Kissimmee Vacation Rentals

(330 rentals)
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$122

avg/night

View Details

Key Amenities

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

About this property

$70/NIGHT JANUARY SPECIAL DUE TO CANCELLATION. FOR 2 ; ADD $5 EACH EXTRA TO MAXIMUM $90/NGHTCHEERY AND BRIGHT. Just what a vacation home should be. 4 bedrooms, 2 bathrooms, great views and just minutes from all the fun. Fully furnished , just bring personal items or things you cannot live ...

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Property Type

Kissimmee House

"Lovely stay"

Really enjoyed our stay, hope to book again! Very clean & great pool which was lovely & warm & well equipped

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3 BR | 2 BA | Sleeps 7 | Quick View

Distance to park: 6 miles to Disney World

$197

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

Sophisticated, stylish, and serene surroundings await at this cozy home in North Kissimmee. Relax in the spacious living room, enjoy gourmet meals in the executive dining room or bask in the Florida sunshine as you work, rest, and play! After a busy day, enjoy your downtime with an immersive experience ...

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Property Type

Kissimmee House

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7 BR | 4.5 BA | Sleeps 14 | Quick View

11

Distance to park: 3 miles to Disney World Parks

$215

avg/night

View Details

Key Amenities

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

About this property

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

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Property Type

Kissimmee House

"Dreams Come True home is amazing & centrally located"

The owners Marisela and Kevin made this booking seamless! They were always responsive and incredible hosts! Really enjoyed their spacious and clean home. It was centrally located and lots of space for ...

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8 BR | 5 BA | Sleeps 16 | Quick View

owner special
Owner special: Great Spring Savings. Up to 20% off stays arriving in the next 45 days

$419

avg/night

View Details

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 . comThe Retreat at Champions Gate - Kissimmee, Florida is a new upscale gated resort community located just 12 miles from Walt Disney World. ...

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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

Welcome to our stunning, larger than average, 5 Bed 4 Bathroom villa with a beautiful view of the conservation area at the rear as background of our private pool. All rooms in the villa are spacious. The villa is furnished and maintained to a very high standard.The villa is located just off US 192 ...

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Property Type

Kissimmee Villa

"Great house"

This house was exactly as expected. It was huge and clean and fit everyone very comfortably! We had some issues with the hot water and the alarm system but the management company responded and acted quickly! ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Introducing 101 Happy Memories Florida Villa, your gateway to unforgettable vacations in the heart of Formosa Gardens, just minutes from the enchantment of Disney World!Step into luxury with our private heated pool and spa, perfect for unwinding after a day of adventure. Thrill-seekers will love our ...

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Property Type

Kissimmee Villa

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Key Amenities

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

About this property

2bd/2ba with the Best View in the amazing community of Storey Lake. Located 10 minutes from Disney Come in and enjoy a unique experience. There is a beautiful waterpark in the community center for you to enjoy. It is the perfect place to relax, have a good time and enjoy all that Orlando has to offer. This ...

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Property Type

Kissimmee Apartment

"2024 vacation"

The house was lovely.. lots of room, clean, bright The resort pool was absolutely beautiful.. my grandson loved his time in the pool .. lot of room to sit around and food at the pool area was really good

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9 BR | 6 BA | Sleeps 18 | Quick View

3

Distance to park: 8 miles to Disney's Animal Kingdom Theme Park

$389

avg/night

View Details

Key Amenities

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

About this property

10% off for five-night stays from July 5-31! Welcome to Magic Moments, a perfect retreat only 8 miles from Disney for large gatherings with friends, family, work groups, or sports teams. Our spacious 9-bedroom villa, located just 20 minutes from Disney, offers an unforgettable experience. With a private ...

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Property Type

Kissimmee Villa

"Amazing family oriented home with everything we needed and more!"

We rented this house for a family vacation and everyone was so impressed with the size of the home and everything it had to offer. The pool area was perfect for kids and the adults. The ensuite was off ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Luxury Villa near Universal Studios and 12 Minutes from Disney with Large Private Pool, Game Room and Free Wifi. LCD TVs and Game Room in the villa complement the upscale furnishings and large pool included in the villa. There is plenty of space to spread out with 4 bedrooms and 3 bathrooms.Welcome ...

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Property Type

Kissimmee Bungalow

"Royal Palms Mansion"

This was the first time we had stayed in this house, we are regular visitors to Orlando and we know the area well. This house is located in our favourite area and is minutes away from Walmart which is a ...

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Key Amenities

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

About this property

Embark on the ultimate Disney vacation at Jurassic Encanto! With elegantly designed thematic rooms, this spacious home provides ample room for larger groups and multiple families. Compete in the epic game room or take in the lake views while relaxing by the luxurious private pool and spa amidst world-class ...

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Property Type

Kissimmee House

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Key Amenities

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

About this property

Sunset Lakes is ideally situated, just 4 miles from Disney World and a short drive from other popular attractions like Universal Studios, Sea World, and more. The proximity to Orlando and other destinations makes it a prime choice for travelers. The gated community offers various amenities such as a community ...

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Property Type

Kissimmee House

"Vacation retreat/$15 Uber to Disney/ HGTV looking retreat"

We are completing our stay in the morning at this beautiful vacation retreat! We brought the family all seven of us ranging from age in two years old to 60 years old. The pool and patio is incredibly maintained, ...

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9 BR | 8 BA | Sleeps 18 | Quick View

10

Distance to park: 3 miles to Disney Animal Kingdom

$616

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Luxurious Southeast Facing - 9 Bedroom and 8 Bathroom in a Prestigious Secure Gated Community • Freshly remodeled and renovated • Sleeps up to a total of 18 • 9 bedrooms, 5 x Master’s and 3 x Themed and ideal for kids • Amazing location 2 miles to (5 minutes) from Disney World ...

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Property Type

Kissimmee House

"Hartley House family gathering"

We have just returned from a great family holiday in Florida we took all our family away for our fiftieth wedding anniversary ,three years late .We stayed at Hartley House ,we have never stayed in a american ...

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3 BR | 2 BA | Sleeps 6 | Quick View

3

Distance to park: 2 miles to Fun Spot America Theme Parks

$122

avg/night

View Details

Key Amenities

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

About this property

Your family will be close to everything when you stay at this centrally-located place.This property it is fully renovated; first-floor unit with a laminate floor, high ceiling in the living room, open floor plan. The kitchen and bathrooms have been upgraded. The whole community was recently replumbed.Nice ...

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Property Type

Kissimmee Townhome

"Great Vacation Home"

We found the townhouse to be nicely decorated with cute little touches, updated, very clean and equipped with all the necessities for a fabulous experience. It's a very safe, quiet, peaceful location, ...

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Key Amenities

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

About this property

Popular Dates in July & August Available*** For smaller groups we offer the opportunity to rent the main house. This area has 4 Bedrooms and 3 Bathrooms Please contact us and ask for a quote ***Our beautiful 3000sq 5 Bed, 4 Bathroom home is located on a generous corner plot. With a south ...

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Property Type

Kissimmee House

"Amazing accommodation and location"

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

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5 BR | 4 BA | Sleeps 10 | Quick View

1

Distance to park: 7 miles to Disney Hollywood Studio

$142

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

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

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Property Type

Kissimmee House

"Very good"

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

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5 BR | 4 BA | Sleeps 12 | Quick View

2

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

$313

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 parks... You grab a refreshing drink, relax in the poolside living area and reminisce about all you did that day.Memories made, job done!Serendipity offers all the comforts you dreamed of putting on your wish List:★ Pool & ...

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Property Type

Kissimmee House

"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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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Property Reference RVH_1021RBalconies, patios, and lanais are not accessible. During 2023 - 2024 there may be construction occurring on the exterior of the building by the homeowners association; contact us for updates Welcome to Seven Eagles Joy. This 3 bed, 3 bath townhome is located in the heart ...

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Property Type

Kissimmee Townhome

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Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

This Disney Villa is a fully furnished home and is one of the best kept turnkey properties you will find in Indian Creek ! Has an airy open floor plan, lots of light. Enjoy the crystal clear South facing pool and the covered lanai on your sunny and warm Florida holidays.This luxurious private home ...

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Property Type

Kissimmee Villa

"Great Experience. Great Location"

Love the location for this house. Only a few miles (on back roads) from the Disney parks, so we go in the morning and return to the house for lunch and a swim then return to the parks in the evening. ...

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Key Amenities

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

About this property

Bring your family and stay at this beautiful vacation home in the Emerald Island Resort community. You will be just minutes away from Walt Disney World® Resort, and all of the nearby theme parks and attractions of Orlando, Florida. This home has 1 King en-suite, 1 queen en-suite and 2 sets of twins.This ...

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Property Type

Kissimmee House

"summer vacation"

My family and i stayed in kissimee florida at lake berkley for 5 days. The time spent was great. the family enjoyed the games that was in the garage and had alot of fun in the pool. would always recommend ...

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10 BR | 8 BA | Sleeps 20 | Quick View

owner special
Owner special: Check out the Spring deals

$531

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

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Key Amenities

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

About this property

Make lifelong memories with your family and experience the bliss of a private home away from home. With the kids’ Frozen- and Avatar-inspired bedrooms, you'll have them squealing in delight! Enjoy luxuries like a fully equipped kitchen, epic game room, an inviting lounge area, children's ...

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Property Type

Kissimmee Townhome

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2 BR | 2 BA | Sleeps 6 | Quick View

2

Distance to park: 2 miles to Disney

$141

avg/night

View Details

Key Amenities

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

About this property

This 2 bedroom, 2 bathroom condo is on the top floor with comfortable furnishings and is quiet for sleeping. An elevator on site. Lots of free parking available for your vehicles. Great value vacation condo sleeps up to 6. The condo includes a fully equipped kitchen with all appliances and utensils. There ...

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Property Type

Kissimmee Condo

"Fabulous Host and Fantastic Accomodations!"

We stayed at this gorgeous condo resort for a week with my family and had a most comfortable and peaceful stay. The bedrooms were perfect for our family and I loved the separate full master bedroom ensuite. ...

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3 BR | 2 BA | Sleeps 6 | Quick View

Distance to park: 7 miles to ESPN WIde World of Sports

$127

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Rentals by owner

About this property

Welcome to your dream vacation destination! This recently renovated condominium is perfectly situated just minutes away from the magical world of Disney. Located in a prime location close to renowned attractions such as ESPN Wide World of Sports Complex, Epcot center, Disney's Blizzard Beach Water ...

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Property Type

Kissimmee Apartment

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Key Amenities

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

About this property

Private Villa on property at Margaritaville Resort, Kissimmee, Fla. - Complimentary Wi-Fi - In-unit washer/dryer - Unassigned parking in the lot in front of the home (motorcycles allowed) Orlando & Airport - Less than 30 minutes from downtown Orlando and Orlando International Airport All Walt ...

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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

Property Reference RVH_1029RExperience luxury and elegance at Bear's Den Delight, a nine-bedroom custom-built retreat located in the highly sought-after Bear's Den neighborhood of Reunion Resort. This spacious and peaceful end lot boasts an extended patio and yard, perfect for a large family ...

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Property Type

Kissimmee House

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4 BR | 2.5 BA | Sleeps 9 | Quick View

10

Distance to park: 10 miles to Disneyworld

$129

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

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

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

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Key Amenities

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

About this property

A fabulous home-base for your trip to Orlando! Just Minutes to Theme Parks.Home Features:* 3 Bedrooms* 1 King, 1 Queen, 2 Full, 1 Twin (Sleeps 7-8) * All New Mattresses * TV's in every bedroom * USBs & Outlets convenient for charging* 3 Bathrooms* All En-Suite * ...

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Property Type

Kissimmee Townhome

"Loved it."

Beautiful House, and a wonderful experience from start to finish! Cant wait to go back! The home was spacious and beautifully decorated and Lisa was a Pleasure to work with, and very helpful.

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Key Amenities

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

About this property

Experience a magical holiday by renting TWO homes across the street from each other to accommodate large groups, teams and reunions! Queen of Hearts is 8 bedrooms and Moana's Minecraft is 7 bedrooms, both in Windsor at Westside Resort. Enjoy private pools, & game rooms in these fabulously equipped ...

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Property Type

Kissimmee House

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4 BR | 4 BA | Sleeps 8 | Quick View

17

Distance to park: 2 miles to Disney

$251

avg/night

View Details

Key Amenities

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

About this property

Wonderfully Themed villa in the beautiful gated community of Windsor Hills, just two miles from Disney. Enjoy complimentary pool & spa heat, themed rooms, and a fun games room in the garage (air hockey, ping ping, foosball)! This is one of very few 4-bedroom units on the resort. We're nice and ...

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Property Type

Kissimmee Villa

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Key Amenities

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

About this property

Villa OverviewNo extra charges!5 bedrooms, 4 full bathroomsSleeps 15 guests~440 square foot Star Wars theme room upstairs with two full over full bunk beds between a 3D TIE Fighter and swirly slideTwin bunk bed with a trundle in the Lego-themed room, complete with multi-color ...

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Property Type

Kissimmee Villa

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Key Amenities

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

About this property

5 star property! Reviews say it all!You will be delighted by the great combination of lux comfort and Disney theming for the whole family! Located in the upscale Emerald Island Resort gated community, our newly remodeled home is a welcome oasis to return to after a long day enjoying the parks. Relax ...

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Property Type

Kissimmee House

"Where to even start!!!"

Whenever we travel, I read reviews. Some reviews you wonder about because no two people seem to see it the same way. However with this house everyone seemed to love it and after staying there I can see ...

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Key Amenities

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

About this property

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

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Property Type

Kissimmee House

"a wonderful place to stay. made our vacation well worth the trip."

i will tell anyone that this is the place to stay in Florida. the house is amazing with everything you will need and want. we had a great time because this house is well stocked and is very clean. just ...

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3 BR | 3 BA | Sleeps 9 | Quick View

11

Distance to park: 5 miles to Animal Kingdom Lodge

$122

avg/night

View Details

Key Amenities

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

About this property

**The private pool is not heated unless requested by the guest. Pool heating is available for an additional fee of $10.00 per day. Pool heating must be arranged and paid for prior to arrival.***No long-term rentals - 14 nights maximum *Minimum rental age is 25 years old (exception for married couples ...

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Property Type

Kissimmee Townhome

"FANTASTIC property!"

This is the place to stay! This rental truly felt like a home away from home. It was a short drive to countless restaurants and shopping...location is perfect! If you're going to Disney, you'll only ...

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4 BR | 2 BA | Sleeps 9 | Quick View

Distance to park: 8 miles to Magic Kingdom Park

$198

avg/night

View Details

Key Amenities

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

About this property

Welcome to the lap of luxury in this exclusive community, OF Rolling Hills in West Kissimmee! where your dreams come true. Nestled within minutes from the famous 192, this immaculate property will take your breath away. Prepare to be enchanted, But that's not all. Step outside, and you'll be ...

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Property Type

Kissimmee House

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Key Amenities

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

About this property

This gorgeous home was completely redesigned in 2023! Experience unforgettable moments with your family at Solara Resort. The kids will delight in our thoughtfully designed themed bedrooms, while others can unwind on the inviting custom patio or enjoy a refreshing swim in the private heated pool.Is ...

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Property Type

Kissimmee House

"AMAZING customer service"

I was skeptical of booking online with a company I wasn't familiar with, however they ended up being so responsive to any concerns or questions I had, including when me and my kids were in the house. It ...

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Key Amenities

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

About this property

Hello, Our vacation home is located in a gated community with a large swimming pool, playground for the children, shuffle board, pool table and a workout room. It’s a duplex with its own separate driveway. There are three bedrooms and two full baths. The kitchen was just fully remodeled in 2022 ...

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Property Type

Kissimmee Villa

"family time"

THIS PLACE WAS AWESOME AND WE ENJOYED IT. QUIET AND PEACEFUL PLACE. I WILL RECOMMEND THIS RESORT TO ALL MY FRIENDS.

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9 BR | 5 BA | Sleeps 18 | Quick View

1
owner special
Owner special: Check out the Spring deals

$473

avg/night

View Details

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 . comThe Retreat at Champions Gate - Kissimmee, Florida is a new upscale gated resort community located just 12 miles from Walt Disney World. ...

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Property Type

Kissimmee House

"Championgate Visit"

Our family visit was one to remember. The rental property at Championsgate was very nice and peaceful. There was plenty of room to accommodate a family of 23. We really had a fantastic time!

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6 BR | 5.5 BA | Sleeps 18 | Quick View

57

Distance to park: 4 miles to Animal Kingdom

$142

avg/night

View Details

Key Amenities

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

About this property

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

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Property Type

Kissimmee House

"Home away from home"

This house is beautiful! I absolutely love that there are 4 master suites and the main master suite being on the ground floor with an entrance to the pool. Perfect for multiple adults. There are also two ...

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Key Amenities

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

About this property

Newly renovated spacious house (not attached or townhome), bright, beautiful, coastal chic design from the moment you walk through the door in Enchanted Hideaway. Enchanted Hideaway is a newly renovated villa that has everything you need to feel right at home like comfortable beds and linens, large open ...

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Property Type

Kissimmee House

"Excellent"

We loved to stay here, the house had everything we may need, my son loved the play room and my daughter to read in the hanging chairs. Very clean and comfortable rooms. We’ll definitely come back

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Key Amenities

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

About this property

Experience the popular "Queen of Hearts" villa in the Windsor at Westside Resort! This home boasts a private heated pool & hot tub, fire pit and outdoor TV. The themed bedrooms are loaded with amazing details. All guests have free access to resort amenities. Your host Vacation Alchemy provides ...

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Property Type

Kissimmee House

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4 BR | 3 BA | Sleeps 8 | Quick View

2

Distance to park: 3 miles to Disney Parks

$121

avg/night

View Details

Key Amenities

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

About this property

This home is thoughtfully furnished. Recently upgraded with a Tempur-Pedic contour supreme king size mattress, LED TV in every bedroom, Frozen themed and Mickey themed twin rooms. This four bedroom luxury home is specifically set up for vacationing guests. The house, just three miles from Disney, is located ...

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Property Type

Kissimmee House

"Vacation"

My family had the pleasure of spending a week at this beautiful vacation home. This home came complete with everything we needed. Very close to all attractions and short distance to shopping. Booking and ...

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Key Amenities

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

About this property

Huge South Facing Rear Deck The Most Exclusive Home in Reunion ResortThis unique, one of a kind, beautiful, private custom Estate Home features over 8,200 sq/ft of luxury accommodation and balconies. This 'WOW!' factor home is private, quiet and not overlooked.Soak up the Florida sun ...

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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

Brand new, very spacious, modern 9-Bed 5-Bath pool home in an exclusive, private gated golf resort. You'll love the feeling of luxury and space throughout the house, the 2 King en-suite master bedrooms, 4 kids themed bedrooms, 3 additional King bedrooms, the games room, the private pool and spa, ...

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Property Type

Kissimmee House

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4 BR | 3 BA | Sleeps 8 | Quick View

9

Distance to park: 4 miles to Disney World

$151

avg/night

View Details

Key Amenities

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

About this property

Welcome to La Casita on the Island (The Little House on the Island) "Our house, our casita" If you want a place to relax and enjoy the beautiful weather of Florida, I invite you to see the "encanto" (charm) that you can experience during your stay at La Casita on the Island.Enjoy ...

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Property Type

Kissimmee House

"Great Villa"

Had a fantastic stay in the villa. Would definitely stay again and highly recommend. It was extremely clean and in a great location near shops, resturaunts and 192 and Disney. Would highly recommend and ...

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Key Amenities

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

About this property

Just 5 minutes away from Disney World, this Cozy, Lux, themed townhouse will be your perfect getaway from Disney while being your neural operation center to Disney, Golf and Orlando itself. Equipped with everything you need to have unforgettable vacations, from a fully equipped Kitchen to cook the best ...

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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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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

This stunning Disney area pool villa offers your family comfortable and convenient accommodations that will make your next Florida vacation a memorable one.Ideal for your next family vacation, this attractive 4 bedroom, 2 bath Disney area vacation home is conveniently located just 10 minutes to the ...

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Property Type

Kissimmee House

"wonderful stay at this villa"

Villa has everything you will need, very spacious and great pool. Nice quiet Resort. We loved it and hopefully one day we can go back....need to start saving.

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4 BR | 3 BA | Sleeps 8 | Quick View

1

Distance to park: 2 miles to Disney's Animal Kingdom

$200

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

4 Bedroom /3 Bath / Pool & Spa Vacation HomeCONTACT US AND REQUEST A DETAILED QUOTE !! No Booking Fees - Book Direct with the HomeownerCheck our Reviews on VRBO - Property #284051

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Property Type

Kissimmee House

"Awesome"

Thank you Awesome Would do again Very close to everything Great pool sand hot tub Felt safe Thank you again

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Property Reference FG_800BR Sunset Mansion This home has been fully renovated in May 2023. With all new flooring and paint throughout the home, all new furniture, mattresses, pillows, bedding, dinnerware and kitchenware.This magnificent 9 bedroom estate home is located in Formosa Gardens Estates ...

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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

Property Reference #RVH_030RThis luxury Mediterranean inspired custom home is on a rare oversized corner lot. This home boasts one of the largest vacation home spillover spas in the whole of central Florida, up to 10 people can relax in the hot jets. Located on the beautiful Tom Watson Independence ...

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Property Type

Kissimmee House

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Kissimmee Vacation Rentals

Kissimmee Weather

 | 

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

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


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

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

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

Top Tips for Traveling to Kissimmee Rentals


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

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

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

Things to Do Nearby Kissimmee House Rentals


Some of the most popular natural areas around Kissimmee are the swamps, which are located in major local bodies of water like Lake Tohopekaliga (known around town as Lake Toho). At Boggy Creek Airboat Adventures, you can experience the swamps from the water and get the thrill of a lifetime on an airboat driven by a local wetlands expert. Get up-close views of gator ponds, discover precious gemstones, and then grab a delicious lunch with the family at Boggy Bottom BBQ! 

Looking to explore a piece of history during your trip to Kissimmee? Medieval Times Dinner & Tournament allows visitors to step into the 11th century for an evening of authentic feasting, jousting, and sword fighting in true medieval style! Enjoy a delicious four-course meal, incredible performances, and a truly unforgettable experience for the entire family.
 
Any vacation to Kissimmee isn’t complete without a trip or two to Old Town, a popular outdoor attraction with opportunities for shopping, dining, and family fun. Old Town is made up of an 18-acre stretch of classic city attractions, including the Old Town Ferris Wheel, the Great Magic Hall, and Mortem Manor, a year-round haunted house that is open for visitors to explore.

Kissimmee Annual Events


Kissimmee is a vibrant area with lots of annual festivals and events to enjoy in and around the city throughout the year. Kissimmee locals and visitors alike flock to the Ford Cuban Sandwich Festival each May near downtown Kissimmee, which celebrates the colorful history of Cuban cuisine in the area. Watch as local dining professionals attempt to build the world’s biggest Cuban sandwich during the event!
 
The Ford Taste of Latino Festival is another local opportunity to celebrate and experience the best in authentic Latin cuisines in Kissimmee. The event features a contest to find the Top Latino Chef as well as plenty of live music and dance performances to enjoy as you taste a variety of Latin dishes. 

Not sure if you’ll be in town for any of Kissimmee’s larger annual events? You can enjoy Show Car Saturday Nights every Saturday night in the city on Margaritaville Boulevard. Check out the city’s best classic cars from a variety of eras and enjoy the plethora of delicious eateries and exciting shops located along the boulevard.

Wining and Dining in Kissimmee  


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

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

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


FAQ

How many vacation rentals are there in/around Kissimmee?

There are 330 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 $55 per night with an average price per night of $174.

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