Kissimmee Vacation Rentals

(330 rentals)
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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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4 BR | 3 BA | Sleeps 10 | Quick View

Distance to park: 2 miles to Walt Disney World

$185

avg/night

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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
  • Pet friendly
  • Pool
  • Private pool

About this property

Get ready to be amazed, because this place is an absolute dream come true! With a whopping 12 bedrooms and room for up to 26 of your closest friends and family, this house is all about sharing good times with those who matter most.Step out onto the back deck, and you'll find a private swimming ...

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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_1069RFor those looking to find a home loaded with luxury, fun, and great views, look no further than Fairway Ridge Joy. This perfectly planned five-bedroom golf view home has everything to offer under one roof, perfect for a great getaway or vacation!From the moment you ...

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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_1078RPlease note that there is construction nearby until mid-November 2023. Please contact us for more information.Adventure and excitement await you in this newly built vacation home, designed with families in mind from top to bottom! Built and designed specifically for ...

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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_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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5 BR | 5 BA | Sleeps 12 | Quick View

1

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

$298

avg/night

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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

"Wonderful home and resort"

This home was super clean and there was so much room. The two kids rooms upstairs are amazing. My kids were in heaven. The game room was so much fun. Always nice to be able to come back after a day at ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

MAGIC HOUSE, is a beautifully furnished 4 bedrooms, 3 bathrooms home with a 26ft x 14ft swimming pool and Spa,. covered lanai. It is only a 3 mile drive to Walt Disney World Resort. It's in easy reach of all other major attractions.MAGIC HOUSE is a luxury villa located in the quiet friendly neighborhood ...

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Property Type

Kissimmee House

"Fun Time with Family"

Home was nice and neat when we arrived. Roomy and close to grocery stores and other shopping areas. Will visit again and recommend to others.

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Key Amenities

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

About this property

Experience the magic of Disney World, Universal Studios, and the very best of Orlando from the comfort of this luxury private resort! Conveniently located in Storey Lake Resort, enjoy the the resort style amenities or explore the world class attractions in Orlando and Kissimmee. Minutes from Disney World, ...

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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

Nestled over at the Bella Vida Resort, just a measly 8 miles away from the magical kingdom of Walt Disney World (yeah, we're basically neighbors!), this 12-bedroom vacation home has room for your whole crew. It can host up to 30 guests at a time, so bring the whole fam!Let's kick things ...

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Property Type

Kissimmee House

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Key Amenities

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

About this property

This luxury villa is perfectly located on the exclusive Emerald Island Resort community less than 3 miles from Walt Disney World, Florida. The property has 7 bedrooms two of which are master bedrooms with en suite bathrooms and a further two and a half bathrooms.This stunning elegant and spacious ...

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Property Type

Kissimmee Villa

"Spacious - great for multiple families"

We had such a great time in this villa, it’s so spacious and perfect for multiple families staying together! It’s great value for the size and location - close to Disney and lots of shopping and dining. ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Welcome to our beautiful townhome villa located at the luxurious 24-Hour Guard-Gated Emerald Island Resort in Kissimmee, Florida. Just 3 miles from Disney World's main gate.No cramped pool deck! No Shade from nearby houses blocking that fabulous Florida Sun! No shortage of pool chairs, tables ...

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Property Type

Kissimmee Townhome

"Vacation"

We had an amazing time and would return again to the property , The management staff where very helpful and accommodating

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Key Amenities

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

About this property

Property Reference # RVH_1085RWelcome to Magical Moments, the luxurious vacation home that awaits you on your next visit to the Central Florida area. This highly sought-after estate boasts seven spacious bedrooms and over 6600 square feet of air-conditioned living space, offering ample room for everyone ...

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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_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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7 BR | 5.5 BA | Sleeps 16 | Quick View

1

Distance to park: 3 miles to Disney World

$308

avg/night

View Details

Key Amenities

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

About this property

"Dory's Magic" is our Emerald Island Resort 7 bed/5.5 bath vacation home offering a fully air-conditioned games room in addition to a south-facing pool/spa and multiple living areas. It offers several complimentary amenities such as a BBQ grill, free full-size crib, pack 'n play, stroller, ...

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Property Type

Kissimmee Villa

"7 bedroom house 8460 Secret Key Cove"

Sri was an outstanding contact ready to help all the time. Place was fantastic for our group of 8. Minor issues where Sri handled. Definite return next year.

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Key Amenities

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

About this property

Nestled over at the Bella Vida Resort, just a measly 5 miles away from the magical kingdom of Walt Disney World (yeah, we're basically neighbors!), this 12 bedroom mansion is big enough to host 24 of your favourite people.Let's kick things off with the amazing back deck. Picture this: a ...

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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
  • 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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Key Amenities

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

About this property

From the minute you pull through the gated entry you will be lost in your dream vacation. Located at the beautiful Veranda Palms Resort, this 26 guest capacity vacation home has everything you could possibly need for a fantastic stay.Let's start with the gorgeous sundeck patio at the back of ...

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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

If this 15 bedroom, 33 guest capacity vacation home isn't big enough, we're jealous you have so many friends!The whole crew will love the backyard swimming pool. It has a spill-over jacuzzi hot tub and a spacious sundeck with lounge chairs. After a swim, why not enjoy a poolside BBQ meal? ...

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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_1071RVacation in style while enjoying this nine bedroom luxury home, built specifically for vacationing in mind. This home can comfortably sleep 20 guests in nine bedrooms, with eight of them having private bathrooms.When you enter the home, you are met with a two story ...

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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_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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Key Amenities

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

About this property

Property Reference #RVH_1059REnjoy sweeping golf views and vacation close to all of the area attractions at Excitement Getaway. This three-story resort home has plenty of space for a family gathering and offers six bedrooms, a private heated pool, and several golf view balconies that allow guests ...

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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

At this 30-guest capacity, 12-bedroom mansion, bedtime will be a blast because these kids bedrooms have some of the coolest beds we've ever seen! For all the Star Wars fans, if you've ever wanted to sleep under an AT-AT, this is your time to shine. Whether storming the battle of Hoth or getting ...

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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 vacation home isn't just a place to stay; it's your own personal wonderland. Step outside, and you'll be greeted by a backyard oasis that dreams are made of – a sparkling swimming pool with a spillover jacuzzi hot tub and a sun-soaked sundeck, complete with lounging chairs that ...

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Property Type

Kissimmee House

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5 BR | 3 BA | Sleeps 12 | Quick View

10

Distance to park: 3 miles to Disney

$188

avg/night

View Details

Key Amenities

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

About this property

5 bedrooms, 3 bathrooms, sleeps 10 - 12.Spacious, 5 bed, 3 bath, luxury villa with Private Pool, Spa +Games Room (pool, air hockey and football tables) Guests have full use of all facilities of the Prestigious Emerald Island Resort, including Club House with pool, spa & licensed Tiki Hut Bar, ...

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Property Type

Kissimmee Villa

"Very Comfortable"

Very comfortable stay! We had a group of 4 adults and 3 kiddos, and each of us enjoyed our stay. House was very clean and well appointed. Owner was a pleasure to deal with, and VERY responsive to our needs. ...

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7 BR | 5 BA | Sleeps 14 | Quick View

4

Distance to park: 7 miles to Disney Magic Kingdom

$257

avg/night

View Details

Key Amenities

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

About this property

*REASONABLE RATES FOR FAMILIES -: We have been renting over 18 Years.SPECTACULAR DISNEY THEME VILLA to make your vacation magical!*SAFE GATED 24 HOUR GUARDED RESORT: Shopping and Restaurants choice of buffets, takeaways or fine dining just 2 mins away, including 24/7 Super Wal-mart. *BEAUTIFUL ...

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Property Type

Kissimmee Villa

"Perfect Lake Berkley Villa for 2 families"

We chose this particular villa as it met many of our non-negotiables; south facing pool, gated community, close to 192 & Poinciana Blvd. From the first enquiry, where we hadn’t purchased flights ( but ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Property Reference #: RVH_323RWelcome to Classic Condo. It is located in the Villas South neighborhood of Reunion. This 3 bedroom, 3 bath vacation rental condo provides beautiful decor and a great location close to Orlando's well-known attractions on top of all the amenities that Reunion Resorts ...

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Property Type

Kissimmee Condo

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4 BR | 3 BA | Sleeps 8 | Quick View

3

Distance to park: 3 miles to Disney World

$167

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Sample the Florida lifestyle in our four-bedroom, three-bathroom spacious air-conditioned villa with 26ft x 13ft privately screened, heated, south-facing swimming pool and spa.Located on the peaceful Indian Creek community, our holiday home is comfortably furnished throughout, only 3 miles away from ...

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Property Type

Kissimmee Villa

"A perfect vacation villa"

We have been travelling to Florida for over 15 years now and this villa is easily one of the best we've had. The location is great, close to every kind of store, restaurant, or attraction you want to go ...

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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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5 BR | 5 BA | Sleeps 10 | Quick View

owner special
Owner special: Ask about a discount for open dates in May!!

$236

avg/night

View Details

Key Amenities

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

About this property

Welcome to Minnie's Mansion! A 5 bd/ 5 bth pool home located in the closest community to Disney World-Windsor Hills Resort!This resort features, $2.1 mil Lagoon Style pool with Zero Depth Entry and Water Slides. Also, with a Water Park for the littles! Clubhouse has Sundry Shop /Deli, Games Room, ...

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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

Villa Fresco - 6 Bed Contemporary Home Located on the Westside of the incredible Reunion Resort within the Fairway Ridge community, and situated on the Jack Nicklaus-designed Tradition Golf Course. Fairway Elegance will fulfill all your vacation wants and needs. The home is located close to all the ...

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Property Type

Kissimmee Villa

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Key Amenities

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

About this property

Welcome to your dream vacation stay! Nestled in a prime location, our 3-bedroom, 2-bathroom condo offers the ultimate blend of comfort and convenience, making it an ideal retreat for families and friends alike. Imagine starting your day in our fully equipped kitchen, brewing a fresh cup of coffee or whipping ...

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Property Type

Kissimmee Condo

"Perfect Spot for a Peaceful Getaway"

I recently stayed at this rental and it was super relaxing. Every morning, I loved having my coffee on the balcony. It was a calm and quiet place, just perfect for starting the day. The rental is cozy and ...

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Key Amenities

  • Air conditioning

About this property

If you’re searching for Orlando vacation rentals that will have plenty of room for your entire family, look no further than Windsor Palms with private pool. This incredible home can fit up to 10 guests between its 4 bedrooms and 3 bathrooms. You’ll find another incredible amenity around every ...

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Property Type

Kissimmee House

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9 BR | 5 BA | Sleeps 18 | Quick View

1
owner special
Owner special: Check out the Spring deals

$566

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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Stunning Lake View House 2mls Disney,free Wi-FI,games room,spa
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4 BR | 2.5 BA | Sleeps 8 | Quick View

1

Distance to park: 3 miles to Disneys Animal Kingdom

$166

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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3 BR | 2 BA | Sleeps 7 | Quick View

9
last minute deal
LAST MINUTE DEAL 5/17 - 6/28: $100 Off Any week

Distance to park: 6 miles to Disney - Animal Kingdom

$122

avg/night

View Details

Key Amenities

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

About this property

This private, lakefront with nature reserve, pool home offers a fusion of luxury, comfort, and convenience. This spacious 3 bedroom and 2 bath home has cathedral ceilings and an open floorplan, with a living room, breakfast nook, and formal dining area. The kitchen is fully outfitted with all the appliances ...

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Property Type

Kissimmee House

"Great Stay at Paradise Cove"

We spent 3 weeks here and we were very impressed with this lovely, clean spacious home. The beds were all very comfortable. The area is near all the restaurants we normally frequent. It’s in a safe quiet ...

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DEAL
Newly Upgraded Disney Themed Vacation Retreat
Viewed

$215

avg/night

View Details

Key Amenities

  • Air conditioning
  • Pool

About this property

Embark on an enchanting journey with our exquisite 5-bedroom home with theme bedrooms and themed out game room that is nestled in the prestigious Windsor Hills community. Ideal for families or groups, this charming retreat promises a perfect blend of luxury and proximity to the magic.? Key Features:?? ...

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Property Type

Kissimmee Villa

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Pool

About this property

Beautiful and clean unit with two queen size beds upstairs, it is part of a recently renovated condo-hotel furnished with modern design and great taste, with fenced pool, playground, gym, and indoor and outdoor dining/resting/seating areasTouristic area, super close to the parks, located on the main 192 ...

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Property Type

Kissimmee Condo

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Key Amenities

  • Air conditioning
  • Pool

About this property

Welcome to our charming townhome in Bella Vida Resort, just a short 8 mile drive from the entrance to Walt Disney World! Make your vacation truly magical with the comfort and convenience of our delightful home. Also, do add to the convenience there is a Walmart Superstore around the corner and many, many ...

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Property Type

Kissimmee House

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5 BR | 4 BA | Sleeps 10 | Quick View

1
owner special
Owner special: Great Spring Savings. Up to 20% off stays arriving in the next 45 days

$155

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Solara Resort - Kissimmee, Florida is an upscale community currently under development just 7 miles from Walt Disney World. This gated resort community sits nestled just outside of Orlando, Florida. During your stay, you will enjoy this well-appointed home that has been designed and decorated to provide ...

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Property Type

Kissimmee House

"Great stay"

Home was just right. Pool , lawn was beautiful the yard well kept garbage was collected on time We enjoy every moment of our stay .We are looking forward to return again in the new year.

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4 BR | 2 BA | Sleeps 8 | Quick View

1

Distance to park: 3 miles to Walt Disney World

$183

avg/night

View Details

Key Amenities

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

About this property

4 Bedrooms| 2 Baths| Sleeps 8|Private Pool|Games Room|Disney-Themed Kids Rooms| Updated Decor|If you’re looking for the perfect home away from home for your family’s perfect Disney vacation, look no further. Our bright, airy house in the desirable 5-star Emerald Island Resort means that ...

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Property Type

Kissimmee House

"Fantastic Villa"

We have recently returned from a fantastic stay at Joanna’s villa and couldn’t recommend highly enough. After a long day of travel the immediate comfort we felt opening the door of what would be our ...

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Key Amenities

  • Air conditioning
  • Pool

About this property

If you're searching for Orlando vacation rentals near Disney, the name of this unit simply says it all: Three-bedroom 2nd Floor condo within minutes from Disney! This unique condo is set up to accommodate six guests between its three bedrooms and two bathrooms. Not only will you be able to benefit ...

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Property Type

Kissimmee Condo

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Key Amenities

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

About this property

5 star Property!Welcome to Sunset Magic Villa!Delightful Windsor at Westside Resort home villa8 bedrooms (2 Downstairs/6 Upstairs) and 6 full bathrooms. Space for up to 16 guests, (stretch out and relax with all the comforts of home) WEST facing private pool ensuring stunning sunset ...

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Property Type

Kissimmee House

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3 BR | 2 BA | Sleeps 7 | Quick View

3
last minute deal
LAST MINUTE DEAL 5/17 - 6/28: $100 Off Any Week

Distance to park: 6 miles to Disney - Animal Kingdom

$119

avg/night

View Details

Key Amenities

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

About this property

The "Sweet Retreat" is just 6 miles to Disney! This "Sweet" Villa has 3 Bedrooms, 2 Baths and sparkling Sunny private pool... Perfect for families & "Sweet" on your feet with all tile in the main rooms & carpet in the bedrooms.The living room feels bright and ...

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Property Type

Kissimmee House

"SWEET RETREAT"

We enjoyed the home very much. The price was right neighborhood is a quiet residential area near everything. The kitchen well equipped with everything one would need! Furniture clean & comfy. Pool ...

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DEAL

Key Amenities

  • Air conditioning
  • Pool

About this property

Welcome to your dream vacation home! Nestled in the heart of the exclusive Storey Lake resort, this modern 4-bedroom townhouse is the perfect retreat for your Disney World or Universal Orlando getaway. With its unbeatable location, luxurious amenities, and a private pool, your vacation experience will ...

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Property Type

Kissimmee House

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6 BR | 4 BA | Sleeps 12 | Quick View

11

Distance to park: 2 miles to Disney World

$397

avg/night

View Details

Key Amenities

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

About this property

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

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Property Type

Kissimmee House

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5 BR | 4 BA | Sleeps 10 | Quick View

Distance to park: 6 miles to Disney World

$206

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

This beautiful 5 bedroom house is located in Crystal cove gated community. Perfect vacation home for families with small children or large groups. This vacation villa offers a sunny private pool, relaxing spa overlooking the lake. There are 2 master suites, private pool, community pool / gym. Pool ...

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Pool

About this property

When you’re searching for Disney vacation rentals, you want a property that’s spacious, luxurious, and full of all the creature comforts of home. This 6 bedroom Avatar themed villa delivers all that and more! Within your home, you’ll have a fully equipped kitchen to whip up some delicious ...

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Property Type

Kissimmee House

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Kissimmee Vacation Rentals

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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!