Kissimmee Vacation Rentals

(330 rentals)
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Key Amenities

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

About this property

New in 2016, Windsor at Westside is a gated vacation rental community close to Disney featuring an 8,000 sq.ft. clubhouse with the Tu Casa Bar & lounge, market & deli, video arcade, sundries shop & fitness center. Other fantastic amenities such as a playground, volleyball court & multi-purpose ...

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Property Type

Kissimmee House

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$145

avg/night

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Key Amenities

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

About this property

Community: Bella Piazza Floors: Second Floor Condo, Elevator Access. NO pets This is a NON SMOKING HOME * Rooms: 3 Bedrooms, 3 Bath rooms. En-suite in Master bedroom.Bed Configuration: King bed(1) King bed(1), Full plus 2 twins., Sleep 8.Flooring: tile throughout with Carpet in the bedrooms.General: ...

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Property Type

Kissimmee House

"Great Location"

Great location near all the major parks. The pool in the gated community was really nice, staff there was excellent. The condo was good. The living room floor was dirty with someone elses bobby pins on ...

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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 8 | Quick View

13

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 ...

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Property Type

Kissimmee Villa

"New Years Getaway"

Stayed month of January..Villa was very well equipped and very comfortable.Location was fantastic being so close to all attractions. Would highly recommend for anybody to stay..

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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

About this property

Property Reference SO_970RParadise awaits you and your family in Solara Gem! Enjoy a relaxing vacation close to all of the major theme parks in this nine-bedroom home, located in Solara Resort.The home features a nice open living area, great for entertaining or gathering with the entire family. ...

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Property Type

Kissimmee House

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2 BR | 2 BA | Sleeps 6 | Quick View

2

Distance to park: 2 miles to Disney

$141

avg/night

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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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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_1052RWelcome to Reunion Getaway! Located in Reunion Resort, and situated within the Fairway Ridge neighborhood. This beautiful 5 bedroom, 4.5 bath is perfect for your friends and family as it is located within minutes from Orlando's world-class attractions. The home is ...

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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_1082RA vacation full of luxury, wonder, and excitement awaits your next trip to The Enchanted Villa. The Enchanted Villa was designed with the vacationing family in mind and provides guests with a vacation full of entertainment and memories all under one roof. Spread out and ...

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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

"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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2 BR | 2 BA | Sleeps 4 | Quick View

owner special
Owner special: Check out the Spring deals

$160

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen

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 ...

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Property Type

Kissimmee Condo

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9 BR | 5 BA | Sleeps 18 | Quick View

1
owner special
Owner special: Check out the Spring deals

$480

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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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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Key Amenities

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

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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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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10 BR | 8 BA | Sleeps 20 | Quick View

owner special
Owner special: Check out the Spring deals

$538

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
  • 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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4 BR | 3 BA | Sleeps 8 | Quick View

16

Distance to park: 4 miles to Disney

$152

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

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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6 BR | 6 BA | Sleeps 12 | Quick View

owner special
Owner special: Check out the Spring deals

$424

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

About this property

Property Reference # RVH_1049RWelcome to Whisper Way Paradise! This beautiful 3 bedroom, 3 bathroom condo is located in The Villas South neighborhood of Reunion Resort (near the center of Reunion Resort). This condo is just steps away from one of Reunion's many playgrounds.The spacious living ...

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Property Type

Kissimmee Condo

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Key Amenities

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

About this property

Property Reference #RVH_1079REnjoy your next vacation in luxury and style, just miles from the theme parks, nestled in the highly sought Reunion Resort. Excitement Escape is the perfect location for your next getaway, boasting six master bedrooms, a private heated pool, golf views, and even your own ...

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Property Type

Kissimmee House

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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
  • 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
  • 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
  • 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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$122

avg/night

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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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7 BR | 5.5 BA | Sleeps 14 | Quick View

2

Distance to park: 5 miles to Disney World

$244

avg/night

View Details

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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6 BR | 5 BA | Sleeps 12 | Quick View

3

Distance to park: 5 miles to Old Town, food,shops and rides

$216

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Spacious air conditioned home on large plot and not overlooked! Living area with 3 sofas and huge TV with cable triple play included and doors to pool deck. Dining tables and chairs enough for all guests and seating at breakfast bar. Refurbished kitchen with granite work tops, stove, microwave, dishwasher, ...

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Property Type

Kissimmee House

"Lovely villa"

We had a wonderful holiday at this villa, the location is perfect both for the setting and for the convenience for access to the attractions and restaurants. Cumbrian Lakes is very peaceful and quiet, perfect ...

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10 BR | 5 BA | Sleeps 20 | Quick View

owner special
Owner special: Check out the Spring deals

$538

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

Show less

Key Amenities

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

About this property

Welcome to our lovely and luxurious townhouse in the sunshine state!Feel at home with your family and friends at our place, located in one of the most exclusive resorts of the area. Enjoy all of the amenities our community has to offer for you to have a wonderful vacation! Visit our water park, mini ...

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Property Type

Kissimmee Apartment

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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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4 BR | 3 BA | Sleeps 10 | Quick View

Distance to park: 2 miles to Walt Disney World

$161

avg/night

View Details

Key Amenities

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

About this property

Our luxury villa is perfectly located, just 2.5 miles away from Walt Disney World's front door. This amazing four bedroom/three bath/fully furnished villa has room for 10 to sleep, dine, and relax in comfort. After the parks or dinner, retreat to your own private pool for a refreshing swim, or the ...

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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

If You're Looking For One Of The Best 5 Bedroom Vacation Homes In Solara Resort or Central Florida, Look No Further!Located just minutes from Orlando's theme parks, shopping, dining, and other area attractions, this luxury villa is located in Solara Resort. Solara Resort is just a 5-minute ...

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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_341RThis beautiful home in the Fairway Ridge neighborhood in Reunion Resort offers serene views of the preserve beyond. Bright and open spaces in a natural color scheme give this home a relaxing and modern feel. Everyone can gather in the great room which includes living, kitchen, ...

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Property Type

Kissimmee House

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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

View Details

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 | 5 BA | Sleeps 12 | Quick View

2

Distance to park: 5 miles to Disney World/Animal Kingdom

$266

avg/night

View Details

Key Amenities

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

About this property

Our Disney vacation villa is furnished to the highest standard and offers your family the luxury of a Five star hotel combined with the relaxed atmosphere of a family vacation home. Soak up the Florida sun on our extended deck where you can relax in the pool and spa, or simply enjoy the shade of the lanai ...

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Property Type

Kissimmee Villa

"Fantastic Stay"

We loved staying at this house it was truly amazing. There were 9 of us altogether, 6 adults and 3 children aged 10,8 & 4. The kids loved the games room and the pool, everything you could wish for in ...

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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
  • Pool

About this property

Property Reference RVH_1054RBalconies, patios, and lanais are not accessible. During 2023 there may be construction occurring on the exterior of the building by the home owners association.This 3 bed, 3 bath townhome is located in the heart of Reunion Resort - Seven Eagles with the magnificent ...

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Property Type

Kissimmee Townhome

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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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4 BR | 3.5 BA | Sleeps 10 | Quick View

12

Distance to park: 5 miles to Animal Kingdom

$118

avg/night

View Details

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
  • Pool
  • Private pool

About this property

Welcome to our stunning townhouse located at 2600 Lodi Crescent in the charming city of Kissimmee, FL. This tastefully furnished property is the perfect choice for your next getaway. Whether you're visiting the magical Walt Disney World or exploring the vibrant attractions of Orlando, our townhouse ...

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Property Type

Kissimmee Townhome

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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 | 2.5 BA | Sleeps 9 | Quick View

10

Distance to park: 10 miles to Disneyworld

$128

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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4 BR | 2.5 BA | Sleeps 8 | Quick View

1

Distance to park: 3 miles to Disneys Animal Kingdom

$164

avg/night

View Details

Key Amenities

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

About this property

Our Home Features are 4 bedrooms consisting of 1 Master suit with en-suite bathroom located on the main level. 1 Queen and 2 twin rooms,1 twin room is themed Winnie the Poo,on the upper level, these bedrooms share the upper bathroom all bedrooms are equipped with TV and DVD player. There is a further ...

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Property Type

Kissimmee Villa

"Tolles Haus"

Hallo, Wir haben hier mit der Familie Urlaub gemacht. Das Haus ist groß genug für acht Personen. Es ist super ausgestattet mit tollem Blick und schönem Pool. Der Vermieter ist sehr um eine tolle Atmosphäre ...

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Key Amenities

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

About this property

Located just minutes from Orlando's theme parks, shopping, dining, and other area attractions, this luxury villa is located in Solara Resort. Solara Resort is just a 5 minute (2.7-mile drive) from a Publix supermarket and restaurantsProperty Summary This property has all that a family needs ...

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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_1083RSituated in the highly sought-after Liberty Bluff neighborhood of Reunion Resort, Liberty Oasis is a brand new, modern, luxurious 5-bedroom 5.5 bath home with Reunion Membership that sits adjacent to the only Reunion Resort greenspace/park. This home includes resort access. ...

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Property Type

Kissimmee House

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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

$388

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

About this property

Property Reference #RVH_1039RWelcome to Fairway Delight! This beautiful property is located at Reunion Resort in the Fairway Ridge neighborhood, a truly beautiful place with world-class amenities such as championship golf courses, infinity pools, a full-service spa, scenic walking trails, fitness ...

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Property Type

Kissimmee House

"Kissimmee"

The home was absolutely adorable. My children loved it as well as my husband and I. Everything was cozy, clean,and ready to use. I will come back everytime I stay.

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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 $56 per night with an average price per night of $172.

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!