Kissimmee Vacation Rentals

(330 rentals)
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4 BR | 2.5 BA | Sleeps 9 | Quick View

10

Distance to park: 10 miles to Disneyworld

$125

avg/night

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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
  • Private pool
  • Rentals by owner

About this property

Imagine a vacation like no other spent in a 9 bedroom, 10 bath custom luxury lakefront pool villa. The Formosa Grand is located in the exclusive gated community of Formosa Gardens Estates and one of the closest communities to Disney (less than 10 minutes!!) No expense was spared in the gorgeous estate ...

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Property Type

Kissimmee Villa

"West Family Reunion"

We had a great time at the mansion. Only a few things I would change. The hot tub price should have been included in the rental agreement.

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Key Amenities

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

About this property

Disney Wood Wonderland*** 7 miles from Disney popular attractions Disney's Animal Kingdom Theme Park and Epcot. Walt Disney World and Magic Kingdom Park.

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Property Type

Kissimmee Villa

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4 BR | 3.5 BA | Sleeps 10 | Quick View

12

Distance to park: 5 miles to Animal Kingdom

$121

avg/night

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Key Amenities

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

About this property

Enjoy Orlando, Florida, home to Disney World, Sea World, Universal Studios, and Islands of Adventure, in style. Our home is within minutes of all the Orlando attractions, golf courses, shopping, and exciting night life. Our richly appointed vacation Townhouse will give you luxurious living and a vacation ...

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Property Type

Kissimmee Townhome

"Cozy stay at townhouse"

My wife, son and I stayed for the month of April. The resort property is well maintained. Garbage is picked up daily and each home has a bin right in front of the home.The condo was very clean upon ...

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Key Amenities

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

About this property

Welcome to our luxurious and spacious vacation home situated in the stunning gated community of Windsor at Westside. This magnificent 5-bedroom, 4.5-bathroom villa boasts everything you need for an unforgettable vacation with your family and friends, Close to theme parks, shopping mall outlets, restaurants ...

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Property Type

Kissimmee House

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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

"Love our Stay"

I have been a vacation renter at this property for 10 plus years now. We absolutely love our stay and we love all the new updates on the home my foster loved that her room was Mickey themed and her bathroom ...

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Key Amenities

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

About this property

This villa is a stunning 5 Bed 3 Bath villa that can comfortably sleep 12 guests.A stunning, larger than average, 5 Bed 3 Bathroom villa with a fantastic private pool. All rooms in the villa are spacious. The villa is furnished and maintained to a very high standard.The villa is spaciously arranged ...

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Property Type

Kissimmee Villa

"Quiet homely villa in a great location"

The villa is in a great location, in a good position to access WDW and Universal, but in a secluded gated community, which means it quiet in the evenings. It really feels like home, not impersonal like ...

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4 BR | 2 BA | Sleeps 7 | Quick View

4

$116

avg/night

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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

"Best vacation ever"

This house has it all! I definitely recommend this villa and it also has a huge swimming pool with hot tub. Villa is beautiful and so convenient to all Disney Parks and shopping. Diane is the best on ...

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Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner

About this property

Excellent location pool community gimnasio walking through complex

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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

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

Popular Dates in July & August AvailableOur 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 ...

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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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Key Amenities

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

About this property

Booking is available from the website in Owner info.Modern architecture, state-of-the-art furnishings, and hip-to-the-minute décor make this 5 bedroom, 5 bath getaway in Storey Lake a bonafide safe haven for luxury and comfort. This home is brimming with amenities, from an action-packed game ...

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Property Type

Kissimmee House

"Great place, nice price!"

The themed kids' rooms and game room are topping on this rental a club house with so much going on for everyone, including pickup/drop off service to and from the club house. Heated pool and gas grill. ...

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3 BR | 2 BA | Sleeps 6 | Quick View

3

Distance to park: 1 miles to Disney Animal Kingdom

$97

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Come and enjoy your vacation in this comfortable condo, right by Disney. Yes Enjoy Three large screen TV's, DVD and free Wi-FI.Yes Beautiful/alluring condo, 1 mile from Disney world and minutes from other attractions, Such as sea world and Universal studio. In Celebration area Florida. Walking ...

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Property Type

Kissimmee Condo

"Great location, clean and comfortable."

We had everything we needed. Excellent communication. Perfect location. Close to the parks as well as restaurants, etc! We will be back.Thanks

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5 BR | 4 BA | Sleeps 10 | Quick View

Distance to park: 7 miles to Disney Hollywood Studio

$150

avg/night

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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

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Key Amenities

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

About this property

BRAND NEW 2023 remodeled 10+ bedroom luxurious home in the Encore/Reunion community. "The Great Escape" is designed for large groups and families who want their vacation home to be part of the adventure!Is this home already booked? Check out our Profile and chose from over a dozen magical ...

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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

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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4 BR | 3 BA | Sleeps 8 | Quick View

16

Distance to park: 4 miles to Disney

$145

avg/night

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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

"Perfect rental for all of our needs!"

This was a Christmas vacation never to be forgotten! We had the time of our lives! My children, grandchildren and I enjoyed the comforts and privacy of a home where we could take in all the theme parks ...

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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

"Home away from home!"

We are regular Airbnb travelers and would rate this stay one of the nicest, best located, and real value of all the places we have stayed. The place was very clean, modern, had everything we needed to feel ...

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9 BR | 8 BA | Sleeps 18 | Quick View

9

Distance to park: 3 miles to Disney Animal Kingdom

$662

avg/night

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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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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

"Fantastic villa"

Absolutely fantastic villa in a great location jusy minutes from Disney (10 minutes at most) really clean luxurious property. Our second holiday here and we will be back in the future. Really has everything ...

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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
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

This stunning 4 Bed 2 Bath Villa enjoys one of the premier positions on Lake Berkley Resort with an unspoilt beautiful view over the lake. Enjoy breakfast, lunch or dinner on the pool patio whilst watching the wildlife on the lake. If you enjoy fishing then you only need to walk a few yards to fish in ...

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Property Type

Kissimmee Villa

"Wonderful house with all the amenities you need for the whole family."

The house is located in a great area, the tidiness and cleanliness is particularly noticeable to us. Moreover, the house is very cozy and tastefully decorated.Kissimee is a cute little town, which takes ...

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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

$506

avg/night

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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
  • Pool
  • Private pool
  • Rentals by owner

About this property

Name Of Home: Walking on Sunshine VillaLocation: Windsor Hills Resort (24/7 guard gated community - Disney World only mins away!)Home Highlights: Recently Renovated Home - Incredible Air Conditioned 80s Game Room - Private South Facing Pool/Spa - Bunk Bedroom with PS5Property Type: Single ...

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Property Type

Kissimmee Villa

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Key Amenities

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

About this property

Experience a magical holiday at this luxe 7-bedroom home! Nestled in Windsor at Westside Resort, you and your loved ones will be a short drive to many attractions. Stretch out into sprawling living areas where comfort awaits you before heading outside for an exciting time - enjoy a dip in your private ...

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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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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

27

$151

avg/night

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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.In the 1st section of Indian Creek you will ...

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Property Type

Kissimmee Villa

"House rental on Santee Dr"

The house was very clean and well furnished. The location is perfect. I dealt with the homeowner Lisa who was professional and returned my text quickly. The pool and hot tub were also very clean. Quiet ...

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Key Amenities

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

About this property

Recently renovated luxury property now available for your next Orlando adventure. Two themed kids bedrooms each sleep 4 kids (or adults), five oversized bedrooms each with king size beds. All bedrooms feature en-suite bathrooms. Two bedrooms downstairs, 5 bedrooms upstairs (including the two themed bedrooms). ...

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Property Type

Kissimmee House

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4 BR | 3 BA | Sleeps 8 | Quick View

8

Distance to park: 4 miles to Disney World

$139

avg/night

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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

"Wonderful house - wonderful hosts."

The house was everything we had hoped for. There was a slight problem with the pool and the hosts quickly returned our money for heating the pool. Love the house and would definitely book again.

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6 BR | 5.5 BA | Sleeps 18 | Quick View

56

Distance to park: 4 miles to Animal Kingdom

$154

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

"Wonderful Disney family home"

This is the second time my family and I have rented this lovely home and will do so again. At one time there were 12 of us, all adults, and nobody felt cramped. The covered lanai around the beautiful pool ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • 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 Condo

"Great family time"

Our family went to florida for a Disney vacation. House was excellent with all the amenities. Clean and pool was great. Greatly recommend

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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 8 | Quick View

2

Inquire for rates

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Key Amenities

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

About this property

Situated in Orlando, within 8 km of Disney's Hollywood Studios and 9 km of Disney's Boardwalk, Windsor Hills Apartment By A3G offers accommodation with free WiFi, air conditioning, a fitness centre and a shared lounge. This property offers access to a patio and free private parking.The apartment ...

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Property Type

Kissimmee Condo

"Great Escape"

I visited to watch softball. The house was a perfect location and has everything I needed. Would stay again.

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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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Key Amenities

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

About this property

Property Reference RVH_1018RMajor Excitement is situated in the Liberty Bluff neighborhood of Reunion Resort, this luxurious 6-bedroom, 6-bath home offers a private pool and much more!With an open-planned floor plan, the living area is bright and spacious with a sofa before a 70-wall-mounted SMART ...

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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_1008RWelcome to Fairway Dream! This beautiful property is located at Reunion Resort in the Fairway Ridge neighborhood, close to Orlando's world-class attractions.Through the foyer, you have access to the second floor and the game room, before it leads you into the ...

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

A Truly Luxurious Executive Retreat, Main Level Features: Quality Ceramic Tile Flooring throughout. Spacious Family Room with Vaulted Ceiling and Corner Leather Sofa.70″ TV with 5.1 surround sound with blue tooth capabilities. Formal Dining Room/ Sitting Area with table for six, Fabulous Kitchen ...

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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

Perfect Family Destination Best lania/pool Minutes to Disney/Attractions/Conveniences Fun/Clean/ComfortableThis is a fantastic house for family getaways! Enjoy the Food and Wine Festivals. Mickey's Not So Scary Halloween Party, Unforgettable Disney Christmas celebration, and everything else ...

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Property Type

Kissimmee House

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Key Amenities

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

About this property

☆☆ HIGHLIGHTS ☆☆️ 3 Fun Kids Bedrooms: Pirate room, Choo-Choo Train room & Enchanted Fortress Room 2 Master Suites Total 8 beds; 3 Kings, 1 Queen + 4 Twins 5 Full Bathrooms: all essential toiletries provided Full Kitchen w/ Island with seating for 4 ️ Coffee bar ️ ...

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Property Type

Kissimmee House

"Nice home, spacious and clea"

The clubhouse was nice as well. Very good experience. Close to restaurants and close to the attractions.

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Our gorgeous 4 bedroom detached single storey villa is perfect for families sleeping a maximum of 10 guests. Located in the gated community of Tuscan Hills, you can enjoy a private south facing pool deck and a fully stocked home of comfort. The single floor living makes it easy and safe for all your families’ ...

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Property Type

Kissimmee Villa

"Wonderful villa"

Had vacation here in July 2023, amazing time, the villa is wonderful. Spacious, clean and modern. Pool area is very relaxing, kids loved it. we will be back. Branda

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

Welcome to our superb 4 bed, 2 bath vacation villa. A perfect place to unwind after a busy day visiting many of the local attractions. Located on Montego Bay Resort.The villa has been furnished to an extremely high standard and will sleep 8. Fully airconditioned throughout and free Wi-Fi.A beautiful ...

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Property Type

Kissimmee Villa

"great stay with family"

Had a week here with family and it was great. Villa is well kept, has everything we needed. Highly recommended and we will stay here again. Percy

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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

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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
  • 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

This home has everything that you, your family and friends will ever need and more! Walt Disney World Resort is only 2 traffic signals away. This luxury South facing pool home, completed in June 2004, has 7 bedrooms, 6 bathrooms and will accommodate 15 people plus infants comfortably. The private pool ...

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Property Type

Kissimmee House

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$293

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Fantastic 2 KING bed EnSuite Villa w heated pool HOT TUB Mins to DisneyFamily-friendly Kissimmee vacation home in Four Corners with water parkContactless one time access code check in! All white linen! Private pool heat up to 104 degree. It’s like a 5 star hotel but better! Pet Friendly ...

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Property Type

Kissimmee House

"Great place"

The owners were very easy to work with. The house was in perfect condition, very clean and well maintained. We had 9 people and plenty of room for everyone. Definitely would recommend the house.

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Key Amenities

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

About this property

Property Reference EMI_1700RA perfect size vacation home for families who wish to stay close to Disney and come home to their own private pool to cool off after a long day at the parks. The decor was professionally updated in June 2022 aand again with further updates such as new flooring, new beds ...

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Property Type

Kissimmee House

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7 BR | 5.5 BA | Sleeps 14 | Quick View

2

Distance to park: 5 miles to Disney World

$244

avg/night

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Key Amenities

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

About this property

Excellent Private Detached Family Vacation home/Villa located in the Prestigious Man Gated Vacation Resort of EMERALD ISLAND RESORTS. SPECIAL DISCOUNTS FOR LONGER STAYS !!! . Monthly bookings during January to April at special rates._________________________________________________________________ This ...

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Property Type

Kissimmee House

"Amazing 7 Bed rooms Villa Near Disney"

Our stay with Family and friens were superb. Cost is just a fraction of what otherwise with any Hotels. VEry large House with 7 Bedrooms and 6 Wash rooms. Own private pool and lanai . Bbq grill was provided ...

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Key Amenities

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

About this property

Escape to a magical 8-bed 6-bath retreat for up to 16 guests at the Windsor at the Westside resort community. This is an entire home rental. Super Mario game room, Beauty and the Beast dining, Paris-themed kitchen, Guardians of the Galaxy primary bedroom. Upstairs: Hollywood, Pirates, Mickey Mouse, Princesses, ...

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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

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 $46 per night with an average price per night of $190.

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