Kissimmee Vacation Rentals

(359 rentals)
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4 BR | 3 BA | Sleeps 8 | Quick View

7
Owner special: Save 10-35% off of Last-Minute Bookings! *Price listed includes already discounted rates

$229

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Storey Lake - Kissimmee is a brand new vacation community located just 4 miles from the magical world of Disney and just minutes to Universal, Sea World and the many water parks in the area. Central Florida is also home to some of the nation's top-rated golf courses and many are within a 10-minute drive ...

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Property Type

Kissimmee Townhome

"My stay :::@" LAKE BERKLEY 2022"

We had fabulous time & I would definitely refer this place to everyone you was so clear about everything & the property Mgr always answered our phone calls loved it 100% satisfied

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool

About this property

A beautiful vacation condo located in a prestigious gated and guarded community, for you to relax and spend time with your family and friends. With the prime location in Kissimmee near Disney World, major parks and restaurants, shops and so much more, this 3BD/2BA condo unit is designed for your best ...

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Property Type

Kissimmee Condo

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8 BR | 5 BA | Sleeps 16 | Quick View

Owner special: Save 10-35% off of Last-Minute Bookings! *Price listed includes already discounted rates

$594

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

The Retreat at Champions Gate - Kissimmee, Florida is a new upscale gated resort community located just 12 miles from Walt Disney World. This luxury home sits nestled just outside of Orlando, Florida and will quickly become one of the most desired locations in the Orlando area. During your stay, you will ...

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Property Type

Kissimmee House

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Key Amenities

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

About this property

Make unforgettable family memories that will last a lifetime on your next stay at our massive and luxurious home! Located near Orlando's attractions, shopping and theme parks, you'll have access to 2 themed game rooms and all the bells & whistles - think gourmet kitchen, huge living area complete ...

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Property Type

Kissimmee Villa

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8 BR | 5 BA | Sleeps 21 | Quick View

Distance to park: 4 miles to Major Disney Theme Parks

$673

avg/night

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Key Amenities

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

About this property

Free pool heating! Sleeps 21. Complimentary access to the luxurious Storey Lake clubhouse. Perfect for families and work trips, staycations and vacations. Four miles to Disney theme parks. Quick access to all of Orlando's attractions. Play Star Wars electronic pinball, pool, and foosball in the spacious ...

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Located just 4 miles west of Walt Disney World® off of Highway 192, Lindfields remains one of the most popular and sought after areas for holiday makers to central Florida. This sub division offers wide boulevards, tranquil lakes and peaceful cul-de-sacs, with little traffic.Established in the ...

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Property Type

Kissimmee Villa

"AWESOME!!"

Love this place. Would def recommend It to anyone !! Awesome location as well. Close to grocery stores and most importantly close to Disney world !! We wanted to stay longer get than 6 nights !

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8 BR | 6 BA | Sleeps 16 | Quick View

3
Owner special: Save 10-35% off of Last-Minute Bookings! *Price listed includes already discounted rates

$369

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen

About this property

Windsor at Westside - Kissimmee, Florida is an upscale gated community located just 10 minutes from Walt Disney World. This luxury home sits nestled just outside of Orlando, Florida, and has quickly become one of the most desired locations in the Orlando area. During your stay, you will enjoy this well-appointed ...

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Property Type

Kissimmee House

"Nice Experience"

This was a nice central location, about 20 miles from Universal and 12 from Magic Kingdom. We had plenty of room for our group of 11. My kids loved the pool, but prepare yourself as the water may be cool. ...

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8 BR | 6 BA | Sleeps 16 | Quick View

4.8 rating on other travel sites

$525

avg/night

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Key Amenities

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

About this property

"This home is so much fun and is the best we have ever stayed in! The 2 theaters were a hit, and my kids could not get enough of the game room. So much to do in there- play pool, foosball, air hockey, shuffleboard, arcade style video games and PS4 games. We also spent so much time enjoying the private ...

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Property Type

Kissimmee House

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9 BR | 6.5 BA | Sleeps 22 | Quick View

4.9 rating on other travel sites
LAST MINUTE DEAL 1/20 - 3/3: Great Last Minutes Rates.

$557

avg/night

View Details

Key Amenities

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

About this property

**Special Offer** 10% off stays of 7 nights or longer. Welcome to Big Top Family Vacation Villa. Located in Solara Resort, this massive, modern, professionally decorated villa has 9 bedrooms, 6.5 bathrooms, sleeps 22 and is located just 8 miles from Disney World. With a Circus themed game room, private ...

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Property Type

Kissimmee Villa

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DEAL

6 BR | 4 BA | Sleeps 14 | Quick View

5.0 rating on other travel sites

$438

avg/night

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Key Amenities

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

About this property

"We have stayed in many Windsor hills homes and this is THE one to stay in! Beautifully decorated, fun and so comfortable!" Beth MARE YOU LOOKING for a very special vacation home? This is it . . . Totally renovated by a professional decorator and includes an incredible game room, a private ...

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Property Type

Kissimmee House

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7 BR | 4.5 BA | Sleeps 14 | Quick View

3

Distance to park: 4 miles to Animal Kingdom

$250

avg/night

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Key Amenities

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

About this property

Conveniently located on the Exclusive Emerald Island Resort. With 7 Bedrooms and 4.5 bathrooms, Berni’s Home from Home can easily accommodate two families travelling together or will give one family plenty of space.Enjoy relaxing by your very own private extended south facing pool or spend some ...

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Property Type

Kissimmee Villa

"Very well maintained home"

This home was lovely and very well kept. Would rent again if the occasion arose that we needed a home this big again.

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4 BR | 2 BA | Sleeps 8 | Quick View

$210

avg/night

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Key Amenities

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

About this property

This is a NON SMOKING HOME *Community: Citrus RidgePets: NO Pets.Rooms: 4 Bedrooms, 2 Bath rooms. En-suite in Master bedroom. Sleeper 8 peopleBed Configuration: Bedroom 1: King size bed with en-suite, and walk in closet. Bedroom 2: Queen size bed. Bedroom 3: 2 Single beds. Bedroom ...

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Property Type

Kissimmee House

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4 BR | 3 BA | Sleeps 8 | Quick View

3

Distance to park: 12 miles to Disney World

$135

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Beautiful lakeside home with a private south facing pool in a gated community 12 miles from Disney. Enjoy fishing in the lake behind the house. Game room with pool table, skeet ball, foosball table and a gaming system with hundreds of old favorites like Pac Man and Mario Brothers. 4 bedrooms and 3 bathrooms. ...

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Property Type

Kissimmee House

"Wonderful home"

This is a beautiful home to stay in. It had all the comforts of your own home, incredible view from the huge pool, lots of wildlife and friendly neighbors. The owners are super nice and so easy to work ...

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6 BR | 4 BA | Sleeps 14 | Quick View

4.9 rating on other travel sites

$514

avg/night

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Key Amenities

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

About this property

"When you walk through the front door, you immediately walk into fun with the adult area's pool table and large TV. And that's just the beginning. There's an awesome game room, 3 themed bedrooms, and in the pool area are a poolside theater and bar counter with TV. You will be totally entertained ...

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

This fabulous 4 Bed Villa is located in a peaceful corner of Lake Berkley Resort with beautiful views to the Conservation Area and one on the lakes at Lake Berkley.The villa is fully equipped with everything you will need including air con throughout, private pool, WiFi, fully equipped kitchen, laundry ...

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Property Type

Kissimmee Villa

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4 BR | 3 BA | Sleeps 8 | Quick View

5

Distance to park: 4 miles to Disney World

$147

avg/night

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Key Amenities

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

About this property

Enjoy Orlando, Florida, home to Disney World, Sea World, Universal Studios, and Islands of Adventure, in style. Conveniently located on the Exclusive Emerald Island Resort. The house is spacious where family can enjoy being together and also have some alone time. Our home is within minutes of all the ...

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Property Type

Kissimmee House

"Family Vacation"

The house and location was perfect. Everyone enjoyed the stay at the house; very spacious for us. The swimming pool was the absolute best. We would definitely stay here again.

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Key Amenities

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

About this property

Amazing 2BD / 2BA in the beautiful community of Storey Lake Resort Style, perfect stay to relax, have a good time with family/friends, and of course, enjoy the parks and many attractions that Orlando offers.Two comfortable rooms accommodate 6 guests: one king bed in Master Suite with smartTV and private ...

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Property Type

Kissimmee Apartment

"Apartments"

Me encantó el apartamento, muy moderno y cómodo. Lo recomiendo para 5-6 personas. Buenísima ubicación.

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3 BR | 2 BA | Sleeps 8 | Quick View

8

Distance to park: 12 miles to All Disney Theme Park

$109

avg/night

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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 it ...

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Property Type

Kissimmee Villa

"Vacation"

our stay her was nice. It had all our basic needs and a nice private pool. We plan to return to this home on our next trip. The only thing we haven't received our deposit yet. But I'm sure it will be soon.

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8 BR | 6 BA | Sleeps 16 | Quick View

4.9 rating on other travel sites

$636

avg/night

View Details

Key Amenities

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

About this property

"This was our first time renting a home for a vacation. This vacation rental has changed our future vacation options forever. Everything about the home and community was A+. The kids didn't want to leave and the grown ups enjoyed the amenities more than the kids. I would recommend this home for rental ...

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Property Type

Kissimmee House

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4 BR | 3 BA | Sleeps 8 | Quick View

Owner special: Save 10-35% off of Last-Minute Bookings! *Price listed includes already discounted rates

$229

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

The Retreat at Champions Gate - Kissimmee, Florida is a new upscale gated resort community located just 12 miles from Walt Disney World. This townhome sits nestled just outside of Orlando, Florida and will quickly become one of the most desired locations in the Orlando area. During your stay, you will ...

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Property Type

Kissimmee Townhome

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10 BR | 8 BA | Sleeps 20 | Quick View

3
Owner special: Save 10-35% off of Last-Minute Bookings! *Price listed includes already discounted rates

$558

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Sonoma 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 and W. Irlo Bronson Memorial Hwy and conveniently located next to "The Loop", a premier shopping ...

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Property Type

Kissimmee House

"Nice place for big family"

We rented this home for Thanksgiving, we had plenty of room, and space for us all. Wonderful club house. The best of all the kids loved the pool. Our own pool.

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Key Amenities

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

About this property

About this spaceWhat makes this listing special? This Premier Vacation Home is perfect for family gatherings, generational family reunions, and for creating lasting memories. You will have access to your own movie theater, private pool, spa and game room. The kids will absolutely love their very ...

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Property Type

Kissimmee House

"The house has enough entertainment for a week."

OMG! The house is amazing! You don’t even need to go to Disney. The house has enough entertainment for a week. Tim was also amazing and very responsive. Our kids had so much fun and it was an unforgettable ...

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Key Amenities

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

About this property

Immerse yourself in this much-beloved world and find the hidden easter eggs in the room as you open the door to Potter's Place. This charming open-concept themed home is ready to make you feel revitalized. From a cleaned, well-maintained space to a fully equipped kitchen to cozy beds and pillows, your ...

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Property Type

Kissimmee Townhome

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Key Amenities

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

About this property

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

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Property Type

Kissimmee Villa

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3 BR | 2 BA | Sleeps 6 | Quick View

Owner special: Save 10-35% off of Last-Minute Bookings! *Price listed includes already discounted rates

$144

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen

About this property

Reunion Resort -Kissimmee, Florida is only 15 minutes to the area's main attraction... Walt Disney World. This gated luxury resort sits nestled just outside of Orlando, Florida and has quickly become one of the most desired resorts in the Orlando area. This home will provide you and your family with an ...

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Property Type

Kissimmee Condo

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9 BR | 5 BA | Sleeps 18 | Quick View

Owner special: Save 10-35% off of Last-Minute Bookings! *Price listed includes already discounted rates

$621

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Storey Lake - Kissimmee is a brand new vacation community located just 4 miles from the magical world of Disney and just minutes to Universal, Sea World, and the many water parks in the area. Central Florida is also home to some of the nation's top-rated golf courses and many are within a 10-minute drive ...

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Property Type

Kissimmee House

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Key Amenities

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

About this property

12 Min Drive to Disney World20 Min Drive to SeaWorld26 Min Drive to Universal StudiosLocated in the gated Storey Lakes resort, this modern 8 bedroom, 5 bathroom home is the perfect place for large groups looking to stay near all the action of central Florida. Aside from an amazing location, ...

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Property Type

Kissimmee Villa

"Excellent stay in the magical mansion!"

Great place, very clean and comfortable. Kids had a blast in the game room and cars room. The movie theater was perfect! Loved the modern and contemporary style of the home with tons of space for everyone ...

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6 BR | 3.5 BA | Sleeps 14 | Quick View

4.8 rating on other travel sites

$495

avg/night

View Details

Key Amenities

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

About this property

"Something for everyone - fun, beauty, and comfort. There's so much to love! Everyone will love the incredible Avengers game room; it is like no other. Plus, all will love the heated pool and spa. Kids will love the themed bedrooms. And, adults will love the professionally decorated beauty of the ...

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Property Type

Kissimmee House

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8 BR | 6 BA | Sleeps 16 | Quick View

4.5 rating on other travel sites

$567

avg/night

View Details

Key Amenities

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

About this property

"Kids and adults love the game room. Really cool. Movie theater in the converted garage is incredible - better than being at a regular movie theater. And, maybe your biggest treat will be the poolside theater. Very pretty and comfortable home and full of fun." Keith C.LOOKING for an incredibly ...

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Property Type

Kissimmee House

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6 BR | 5.5 BA | Sleeps 18 | Quick View

54

Distance to park: 4 miles to Animal Kingdom

$219

avg/night

View Details

Key Amenities

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

About this property

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

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Property Type

Kissimmee House

"Fantastic Disney Vacation Rental Home"

We throughly enjoyed our stay in your lovely home! The location was perfect, as it allowed us to get to and from the parks in minimal time. We loved having the 4 master bedrooms with their own private bathrooms! ...

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Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Our beautiful 3 bedroom, 2 bathroom pool home is ideally located in thequiet residential community of Liberty Village, Kissimmee. Conveniently situated close to Disney and the other major theme parks. There are several restaurants, shopping and World-Class Golf is nearby.The villa sits on a ...

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Property Type

Kissimmee Villa

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6 BR | 4 BA | Sleeps 12 | Quick View

4.7 rating on other travel sites
LAST MINUTE DEAL 1/18 - 3/1: 25% off this month!

Distance to park: 2 miles to Disney World

$435

avg/night

View Details

Key Amenities

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

About this property

Welcome to Oasis by KLMJ Sunshine! Completely renovated (2022), this villa is in the #1 location in the beautiful gated community of Windsor Hills, just two miles from Disney. Enjoy complimentary pool & spa heat, themed rooms, and the only private Virtual Reality studio in the area! This is the 2nd ...

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Property Type

Kissimmee Villa

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DEAL

3 BR | 2 BA | Sleeps 8 | Quick View

3

Distance to park: 12 miles to All Disney Theme Park

$109

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 it ...

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Property Type

Kissimmee Villa

"2021 vacation"

A well kept nice home. Everything as shown in the pictures. Excellent communication from owner and the property manager.

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5 BR | 4 BA | Sleeps 12 | Quick View

2
LAST MINUTE DEAL 1/19 - 2/17: Discounted Rates for January/February

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

$377

avg/night

View Details

Key Amenities

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

About this property

Imagine coming home at the end of an exhilarating day at the theme parks...You grab a refreshing drink from the fridge, flake out on the sofa in the outdoor living area right by the pool and reminisce about all the amazing things you did that day.The kids are splashing around in the pool, you ...

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Property Type

Kissimmee House

"Family Birthday Vacation"

Everything was great! The house was very spacious. The back area a bit small but still great! We had a blast!

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DEAL

4 BR | 2 BA | Sleeps 7 | Quick View

2

$150

avg/night

View Details

Key Amenities

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

About this property

WELL CARED FOR HOME IN LOVELY COMMUNITY. HOME BACKS TO CONSERVATION SO YOU ARE NOT OVERLOOKED AND IS A FEW STEPS FROM RETENTION POND WITH POND VIEWS FROM THE POOL DECK. SHADED PATIO WITH TABLE AND CHAIRS .KING, KING AND 4 TWIN BEDS WITH THEMED TWIN BEDROOMS - LITTLE MERMAID AND DORY. TV IN ALL ...

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Property Type

Kissimmee House

"Excellent villa in great location."

Very good villa for our two week holiday. The villa was equiped with everything we needed for our holiday. Host was very friendly and helpful. Happy to return for a future visit.

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5 BR | 5 BA | Sleeps 10 | Quick View

Owner special: Save 10-35% off of Last-Minute Bookings! *Price listed includes already discounted rates

$352

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

The Retreat at Champions Gate - Kissimmee, Florida is a new upscale gated resort community located just 12 miles from Walt Disney World. This luxury home sits nestled just outside of Orlando, Florida and will quickly become one of the most desired locations in the Orlando area. During your stay, you will ...

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Property Type

Kissimmee House

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8 BR | 5 BA | Sleeps 16 | Quick View

Owner special: Save 10-35% off of Last-Minute Bookings! *Price listed includes already discounted rates

$635

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

The Retreat at Champions Gate - Kissimmee, Florida is a new upscale gated resort community located just 12 miles from Walt Disney World. This luxury home sits nestled just outside of Orlando, Florida and will quickly become one of the most desired locations in the Orlando area. During your stay, you will ...

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Property Type

Kissimmee House

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5 BR | 5 BA | Sleeps 12 | Quick View

5.0 rating on other travel sites

$479

avg/night

View Details

Key Amenities

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

About this property

"We just got home from our 1 week stay and are already wishing we were back! The home was beautiful and looked just as pictured in the listing. We were very close to the parks and shopping but yet felt like we were secluded. The neighborhood is wonderful and was great for walks. The pool and game ...

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Property Type

Kissimmee House

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4 BR | 3 BA | Sleeps 8 | Quick View

15

Distance to park: 4 miles to Disney

$149

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Magical Dreams come true in our elegant private 4 bedroom villa, 3 bathroom, all located on one floor, Quiet upgraded comforts of home and luxuries of an exceptionally rated vacation resort/hotel. Newly resurfaced and freshly painted pool and spa is sure to impress. There will be no waiting in line ...

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Property Type

Kissimmee House

"Had everything we needed"

Property was very clean and the beds were comfortable. The heated pool & the hot tub were awesome, especially after being on our feet at the Disney parks, plus our kids loved swimming on our off day. Overall ...

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Key Amenities

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

About this property

A beautiful vacation condo located in a prestigious gated and guarded community, for you to relax and spend time with your family and friends. With the prime location in Kissimmee near Disney World, major parks and restaurants, shops and so much more, this 3BD/2BA condo unit is designed for your best ...

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Property Type

Kissimmee Villa

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Key Amenities

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

About this property

Our beautiful 3000sq 5 Bed, 4 Bathroom home is located on a generous corner plot. With a south facing Pool and stunning views over the second tee of the Arnold Palmer Golf Course on Reunion ResortThe open plan living area is comfortably furnished and has a wood look tiled floor. Flat screen tv. ...

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Property Type

Kissimmee House

"Beautiful"

We had such a wonderful vacation at this home! It was big enough for all of us, clean and equipped fully with everything that we needed. Vicky and Jackie were just a text away if we needed anything or just ...

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Key Amenities

  • Air conditioning

About this property

Looking to take the Family on an unforgettable vacation? Then look no further! This luxurious, single story home has it all! A well appointed game room, modern and colorful design, and a private pool & spa with covered lanai! Best of all, this home is only about 10 minutes away from the theme parks!Nestled ...

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Property Type

Kissimmee Villa

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Key Amenities

  • Air conditioning
  • Pool

About this property

*Updated Cleaning Standards - Your Safety is Our Primary Concern* Due to the COVID-19 health and safety concerns, we are taking additional steps to ensure you and all our guests are safe. We are focusing extra attention on high-traffic & high-touch areas, such as counter tops & surfaces, railings, ...

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Property Type

Kissimmee Townhome

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4 BR | 3 BA | Sleeps 8 | Quick View

20

$140

avg/night

View Details

Key Amenities

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

About this property

Indian Creek Disney Retreat is a beautiful 1800SF, well maintained home in the Indian Creek subdivision which is literally on Disney's doorstep and your home away from home. Indian Creek is not a gated community but has a lot of community amenities.COVID-19 Precaution Implementations: We have installed ...

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Property Type

Kissimmee Villa

"Comfortable House for Disney Park Trip"

The house was very comfortable, spacious and clean. It was near the Disney parks and had everything we needed to prepare breakfast and some late night dinners. We didn't spend much time at the house as ...

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

If cozy decor, epic themed bedrooms, and multiple entertainment quarters are at the top of your vacation checklist, look no further than this adorable villa—located just minutes from Disney World in the amazing new Solara Resort! The kids will marvel at the wizard-themed bedroom, featuring life-sized ...

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Property Type

Kissimmee House

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6 BR | 4 BA | Sleeps 14 | Quick View

5.0 rating on other travel sites

$475

avg/night

View Details

Key Amenities

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

About this property

ARE YOU LOOKING for a just renovated beautiful vacation home that is full of fun? This is it . . . Avenger theme game room - South facing (plenty of sun) private saltwater pool and spa - Poolside movie theater - Themed kids bedrooms - And much more. Also, it's located in Windsor Hills Resort - the closest ...

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Private pool

About this property

RECENTLY REFURBISHEDLuxurious Windsor Palms with an extra wide cul de sac lot and with a pool that is not overlooked. Our guests enjoy terrific privacy in one of the premier resorts in the Disney vicinity. We have a south facing pool with kiddy pool and stand alone hot tub. Numerous child friendly ...

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Property Type

Kissimmee Villa

"Relaxing vacation"

We just spent a week at this house. There were 5 adults and plenty of room for all of us. It was great having a full kitchen to cook our meals and Walmart was very close for groceries. The house was ...

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10 BR | 8 BA | Sleeps 20 | Quick View

4
Owner special: Save 10-35% off of Last-Minute Bookings! *Price listed includes already discounted rates

$677

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Sonoma 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 and W. Irlo Bronson Memorial Hwy and conveniently located next to "The Loop", a premier shopping ...

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Property Type

Kissimmee House

"Awesome house!"

We held our annual Married Couples Retreat. It was above and beyond all of my expectations. More than enough room for everyone that no one was on top of each other. Definitely will yes again!

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6 BR | 4 BA | Sleeps 14 | Quick View

4.8 rating on other travel sites

$501

avg/night

View Details

Key Amenities

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

About this property

"What a delightful home! It exceeded all of our expectations...There was a television in almost every room, two living rooms with comfortable seating, coffee bar, game room, fun children's bedrooms with a "secret room", pool with large movie screen, and plenty of outdoor loungers and seating...I ...

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Property Type

Kissimmee House

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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."

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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Kissimmee Vacation Rentals

Kissimmee Weather

 | 

7222°  489°
JANUARY
7323°  499°
FEBRUARY
7725°  5312°
MARCH
8228°  5814°
APRIL
8731°  6418°
MAY
9032°  7021°
JUNE
9233°  7222°
JULY
9233°  7222°
AUGUST
9032°  7122°
SEPTEMBER
8429°  6518°
OCTOBER
7926°  5714°
NOVEMBER
7323°  5010°
DECEMBER

Soak up the Sun on Your Next Trip to Kissimmee Vacation Rentals

There’s nothing quite like a vacation to sunny Florida, a unique and inviting state with a huge variety of distinctive cities and natural areas to explore. One popular vacation destination in Florida is Kissimmee, a charming city with plenty to see and do just south of the Orlando metropolitan area. 

Kissimmee has a lot more to offer visitors than just excellent weather year-round. With a huge variety of scenic nature, shopping opportunities, and outdoor activities, Kissimmee itself has lots to offer every member of the family, not to mention its extremely close proximity to some of Orlando’s biggest amusement parks. 

You could stay in a busy hotel during your trip to Kissimmee, but then you wouldn’t be able to get a truly immersive experience of local city life. Kissimmee vacation rentals allow you to enjoy Kissimmee from inside its authentic residential neighborhoods. Additionally, having your own home to live in rather than a jam-packed hotel will provide some much-needed peace and quiet during your vacation. It will also offer plenty of space for the whole family to spread out.  

Top Tips for Traveling to Kissimmee Rentals

Like most other Florida cities, Kissimmee enjoys sunshine and clear skies throughout the majority of the year. However, the tropical climate of the state means that bouts of rain can occur throughout the seasons, particularly during the summer months, peaking in August. 

In addition to a higher likelihood of rain, the summer season in Kissimmee tends to be the most humid time of year. That’s why most vacationers choose mid to late spring or early autumn to make their trip to the city. At those times of the year, vacationers can enjoy great weather and lots of outdoor activities. 

Though the Kissimmee Gateway Airport is located centrally within the city, most vacationers taking commercial flights will fly into Orlando International Airport. It is located roughly 17 miles northeast of the city center, about halfway between Kissimmee and Orlando. Vacationers coming in from elsewhere in Florida can access Kissimmee by road using U.S. Route 192 and U.S. Route 441.

Things to Do Nearby Kissimmee House Rentals

Some of the most popular natural areas around Kissimmee are the swamps, which are located in major local bodies of water like Lake Tohopekaliga (known around town as Lake Toho). At Boggy Creek Airboat Adventures, you can experience the swamps from the water and get the thrill of a lifetime on an airboat driven by a local wetlands expert. Get up-close views of gator ponds, discover precious gemstones, and then grab a delicious lunch with the family at Boggy Bottom BBQ! 
Looking to explore a piece of history during your trip to Kissimmee? Medieval Times Dinner & Tournament allows visitors to step into the 11th century for an evening of authentic feasting, jousting, and sword fighting in true medieval style! Enjoy a delicious four-course meal, incredible performances, and a truly unforgettable experience for the entire family. 
Any vacation to Kissimmee isn’t complete without a trip or two to Old Town, a popular outdoor attraction with opportunities for shopping, dining, and family fun. Old Town is made up of an 18-acre stretch of classic city attractions, including the Old Town Ferris Wheel, the Great Magic Hall, and Mortem Manor, a year-round haunted house that is open for visitors to explore.
Kissimmee Annual Events

Kissimmee is a vibrant area with lots of annual festivals and events to enjoy in and around the city throughout the year. Kissimmee locals and visitors alike flock to the Ford Cuban Sandwich Festival each May near downtown Kissimmee, which celebrates the colorful history of Cuban cuisine in the area. Watch as local dining professionals attempt to build the world’s biggest Cuban sandwich during the event! 
The Ford Taste of Latino Festival is another local opportunity to celebrate and experience the best in authentic Latin cuisines in Kissimmee. The event features a contest to find the Top Latino Chef as well as plenty of live music and dance performances to enjoy as you taste a variety of Latin dishes. 
Not sure if you’ll be in town for any of Kissimmee’s larger annual events? You can enjoy Show Car Saturday Nights every Saturday night in the city on Margaritaville Boulevard. Check out the city’s best classic cars from a variety of eras and enjoy the plethora of delicious eateries and exciting shops located along the boulevard.

Wining and Dining in Kissimmee  

Between your outdoor activities and trips to local amusement parks while in Kissimmee, you’re sure to need some satisfying food and refreshing drinks to complete your perfect day. Luckily, Kissimmee is home to some of the best restaurants that Florida has to offer, combining authentic local flavors with worldly cuisine. 

To start your day off right with a delicious and hearty breakfast, look no further than Woodsby’s Countryside Café. This spot has authentic, cozy diner vibes to spare, not to mention a stacked menu of classic breakfast favorites, coffee bar items, and unique dishes you won’t want to miss out on. 

Tarantino’s Italian Restaurant is a great choice for a vacation date night or simply a nice dinner out with the family. A hearty Italian meal is a great way to finish a fun day of activities, and you’re sure to get that and more at Tarantino’s. If you bring the family along, you can take advantage of the takeout dinner special, which feeds four and includes a massive entrée, salad, and garlic bread.


FAQ

How many vacation rentals are there in/around Kissimmee?

There are 359 Kissimmee vacation rentals available on FloridaRentals.com. From house rentals to villa rentals and beyond, find a unique vacation rental for you to enjoy a memorable vacation in Florida.

How much does it cost to rent a vacation rental in Kissimmee?

There are vacation rentals available in Kissimmee for as low as $85 per night with an average price per night of $251.

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