Kissimmee Vacation Rentals

(260 rentals)
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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

$155

avg/night

$155
avg per night
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Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

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

Distance to park: 7 miles to Disney Hollywood Studio

$146

avg/night

$146
avg per night
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Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Beautiful, clean and spacious 5 bedroom and 4 bath house in the most sought after community near Disney! 10 minutes drive to Disney and you can hear the Disney fireworks at night. Close to stores, restaurants and tons of shops. The house was renovated and professionally designed recently. The house has ...

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Property Type

Kissimmee House

Featured review

"Very good"

The trip was great me and my family really had fun and enjoyed ourselves we will be coming back soon.

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

$345

avg/night

$345
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

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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Kissimmee Villa

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

$379

avg/night

$379
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

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

Featured review

"2nd time still a charm"

We enjoyed a stay here 3 years ago and we lucky enough to find it available again in 2024. We can't say enough except that the property was somehow even an improvement over the 1st time. This is a great ...

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Kissimmee House
3 BR | 3.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3.5 bathrooms

$214

avg/night

$214
avg per night
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Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Luxury vacation homes accommodations feature contemporary interiors, located in Magic Village gated community only 5 minutes away from Disney’s Animal Kingdom. Step into your private villa at Magic Village Yards and discover a chic and contemporary yet invitingly cozy sanctuary. All Bedrooms are ...

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Property Type

Kissimmee House

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

$217

avg/night

$217
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

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

$128

avg/night

$128
avg per night
View Details

Key Amenities

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

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

$188

avg/night

$188
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Our villa is beautifully furnished and airconditioned and has a heated swimming pool and spa for that morning swim and for you family’s personal enjoyment there is a security fence to protect the young ones. A covered lanai on an extended pool deck includes a large table with seating for four plus ...

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Property Type

Kissimmee Villa

Featured review

"Excellent Villa"

Well equiped, excellent location, friendly and helpful estate. The villa was one of the best we have hired over the past 20 years. The gated estate was first class, helpful and friendly clubhouse. Close ...

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

$459

avg/night

$459
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

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

Distance to park: 4 miles to Disney World

$159

avg/night

$159
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

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

$373

avg/night

$373
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

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

$197

avg/night

$197
avg per night
View Details

Key Amenities

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

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

$354

avg/night

$354
avg per night
View Details

Key Amenities

  • Private pool
  • Rentals by owner
  • WiFi

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 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
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

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

Distance to park: 5 miles to Animal Kingdom

$111

avg/night

$111
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

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

$396

avg/night

$396
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

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

$218

avg/night

$218
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

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

$301

avg/night

$301
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

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

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Property Type

Kissimmee House

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

Distance to park: 4 miles to Disney

$226

avg/night

$226
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

"Boutique style very spacious Town house, ideally located in Magic Village community……right next to Disney’s parks like Magic Kingdom. All Units have unique furnishings, complete kitchens with gas range, living, and dining rooms with vaulted ceilings. Full size laundry room, extra ...

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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

$337

avg/night

$337
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

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
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

$202

avg/night

$202
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

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 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
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

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

Distance to park: 2 miles to Disney

$150

avg/night

$150
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

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

Distance to park: 7 miles to Walt Disney World

$214

avg/night

$214
avg per night
View Details

Key Amenities

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

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 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
  • Private pool
  • WiFi

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

$321

avg/night

$321
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

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
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
  • Private pool
  • WiFi

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

$144

avg/night

$144
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

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

$144

avg/night

$144
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

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

$322

avg/night

$322
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

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! Recently refurbished inside. Bedrooms ...

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

$162

avg/night

$162
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

MAGIC HOUSE, is a beautifully furnished 4 bedrooms, 3 bathrooms home with a 26ft x 14ft swimming pool and Spa,. covered lanai. It is only a 3 mile drive to Walt Disney World Resort. It's in easy reach of all other major attractions. MAGIC HOUSE is a luxury villa located in the quiet friendly neighborhood ...

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Property Type

Kissimmee House

Featured review

"Fun Time with Family"

Home was nice and neat when we arrived. Roomy and close to grocery stores and other shopping areas. Will visit again and recommend to others.

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

$966

avg/night

$966
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

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

"50th birthday celebration"

We booked this for my husbands 50th birthday getaway and it was all we imagined! The place was very spacious and the owner was easy to communicate with. The pool and the outdoor living areas are spectacular. ...

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Kissimmee Villa
3 BR | 3.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3.5 bathrooms

Distance to park: 4 miles to Disney

$238

avg/night

$238
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to Magic Village Views, part of Trademark Collection by Wyndham. "Boutique style 3BDR very spacious Town house, ideally located in Magic Village community……right next to Disney’s parks like Magic Kingdom. All Units have unique furnishings, complete kitchens with gas range, ...

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Property Type

Kissimmee Villa

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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

$704

avg/night

$704
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

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

$170

avg/night

$170
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Water View and Outdoor Spa! Stay close to just about everything and enjoy easy access to our world-renowned theme parks, exciting golf, mega shopping and exceptional dining. Ideal for your next family vacation, this attractive 4 bedroom, 3 bath Disney area vacation home is conveniently located just ...

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Property Type

Kissimmee Villa

Featured review

"Our Walt Disney World vacation"

The villa was absolutely wonderful as well as the pool and exactly as shown on the site picture. We were in Florida for 10 nights. The company which takes care of the site was also great, they responded ...

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

Distance to park: 4 miles to Disney

$217

avg/night

$217
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

You will love it here in our Boutique styled Condos featuring contemporary interiors, located in Magic Village gated community only 5 minutes away from Disney’s Animal Kingdom. Step into your private villa and discover a chic and contemporary yet invitingly cozy sanctuary. All three bedrooms are ...

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Property Type

Kissimmee House

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Kissimmee Villa
4 BR | 4.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4.5 bathrooms

Distance to park: 4 miles to Disney Theme Parks

$233

avg/night

$233
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Welcome to Magic Village Views, part of Trademark Collection by Wyndham. This 4 Bedroom 4.5 Bath Luxury Townhouse Villas is a must stay. located in an ideally located gated community……right next to Disney’s parks. All Units are En-Suites with unique furnishings, complete kitchens, ...

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Property Type

Kissimmee Villa

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

$219

avg/night

$219
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Charming brand new 4 br, 3 bath townhouse with pool. Located in the desirable Storey Lake Resort, in the new quiet Preserve Area, It has capacity for 12 guests. Storey Lake has a resort-style clubhouse full of amenities and fun for families, including a business center, basketball court, ping pong table, ...

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Property Type

Kissimmee House

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

$169

avg/night

$169
avg per night
View Details

Key Amenities

  • Air conditioning
  • WiFi

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

$337

avg/night

$337
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

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

$177

avg/night

$177
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

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

$238

avg/night

$238
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

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

$155

avg/night

$155
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

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

$91

avg/night

$91
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

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
4 BR | 2.5 BA | Sleeps 9 | Quick View
Sleeps 9, 4 bedrooms, 2.5 bathrooms
10 reviews

Distance to park: 10 miles to Disneyworld

$138

avg/night

$138
avg per night
View Details

Key Amenities

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

About this property

Our villa is modern style furnished, has everything you would expect in a holiday home, 4 bedrooms, 2 with king-size beds, 1 with single bed´s, 1 with triple bunk bed all with private TV. 2 bathrooms, 1 guest toilet, fully equipped kitchen, etc. with ceran stove, fridge, oven, microwave, coffee ...

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Property Type

Kissimmee House

Featured review

"Looking for a great vacation rental for the kids? This is it!!"

What a nice house! It has everything you could want in a vacation home. A very nice pool, patio and attached BBQ area with gas grill, literally a ton of DVD's to keep everyone entertained in the evening, ...

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Kissimmee Villa
6 BR | 4 BA | Sleeps 12 | Quick View
Sleeps 12, 6 bedrooms, 4 bathrooms
2 reviews

$200

avg/night

$200
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Beautiful two-story home with 6 bedrooms and 4 bathrooms. This home is situated on a quiet street within the Solterra Resort. It boasts modern open plan living. It has an additional outdoor balcony space along with a large private pool and spa, loungers, outdoor table and chairs with an optional BBQ ...

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Property Type

Kissimmee Villa

Featured review

"Amazing villa"

Totally overwhelmed, villa is amazing, very spacious. Highly recommended. We will book this villa again next family gathering. jim

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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

$169

avg/night

$169
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

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

$163

avg/night

$163
avg per night
View Details

Key Amenities

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

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
3 BR | 2.5 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2.5 bathrooms
1 review

$79

avg/night

$79
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

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

Featured review

"Quite friendly"

Great property courteous prompt service and flexible payment options. Close to many attractions. All around a pleasant get away.

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Kissimmee House
7 BR | 6 BA | Sleeps 15 | Quick View
Sleeps 15, 7 bedrooms, 6 bathrooms

$302

avg/night

$302
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Stunning, designer furnished 7th Heaven Villa! This home has everything that you, your family and friends will ever need and more! Walt Disney World Resort is only 2 traffic signals away. This luxury South facing pool home, completed in June 2004, has 7 bedrooms, 6 bathrooms and will accommodate 15 people ...

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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 260 Kissimmee vacation rentals available on FloridaRentals.com. From villa rentals to house 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 $65 per night with an average price per night of $188.

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!