studios. The ground floor of this villa is an open concept with a living area featuring a 65" Smart 4k tv. The granite countertop kitchen boasts all new 2022 stainless appliances. ...

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Property Type

Kissimmee Villa

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Kissimmee Villa
7 BR | 6.5 BA | Sleeps 16 | Quick View
Sleeps 16, 7 bedrooms, 6.5 bathrooms

$295

avg/night

$295
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

WELCOME To “Rebel Flamingo” at Solara Resort by Shine Villas! Sleeps Up to 16 Adults and 1 Baby (Premium Wooden Crib in ‘Mom Haven’ in downstairs master). - PREMIUM Home Size - Premium Games Room with AC and Dual X Box Setup with Included Games Subscription! - Premium ...

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Property Type

Kissimmee Villa

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Kissimmee House
7 BR | 4.5 BA | Sleeps 14 | Quick View
Sleeps 14, 7 bedrooms, 4.5 bathrooms

$460

avg/night

$460
avg per night
View Details

Key Amenities

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

About this property

Perfect Family Destination Best lania/pool Minutes to Disney/Attractions/Conveniences Fun/Clean/Comfortable This is a fantastic house for family getaways! Enjoy the Food and Wine Festivals. Mickey's Not So Scary Halloween Party, Unforgettable Disney Christmas celebration, and everything else ...

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Property Type

Kissimmee House

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Kissimmee House
7 BR | 6 BA | Sleeps 16 | Quick View
Sleeps 16, 7 bedrooms, 6 bathrooms

$483

avg/night

$483
avg per night
View Details

Key Amenities

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

About this property

Experience a magical holiday at this luxe 7-bedroom home! Nestled in Windsor at Westside Resort, you and your loved ones will be a short drive to many attractions. Stretch out into sprawling living areas where comfort awaits you before heading outside for an exciting time - enjoy a dip in your private ...

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Property Type

Kissimmee House

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Kissimmee House
6 BR | 4 BA | Sleeps 14 | Quick View
Sleeps 14, 6 bedrooms, 4 bathrooms
3 reviews

$320

avg/night

$320
avg per night
View Details

Key Amenities

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

About this property

Welcome to your ultimate themed vacation experience in the heart of Kissimmee, Florida! Prepare to embark on an extraordinary journey as you step into this spectacular 6-bedroom, 4-bathroom house in the prestigious Windsor Hills community. This newly listed paradise has been meticulously designed to immerse ...

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Property Type

Kissimmee House

Featured review

"Two week stay"

We stayed for two weeks in August/September. Great house and location to the parks. Kids enjoyed the pool table and game systems. Would book again.

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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 259 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 $27 per night with an average price per night of $185.

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