Kissimmee Vacation Rentals

(330 rentals)
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Key Amenities

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

About this property

Windsor at Westside Resort is one of the newest and most luxurious resort communities in the Orlando/Kissimmee,Developed by one of the nation's largest developer , the Pulte Homes. Just 8 miles from Disney, and within easy reach to all the attractions, shopping, and dining in the Disney area, this ...

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Property Type

Kissimmee House

"Excellent luxurious home"

First class all the way and we will do it again!! It was a beautiful home and everything that was advertised was true.

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3 BR | 2 BA | Sleeps 6 | Quick View

2

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

$102

avg/night

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Key Amenities

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

About this property

Welcome to the Sun Lake Resort. This 1500 sqft 3bedroom/2bathroom unit is on 2nd floor. The beautiful condo faces to sun lake and it has a spacious screened patio with an amazing view. It only takes 1 minute walk to a plaza for shopping and restaurants which is very convenient ! More importantly, you ...

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Property Type

Kissimmee Condo

"Larry’s Villas, Kissimmee, Florida"

Loved the area! Easy access to restaurants and attractions! The condo was very clean! Needs some bathroom updates! There was a problem with the wifi and eventually was rectified!

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Property Reference Code RVH_333R Welcome to Whisper Delight located in Reunion Resort. This beautiful condo comes with 3 bedrooms and 3 bathrooms ideal for up to 6 guests to stay. From all the luxury that Reunion Resort offers to the strategic location close to Orlando's known attractions, this ...

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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

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

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Property Type

Kissimmee Townhome

"Loved it."

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

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Key Amenities

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

About this property

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

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Property Type

Kissimmee Townhome

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Key Amenities

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

About this property

Property Reference: RVH_357RWelcome to Leisure at Fairway. Located in Reunion Resort, and situated within the Fairway Ridge neighborhood. This beautiful 5-bedroom, 5.5 bath is perfect for your friends and family as it is located within minutes from Orlando's world-class attractions.The lanai ...

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Property Type

Kissimmee House

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Key Amenities

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

About this property

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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9 BR | 6 BA | Sleeps 18 | Quick View

3

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

$392

avg/night

View Details

Key Amenities

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

About this property

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

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Property Type

Kissimmee Villa

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

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

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$122

avg/night

View Details

Key Amenities

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

About this property

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

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Property Type

Kissimmee House

"Lovely stay"

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

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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_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_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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6 BR | 6 BA | Sleeps 12 | Quick View

owner special
Owner special: Check out the Spring deals

$218

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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3 BR | 2 BA | Sleeps 6 | Quick View

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

$127

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Rentals by owner

About this property

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

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Property Type

Kissimmee Apartment

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • 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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8 BR | 6 BA | Sleeps 16 | Quick View

4

Distance to park: 8 miles to Disney Animal Kingdom

$280

avg/night

View Details

Key Amenities

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

About this property

Windsor at Westside Resort is one of the newest and most luxurious resort communities in the Orlando/Kissimmee, Developed by one of the nation's largest developer , the Pulte Homes. Just 8 miles from Disney, and within easy reach to all the attractions, shopping, and dining in the Disney area, this ...

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Property Type

Kissimmee House

"Quite and comfortable"

Nice area, quite and convenient to many attractions many restaurants close by.nice pool and hot tub and gym in clubhouse.

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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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4 BR | 3 BA | Sleeps 8 | Quick View

6

Distance to park: 6 miles to Disney,Seaworld

$116

avg/night

View Details

Key Amenities

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

About this property

Welcome to the beautiful Coral Cay resort ! It is one of the most popular resort destinations in the Kissimee/Orlando area for its proximity to theme parks and other major attractions. Situated 6 miles from Disney,1 mile to walmart and target, 8 miles to seaworld and convention center.This 1500 sqft ...

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Property Type

Kissimmee Townhome

"Second stay"

This is a nice place. Well kept and clean. There is 3 pools but not enough lounge chairs. The room was nice. Needed to buy a frying pan there is not enough kitchen gadgets and the cups for coffee are very ...

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Key Amenities

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

About this property

Property Reference RVH_354RWelcome to Radiant Luxury! This is a breath-taking home designed to offer comfort, entertainment, and luxury, overlooking Reunion Resort's signature Tom Watson golf course.As you step inside, you will notice the attention to detail made when decorating this home. ...

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Property Type

Kissimmee House

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6 BR | 4 BA | Sleeps 14 | Quick View

2
owner special
Owner special: Discounted Rates avaliable for last minute bookings!!!

$280

avg/night

View Details

Key Amenities

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

About this property

Welcome to your ultimate themed vacation experience in the heart of Kissimmee, Florida! Prepare to embark on an extraordinary journey as you step into this spectacular 6-bedroom, 4-bathroom house in the prestigious Windsor Hills community. This newly listed paradise has been meticulously designed to immerse ...

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Property Type

Kissimmee House

"Wonderful place"

Omg we loved the house and how nice everything was it really felted like we were back home I definitely will be booking again with this company we really enjoyed our stay such lovely place

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5 BR | 3 BA | Sleeps 10 | Quick View

3

Distance to park: 6 miles to Disney,Seaworld

$124

avg/night

View Details

Key Amenities

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

About this property

Welcome to the beautiful Coral Cay Resort. It is one of the most popular resort destinations in the Kissimmee/Orlando area for its proximity to the theme parks and other major attractions. Situated 6 miles from Disney World, 1 mile to Walmart and target. 8 miles to Seaworld and Convention center. Minutes ...

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Property Type

Kissimmee Townhome

"Comfortable place to stay....."

We stayed here while in Florida for my daughter's dance competition. It was so nice to come "home" after a long day of dance. I loved that the driveway was right up to the door. I also loved that it ...

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10 BR | 5 BA | Sleeps 20 | Quick View

owner special
Owner special: Check out the Spring deals

$540

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Be sure to visit our website to check availability on all our homes! Save our page for future vacations to the Orlando area!Visit us at lostinthemagic . comThe Retreat at Champions Gate - Kissimmee, Florida is a new upscale gated resort community located just 12 miles from Walt Disney World. ...

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Property Type

Kissimmee House

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Key Amenities

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

About this property

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
  • 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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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

About this property

Property Reference Code #XBV_1901RWelcome to Bella Vida Paradise! This magnificent vacation home located in Bella Vida Resort has 4 bedrooms, 4 bathrooms, a private pool, and much more.On the first floor, you will find a dining table for 6 and an extra bistro table for 2. The living room offers ...

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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
  • 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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8 BR | 6 BA | Sleeps 16 | Quick View

1
owner special
Owner special: Book 7 Nights or More & Enjoy 15%! Offer not valid with any other discounts.

$217

avg/night

View Details

Key Amenities

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

About this property

Enjoy a whimsical getaway when you book a stay at this sleek, refreshing, 8-bedroom, 6-bathroom vacation rental home. Take a dip in the private pool, fix up something tasty in the fully equipped kitchen, play a game of pool in the game room, or head to the community fitness center for a quick workout. ...

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Property Type

Kissimmee House

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Key Amenities

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

About this property

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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4 BR | 3 BA | Sleeps 8 | Quick View

15

Distance to park: 3 miles to Mgm

$125

avg/night

View Details

Key Amenities

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

About this property

Beautiful 4 bedroom /3 bath private villa only 3 miles to Disney and other parks. Including heated pool/jacuzzi and game room. Free wifi and phone use in USA and Canada and PR. Fully furnished with all kitchen needs . Greatest location to shopping , all major restaurants and stores including supermarkets ...

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Property Type

Kissimmee Villa

"Great Location!"

This location is great! A few minutes drive to good restaurants (Carrabbas, Olive Garden, Outback, Bonefish Grill, Texas Road House, Red Lobster) and all the usual fast food places. This house is well ...

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7 BR | 6 BA | Sleeps 14 | Quick View

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

$251

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

"Awesome Stay"

This house was the perfect holiday stay, lots of space and no problem at all.Only thing missing was a game table, we love game nights.

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4 BR | 4 BA | Sleeps 8 | Quick View

17

Distance to park: 2 miles to Disney

$257

avg/night

View Details

Key Amenities

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

About this property

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

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Property Type

Kissimmee Villa

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Key Amenities

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

About this property

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

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Property Type

Kissimmee House

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4 BR | 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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9 BR | 5 BA | Sleeps 18 | Quick View

1
owner special
Owner special: Check out the Spring deals

$482

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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9 BR | 8 BA | Sleeps 18 | Quick View

10

Distance to park: 3 miles to Disney Animal Kingdom

$618

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

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

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Property Type

Kissimmee House

"Hartley House family gathering"

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

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Key Amenities

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

About this property

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

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Property Type

Kissimmee House

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

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

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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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$111

avg/night

View Details

Key Amenities

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

About this property

Close to the Attractions but away from the crowds. 4 bedroom/3 bath single story home on "lake". Ducks, Sandhill Cranes, sometimes a falcon, turtles. King, king, and 4 twin beds, TV in all bedrooms, WiFi, FREE US, Canada and US Territory phone calls. Fully furnished. Not suitable for ...

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Property Type

Kissimmee House

"Great Location for your stay."

The home was very comfortable and dealing with the owner was a breeze. Check in was very easy and the location is ideal for Disney and Universal visitors. Nice lake view and several chairs for outdoor seating. ...

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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_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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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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2 BR | 2 BA | Sleeps 6 | Quick View

2

Distance to park: 2 miles to Disney

$141

avg/night

View Details

Key Amenities

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

About this property

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

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Property Type

Kissimmee Condo

"Fabulous Host and Fantastic Accomodations!"

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

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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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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
  • 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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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!