Kissimmee Vacation Rentals

(326 rentals)
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Key Amenities

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

About this property

*** 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 facing Pool and stunning views over the second ...

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Property Type

Kissimmee House

"Amazing accommodation and location"

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

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Key Amenities

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

About this property

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

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Property Type

Kissimmee House

"summer vacation"

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

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4 BR | 3 BA | Sleeps 8 | Quick View

9

Distance to park: 4 miles to Disney World

$151

avg/night

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Key Amenities

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

About this property

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

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Property Type

Kissimmee House

"Great Villa"

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

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Key Amenities

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

About this property

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

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Property Type

Kissimmee House

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Key Amenities

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

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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9 BR | 8 BA | Sleeps 18 | Quick View

10

Distance to park: 3 miles to Disney Animal Kingdom

$617

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Mickey's Oyster is a luxurious oasis designed to make your Disney World vacation unforgettable. Nestled in a prestigious, gated community just minutes away from the magic, this freshly remodeled and renovated home offers an enchanting escape with all the comforts of a five-star resort. Luxurious ...

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Property Type

Kissimmee House

"Hartley House family gathering"

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

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • 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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6 BR | 6 BA | Sleeps 12 | Quick View

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

$203

avg/night

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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

Fairway Retreat is a home that truly lives up to its name and more. This five-bedroom custom-designed vacation home offer sweeping Fairway views and tons of fun and excitement all under one roof. This home is sure to set the bar of expectations much higher for future getaways for you and your family.When ...

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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_1021RBalconies, patios, and lanais are not accessible. During 2023 - 2024 there may be construction occurring on the exterior of the building by the homeowners association; contact us for updates Welcome to Seven Eagles Joy. This 3 bed, 3 bath townhome is located in the heart ...

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Property Type

Kissimmee Townhome

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Key Amenities

  • Air conditioning
  • 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

$534

avg/night

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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

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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3 BR | 2 BA | Sleeps 6 | Quick View

2

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

$100

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
  • 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 8 | Quick View

15

Distance to park: 3 miles to Mgm

$125

avg/night

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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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Key Amenities

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

About this property

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

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Property Type

Kissimmee Townhome

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Key Amenities

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

About this property

Property Reference WW_718ARWelcome to Westside Deluxe. You and your family will immediately love this wonderful vacation home from the moment you take a step inside. The great room has a large plush sofa and chairs for everyone to gather around and watch TV together. The decor is modern and accented ...

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Property Type

Kissimmee House

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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

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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
  • 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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7 BR | 5.5 BA | Sleeps 14 | Quick View

2

Distance to park: 5 miles to Disney World

$244

avg/night

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Key Amenities

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

About this property

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

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Property Type

Kissimmee House

"Amazing 7 Bed rooms Villa Near Disney"

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

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Key Amenities

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

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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8 BR | 4 BA | Sleeps 16 | Quick View

12

Distance to park: 6 miles to Disney

$383

avg/night

View Details

Key Amenities

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

About this property

AMAZING Pool Deck Extension cira 2023! Its the BIGGEST pool deck at the resort! Plus JAW DROPPING, Fancy, Fun, Fountain Jets w/ LED lighting, high-end glass tile & a Mickey Mosaic giving you an ULTIMATE luxury pool experience. This SALT WATER POOL/SPA will leave your skin feeling soft w/ no eye-sting ...

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Property Type

Kissimmee Villa

"Amazing house"

We had an amazing time and the house had everything we needed and wanted for our vacation in Florida. If you are going to Florida we recommend this house. It's has a great pool and patio and can accommodate ...

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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
  • Rentals by owner

About this property

A beautiful vacation condo located in a prestigious gated and guarded community, for you to relax and spend time with your family and friends. With the prime location in Kissimmee near Disney World, major parks and restaurants, shops and so much more, this 3BD/2BA condo unit is designed for your best ...

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Property Type

Kissimmee Condo

"Great family time"

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

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

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

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

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Property Type

Kissimmee Townhome

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Key Amenities

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

About this property

Enjoy comfort during your next vacation in this gorgeous 6 bedroom 4.5 bath, the perfect home for you and your family to stay in. One Queen bedroom is located in the annex with seperate entrance, ideal for grand parents wanting extra privacy. Located in Reunion Resort, allows for you to easily access ...

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Property Type

Kissimmee House

"Was awesome experience"

We had an amazing time it came with everything we needed in the kitchen and also through out the house we had a blast and will definitely be back

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5 BR | 3 BA | Sleeps 10 | Quick View

2

Distance to park: 6 miles to Disney kingdom

$122

avg/night

View Details

Key Amenities

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

About this property

Welcome to Coral Cay Resort! Coral Cay resort Situated 6 miles from Disney World, 1 mile to Walmart and target. 0.5 mile off highway 192.Seaworld and Convention Center are 8 miles away.Just minutes from Orlando's vast array of theme parks, fabulous dining options and world-class shopping.Our ...

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Property Type

Kissimmee Townhome

"Vacation was beautiful!"

We had an awesome week in Florida! The house was amazing! The owners were awesome!!!!’ 6 stars! My family and myself will book again very soon!!

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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

Luxury five star villa with 4 bedrooms, 2 bathrooms, and a private swimming pool Our luxury 4 bedroom home is located within the top rated community of Lake Berkley.The villa is furnished to a very high standard and is fully Air-conditioned throughout keeping the villa cool in the warm Florida ...

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Property Type

Kissimmee Villa

"Comforts of Home"

The mattresses and blankets were fantastic. Everything was very clean, and I loved the themed rooms. The pool was great too, with floats and towels for everyone. The only thing I think could have been improved ...

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5 BR | 3 BA | Sleeps 10 | Quick View

5

Distance to park: 6 miles to Disney,Seworld

$120

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 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 gorgeous ...

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Property Type

Kissimmee Townhome

"Thank you"

The property my children and I stayed at for 6 months was amazing. Would definitely recommend this rental again. Five stars.

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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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2 BR | 2 BA | Sleeps 4 | Quick View

owner special
Owner special: Check out the Spring deals

$158

avg/night

View Details

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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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 SL_660RStep inside the enchanted doors of this magnificent abode and be transported to a world of wonder and delight. Nine luxurious bedchambers and five opulent bathrooms await your arrival for a family sojourn like no other.The heart of the home, the modern kitchen, is a place ...

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Property Type

Kissimmee House

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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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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
  • 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
  • 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

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_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
  • 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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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

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 pool, hot tub, BBQ, and themed bedrooms, including ...

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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

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

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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3 BR | 2 BA | Sleeps 8 | Quick View

13

Distance to park: 12 miles to All Disney Theme Park

$109

avg/night

View Details

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
  • 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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Kissimmee Apartment

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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 326 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 $57 per night with an average price per night of $171.

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