Kissimmee Vacation Rentals

(280 rentals)
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❤EIR Fun House Pool/Arcade/Theatre/GameRoom 15min/4mi to Disney

$550

avg/night

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Key Amenities

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

About this property

Relax

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Property Type

Kissimmee Villa

"Great House"
Reviewed April 20, 2021

This is a clean home that is very well equipped for a nice stay and my family and I really enjoyed it!

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6BR/5.5Bath/4Miles to DisneyAK/$129 Specials/FreeSpa/Lanai

6 BR | 5.5 BA | Sleeps 18 | Quick View

48

Distance to park: 4 miles to Animal Kingdom

$176

avg/night

View Details

Key Amenities

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

About this property

Summary of this House’s best features (from 200+ Guest Reviews) • Less than a 4-mile drive to Disney World’s Animal Kingdom • Two leather couches and a recliner with a total of 5 power reclining seats • Privacy on the pool deck with flowering hedge-plants along the perimeter • A ...

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Property Type

Kissimmee House

"Absolutely WONDERFUL Vacation Home!"
Reviewed October 25, 2021

Our recent stay was the second time we booked John's incredible vacation home. We were pleased to see so many upgrades in the home since our last stay. Everything in the house was in perfect working order ...

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Toy Story Tower

6 BR | 4 BA | Sleeps 14 | Quick View

1

Distance to park: 5 miles to Disney World

$255

avg/night

View Details

Key Amenities

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

About this property

Toy Story Tower is an imposing, six bedroom vacation home located within the prestigious gated community of Windsor Hills Resort. Here, you can enjoy the very best in luxurious accommodation all while being located just minutes from Walt Disney World Resort as well as many other great attractions. As ...

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Property Type

Kissimmee House

"June vacation"
Reviewed July 8, 2021

House was very nice and clean. Really no problems but the hot tub piece had to be ordered for heat that we paid for extra but it was ok because it was hot enough outside. We stay at wondsor hills every ...

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South facing heated pool and spa

6 BR | 4 BA | Sleeps 12 | Quick View

6

Distance to park: 3 miles to Disney World

$265

avg/night

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Key Amenities

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

About this property

Situated in the Window Hills resort community about 2 miles from Disney, this 6-bedroom, 4-bath vacation rental home specializes in providing fantastic Florida vacations! With 2,812 square feet and accommodations for 14, guests can enjoy not only the private pool and spa in the enclosed lanai but also ...

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Property Type

Kissimmee House

"Girls Trip 2020"
Reviewed July 24, 2020

My friends and I absolutely loved this home ...it was perfect for the 8 of us. I WOULD DEFINITELY RENT AGAIN!!

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Storey Lake-4797CEKCCJGIL

5 BR | 5 BA | Sleeps 10 | Quick View

1

$176

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

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

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Property Type

Kissimmee Townhome

"Summer Vacation"
Reviewed July 28, 2020

The house was beautiful.... very clean.... excellent location!!!! My children really enjoyed the resorts pool and lazy river!!!! Will definitely visit again!

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Updated Family Vacation Home, Only 4 Mi to Disney, 8 BR, Priv. Pool & Game Room

8 BR | 4.5 BA | Sleeps 16 | Quick View

7

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

$261

avg/night

View Details

Key Amenities

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

About this property

Mickey's Mansion happily presents two of our newly updated, professionally hand painted, themed twin bedrooms sure to please Star Wars and Frozen fans of all ages. The Star Wars room gives the feel of being in a spaceship looking out into outer space surrounded by stars and planets while being watched ...

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Property Type

Kissimmee House

"Family Vacation"
Reviewed September 21, 2021

I brought my family to Florida for a vacation. My 95 year old grandmother enjoyed the trip as well as everyone else. The house was just as it was stated on the site. The Wilson’s were very tentative to ...

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Lakeside pool villa, kissimmee 3 miles disney

$196

avg/night

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Key Amenities

  • Air conditioning
  • Private pool

About this property

Location, Location, Location, situated just 3 miles from Disneys Animal Kingdom and less than a mile from the Formosa gardens shopping area and restaurants on the US192 you are perfectly placed to hit the parks before the rush, come home to cool down by the pool for dinner and hit the parks again for ...

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Property Type

Kissimmee Villa

"Lovely Villa, Great Location"
Reviewed June 14, 2019

Really nice villa. Plenty of living space. Sleeps up to 12 but there were 7 of us so it was really roomy.Pool area is so nice, with a view over a lake with lots of wildlife to see. Pool also has a colour ...

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Nice 7 BR/5 BA Luxury Villa with POOL/SPA,Wi-Fi,LCD TVs, BBQ,3 miles to Disney

7 BR | 4.5 BA | Sleeps 16 | Quick View

6

Distance to park: 3 miles to Disney world

$149

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pets allowed
  • Pool

About this property

Newly furnished luxurious 2-story Villa home opens its door to welcome you! This villa is furnished with two master suite and one large bedroom with upscale King-size beds; two bedrooms with queen-size beds; and two bedrooms with two twin-beds each. All bedding and mattresses are Brand New with top quality ...

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Property Type

Kissimmee Villa

"House rental"
Reviewed July 30, 2021

Once again very pleased with Ann service this is my third years renting from her for our family vacation and can’t complain the house was awesome very spacious for all my family close by to a lot of restaurants ...

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FABULOUS HOUSE NEAR DISNEY WITH PRIVATE POOL!

7 BR | 5.5 BA | Sleeps 14 | Quick View

Distance to park: 5 miles to Disney World

$245

avg/night

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Key Amenities

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

About this property

DOWNSTAIRS FORMAL LOUNGE & DINING. The front entrance lobby leads into the formal lounge and dining areas - ideal luxurious surroundings. We offer another detached house in Solana Resorts aswell. KITCHEN/BREAKFAST AREA The large open plan fully equipped kitchen contains all the modern appliances ...

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Property Type

Kissimmee House

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Our Goal:- Make your stay Enjoyable! Sleeps 20 - Heated Saltwater Pool & Spa

8 BR | 6 BA | Sleeps 20 | Quick View

2

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

$364

avg/night

View Details

Key Amenities

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

About this property

You can Book the property by clicking on the link which you can find under " OWNER INFO "Enjoy your vacation in this lovely and spacious home with large screened in patio which flows into Heated Saltwater Pool & Spa. You will love your stay in this 8 bedroom x 6 bath home as we understand ...

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Property Type

Kissimmee House

"Very Nice Villa"
Reviewed December 29, 2020

This Villa was beautiful. The property managers were very helpful in clarifying any doubts that I had. They were quick and super nice. The pool was nice and heated. The spa was my favorite part.

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Luxury Windsor Hills 3/2 Condo

3 BR | 2 BA | Sleeps 6 | Quick View

5

Distance to park: 2 miles to Disney

$100

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool

About this property

Windsor Hills is one of the greatest gated community located within the heart of Orlando’s premier tourist attractions. Windsor Hills boasts the closest proximity to Central Florida's theme parks. Windsor Hills has all the amenities of a Five Star Hotel or Resort.Our 3 bed/2 bath (1 king, 1 ...

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Property Type

Kissimmee Apartment

"Excellent resort facilities"
Reviewed March 24, 2020

Resort was excellent with all the Disney attractions. Plus all the restaurants nearby and the Walmart store just one half mile away. The pool area was very large and accommodated all the guests. Very well ...

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Resort living while visiting the theme parks and next door to Margaritaville

$154

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Our beautiful FOUR-BEDROOM, THREE-BATHROOM, luxury home is located at the gated community of Emerald Island Resort, surrounded by lush Florida vegetation, is the one of the latest full-facility resort in the Disney area. The winding, palm-lined road that leads to the impressive entry to the resort gives ...

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Property Type

Kissimmee House

"Wonderful Home"
Reviewed August 3, 2021

Home was great. Have stayed in emerald Island multiple times and this home was one of our favorites.

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Enchanted Emerald Oasis (At the gates of Disney World)!

7 BR | 4.5 BA | Sleeps 16 | Quick View

1

Distance to park: 3 miles to Disney World Resort

$272

avg/night

View Details

Key Amenities

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

About this property

Welcome to the Enchanted Emerald Oasis! The perfect vacation rental home for you, your family and friends! Located in the upscale Emerald Island Resort, just outside of the gates of Disney World theme parks, minutes to Universal Studios Orlando, Sea World and so much more in the Orlando area! Also, ...

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Property Type

Kissimmee Villa

"Can’t wait to go back!"
Reviewed January 18, 2020

Awesome property that was simply perfect for our extended family trip to Disney. Over half of our group flew in from Ireland and the remainder of us are Irish living here in the states. Comfortable, clean, ...

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Beautiful 3 bedroom villa. Close to Disney. Free BBQ/Grill

$105

avg/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

"Amazing Summer Stay"
Reviewed August 24, 2021

House was everything we hoped for, pool, kitchen, bedrooms were all lovely. Will definitely recommend to anyone visiting Florida.

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HOME AWAY FROM HOME- ENJOY THE VIEW

$133

avg/night

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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

"Our favourite place"
Reviewed September 28, 2021

Two years we have not been able to get there we have rebooked for next May the couple that own the Villa have been so kind and patient with us and we really appreciate them we just can’t wait to get there

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West Reunion Estate | Games Room, Theater and South Facing Pool!

$356

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

Situated within the West-side of the exclusive Reunion Resort and Just 6 miles from the gates of Disney World!Pull up to your home away from home, and prepare to indulge in luxury. This home has been furnished with no expense spared. This beautiful home boasts a rare combination of characteristics ...

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Property Type

Kissimmee House

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Family Disney villa pool/spa 5 bds 15 Mins to Disney

5 BR | 4 BA | Sleeps 12 | Quick View

5

Distance to park: 6 miles to Disney Animal Kingdom

$183

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

***FREE WIRELESS INTERNET JUST BRING YOUR MOBILE DEVICES** ***FREE NATIONAL AND INTERNATIONAL LANDLINE PHONE CALLS***Sleeps a maximum 12 guests, with a maximum of 8 guests over the age of 14 years oldIn these strange times we are doing all we can to ensure our home is safe for your stay. We ...

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Property Type

Kissimmee House

"Lovely home"
Reviewed August 3, 2021

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

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Affordable Disney Villa - just 5 minutes to Disney

$143

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Our property maintains a gap of 3 days between each booking for health safety measures during this crisis and we also follow stated mandated cleaning procedures and guidelines after each guest checks out.This Disney Villa is a fully furnished home and is one of the best kept turnkey properties you ...

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Property Type

Kissimmee Villa

"Perfection vacation getaway"
Reviewed March 24, 2020

I rented this house for my 1 week vacation to Disney and Universal Studios and was truly impressed by all it offered. To start the location was perfect, as it was close to both theme parks (being minutes ...

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7 bedroom with a special discount

$224

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly

About this property

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

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Property Type

Kissimmee House

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Palm Tree Villa Florida, 5 Star Review Rating with Pool Lift & Wheel in Shower

$180

avg/night

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Key Amenities

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

About this property

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

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Property Type

Kissimmee Villa

"Great home to stay for a vacation. The home met our expectations, clean and family ready."
Reviewed August 10, 2021

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

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Lakeview Retreat, luxury villa, large pool, game room , pet friendly

6 BR | 5 BA | Sleeps 12 | Quick View

1

Distance to park: 4 miles to Disney Animal kingdom

$305

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pets allowed
  • Private pool

About this property

Luxury 6 bed 5 bath Villa with large south west facing pool, just 4 miles from Disney! Our wonderful villa can sleep up to 12 guests. Situated in the prestigious gated upscale community of Formossa Gardens, where properties enjoy spacious garden plots giving privacy, your wonderful pool home has a ...

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Property Type

Kissimmee House

"Wonderful Home"
Reviewed December 3, 2020

We were very happy with this home. Very clean and well kept. The pool was beautiful, especially at sunset. The parks were only a short drive away. The best part was we could bring our beautiful boy Sawyer ...

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Windsor Palms Resort-2334CISPDITHP

$110

avg/night

View Details

Key Amenities

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

About this property

Be sure to visit our website to check availability on all our homes! Save our page for future vacations to the Orlando area!Visit us at lostinthemagic . comWindsor Palms Resort- Kissimmee, Florida is an upscale gated community located just 2 miles from Walt Disney World. This luxury resort sits ...

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Property Type

Kissimmee Townhome

"Perfect spot for a get-away with your family."
Reviewed March 27, 2021

My expectations were exceeded. Actually, my wife and my children keep asking me to go back. I am looking forward to booking again in April 2021.

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Family Fun | Games Room & No Rear Neighbors

$286

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

This expansive 3,909sq. ft home can also sleep 18 comfortably, set within a luxury resort. With 9 bedrooms and 5 bathrooms, this is a perfect home for a large family or group vacation. Your family will love relaxing in the Florida sun by the pool!The living area has an open floor plan, you will find ...

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Property Type

Kissimmee Villa

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Luxury Sunset View 8 bed pool home, water views, game room, pet friendly

8 BR | 6 BA | Sleeps 16 | Quick View

2

Distance to park: 4 miles to Animal Kingdom

$313

avg/night

View Details

Key Amenities

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

About this property

This is the one you've been looking for! Your holiday home from home - our fabulous luxury villa with private pool and spa is situated in the gated resort community of Windsor at Westside, conveniently situated approximately 10-15 mins from Disney and close to Golf at Champions Gate. Up to 16 people can ...

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Property Type

Kissimmee Villa

"Spring Break Retreat"
Reviewed March 12, 2021

We were looking for a place to spread out, have a heated pool, and be close to the parks. This place delivered all that and more. When we arrived, the place was clean and ready for our visit. We cooked ...

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Beautiful lakeside villa with private pool.

$74

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Beautiful south facing lakeside villa with solar and electric heated pool. Great location for all the theme parks, Disney 20 mins, Seaworld 15mins, Universal 30 mins and Cocoa Beach/Kennedy Space Centre 45 mins. Local English management contact and fully inspected/licensed by the Florida Hotels Board. ...

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Property Type

Kissimmee Villa

"Peaceful, Beautiful, Spacious surroundings."
Reviewed September 22, 2021

We are more than pleased with the spacious, clean home in a peaceful and safe neighborhood. The home could not be in a better neighborhood. It is very close to anything kids and adults would want during ...

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Luxury Legacy Dunes condo close to Disney, Golf and Orlando Fun!

4 BR | 2 BA | Sleeps 9 | Quick View

1

Distance to park: 5 miles to Disney World

$102

avg/night

View Details

Key Amenities

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

About this property

Superb Remodeled 4 bedroom condo at 2 bedroom price! Legacy Dunes Resort. 4 bedroom/2 bathroom 1400 sq ft condo with screened balcony and children's playground & lake view. Easily accessible for the entire family so you can bring Grandma and Granddad. Or two couples each with two children, or groups ...

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Property Type

Kissimmee Condo

"Recently renovated 4 bedroom condo in a great complex, close to everything."
Reviewed January 29, 2019

This is our third extended stay in this unit. We enjoy the closeness to Disny as well as the closeness to grocery shopping and most of the chain restaurants. This gated complex is set back from Route 192 ...

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Holiday villa with pool and entertainment, 10 min to Disneyworld, Orlando, etc.

4 BR | 2.5 BA | Sleeps 9 | Quick View

5

Distance to park: 10 miles to Disneyworld

$120

avg/night

View Details

Key Amenities

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

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

"Great place"
Reviewed April 7, 2021

Lots of space out of the Hustle and bustle but close enough for a small drive to get to everything needed kids love the pool

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Mad Men Magic Kingdom House *Pool&Spa* 6mi to Disney*Dog and Family Friendly*

$273

avg/night

View Details

Key Amenities

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

About this property

As you step through the front door of this 2800-square-foot home, you are immediately drawn to the unique geometric wall design and mid-century modern decor throughout the house. The lighting is spectacular as you enter the great room and look through the two sliding glass doors onto the patio where the ...

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Property Type

Kissimmee Villa

"Amazing!"
Reviewed February 4, 2021

Had the most amazing time here with my family! My daughter had an amazing birthday. Rebecca is amazing and made sure to go above and beyond to make our stay extra special. Rebecca responded to every question ...

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Kissimmee Vacation Rental - Disney Home to Rent

$114

avg/night

View Details

Key Amenities

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

About this property

Our luxury Kissimmee vacation villa will comfortably sleep 10 people. It is fully air-conditioned for your comfort, and has a very roomy and spacious floor plan. It has 2 lounge areas (one with 2 full sofas, and a ceiling fan, the other with a love seat and a sofa bed), both have cable T.V. The kitchen ...

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Property Type

Kissimmee Villa

"We are Home"
Reviewed April 19, 2021

Enjoyed my stay at this property it was very homey for me and my family. Only one question if the filters was changed in the home all of our sinuses went haywire even down to the babies. It could be the ...

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3BR 1st Floor Condo Near Disney, Steps from Pool, Loaded with Amenities

$85

avg/night

View Details

Key Amenities

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

About this property

Built in 2002, Windsor Palms Resort is a gated community approximately five miles from Disney. This luxury complex has a 7500 square foot clubhouse, basket ball courts, volleyball courts, children's play area, large swimming pool, splash pad, hot tub, picnic and barbecue area, outdoor bar, convenience ...

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Property Type

Kissimmee Condo

"Disney trip"
Reviewed January 5, 2020

Our stay was wonderful! Clean, close to Disney, beautiful pool! Loved it!! Check-in was easy and quick. Everyone was very polite and helpful.

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5 Bed 3 Bath Luxury Emerald Island Villa - Pool,Spa Games Room

5 BR | 3 BA | Sleeps 12 | Quick View

2

Distance to park: 3 miles to Disney

$151

avg/night

View Details

Key Amenities

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

About this property

5 bedrooms, 3 bathrooms, sleeps 10 - 12.Spacious, 5 bed, 3 bath, luxury villa with Private Pool, Spa +Games Room (pool, air hockey and football tables) Guests have full use of all facilities of the Prestigious Emerald Island Resort, including Club House with pool, spa & licensed Tiki Hut Bar, ...

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Property Type

Kissimmee Villa

"Great experience"
Reviewed April 8, 2021

We had a great experience dealing with Ian he is professional and responded right away if we needed anything , the house was clean and organized when we got there. Everything worked out as planned. Would ...

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Special price for February, dont miss it !

$138

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

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

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Dreams Come True

7 BR | 4.5 BA | Sleeps 14 | Quick View

Distance to park: 3 miles to Disney Land Parks

$256

avg/night

View Details

Key Amenities

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

About this property

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

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Property Type

Kissimmee House

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Florida - Sunsations Condo Rental

3 BR | 2 BA | Sleeps 8 | Quick View

Distance to park: 5 miles to Disneyworld and Disney Springs

$94

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pets allowed
  • Pool
  • Rentals by owner

About this property

You have arrived in the "Vacation Capital of the World" and you're going to love staying in our luxury, three bedroom, two bath, fully equipped vacation condo rental situated near DisneyWorld and all other theme park attractions. The property rental is located within the resort community of ...

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Property Type

Kissimmee Condo

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Disney Vacation Rental/heated pool - call for Specials now

4 BR | 3 BA | Sleeps 8 | Quick View

7

Distance to park: 3 miles to Mgm

$119

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pets allowed
  • Private pool

About this property

Beautiful 4 bedroom /3 bath private villa only 3 miles to Disney and other parks. Including heated pool/jacuzzi and game room. Free wifi and phone use in USA and Canada and PR. Fully furnished with all kitchen needs . Greatest location to shopping , all major restaurants and stores including supermarkets ...

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Property Type

Kissimmee Villa

"Perfect , clean and close to everything"
Reviewed September 28, 2021

I had stayed at this home once before. The beds are comfortable. Home was clean and pool was warm. Exactly as I had hoped. Thank you Yona

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Sunshine Memories Villa. ☀️❤️ Magical Family Retreat near Disney w/Waterpark

$305

avg/night

View Details

Key Amenities

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

About this property

Welcome to Sunshine Memories Villa, where you will have an amazing vacation enjoying all that the Orlando area has to offer. Our 5-bedroom 5-bathroom villa is located less than 10 minutes away from Disney in the beautiful gated resort of Windsor Hills. As you step inside the foyer of your vacation home ...

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Property Type

Kissimmee Villa

"Don’t worry, be happy"
Reviewed August 7, 2020

Even with all that’s going on, this was a blessing in disguise. Really needed this and everything was perfect. You can’t live your life in fear, just be cautious in all you do. No complaints whatsoever. ...

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South facing 5 Bed 3 Bath - pool vacation rental Villa near Disney

$155

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Planning to visit Disney during 2021/22/23How would you like to rent our 5 bed 3 bath rental villa.It has its own south facing screened private swimming pool that is located on the exclusive Lake Berkley gated Resort in Kissimmee, Orlando, Florida.We are just minutes from the theme parks ...

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Property Type

Kissimmee Villa

"Great weather and the pool was wonderful!"
Reviewed March 19, 2020

Gated community was wonderful and secure. Walking in neighbourhood around the lake was very peaceful. House size was nice, updated furniture was one suggestion in living room and beds in general. ...

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4767 Terra Esmeralda Townhouse

3 BR | 2.5 BA | Sleeps 8 | Quick View

$118

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

About this property

You have arrived in the "Vacation Capital of the World" and you're going to love staying in our luxury, 3 bedroom, 2.5 bath, fully equipped vacation townhouse rental situated near DisneyWorld and all other theme park attractions. The property rental is located within the resort community at ...

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Property Type

Kissimmee Townhome

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Amazing pool home, Hardwood Floors, Game room, SAFETY POOL FENCE. Has It All!!!

$158

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

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.This Beautiful home is well situated, close to all major attractions and amenities, ...

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Property Type

Kissimmee House

"Great Villa for my needs"
Reviewed November 16, 2019

I volunteer each year at GKTW in Kissimmee so Mark's villa for perfect for my needs. Used 3 of the 4 bedrooms with guests so we all had bathrooms as well - important for our early starts! A few things cropped ...

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Beautiful Lake View Villa With Private Pool And Games Room

$125

avg/night

View Details

Key Amenities

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

About this property

Situated on the beautiful gated Resort, our luxury 4 bed villa has a west facing pool deck overlooking a tranquil lake, ideal for relaxing after a days out in the theme parks or one of the many shopping malls. Sleeping 8 people in comfort with 4 bedrooms: 1 king sized double with en suite shower room ...

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Property Type

Kissimmee Villa

"Clean, spacious, convenient"
Reviewed April 13, 2021

The house was clean and roomy in gated, safe community with easy access to stores, restaurants, and many things to do in the Orlando/ Kissimmee area.We had a fantastic stay and look forward to returning ...

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4/3 Lake-Front Townhome w/Private Pool at Storey Lake Resort

$178

avg/night

View Details

Key Amenities

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

About this property

Private 2 story home with 4 Bedroom/3 Bathroom with heated pool has all of the spacious and convenient accommodations for your entire family vacation. Storey Lake is very close to all of the major attractions of Disney World, Epcot, Animal Kingdom, Disney Water Parks, Universal Studios and Sea-World.The ...

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Property Type

Kissimmee Townhome

"Satisfied"
Reviewed June 21, 2021

The unit looks just like the pictures. Robert was very helpful and professional. I would definitely stay there again. The property is accessible to everything.

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OUR LUXURY HOME IN THE SUN WITH LARGE SOUTH FACING 34ft x 18ft POOL

4 BR | 3 BA | Sleeps 8 | Quick View

16

Distance to park: 12 miles to Disney

$117

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Due to the Covid-19 pandemic. PLEASE CHECK CURRENT FLORIDA CDC GUIDELINES for the latest travel information.Since Covid-19 hit the US, we are now required to give our Management Company at least 2 days notice to enable them to prepare our home ready to receive guests.Stay safe ———————————WELCOME ...

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Property Type

Kissimmee Villa

"House reviews"
Reviewed July 24, 2021

My family enjoyed this spacious family vacation home. The kids enjoyed the pool and watching the fireworks at night from Disney. Also, we will recommend this home to our family & friends.

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Disney Palms

3 BR | 2 BA | Sleeps 9 | Quick View

1

Distance to park: 4 miles to Walt Disney World

$108

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool

About this property

This is a beautiful 3 bedroom 2 bath condo just 20 min from Disney, is loaded with beauty and fun! While you can entertain in the condo itself, the Clubhouse holds a whirlwind of fun! Outside you have a playground, tennis court and walking trails; inside the Clubhouse you have a movie theater, tons of ...

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Property Type

Kissimmee House

"prefect place to relax"
Reviewed December 13, 2020

We were at the home in November. We really enjoyed it. The home is big and real clean and there is lot's of room to move around. The location is fantastic, nice community, close to everything. Real quick ...

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StarLakeVilla, 4 Bedroom Villa with Private Pool & Games Room. Near Disney

4 BR | 3 BA | Sleeps 8 | Quick View

2

Distance to park: 3 miles to Walt Disney Animal Kingdom

$139

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Welcome to our 4 bed single storey air conditioned home in Rolling Hills, Kissimee. It is just 10 mins (real time) to Disney Main Gate. It is situated on a part residential, part visitors estate, with lake views at the rear, in a quiet neighbourhood, close to Formosa Gardens.The pool overlooks the ...

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Property Type

Kissimmee Villa

"Great Home!"
Reviewed August 27, 2021

From before booking and after David was GREAT! Quick responses and very detailed answers to questions asked. The home was great for our week stay, many things to do and eat nearby and the pool was the cherry ...

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Villa own pool and close to Disney. Only $90 per night

$90

avg/night

View Details

Key Amenities

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

About this property

Welcome to VIPvilla Johanna and Stephen thank you for visiting our website of hand-picked 5 Star quality villas. We manage the bookings for 50 private villa owners on this website and we can personally assure you that you will be delighted with any of the villas offered to you. We have many repeat ...

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Property Type

Kissimmee Villa

"Awesome vacation home."
Reviewed September 23, 2021

We had a great time in this lovely home. Very clean, updated, and had all the likings to home that we needed. Truly enjoyed the pool. Will definitely be using again.

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491-Luxury Villa with Pool & Spa By Disney. 491-Luxury Reunion Villa By Disney

$497

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Luxury Reunion Villa By Disneyhis 8 bedrooms 7 bathrooms Contemporary Villa is located very close to Disney, a perfect choice for family and friends wanting an Orlando vacation. Sleeping up to 18 guests, this home has 3 owner suites with bathroom also 2 additional queen bedroom with en suite bathroom. ...

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Property Type

Kissimmee Villa

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331 - Luxury Villa With Pool & Spa By Disney. 331 - Luxury Villa W / Pool

$454

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Perfectly furnished and properly maintained villa with private pool, hot tub and many more for a comfortable stay near Disney! This is a perfect eight bed/ seven bath Villa for your family reunion or a group of friends retreat. Our spacious villa is just a few miles away from Disney World. You won't regret ...

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Property Type

Kissimmee Villa

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South Facing Lake View Villa With Private Pool, Spa, Games Room on Lake Berkley

$259

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

We have availability. Sorry no pets or smokers. Good discount off list price for all rentals of 5 nights and more in October and November. Welcome to “Hibiscus on the Lake” our true south facing villa with stunning, uninterrupted views of the largest lake on Lake Berkley resort in Kissimmee. ...

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Property Type

Kissimmee Villa

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480-Luxury Villa with POOL & SPA by Disney. 480-Villa with POOL /SPA

$378

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Large and luxury villa with 6 bedrooms, 6.5 bathrooms,Every room has its own bathroom, 8 beds, several family areas, themed bedrooms, flat TV in each bedroom, and sleeps up to 16 guests! This vacation home is built to impress; plenty of space, modern furnishings, private pool and spa, located in Orlando ...

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Property Type

Kissimmee Villa

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Sunrise Pleasure at Emerald Island Resort

4 BR | 3 BA | Sleeps 10 | Quick View

6

Distance to park: 3 miles to Disney World

$138

avg/night

View Details

Key Amenities

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

About this property

4 Bedroom (2 master suites) 3 full baths, separate living and family rooms, will sleep up to 10 people. Decor in this house is Timeless!!The game room includes an 8 foot pool table, foosball table, poker table. The private pool deck provides a distant view of the nightly DisneyWorld fireworks display ...

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Property Type

Kissimmee House

"Long visit"
Reviewed July 28, 2021

We stayed here for over 3mo. It was great location with lots of rooms, 4 Br 2 sitting rooms. Nice solar heated pool. Owners where great to work with. Emerald Isle Resort is a nice gated community. Close ...

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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

Find your ideal Kissimmee vacation rental today
 
Aiming to take an incredible vacation to this year? Ditch the traditional hotel and opt for one of our Kissimmee vacation rentals instead. We have plenty of condos available in Kissimmee on FloridaRentals.com. Whether you’re looking for luxury Kissimmee villa rentals or kid-friendly mansions with an arcade, you can find it on our site.
 
Kissimmee, Florida travel advice
 
A short drive south of Orlando finds you in sunny, friendly Kissimmee. Here you’ll be near all the theme parks, but you’ll be away from the bustling crowds. Rentals will cost less than a stay in Orlando, so you’ll have extra cash to spend on park tickets and meals. This area also offers activities for those who love outdoor exploration, with exotic plants and animals in the local nature preserves.
 
Top attractions
 
The Florida theme parks are the major draw for visitors to the area. Walt Disney World, Universal Studios, SeaWorld, and the Wizarding World of Harry Potter draw millions of families every year. 
 
The fun doesn’t stop as kids and adults alike can mingle with their favorite characters, feel the chills and thrills of amusement rides, and cool off in the area’s water parks. If the theme parks don’t meet your need for speed, spend an afternoon at Fun Spot America. With two unique go-kart tracks and 18 rides you’ll be dizzy with delight. 
 
The Museum of Military History offers exhibits that highlight the bravery and humanity of the men and women who have served in the armed forces. Genuine artifacts, military relics, photographs and memorable accounts by former soldiers are on display here.
 
For some Florida history, stop in to Osceola County Pioneer Village and Museum. This museum features many exhibits depicting life in the 19th century. The Pioneer Village has a general store, blacksmith shop, one room schoolhouse, and nature preserve.
 
Family-friendly activities
 
Strap on your hiking boots and take off on the Shingle Creek Regional Trail. The trail offers a beautiful, natural environment for cyclists, pedestrians, canoeists/kayakers, bird watchers and other nature lovers.  A wide variety of habitats on the trail include Lake Tohopekaliga waterfront and islands, a pristine cypress swamp, an orange grove and wild grasslands.
 
For a more cuddly experience, Green Meadows Petting Farm has over 50 acres of animals to greet and family rides. If you’re visiting during spring training, stop in to see the Houston Astros practice as Osceola County Stadium. 
 
Of course, the options for fun aren’t limited to the parks. For golfers, Central Florida is a veritable paradise. With dozens of award-winning courses within a few square miles, you should definitely pack your clubs when visiting. If your family prefers mini-golf you have plenty of options, too. 
 
Kissimmee Lakefront Park features a playground and splash park for kids, BBQ grills for a cookout, and fishing piers. For more along these lines, nearby St. Cloud Lakefront Park and Beach offers a family picnic area and volleyball court. Located along the breathtaking Lake Tohopekaliga, these parks are great options to spend a relaxing afternoon.
 
Spend your evenings in Old Town Kissimmee, where every Saturday night there is a classic car cruise through the city streets, accompanied by a live band. In Old Town you’ll also find everything from high end retailers to souvenir shops. There is live music playing almost every night, and restaurants offering pizza, Tex-Mex, or anything in between. 
 
Annual events
 
Osceola Heritage Park has a variety of world-class shows and sporting events. You'll find the Silver Spurs Rodeo here, too. It's a real crowd pleaser, offering a taste of the Wild West and reflective of the area's ranching heritage. You can watch bull riding, bronco bucking, barrel racing, steer wrestling, team roping, and even those funny rodeo clowns.
 
Kissimmee vacation home rentals on FloridaRentals.com
 
Booking one of our vacation homes in Kissimmee on FloridaRentals.com can save you 15% over our competitors. Plus, we have a wide array of inventory appealing to any group size or traveler tastes. Book today!


FAQ

How many vacation rentals are there in/around Kissimmee?

There are 280 Kissimmee vacation rentals available on FloridaRentals.com. From house rentals to cottage rentals to beach condos 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 $34 per night with an average price per night of $186.

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

What are the best vacation rentals in Kissimmee?

Visitors give great reviews to these top-rated Kissimmee vacation rentals available on FloridaRentals.com:
Indian Creek Retreat: Well maintained home in the Indian Creek subdivision which is literally on Disney's doorstep and your home away from home.
Casa Bonita: 'Casa Bonita' which means 'Beautiful Home' is a beautifully furnished four bedroom, three bathroom home with a 26 ft x 14 ft swimming pool.
Mickey's Villa: This beautiful 5-Bed 4-Bath home located in the very popular community of Indian Creek is one of only three homes in the development with a Mickey Pool.


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