Kissimmee Vacation Rentals

(258 rentals)
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Kissimmee House
6 BR | 5.5 BA | Sleeps 18 | Quick View
Sleeps 18, 6 bedrooms, 5.5 bathrooms
58 reviews

Distance to park: 4 miles to Animal Kingdom

$178

avg/night

$178
avg per night
View Details

Key Amenities

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

About this property

Some of the best features of this house from Guest Reviews • Beautiful Vinyl Plank Flooring in all bedrooms, halls and on the steps • Less than a 4-mile drive to Disney World’s Animal Kingdom Theme Park • Two leather couches and a recliner with a total of 5 power reclining seats • ...

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Property Type

Kissimmee House

Featured review

"Spacious, well-appointed house in a great location close to the Disney Parks."

The owner provided very detailed and helpful information regarding the house, the Orlando area and the Disney parks before we arrived. The house was very clean and tidy and all the rooms were as described. ...

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Kissimmee Villa
6 BR | 5.5 BA | Sleeps 12 | Quick View
Sleeps 12, 6 bedrooms, 5.5 bathrooms
1 review

$294

avg/night

$294
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

Welcome to WellerDen at Reunion Resort! Just 12 Miles from Walt Disney World Resort. This Two story home has 6 bedrooms, 5.5 bathrooms South East facing pool and much more to enjoy your Florida vacation in the Resort community of Reunion Resort and Spa! SPECIAL FEATURES * Air Conditioned throughout * ...

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Property Type

Kissimmee Villa

Featured review

"Not Bad"

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

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

$347

avg/night

$347
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 House
7 BR | 4.5 BA | Sleeps 14 | Quick View
Sleeps 14, 7 bedrooms, 4.5 bathrooms
13 reviews

Distance to park: 3 miles to Disney World Parks

$247

avg/night

$247
avg per night
View Details

Key Amenities

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

About this property

This is a spacious vacation rental home located in Orlando, perfect for large families of up to 14 guests. The house has 7 bedrooms and 4.5 bathrooms, including two King Master Suites, one on each floor. The first-floor suite features a walk-in shower and a separate garden tub. Bedroom 3 and 4 have King ...

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Property Type

Kissimmee House

Featured review

"Brilliant villa and location"

What a lovely place Be Our Guest is, weve just come back and are depressed now..... The villa was well kept, equiped, clean & pleasant. The owner and the management company couldnt do enough for us. The ...

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Kissimmee Villa
4 BR | 2.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 2.5 bathrooms
1 review

Distance to park: 3 miles to Disneys Animal Kingdom

$191

avg/night

$191
avg per night
View Details

Key Amenities

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

About this property

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

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Property Type

Kissimmee Villa

Featured review

"Tolles Haus"

Hallo, Wir haben hier mit der Familie Urlaub gemacht. Das Haus ist groß genug für acht Personen. Es ist super ausgestattet mit tollem Blick und schönem Pool. Der Vermieter ist sehr um eine tolle Atmosphäre ...

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

$956

avg/night

$956
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 Villa
7 BR | 6 BA | Sleeps 14 | Quick View
Sleeps 14, 7 bedrooms, 6 bathrooms
3 reviews

$332

avg/night

$332
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 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 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

$206

avg/night

$206
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 Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
2 reviews

Distance to park: 2 miles to Disney

$132

avg/night

$132
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 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 Villa
6 BR | 5 BA | Sleeps 12 | Quick View
Sleeps 12, 6 bedrooms, 5 bathrooms
1 review

$262

avg/night

$262
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 House
7 BR | 6.5 BA | Sleeps 16 | Quick View
Sleeps 16, 7 bedrooms, 6.5 bathrooms
1 review

$478

avg/night

$478
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
5 BR | 4.5 BA | Sleeps 15 | Quick View
Sleeps 15, 5 bedrooms, 4.5 bathrooms

$220

avg/night

$220
avg per night
View Details

Key Amenities

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

About this property

Welcome to our luxurious and spacious vacation home situated in the stunning gated community of Windsor at Westside. This magnificent 5-bedroom, 4.5-bathroom villa boasts everything you need for an unforgettable vacation with your family and friends, Close to theme parks, shopping mall outlets, restaurants ...

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Property Type

Kissimmee House

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

$160

avg/night

$160
avg per night
View Details

Key Amenities

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

About this property

POOL SAFETY FENCE!!!! - Florida law requires that doors leading out to the pool have an alarm. THAT IS NOT ENOUGH!. If you are traveling with children please make sure the house you are renting has a pool safety fence. WE HAVE A NO PET POLICY FOR ALERGY REASONS This Beautiful home is well situated, ...

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Property Type

Kissimmee House

Featured review

"Florida 2024"

This was a nice peaceful place just didn't like the holes outside screen for the pool n no baking dishes..we like to bake

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Kissimmee Townhome
4 BR | 3.5 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 3.5 bathrooms
12 reviews

Distance to park: 5 miles to Animal Kingdom

$113

avg/night

$113
avg per night
View Details

Key Amenities

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

About this property

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

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Property Type

Kissimmee Townhome

Featured review

"Cozy stay at townhouse"

My wife, son and I stayed for the month of April. The resort property is well maintained. Garbage is picked up daily and each home has a bin right in front of the home. The condo was very clean upon ...

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Kissimmee Villa
8 BR | 6 BA | Sleeps 23 | Quick View
Sleeps 23, 8 bedrooms, 6 bathrooms

$355

avg/night

$355
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

Welcome to Camp Mickey at Solara Resort by Shine Villas. This home has it All. Private Pool and Spa Overlooking Water, Media Loft Area with Arcade Machine, Air-Conditioned Pool Room. Camp Mickey Bunk Room and Star Wars bedroom is just the start! This beautiful property comfortably provides accommodation ...

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Property Type

Kissimmee Villa

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

$326

avg/night

$326
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 House
5 BR | 3.5 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 3.5 bathrooms

$195

avg/night

$195
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Welcome to your own private retreat at Westside! This beautiful five bedroom vacation home is the perfect getaway for families or groups of up to 10 guests. This vacation home is just minutes away from popular attractions like Disney World, Universal Studios, etc. along with all major restaurants and ...

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Property Type

Kissimmee House

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

$223

avg/night

$223
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

"Amazing accommodation and location"

Spacious, well equipped home in an amazing golf resort. Master suite was stunning with huge bathroom and balcony overlooking the second tee. Very well situated for Disney and Universal studios. Nice pool ...

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Kissimmee Villa
5 BR | 5 BA | Sleeps 12 | Quick View
Sleeps 12, 5 bedrooms, 5 bathrooms
16 reviews

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

$325

avg/night

$325
avg per night
View Details

Key Amenities

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

About this property

☆☆ HIGHLIGHTS ☆☆ ✹ 5 spacious bedrooms w/ smart TVs: 2 kings, 1 queen, 1 full, 3 twins ✹ 5 full bathrooms ✹ Fully stocked kitchen w/ modern appliances ✹ Large living room w/ flat-screen TV + DVD player ✹ Fun game room w/ basketball, Lego table, skee ball + more ✹ Heated pool ...

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Property Type

Kissimmee Villa

Featured review

"EXCELLENT"

This location was perfect for our family while staying close to the Disney Park. It had all the amenities for two families plus more. The pool and hot tub were a wonderful addition. The game room was a ...

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

$170

avg/night

$170
avg per night
View Details

Key Amenities

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

About this property

Ideal for your next family vacation, this attractive 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. Florida’s famous beaches are just a quick 45 minutes ...

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Property Type

Kissimmee Villa

Featured review

"Very nice house"

We had an amazing stay at this very nice house. Everything was perfect. We enjoyed the pool very much. House is in great loaction. Hope we can stay again in couple of years. Pam

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

$130

avg/night

$130
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 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
4 BR | 4 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 4 bathrooms
2 reviews

$295

avg/night

$295
avg per night
View Details

Key Amenities

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

About this property

Name Of Home: Walking on Sunshine Villa Location: Windsor Hills Resort (24/7 guard gated community - Disney World only mins away!) Home Highlights: Recently Renovated Home - Incredible Air Conditioned 80s Game Room - Private South Facing Pool/Spa - Bunk Bedroom with PS5 Property Type: Single ...

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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

$179

avg/night

$179
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 Townhome
3 BR | 2.5 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Gorgeous 3 bedroom townhome in a gated resort community with many activities. The home is located right across the street from one of the pools and playground.

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Property Type

Kissimmee Townhome

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

$278

avg/night

$278
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 Villa
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms
13 reviews

Distance to park: 12 miles to All Disney Theme Park

$109

avg/night

$109
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

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

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Property Type

Kissimmee Villa

Featured review

"New Years Getaway"

Stayed month of January..Villa was very well equipped and very comfortable.Location was fantastic being so close to all attractions. Would highly recommend for anybody to stay..

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

$329

avg/night

$329
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
9 BR | 5 BA | Sleeps 28 | Quick View
Sleeps 28, 9 bedrooms, 5 bathrooms

$346

avg/night

$346
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 * * Hot Tub Heat Included at no extra cost * Walking Distance and access to the brand Second ‘Pirate’ Water Park at Storey Lake Resort* - Find Your Amazing ...

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Property Type

Kissimmee Villa

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

$214

avg/night

$214
avg per night
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 House
7 BR | 6 BA | Sleeps 16 | Quick View
Sleeps 16, 7 bedrooms, 6 bathrooms

$467

avg/night

$467
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
9 BR | 7 BA | Sleeps 16 | Quick View
Sleeps 16, 9 bedrooms, 7 bathrooms

$345

avg/night

$345
avg per night
View Details

Key Amenities

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

About this property

Located in the exclusive Encore community. This beautiful and luxurious vacation home is a 2-story home with 9 bedrooms, 7 bathrooms, a laundry room, game room, and a pool with hotube. It is completely fenced. The house has a capacity for 18 guests. This stylish place to stay is perfect for group trips. Charming ...

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Property Type

Kissimmee House

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

$139

avg/night

$139
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

Sweet Suite @ – Sleeps 6. (#903) Sleeps up to 6 Master Suite has a King Bed with large TV, fabulous en-suite and large walk in shower, double vanity bathroom and walk in closet space. Sleeps 2 Second bedroom, also with TV with custom wall art, has a full size over full size ...

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Property Type

Kissimmee Condo

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

$517

avg/night

$517
avg per night
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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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Kissimmee House

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Kissimmee Villa
5 BR | 4 BA | Sleeps 12 | Quick View
Sleeps 12, 5 bedrooms, 4 bathrooms

$170

avg/night

$170
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

The spacious two storey 5 bed, 4 bath fully air-conditioned home has a south facing pool. There is an extended pool deck for all day sun and has a spacious covered lanai for alfresco dining and poolside entertaining. This well-equipped and newly furnished home caters for all your holiday needs with ...

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Property Type

Kissimmee Villa

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Kissimmee Condo
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom

$91

avg/night

$91
avg per night
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Key Amenities

  • Air conditioning
  • Kid friendly
  • Pool

About this property

Beautiful and clean unit with two queen size beds upstairs, it is part of a recently renovated condo-hotel furnished with modern design and great taste, with fenced pool, playground, gym, and indoor and outdoor dining/resting/seating areasTouristic area, super close to the parks, located on the main 192 ...

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Property Type

Kissimmee Condo

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

$135

avg/night

$135
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

Catch the Disney and Epcot Fireworks at Night from your top floor private balcony, Resort Living by Day! Sleeps up to 8 when using the bunk room trundle and the pull out sofa bed. Master Suite has a King Bed with fabulous en-suite, large walk in shower, double vanity bathroom and walk in closet ...

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Property Type

Kissimmee Condo

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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
5 BR | 4 BA | Sleeps 12 | Quick View
Sleeps 12, 5 bedrooms, 4 bathrooms
2 reviews
last minute deal
LAST MINUTE DEAL 10/26 - 12/7: Discounted Rates for remaining 2024 dates. Message for quote :)

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

$342

avg/night

$342
avg per night
Offer for: Oct 26 - Dec 7:
Discounted Rates for remaining 2024 dates. Message for 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 Condo
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
21 reviews

Distance to park: 2 miles to Disney World

$168

avg/night

$168
avg per night
View Details

Key Amenities

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

About this property

Welcome to Escape by KLMJ Sunshine! This is a completely renovated 3-bedroom condo in the beautiful gated community of Windsor Hills, just two miles from Disney. Enjoy the massive heated pool, brand new water park, large playground, tennis and basketball courts, mini-golf, arcade, movie theatre, fitness ...

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Property Type

Kissimmee Condo

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

$188

avg/night

$188
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 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
4 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 4 bedrooms, 2 bathrooms
9 reviews

$116

avg/night

$116
avg per night
View Details

Key Amenities

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

About this property

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

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Property Type

Kissimmee House

Featured review

"Wonderful stay"

Traveled from the UK. Villa was a little dated but was very clean and the beds comfortable. Pool was a great hit with our teenagers. Parks were easy to get to from the villa. We had a great stay and ...

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

$165

avg/night

$165
avg per night
View Details

Key Amenities

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

About this property

Welcome to our stunning spacious 5 bedroom, 4 bath home located in the much sought after community of Tuscan Hills near Disney This beautiful home offers 2 masters en-suite bedrooms and 3 sitting rooms. Full air con and hi-speed WiFi throughout. The villa uniquely has 3 sitting rooms, two of ...

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Property Type

Kissimmee House

Featured review

"Great Home… Great location"

My family and I just spent a week in this lovely home. It was nicely decorated, well-maintained, and had everything in a well stock kitchen that one would need for fixing meals. The pool/spa was great and ...

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

$120

avg/night

$120
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 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 258 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 $183.

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