Kissimmee Vacation Rentals

(343 rentals)
The Floridian : Ultra Luxuary 5BR Pool Home, 2 Master Suites, Sleeps 12!

$239

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool

About this property

Enjoy our three-thousand square foot, custom luxury pool home, less than four miles from Disney World. We offer two master suites with king-size beds (one with Jacuzzi), two queen-bedrooms, one twin-bedroom, and queen size pullout-couch, all on one floor. This is not your typical Rolling Hills house. ...

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Property Type

Kissimmee House

"Our Dream Vacation"
Reviewed July 30, 2018

This home was PERFECT for my family! It was very spacious and had everything we needed to make us comfortable. Very close to Disney and close to a lot of nice eating places we could not have chosen a ...

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*Fabulous South Facing Lake View 6 Bed Villa*

$228

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool
  • Rentals by Owner

About this property

Sunset Villa, located in the ideally situated community of Sunset Lakes, offers you and your party the unique opportunity to spend your Florida vacation in a quiet rural setting, yet only a short drive away from the theme parks, restaurants, shopping malls and all the many attractions Orlando has to offer.Sunset ...

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Property Type

Kissimmee Villa

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Encantada Resort Townhouse with pool 3 bedrooms

$99

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

This amazing townhouse located at Encantada Resort has been recently upgraded. The fully equipped kitchen has new granite countertops and everything you need to eat at home or prepare some snacks for the parks. There is a dining set for 6 that shares the open plan with the living room where there is a ...

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Property Type

Kissimmee Townhome

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

4 BR | 2 BA | Sleeps 10 | Quick View

1
Owner special: Book 12 nights between May 14 and May 30 and we will INCLUDE ONE NIGHT FREE!

Distance to park: 5 miles to Disney World

$69

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • 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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6 bed luxury villa, SOUTH facing pool/hot tub, Themed Rooms, 2 miles to Disney

6 BR | 4 BA | Sleeps 13 | Quick View

1

Distance to park: 3 miles to Animal Kingdom

$200

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool

About this property

This Villa has been beautifully refurbished . The property is Located just 2 miles from Disney World with a large SOUTH facing pool (heating extra) , kids paddling pool, stand alone hot tub (extra charge to use $15 per night)and large deck that is not overlooked and backs onto a lake with sun loungers ...

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Property Type

Kissimmee Villa

"Awesome vacation home"
Reviewed August 15, 2019

This villa is just as described. There was grandparents, grown children, grandchildren and great grandchildren with plenty of room for everyone A Disney princess room my great granddaughters loved dressing ...

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Enchanted Disney Villa Oasis

6 BR | 5 BA | Sleeps 12 | Quick View

Distance to park: 3 miles to Disneyworld

$245

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool
  • Rentals by Owner

About this property

Welcome to your own private Oasis on the outskirts of Disneyworld! Enjoy your own 6 bedroom Villa with room for all your family while you visit some of the happiest places on Earth!WE ARE CURRENTLY BOOKED OUT THROUGH JANUARY 9TH, 2020! ONLY OPEN DATES ARE: NOV 16-24TH DEC 1-5TH JAN 9-17PLEASE ...

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Property Type

Kissimmee Villa

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

$125

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • 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

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Exquisite Mallard Creek Villa

4 BR | 2 BA | Sleeps 8 | Quick View

2

$93

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Our Villa design was selected and built specifically to make your vacation experience exceptional.The very Private 30ft X 15ft Pool and huge sundeck is a real treat and perfect for relaxing around after a long day at the theme parks or a day spent teeing off on the greens.Close to all the theme ...

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Property Type

Kissimmee Villa

"Decent pool"
Reviewed July 12, 2018

We liked the pool that the house has.

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6BR/5.5Bath/4Miles to DisneyAK/$99 Specials/FreeSpa/Lanai

6 BR | 5.5 BA | Sleeps 19 | Quick View

16

Distance to park: 4 miles to Animal Kingdom

$99

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool
  • Rentals by Owner

About this property

We have just a few openings for the balance of the year: Oct 5 to 10 for $99/night; Oct 29 to Nov 2 for just $99/night; and Nov 9 to 14 for $119/night. We also have the week of Thanksgiving open. Go to , watch the video and submit a request for a quote.Summary of this House’s best features ...

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Property Type

Kissimmee House

"Impressive"
Reviewed September 9, 2019

The house is beautiful and great for the family. My teenagers loved it. The pool was very relaxing especially with the heated tub. Definitely will be back with my family.

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Minutes From Mickey - 3Bed 3Bath Townhome with South Facing Pool

3 BR | 3 BA | Sleeps 6 | Quick View

7

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

$110

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool
  • Rentals by Owner

About this property

“Minutes-From-Mickey” is our beautiful townhome, situated in the 5-Star Windsor Palms Resort community less than 4 miles from Walt Disney World in sunny Central Florida, giving quick and easy access to the area’s many theme and water parks, golf courses, restaurants, shopping and other ...

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Property Type

Kissimmee Townhome

"We loved the townhome"
Reviewed May 17, 2019

We arrived on May 5, 2019 and for the next 10 days we totally felt at home in Jane's lovely, clean townhome. All the amenities were there for us - a fully ready-to live in environment (we just had to add ...

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Four Bedroom Family Vacation Home Close to Disney!

4 BR | 2.5 BA | Sleeps 8 | Quick View

3

Distance to park: 4 miles to Disney World

$130

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool

About this property

Great vacation home just three miles from the gates of Disney! Flat screen TV's in living room and all 4 bedrooms. Free wireless hi-speed internet and cable TV. HD TV in living room and all bedrooms. King bedroom has a flat screen 50" TV and 2 additional bedrooms have a built in DVD player in the ...

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Property Type

Kissimmee House

"Excellent Stay"
Reviewed August 15, 2019

Kay’s Retreat was the perfect destination for our recent vacation! Everything was perfect. She thought of everything we might need during our stay. The house was clean and comfortable. Will absolutely ...

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Toy Story Tower

6 BR | 4 BA | Sleeps 14 | Quick View

Distance to park: 5 miles to Disney World

$243

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • 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

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Beautiful 3 Bedroom 2 Bathroom Townhouse. Amazing Resort. Minutes to Disney.

3 BR | 2 BA | Sleeps 6 | Quick View

2
Owner special: STAY 6 NIGHTS GET THE 7TH NIGHT FREE ON ALL NON HOLIDAY WEEKS.

Distance to park: 5 miles to Walt Disney World

$99

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Rentals by Owner

About this property

Beautiful 3 Bedroom 2 Bathroom Townhouse just off of 192 in Kissimmee, Fl. Minutes to Walt Disney World, Universal Studios, Sea World, Outlet shopping. You can walk to great restaurants and shopping. The Townhouse has 3 bedrooms and 2 bathrooms. The living room/dining area has a sofa and sofa sleeper ...

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Property Type

Kissimmee Condo

"The place was beautiful and clean but best of all the owner s responded right away to my questions."
Reviewed July 27, 2019

The place exceed our expectations. We'll definitely recommend this place or website to families and friends

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Affordable Home Near Disney World

$100

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool
  • Rentals by Owner

About this property

Indian Creek Disney Retreat is a beautiful 1800SF, well maintained home in the Indian Creek subdivision which is literally on Disney's doorstep and your home away from home. Indian Creek is not a gated community but has a lot of community amenities.In the 1st section of Indian Creek you will find ...

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Property Type

Kissimmee Villa

"Great Vacation"
Reviewed August 6, 2019

Attractions was good area was good everything about the trip was good my family and i had a good time we really enjoy our self cant wait for next year.

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Family Friendly Golf View Home, South Facing Pool & Tiki Bar

$169

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

Our beautiful 5 Bed, 4 Bathroom home is located on a generous corner plot. With a south facing Pool and stunning views over the second tee of the Arnold Palmer Golf Course on Reunion ResortIncluded within the rental is a one bedroom Guest Suite, ideally used for extended family.4 Bedrooms are ...

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Property Type

Kissimmee House

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Enjoy resort style living in this outstanding brand new lakeside home

$139

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

This two story 2 bedroom 2 & 1/2 bathroom townhome is located in Regal Oaks: the perfect location for your next Orlando getaway. Situated right behind Old Town with Fun Spot right next door, entertainment abounds. Take a stroll down the brick lined street of Old Town and wander into one of the specialty ...

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Property Type

Kissimmee Townhome

"Inquiry for rental for 2020 winter season"
Reviewed April 3, 2019

/we inquired to rent for February and March 2020 they wanted the full price paid now we expect to pay a deposit but not the full amount we have never encountered this before.

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LUXURIOUS 14B 13BA PRIVATE POOL/PATIO Sonoma Resort-2613CYA - Property 4831

$515

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Be sure to visit our website to check availability on all our homes!Visit us at lostinthemagic . comSonoma Resort - Kissimmee, Florida is only 15 minutes to the area's main attraction... Walt Disney World. This brand new resort community sits nestled just outside of Orlando, between W. Osceola ...

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Property Type

Kissimmee House

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***At Disney's Door*** Just 5 minutes to Animal Kingdom!

4 BR | 3 BA | Sleeps 10 | Quick View

1

Distance to park: 3 miles to Animal Kingdom, DIsney World

$193

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool
  • Rentals by Owner

About this property

Enjoy a magical Disney-style vacation at this luxurious Emerald Island Resort house. This luxurious private home includes a custom-built over-sized south-facing pool with Jacuzzi/spa. Constructed in the elegant Emerald Island Resort, this house offers all the latest features in vacation rentals. With ...

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Property Type

Kissimmee House

"Excellent Experience"
Reviewed February 27, 2018

This was a last minute booking so we were very pleased that Nancy could accommodate us.Having stayed here before we knew the villa and the service that Nancy would provide and once again we were not disappointed. ...

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Mickey's Villa -- New home now available! Wide-open calendar! Low rates!

5 BR | 4 BA | Sleeps 11 | Quick View

7

Distance to park: 4 miles to Disney World

$134

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly

About this property

Florida State License DWE5910390 (Near Disney) COME SWIM WITH MICKEY! 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. Featuring two en-suites with private baths and three other bedrooms and two ...

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Property Type

Kissimmee House

"Wonderful Stay"
Reviewed August 19, 2019

Loved the place. It was all that we needed to relax and unwind. The house was in great shape and it was a great location. Just minutes away from anything we needed. Walmart being right around the corner ...

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Formosa Gardens Villa

4 BR | 3 BA | Sleeps 6 | Quick View

$165

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool

About this property

Our Formosa Gardens Villa is a luxurious four bed/three bath executive home on the prestigious gated community of Formosa Gardens Estate, genuinely 2 miles (about 5 minutes) from Disney World. Our home is situated on a large 1/3rd acre lot with palm trees and shrubs affording privacy and a Floridian outlook ...

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Property Type

Kissimmee House

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Lovely 4 BR 2.5 bath townhouse with lakeview in a gated community near Disney

$120

per night

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Key Amenities

  • Air Conditioning
  • Pool

About this property

Fully furnished townhouse condo with 2 master suites. Sleeps 8. Located in a gated community called Coral Cay Resort. Parking for 3 vehicles. Wonderful heated pool and spa, 2 playgrounds, barbecue pits. Pets allowed to 30 lbs. There is a pet fee. Clubhouse has a gym, theater, reading area. Quiet community. ...

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Property Type

Kissimmee Townhome

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

$200

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

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

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Brand new 8br/6ba pool villa , Close to Disney

8 BR | 6 BA | Sleeps 18 | Quick View

5
Owner special: Last minutes deal from $260/nt

Distance to park: 8 miles to Disney World

$257

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

Windsor at Westside Resort is one of the newest and most luxurious resort communities in the Orlando/Kissimmee,Developed by one of the nation's largest developer , the Pulte Homes. Just 8 miles from Disney, and within easy reach to all the attractions, shopping, and dining in the Disney area, this 24 ...

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Property Type

Kissimmee House

"Wonderful Family Vacation"
Reviewed July 14, 2019

My family vacation was wonderful and the house was amazing! I definitely look forward to renting a home for my family's next vacation trip!⭐⭐⭐⭐⭐

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The Princess Villa in Emerald Island Close to Disney World

$200

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool
  • Rentals by Owner

About this property

Welcome to our beautiful villa close to Disney World . Our home fully is fully furnished and all the amenities to make your stay very enjoyable and comfortable. We have 2 kids theme rooms that little kids will enjoy sleeping in. We have 3 bunk beds in each of the theme rooms. In the garage has been ...

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Property Type

Kissimmee Villa

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Discover newly refurbished 4 BR Windsor Palms Resort

4 BR | 3 BA | Sleeps 9 | Quick View

Distance to park: 10 miles to Walt Disney World

$140

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

Enjoy Windsor Palms, featuring gated resort style living at its finest! This beautiful, Orlando vacation resort is just 3 miles (4.5 km) from the gates of Walt Disney World. The perfect location for families to enjoy Disney Magical Gatherings. Our totally remodeled and renovated home provides lots of ...

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Property Type

Kissimmee House

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Villa Cosy Kissimmee - Disney

3 BR | 2 BA | Sleeps 6 | Quick View

4

$95

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool
  • Rentals by Owner

About this property

Welcome to Villa Cosy Kissimmee! You will be seduced by our charming villa fully equipped for your stay. Conveniently located in the community of Creekside, in a family villa. Whether it is for a sensational vacation with the Orlando parks or just to enjoy the bright sunshine of Florida our home is ...

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Property Type

Kissimmee Villa

"Lovedddddd it!"
Reviewed June 18, 2019

awesome house I loved our stay me and my family enjoyed the pool and fools ball table in garage will most certainly rent again!

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Gigantic Pool 6 BR 4 BA, Two Themed Bedrooms, XBox/Games room

6 BR | 4 BA | Sleeps 13 | Quick View

Distance to park: 3 miles to Disney World Animal Kingdom

$249

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool
  • Rentals by Owner

About this property

Welcome to BigPoolVilla!Our 6 bed (3 en-suite masters) 4.2 bath villa (with a spectacular pool) is where you want to be - as close to Disney as it gets, only at 2 miles from Disney in the prestigious Rolling Hills at Formosa Gardens Estate on a QUIET street.The Pool is Gigantic it's in the top ...

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Property Type

Kissimmee Villa

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Sunset View

4 BR | 2.5 BA | Sleeps 8 | Quick View

1

Distance to park: 10 miles to Sea World

$120

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool
  • Rentals by Owner

About this property

If spaciousness is what you desire then Sunset View with over 2000 square feet of living area, is what you have been searching for. This large well equipped, fully air conditioned, 4 bedroom 2 1/2 bathroom home is set on a 1/5 acre plot with a larger than average 30 x 15 ft south west facing pool which ...

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Property Type

Kissimmee House

"Awesome property"
Reviewed May 14, 2018

Great property. Well maintained. Very pleasant and easy to deal with owner. Highly recommended

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Lakeside pool villa, kissimmee 3 miles disney

$171

per night

View Details

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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EVERYTHING HERE IS ON THE SECOND FLOOR; 5 BEDROOMS AND 4 BATHROOMS

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

EVERYTHING HERE IS ON THE SECOND FLOOR; 5 BEDROOMS AND 4 BATHROOMS; GREAT FLOORPLAN WHERE EVERY BEDROOMIS CONNECTED TO A BATHROOM. TWO BEDROOMS ARE MASTER BEDROOMS AND THE OTHER 4 BEDROOMS ARE BOTH SET UPAS JACK N JILL. IF ONLY 5 BEDROOMS IN THE HOUSE WERE USED, IT COULD BE SET UP AS ALL THOSE ...

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Property Type

Kissimmee Apartment

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SPECTACULAR, NEW, NEAR DISNEY AND LOW $'S!!

3 BR | 2 BA | Sleeps 6 | Quick View

Distance to park: 4 miles to Disney World

$125

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

This beautiful, professionally designed and furnished ground floor (no steps) Disney World area home has just been completed and is ready and waiting for you and your family!This amazing home sleeps up to 6 and it's just 12 minutes from Disney World and only 15-20 minutes from Universal, Sea World, ...

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Property Type

Kissimmee Condo

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2 bedroom Resort Luxury Condo. 4721C

$89

per night

View Details

Key Amenities

  • Air Conditioning
  • Kid Friendly
  • Pool
  • Private Pool

About this property

1 King, 1 bunk bed (Full over Full) Welcome to this brand new luxury 2 bedroom Resort Condo in the fabulous Storey Lake Resort community close to the parks. This Condo features a King suite and a bedroom with bunk beds for the kids.Only minutes to Disney, Seaworld, Universal Orlando, Premium Outlets ...

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Property Type

Kissimmee House

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Perfect 9 Bed Resort Vacation Home. 8899

$189

per night

View Details

Key Amenities

  • Air Conditioning
  • Kid Friendly
  • Pool
  • Private Pool

About this property

6 kings, 2 full, 2 twin, 1 bunk with trundle Introducing our newest 9 bedroom luxury Resort home in the fantastic Windsor at Westside Resort.No expense has been spared to furnish this 9 bedroom home with 2 bedrooms on the main floor and an additional 7 bedrooms on the second floor.You will ...

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Property Type

Kissimmee House

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Holiday Rest

3 BR | 2 BA | Sleeps 7 | Quick View

1

$98

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool
  • Rentals by Owner

About this property

Thinking about taking a Florida Vacation? Why not stay at our wonderful 1950 Sq ft property with three spacious bedrooms two bathrooms. Feature a fantastic floor plan with ceramic Tiles throughout. Master bedroom has a King sized bed, TV, Jacuzzi, stand up shower, his /her sink and a walk in closet. ...

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Property Type

Kissimmee House

"Our vacation house"
Reviewed February 19, 2018

Found the property very nice, close to all our vacation needs, owner and property manager attentive and friendly, on a personal note the pool did not get warm enough for my taste, good experience

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Modern Private Pool Home with Amazing Golf View. 733

$189

per night

View Details

Key Amenities

  • Air Conditioning
  • Kid Friendly
  • Pool
  • Private Pool

About this property

3 Kings, 2 Full, 1 Bunk Full over Twin Welcome to our newest addition to Reunion Resort. Enter this luxurious 5 bedroom 4 bath pool home in the prestigious Reunion Golf Resort.This brand new home has just been newly finished and furnished and is now ready to reserve today.Enjoy the magnificent ...

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Property Type

Kissimmee House

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

$75

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • 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, olympic-size swimming pool, toddler pool, hot tub, picnic and barbecue area, outdoor bar, convenience ...

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Property Type

Kissimmee Condo

"Fantastic, close to everything you'll need for a super holiday"
Reviewed June 25, 2019

It's 5 minutes drive to the Disney parks and has a great selection of dinning, close to the condo. The condo was smartly furnished and has everything you could need for a great holiday. It couldn't be any ...

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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

3

Distance to park: 10 miles to Disneyworld

$120

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • 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

"Home Away From Home"
Reviewed July 10, 2019

We Loved this home. This is the best vacation home!! It is wonderfully themed and has everything you would need!! We went down for a week and had 3 small children and they could have cared less if we went ...

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Homestead Vista - Arcade Room, Amazing Custom Bunk Beds & Golf Course Views

$399

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

This luxury custom home is located right on the stunning Reunion Resort golf course and just 6 miles to the gates of Disney.Enjoy one of the best outlooks in Reunion from the southeast facing pool deck, unobstructed views of holes #7 and #8 of the beautiful Tom Watson golf course. The private pool ...

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Property Type

Kissimmee House

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Heritage Charm - 3 Bedroom Luxury Condo | Top Floor with Amazing Views

$89

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly

About this property

This spectacular third floor 3 bed, 2 bath 1,352 sq ft. condo in Heritage Crossing has amazing views over 5 different holes on the Reunion Palmer golf course. Enjoy beautiful sunsets from your own private balcony with the magnificent heritage crossing pool and hot tub just a few steps away. The living ...

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Property Type

Kissimmee Condo

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

$99

per night

View Details

Key Amenities

  • Air Conditioning
  • Full 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

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Fairway Joy | 5 Bedroom Pool Home with Extended Pool Deck and Conservation Views

$209

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

This luxurious and comfortable home is located in Reunion Resort and has 3,203 square feet of living space, complete with a pool and balcony. The location of this property allows you to enjoy the resort’s many amenities and attractions that central Florida has to offer.This vacation home is ...

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Property Type

Kissimmee Villa

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3 Miles From Disney - Pet Friendly - Free Wifi - Grill - AC - Baby Equipment

$186

per night

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Key Amenities

  • Air Conditioning
  • Kid Friendly
  • Pet Friendly
  • Pool
  • Private Pool

About this property

The large, fully-equipped kitchen is complete with a microwave and dishwasher! The home’s layout is perfect for watching the fun going on in the pool area from the living room, dining area and kitchen! The fully equipped kitchen offers everything you need to feel at home; both a Kuerig coffee maker ...

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Property Type

Kissimmee House

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True Champion | 4 Bedroom Pool Home in Champions Gate

$139

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Enjoy these amenities and more at The Retreat, only 6 miles from Reunion and 12 miles to the gates of Disney World®.Cool off and relax in the private pool after you’ve been out on your Orlando adventures. The whole family is sure to enjoy this home during vacation. Book this home today!

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Property Type

Kissimmee House

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Solterra Paradise Villa | Extended Pool Deck, Movie Room, Amazing Kids Bedrooms

$599

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

Located just minutes from Orlando's theme parks, shopping, dining and other area attractions, this luxury villa is located in Solterra Resort. Solterra resort is just a 5 minute (2.5-mile) drive from a Publix supermarket and other stores. There is also an IMAX movie theater and many other stores such ...

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Property Type

Kissimmee Villa

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Ultimate Villa | Huge South Facing Deck, Movie Room, Multiple Arcades, Tiki Bar

$799

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

SR_910RLocated just minutes from Orlando's theme parks, shopping, dining and other area attractions, this luxury villa is located in Solterra Resort. Solterra resort is just a 5 minute (2.5-mile) drive from a Publix supermarket and other stores. There is also an IMAX movie theater and many other stores ...

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Property Type

Kissimmee Villa

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Champions Escape | 2 Kids Bedrooms and Games Room with Pool Table, Screened Pool

$240

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

airs you will find the master suite featuring a king bed with large en-suite bathroom with walk in showers and large counter space. There is a second bedroom downstairs with king bed and attached shared bathroom.Upstairs you will find the additional 6 bedrooms, 2 of which are kids themed rooms, a ...

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Property Type

Kissimmee House

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Orlando Disney Vacation 1,2 & 3 Bedroom Condos at Orange Lake Resort Send to a

$157

per night

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Key Amenities

  • Air Conditioning
  • Kid Friendly

About this property

Stay in one of Florida's finest and one of a kind resorts, Orange Lake Country Club. I was in awe from the first time I visited back in 2006 and have returned every year since. Can book 1, 2 and 3 bedroom Condos if contacted at least 3 months prior to travel. The 5 Star accommodations has everything needed ...

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Property Type

Kissimmee House

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3 Miles From Disney - Pet Friendly - Free Wifi - Grill - AC - Baby Equipment

$186

per night

View Details

Key Amenities

  • Air Conditioning
  • Kid Friendly
  • Pet Friendly
  • Pool
  • Private Pool

About this property

Sleeps 8-10. Beachy decor. 2 master suites (one king / one queen) both with private bathrooms. 2 twin bedrooms / 2 twin beds each share the 3rd bathroom. Queen sofa sleeper in the living room. Private pool and free standing hot tub. Extra large fenced rear yard. Great for kids and pets (2-3 pet with paid ...

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Property Type

Kissimmee House

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Reunion Manor | Luxury 8 Bed Home, Custom Kids Bedrooms, Balcony w/ great views

$740

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Private Pool

About this property

Truly one of a kind custom, luxury home situated inside of the world famous Reunion Resort. The home is located within the well established Homestead community boasting spectacular views of the Independence golf course.Stepping into the grand entrance of the exquisitely designed home, you will be ...

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Property Type

Kissimmee House

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Golden Villa | 6 Bed 4 Bath Pool Home with Golf Course Views in Reunion Resort

$235

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

Enjoy comfort during your next vacation in this gorgeous 6 bedroom 4.5 bath, the perfect home for you and your family to stay in. Located in the Reunion Resort allows for you to easily access world-famous theme parks and attractions.As soon as you pull into the driveway of your new vacation home you’ll ...

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Property Type

Kissimmee Villa

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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 20% over our competitors. Plus, we have a wide array of inventory appealing to any group size or traveler tastes. Book today!