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Kissimmee Vacation Rentals

(219 rentals)
Kissimmee House
Sleeps 6, 4 bedrooms, 2 bathrooms
14 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

CHEERY 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 without. Located in Eagle Pointe, a well sought-after vacation home community. Just minutes from what...

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Featured review

"Well equipped villa in a beautiful setting"

Beautiful setting, overlooking a lake with bird life to watch, and quiet neighbourhood. 15 minute easy access to 2 large supermarkets and a variety of eateries. Villa itself is large with plenty of space,...

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$120
avg per night
Kissimmee Villa
Sleeps 6, 3 bedrooms, 3.5 bathrooms

Distance to park: 4 miles to Disney

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to Magic Village Views, part of Trademark Collection by Wyndham. "Boutique style 3BDR very spacious Town house, ideally located in Magic Village community……right next to Disney’s parks like Magic Kingdom. All Units have unique furnishings, complete kitchens with gas range,...

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$240
avg per night
Kissimmee House
Sleeps 10, 5 bedrooms, 4 bathrooms
6 reviews

Distance to park: 7 miles to Disney Hollywood Studio

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Beautiful, clean and spacious 5 bedroom and 4 bath house in the most sought after community near Disney! 10 minutes drive to Disney and you can hear the Disney fireworks at night. Close to stores, restaurants and tons of shops. The house was renovated and professionally designed recently. The house has...

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Featured review

"60th birthday gathering"

So it was my wife's 60th birthday and we wanted something very nice so we contacted Mrs. Jun and she was very nice . We we arrived at the home it was just what we were looking for. The home very spacious...

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$153
avg per night
Kissimmee Villa
Sleeps 14, 7 bedrooms, 5 bathrooms
6 reviews

Distance to park: 7 miles to Disney Magic Kingdom

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

* Gated and Guarded Resort 7 -10 minutes to Disney * Stunning Lake Views from Enclosed Pool Deck * Pool with 24 Hour Spa on Over ride - Handrails * Lots of Baby Equipment - Free to Use * 2 Lounges - Leather sofas * Game Room Disney Themed -Air conditioned - Slate Bed Pool Table *New Gaming Station...

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Featured review

"Great place to stay"

Our family of 10 rented this property. The host was unbelievable and assisted us every step of the way. The property is clean and neat with everything you could need. Its location is excellent for the parks....

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$264
avg per night
Kissimmee Condo
Sleeps 8, 3 bedrooms, 2 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

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

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Featured review

"Vacation"

We stayed there in 2024 and it was amazing to stay there and experience all that fun. We will definitely be back again. Thanks again

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$147
avg per night

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Kissimmee House
Sleeps 14, 7 bedrooms, 5.5 bathrooms
1 review

Distance to park: 5 miles to Animal Kingdom

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Peaceful Private Getaway – Private Pool and Hot Tub - (6) NIGHT MINIMUMWelcome to Islands of Magic @ , a spacious and family-friendly vacation home just 5 miles from Walt Disney World! Perfect for large families, group getaways, or multi-family trips, this beautifully designed home offers...

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Featured review

"Best Vacation Home"

Renting this beautiful house was a breeze!! We were very happy that after checking out at least a dozen houses, we all agreed on this one!! We wanted a big house with lots of bedrooms/bathrooms! We got...

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$232
avg per night
Special Offer
Kissimmee House
Sleeps 16, 8 bedrooms, 6 bathrooms
2 reviews

Key Amenities

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

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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Featured review

"Kissimmee Home/Windsor"

My family & I enjoyed our stay at this lovely home during the summer time. This house gave us an enjoyable experience that we will all remember. We didnt have any problems with the house and we hope to...

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$323
avg per night
Kissimmee Villa
Sleeps 8, 4 bedrooms, 4.5 bathrooms

Distance to park: 4 miles to Disney World

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to Magic Village Views, part of Trademark Collection by Wyndham. With a stay in a luxury condominium in an ideally located community, you won’t run out of exciting things to do and thoughtful amenities to enjoy. The hotel’s ideal location is right next to Disney’s parks. You’ll...

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$246
avg per night
Kissimmee Villa
Sleeps 16, 7 bedrooms, 5.5 bathrooms
1 review

Distance to park: 3 miles to Disney World

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

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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Featured review

"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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$307
avg per night
Kissimmee House
Sleeps 9, 4 bedrooms, 2.5 bathrooms
12 reviews

Distance to park: 6 miles to Disneyworld

Key Amenities

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

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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Featured review

"The way to go"

Very nice house. Pool heat price could be about 10 $ The extra cost hurts. Always need hangers.towels and a extra fridge in garage would be handy. Location close to shopping and restaurants Not good...

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$139
avg per night
Kissimmee Townhome
Sleeps 10, 4 bedrooms, 3.5 bathrooms
17 reviews

Distance to park: 5 miles to Animal Kingdom

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

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

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Featured review

"Great!"

We love staying here. Close to everything, clean, spacious and reasonable priced. The area is quite and we have never had a problem. We have stayed here twice now and will cont when we visit Florida.

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$118
avg per night
Kissimmee House
Sleeps 18, 6 bedrooms, 5.5 bathrooms
58 reviews

Distance to park: 4 miles to Animal Kingdom

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Some of the best features of this house from Guest Reviews • Beautiful Vinyl Plank Flooring in all bedrooms, halls and on the steps • Less than a 4-mile drive to Disney World’s Animal Kingdom Theme Park • Two leather couches with a total of 4 power reclining seats • Privacy...

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Featured review

"Fantastic Stay for Extended Family Vacation"

Words fail me as to describe what an incredible time we had at the Diamond on the Island Vacation Home. Having rented houses in the Kissimmee area many times, this was the first time we rented a house...

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$197
avg per night
Kissimmee Condo
Sleeps 4, 1 bedroom, 1 bathroom

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

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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$90
avg per night
Kissimmee House
Sleeps 8, 4 bedrooms, 4 bathrooms

Distance to park: 4 miles to Disney

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

"Boutique style very spacious Town house, ideally located in Magic Village community……right next to Disney’s parks like Magic Kingdom. All Units have unique furnishings, complete kitchens with gas range, living, and dining rooms with vaulted ceilings. Full size laundry room, extra...

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$222
avg per night
Kissimmee Villa
Sleeps 26, 9 bedrooms, 10 bathrooms
17 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

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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Featured review

"A Christmas To Remember"

My Family and I So Enjoyed This Beautiful Mansion For The Week Of Christmas. The Entry/Foyer was decorated with a beautiful tall Christmas Tree. As well as Christmas Decor around the house. Which was an...

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$956
avg per night
Kissimmee House
Sleeps 14, 7 bedrooms, 5.5 bathrooms
2 reviews

Distance to park: 5 miles to Disney World

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

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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Featured review

"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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$207
avg per night
Kissimmee House
Sleeps 8, 4 bedrooms, 3 bathrooms
9 reviews

Distance to park: 4 miles to Disney World

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

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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Featured review

"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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$157
avg per night
Kissimmee House
Sleeps 6, 3 bedrooms, 3.5 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Luxury vacation homes accommodations feature contemporary interiors, located in Magic Village gated community only 5 minutes away from Disney’s Animal Kingdom. Step into your private villa at Magic Village Yards and discover a chic and contemporary yet invitingly cozy sanctuary. All Bedrooms are...

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$212
avg per night
Kissimmee Townhome
Sleeps 8, 3 bedrooms, 2.5 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

About this property

You have arrived in the "Vacation Capital of the World" and you're going to love staying in our luxury, 3 bedroom, 2.5 bath, fully equipped vacation townhouse rental situated near DisneyWorld and all other theme park attractions. The property rental is located within the resort community...

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Featured review

"Beautiful Condo! Exactly as shown!"

We are a retired couple who stayed for 3 months from Jan to March. Beautiful Condo, exactly as pictured. Furniture is very comfy. Close to all attractions. We felt very safe. Publix and Walmart are...

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$105
avg per night
Kissimmee Villa
Sleeps 8, 4 bedrooms, 3 bathrooms
4 reviews

Key Amenities

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

About this property

Palm Tree Villa Florida, is tucked away in the much sought after location of Doral Woods. This large 4 Bedroom, 3 Bathroom villa, is ideal for making the perfect vacation.This is our own holiday home, so the furnishings are to a high standard, as you can see from the pictures and video. Fully Air...

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Featured review

"Lovely Villa with a lot of extras !"

Beautiful place for a relaxing holiday or just 15 minutes away from the Disney and Resorts area . The home was perfect and the welcome package was great. Andy was great and checked in on us during our stay....

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$184
avg per night
Kissimmee House
Sleeps 6, 4 bedrooms, 3 bathrooms
17 reviews

Key Amenities

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

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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Featured review

"Unreal stay"

We had a great week and it was everything they said it was. Stayed in the location before and we will definitely book again.

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$121
avg per night
Special Offer
Kissimmee House
Sleeps 14, 6 bedrooms, 4 bathrooms
4 reviews

Key Amenities

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

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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Featured review

"Amazing"

This was an amazing experience for my kids and I. I would definitely choose again!!!!!!!!!!!!!!!!!!!

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$324
avg per night
Kissimmee House
Sleeps 12, 5 bedrooms, 5 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

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

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Featured review

"Great place, nice price!"

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

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$231
avg per night
New
Kissimmee Villa
Sleeps 14, 6 bedrooms, 4 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Just 10 minutes from Disney, this 6BR home has it all—Minions, Avatar, and Guardians of the Galaxy-themed kids' rooms, a hidden Mario game room, and luxe king suites. Outside, enjoy a private screened pool and spa with free heat, a full outdoor kitchen, firepit lounge, movie screen, sauna,...

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Special Offer
Kissimmee House
Sleeps 10, 3 bedrooms, 2 bathrooms
25 reviews

Key Amenities

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

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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Featured review

"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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$167
avg per night
Kissimmee Villa
Sleeps 8, 4 bedrooms, 4.5 bathrooms

Distance to park: 4 miles to Disney Theme Parks

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Welcome to Magic Village Views, part of Trademark Collection by Wyndham. This 4 Bedroom 4.5 Bath Luxury Townhouse Villas is a must stay. located in an ideally located gated community……right next to Disney’s parks. All Units are En-Suites with unique furnishings, complete kitchens,...

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$245
avg per night
Kissimmee Villa
Sleeps 14, 7 bedrooms, 6 bathrooms
4 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Introducing 101 Happy Memories Florida Villa, your gateway to unforgettable vacations in the heart of Formosa Gardens, just minutes from the enchantment of Disney World!Step into luxury with our private heated pool and spa, perfect for unwinding after a day of adventure. Thrill-seekers will love our...

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Featured review

"2nd time still a charm"

We enjoyed a stay here 3 years ago and we lucky enough to find it available again in 2024. We can't say enough except that the property was somehow even an improvement over the 1st time. This is a great...

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$313
avg per night
Kissimmee Apartment
Sleeps 4, 1 bedroom, 1 bathroom

Distance to park: 7 miles to Disney World

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

1/1 Condo. Queen sofabed in living room. Queen bed in master with desk and chair. Full kitchen. Just 7 miles from Disney, centrally located. Gated community , Complex has 2 pools, gym, tennis courts. Laundry room with full size washer/dryer in unit. Free wifi and streaming. Second floor unit.No elevators. No...

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$81
avg per night
Kissimmee House
Sleeps 16, 9 bedrooms, 7 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Located in the exclusive Encore community. This beautiful and luxurious vacation home is a 2-story home with 9 bedrooms, 7 bathrooms, a laundry room, game room, and a pool with hotube. It is completely fenced. The house has a capacity for 18 guests. This stylish place to stay is perfect for group trips. Charming...

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$383
avg per night
Kissimmee House
Sleeps 10, 5 bedrooms, 4 bathrooms
9 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

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 ***Newly painted throughput New wood/plank flooring currently be fitted in the main house upper floor. This will make the main house carpet...

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Featured review

"Excitement Place at Christmas time was Incredible!"

Knowing at the beginning of 2024 that we were going to take a family vacation to Disney World with all of our children and grandchildren over the Christmas 2024 Holiday, we would need accommodations for...

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$223
avg per night
Kissimmee Villa
Sleeps 12, 6 bedrooms, 5 bathrooms
1 review

Distance to park: 5 miles to Disney’s Animal Kingdom

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to your elegant vacation retreat in Emerald Island Resort, Orlando, FL! This spacious 6-bedroom, 5-bathroom home has been recently upgraded and is located just 3 miles from Walt Disney World and only minutes from top attractions like Universal Studios, SeaWorld, and Old Town Kissimmee. With plenty...

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Featured review

"Wonderful stay"

We rented this property for the month of February 2025. As a family of 9 with Grandparents, parents and 2 young grandchildren, we found the villa to be spacious without feeling cavernous. It was well...

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$250
avg per night
Kissimmee Villa
Sleeps 8, 4 bedrooms, 2 bathrooms
8 reviews

Distance to park: 7 miles to Walt Disney World

Key Amenities

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

About this property

Welcome to our Florida villa, the Lake House at Sunset Lakes. The Lake House at Sunset Lakes is an upscale rental villa in the greater Orlando Florida area, minutes away from Disney’s Magic Kingdom and theme parks, your choice of fine golf courses and many other attractions. This four bedroom house...

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Featured review

"A Gem"

Second visit to the Lake House. Clean, well stocked, nice hot pool and beautiful views of the lake. The owners and the management company responsive to every need.Thanks so much Carole & Brian

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$210
avg per night
Kissimmee Villa
Sleeps 8, 3 bedrooms, 2 bathrooms
15 reviews

Distance to park: 12 miles to All Disney Theme Park

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

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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Featured review

"Wonderful Vacation"

We enjoyed a lot during our stay. Everything was perfect! Thank you Mariana for making our stay excellent.

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$134
avg per night
New
Special Offer
Kissimmee House
Sleeps 12, 6 bedrooms, 5 bathrooms
4 reviews

Distance to park: 5 miles to Disney

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Whether you are planning a family vacation, reunion with friends and family, or couples' retreat, Paradise Cove offers everything you need for an unforgettable stay!! Book your stay today and start making memories....This 6BR/5B spacious home is located in a secure gated family friendly resort...

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$301
avg per night
Kissimmee Villa
Sleeps 12, 6 bedrooms, 3.5 bathrooms
1 review

Key Amenities

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

About this property

Bring your family to this stunning 6BR 3.5BA in the luxurious gated community just minutes from the world-famous Disney World. Have hours of fun in the game room and scenic pool backyard, or set out to explore local theme parks, golf clubs, restaurants, shops, and more!6 Comfy Bedrooms (2 Themed) ...

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Featured review

"Wonderful Stay!"

The house was lovely and had everything we needed for my family of 6 week long stay. Kitchen was well stocked with everything we needed, house and pool were clean, and the beds were comfortable. The 80s...

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$261
avg per night
Kissimmee House
Sleeps 16, 7 bedrooms, 4 bathrooms
68 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

A tropical oasis in Central Florida. Come experience all the details this home away from home has to offer, with the added benefit of being centrally-located to the best attractions in Orlando.Discover magic and family fun at this elegant Emerald Island Resort escape. Perfect for a group getaway,...

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$453
avg per night
Kissimmee Villa
Sleeps 12, 6 bedrooms, 5 bathrooms

Distance to park: 7 miles to Disney's Animal Kingdom Theme Park

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Experience Luxury and Comfort at Our 6-Bedroom, 3,200 sq. ft. Villa – Perfect for Families and Groups!Escape to our stunning luxury villa, featuring 6 spacious bedrooms (9 beds) and 3,200 sq. ft. of beautifully appointed living space. With 2 luxurious en-suites, 3 king-sized beds, 2 cozy living...

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$194
avg per night
Kissimmee Villa
Sleeps 8, 4 bedrooms, 2 bathrooms
9 reviews

Distance to park: 5 miles to Walt Disney World

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Located in the 5 star gated (guarded) resort of Windsor Palms, this 4 bedroom home is minutes away from Disney World, Universal Studios, and other major attractions. Keyless entry for easy access.You'll find all the comforts of home including a private pool, flat screen HDTVs, XBOX 360 and N64,...

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Featured review

"Great Experience"

We stayed at Don’s villa in late July-early August of this year. True to its description, the villa not only met our expectations but surpassed it. As regular repeat guests who have stayed at Windsor...

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$200
avg per night
Special Offer
Kissimmee Condo
Sleeps 6, 3 bedrooms, 2 bathrooms
4 reviews

Distance to park: 1 miles to Disney Animal Kingdom

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

About this property

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

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Featured review

"Great place"

We love the place. Close to everything we needed. The place is spacious. Will rent again in the future. Frank was an awesome host.Gregory and Ghyslaine From Aruba

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$97
avg per night
Kissimmee Villa
Sleeps 12, 5 bedrooms, 4 bathrooms
2 reviews

Distance to park: 3 miles to Disney World

Key Amenities

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

About this property

A luxurious 5 bedroom 4 bath villa with south-facing pool situated in luxury Emerald Island Resort Orlando. Located a short distance from the popular destinations such as Disney World, Sea World and Universal Studios and accommodates 10-12 guests.This tastefully-decorated 5 bedroom/4 bath vacation...

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Featured review

"Excellent vacation & house"

we were a family of 10 staying in this beautiful house was well equipt with everything we needed room was a big hit ..The heated pool was sure a big catcher the 4 children loved it so did the adults.....

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$250
avg per night
Kissimmee House
Sleeps 10, 4 bedrooms, 3 bathrooms
5 reviews

Key Amenities

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

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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Featured review

"Fabulous home"

The home was comfortable for our big group. The kitchen was well stocked with utensils, cookie sheets, and bowls. We were able to make our Christmas brunch! The game room was fun for the teens. The location...

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$168
avg per night
New
Kissimmee Townhome
Sleeps 8, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

About this property

Welcome to your perfect Orlando retreat! Located in the heart of the action, our spacious 3-bedroom, 3-bathroom townhome is just minutes from Disney World, Universal Studios, and other top theme parks — and only 30 minutes from Orlando International Airport (MCO).

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$117
avg per night
Kissimmee Bungalow
Sleeps 9, 4 bedrooms, 3 bathrooms
6 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Amazing Villa near Universal Studios and 15 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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Featured review

"The house was fantastic and a great location."

The house was very easy to find, quiet neighborhood and Walmart was 2 minutes away. The was neat and tidy with all kitchen amenities needed to prepare a home cook meal. The Air conditioner was the best,...

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$123
avg per night
Kissimmee Villa
Sleeps 8, 4 bedrooms, 3 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to M&M Dream Villa – Just 3 Miles from Disney! Experience peace, play, and pure comfort at this quiet and relaxing 4-bedroom retreat, perfect for families and Disney lovers alike.M&M Dream Villa – 4BR Family Retreat Just Minutes from DisneyWelcome to M&M Dream...

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Featured review

"We had a great holiday at Crushes Crash Pad."

We had a great holiday at Crushes Crash Pad.The villa is very well equipped and has everything you could possibly need (and more) to make your stay enjoyable. The location couldn’t be better, being...

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$280
avg per night
Kissimmee Villa
Sleeps 8, 4 bedrooms, 3 bathrooms
6 reviews

Distance to park: 3 miles to Disney World

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

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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Featured review

"Will come back whenever in area"

Very spacious Villa in excellent location with quiet neighbourhoud. Next Walmart and restaurants only a few minutes away. Check-In easy. Good communication with hosts and fast answers. We loved the atmosphere...

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$166
avg per night
New
Kissimmee House
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

About this property

***FULLY FURNISHED*** 3 bedroom, 2 bathroom house in Kissimmee. Amenities included: central air, central heat, dishwasher, hardwood floors, pool, stainless steel appliance, updated kitchen, washer dryer, and yard. Utilities included: internet. Is pet friendly. Date Available: Oct 8th 2025. $3,000/month...

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$100
avg per night
Kissimmee House
Sleeps 14, 7 bedrooms, 4.5 bathrooms
1 review

Key Amenities

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

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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Featured review

"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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$450
avg per night
Kissimmee Villa
Sleeps 8, 4 bedrooms, 3 bathrooms
29 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Indian Creek Disney Retreat is a beautiful 1800SF, well maintained home in the Indian Creek subdivision which is literally on Disney's doorstep and your home away from home. Indian Creek is not a gated community but has a lot of community amenities.In the 1st section of Indian Creek you will...

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Featured review

"Beautiful rental on Santee Drive"

It is our 2nd time staying in this rental home. It does not disappoint. The home is very clean and well equipped. The owner is quick to respond and always pleasant. The outdoor space ( pool and hot tub)...

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$141
avg per night
Kissimmee House
Sleeps 6, 3 bedrooms, 3 bathrooms
1 review

Distance to park: 4 miles to Disney

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

You will love it here in our Boutique styled Condos featuring contemporary interiors, located in Magic Village gated community only 5 minutes away from Disney’s Animal Kingdom. Step into your private villa and discover a chic and contemporary yet invitingly cozy sanctuary. All three bedrooms are...

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Featured review

"Best vacation rental ever!"

This property was absolutely gorgeous, spacious, private and quiet! We stayed for 11 days and wish we could've stayed for 11 more. The amenities are just like being in your own home - we did go to Walmart...

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$216
avg per night
Kissimmee Villa
Sleeps 8, 4 bedrooms, 2.5 bathrooms
1 review

Distance to park: 3 miles to Disneys Animal Kingdom

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

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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Featured review

"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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$207
avg per night
Full map
Map

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

FAQ

Proximity to Attractions

How close are Kissimmee rentals to the main entrance of Walt Disney World versus Orlando rentals?

Some Kissimmee vacation rentals are only 12 miles from Walt Disney World. Orlando rentals are a little further away from the amusement park at around 20 miles.

What is the average drive time from Kissimmee to Universal Studios or SeaWorld?

The average drive time from Kissimmee to Universal Studios is 23 minutes, while the average drive to SeaWorld takes 25 minutes.

Are there Kissimmee communities that offer shuttle services to the theme parks?

Yes. Encore Resort Condo, Wyndham Bonnet Creek Resort Condo, and Champions Gate Condo are some of Kissimmee’s vacation rentals offering shuttle service to Walt Disney World, Universal Studios, SeaWorld, and other attractions.

How bad is the traffic on US-192 or I-4 when driving from Kissimmee to the parks?

Both US-192 and I-4 are busy roadways leading to the parks. Traffic is heavier or lighter depending on the day of the week and the time of day. Weekday mornings, early evenings, and Saturdays are especially crowded.

Property Type & Communities

What are the most popular resort communities in Kissimmee (e.g., Reunion, ChampionsGate, Windsor Hills)?

Champions Gate, Reunion, Emerald Island, Windsor Hills, and Indian Creek are all popular resort communities in Kissimmee.

What kind of exclusive amenities do these large resort communities offer?

Some exclusive amenities include a clubhouse, tennis courts, a fitness center, a movie theater, a sauna, and a marketplace to purchase food.

Is it better to stay in a large resort or a smaller, non-gated community in Kissimmee?

The answer depends on your preferences. A smaller, non-gated community in Kissimmee offers fewer amenities than a large resort but still has a collection of fun activities nearby.

What are the main differences between staying in Kissimmee versus staying in Orlando?

Orlando is a large, bustling city full of restaurants, shops, and attractions, while Kissimmee is less crowded with a more family-friendly atmosphere. Though both cities are close to the major parks, Kissimmee is closer to Disney World, whereas Orlando is closer to Universal Studios.

Amenities & Features

What size homes are typically available for rent in Kissimmee?

The typical Kissimmee vacation home has four bedrooms and ranges from 1,980 to 2,000 square feet.

Do most house rentals come with a private, screened-in pool and lanai?

Though most house rentals come with a private, screened-in swimming pool, not all of them have a lanai.

Are multi-generational homes with multiple master suites common?

Yes, multiple master suites are common in Kissimmee vacation homes for rent.

What are some unique amenities to look for in Kissimmee homes, like private movie theaters or elaborate game rooms?

Check listings for unique amenities in Kissimmee house rentals such as EV chargers, gardens, balconies, ping pong tables, pool tables, game rooms, and heated pools.

Booking & Cost

Is it generally more affordable to rent a large house in Kissimmee compared to a similar one in Orlando?

Yes, when comparing similar homes in these two Florida cities, Kissimmee house rentals are the more affordable option.

What are the typical resort fees or community access fees I should budget for?

The typical resort fee is around $40 per day.

Are there any "hidden costs" associated with Kissimmee rentals, like pool heating or BBQ grill rental?

Studying the “Fees” section of a Kissimmee rental’s listing can help you avoid any surprise costs. Some owners list fees for services like pool heating, damage protection, and pets.

What is the best time of year to find deals on Kissimmee vacation homes?

September and October are the best times to find deals on Kissimmee vacation homes because fewer people are booking rentals.

Kissimmee Specifics

What attractions are there to see in Kissimmee itself, outside of the major theme parks?

Boggy Creek Airboat Adventures, Gatorland, Shingle Creek Regional Park, Congo River Golf, and Lake Tohopekaliga (Lake Taho) are all unique attractions in Kissimmee.

What are the best places for shopping and dining in the Kissimmee area?

The Promenade at Sunset Walk, The Crosslands, and Universal CityWalk are some of the best places for shopping, dining, or both.

How does the vibe of Kissimmee differ from the International Drive area in Orlando?

Orlando’s International Drive has a high-energy vibe with dozens of shops, restaurants, shows, spas, and other attractions. While Kissimmee has its own collection of shops, eateries, and attractions, the city’s vibe is more laid-back.

Are there any good nature-based activities, like airboat tours, that are easily accessible from Kissimmee?

Yes. Wild Florida Adventure Park, Gatorland Bird Rookery, and horseback riding sessions at Lazy H Ranch give visitors the opportunity to admire Kissimmee’s natural environment.