Kissimmee Vacation Rentals

(336 rentals)
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Key Amenities

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

About this property

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

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Property Type

Kissimmee House

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Key Amenities

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

About this property

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

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

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

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Property Type

Kissimmee House

"Fun Time with Family"

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

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Key Amenities

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

About this property

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

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Property Type

Kissimmee House

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7 BR | 4.5 BA | Sleeps 14 | Quick View

12
owner special
Owner special: ** 20th April - 18th May 2024** $150 +taxes per night

$178

avg/night

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Key Amenities

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

About this property

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

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Property Type

Kissimmee Villa

"Spacious - great for multiple families"

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

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5 BR | 5 BA | Sleeps 12 | Quick View

1

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

$298

avg/night

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Key Amenities

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

About this property

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

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Property Type

Kissimmee Villa

"Wonderful home and resort"

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

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Key Amenities

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

About this property

Escape to a magical 8-bed 6-bath retreat for up to 16 guests at the Windsor at the Westside resort community. This is an entire home rental. Super Mario game room, Beauty and the Beast dining, Paris-themed kitchen, Guardians of the Galaxy primary bedroom. Upstairs: Hollywood, Pirates, Mickey Mouse, Princesses, ...

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

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Property Type

Kissimmee House

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Key Amenities

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

About this property

Property Reference RVH_1082RA vacation full of luxury, wonder, and excitement awaits your next trip to The Enchanted Villa. The Enchanted Villa was designed with the vacationing family in mind and provides guests with a vacation full of entertainment and memories all under one roof. Spread out and ...

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Property Type

Kissimmee House

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Key Amenities

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

About this property

Property Reference RVH_1078RPlease note that there is construction nearby until mid-November 2023. Please contact us for more information.Adventure and excitement await you in this newly built vacation home, designed with families in mind from top to bottom! Built and designed specifically for ...

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

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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5 BR | 3 BA | Sleeps 12 | Quick View

10

Distance to park: 3 miles to Disney

$188

avg/night

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Key Amenities

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

About this property

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

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Property Type

Kissimmee Villa

"Very Comfortable"

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

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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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5 BR | 5 BA | Sleeps 10 | Quick View

owner special
Owner special: ASK ABOUT A DISCOUNT FOR OPEN DATES IN MAY!!

$241

avg/night

View Details

Key Amenities

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

About this property

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

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Property Type

Kissimmee Villa

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7 BR | 5 BA | Sleeps 14 | Quick View

4

Distance to park: 7 miles to Disney Magic Kingdom

$260

avg/night

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Key Amenities

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

About this property

*REASONABLE RATES FOR FAMILIES -: We have been renting over 15 Years.SPECTACULAR DISNEY THEME VILLA to make your vacation magical!*SAFE GATED 24 HOUR GUARDED RESORT: Shopping and Restaurants choice of buffets, takeaways or fine dining just 2 mins away, including 24/7 Super Wal-mart. *BEAUTIFUL ...

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Property Type

Kissimmee Villa

"Perfect Lake Berkley Villa for 2 families"

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

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Key Amenities

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

About this property

Beautiful 4 bedroom/3 bathroom house in the luxurious Emerald Island Resort - Only ~ 4 miles from Disney & close to other major attractions! This home is equipped with a heated private pool, spa & game room. There is a large SMART TV in the living room & in each bedroom. There are queen beds ...

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Property Type

Kissimmee House

"Clean, comfortable and aesthetically pleasing"

We stayed for about 2 weeks. Home is extremely comfortable with enough of everything we needed. The owners are easy to work with and the property management very responsive. The location is superb for all ...

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Key Amenities

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

About this property

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

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Property Type

Kissimmee House

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Key Amenities

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

About this property

Property Reference RVH_1071RVacation in style while enjoying this nine bedroom luxury home, built specifically for vacationing in mind. This home can comfortably sleep 20 guests in nine bedrooms, with eight of them having private bathrooms.When you enter the home, you are met with a two story ...

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Property Reference #: RVH_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
  • 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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4 BR | 3 BA | Sleeps 8 | Quick View

3

Distance to park: 3 miles to Disney World

$173

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

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

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Property Type

Kissimmee Villa

"A perfect vacation villa"

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

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Key Amenities

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

About this property

Villa OverviewNo extra charges!5 bedrooms, 4 full bathroomsSleeps 15 guests~440 square foot Star Wars theme room upstairs with two full over full bunk beds between a 3D TIE Fighter and swirly slideTwin bunk bed with a trundle in the Lego-themed room, complete with multi-color ...

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Property Type

Kissimmee Villa

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7 BR | 5.5 BA | Sleeps 16 | Quick View

1

Distance to park: 3 miles to Disney World

$308

avg/night

View Details

Key Amenities

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

About this property

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

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Property Type

Kissimmee Villa

"7 bedroom house 8460 Secret Key Cove"

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

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Key Amenities

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

About this property

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

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Property Type

Kissimmee Villa

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Key Amenities

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

About this property

Your family will be close to everything when you stay at this centrally-located place. Welcome to the perfect vacation place at Encore Resort. Luxurious, 2 story house, 8 bedroom, 7 bathroom with Pool, Perfect place to vacation near Disney. A great destination for family and friend reunions. Minutes ...

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Property Type

Kissimmee Villa

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

After. *** Location Location Location*** It’s all about. ‘The View’The uninterrupted view of the 14 acre lake and bird island, takes unwinding by the pool to a new level! Relax on a sun bed, or perhaps get wrinkly in the spa whilst ...

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Property Type

Kissimmee Villa

"What a view"

In July 2023 we stayed at Winter Haven a fantastic villa in Lake Berkley which had enough room for 8 of us comfortably. The guys partially liked the games room/pool room, and we all loved to pool and jacuzzi, ...

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2 BR | 2 BA | Sleeps 6 | Quick View

4
owner special
Owner special: $90 per night including taxes for 2 bedroom condo between May 11 and May 21 (minimum 7 nights).

Distance to park: 5 miles to Disney World

$98

avg/night

View Details

Key Amenities

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

About this property

Our lakeside condo is on the ground floor and has a screened lanai seating area for your enjoyment. The living room is quite spacious and has a flat screen television, a DVD player, a queen sleeper sofa bed, and has seating for up to six guests. The dining area also has seating for six. Save money by ...

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Property Type

Kissimmee Condo

"Very Comfortable and Quiet Long Term Stay"

We spent 6 weeks in Mary's Ground Floor 4 Bedroom Condo at Legacy Dunes. The condo is spacious and tastefully decorated, it is very clean and well equipped with all we needed for a comfortable long term ...

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Key Amenities

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

About this property

Private 2 story home with 4 Bedroom/3 Bathroom with private pool which has all of the spacious and convenient accommodations for your entire family vacation. Storey Lake is near to all of the major parks & attractions of Disney World, Epcot, Animal Kingdom, Disney Water Parks, Universal Studios and ...

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Property Type

Kissimmee Townhome

"Great place"

We stayed here for a tournament at Orange County Convention and this was a perfect location and the amenities were amazing!! We loved this townhouse and would love to stay here again

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14 BR | 14.5 BA | Sleeps 40 | Quick View

$976

avg/night

View Details

Key Amenities

  • Air conditioning
  • Pool

About this property

Are you a sports enthusiast? Welcome to the Sports bowling villa! Each room is themed around a different sport–from polo, to baseball, to football and others–it will be hard to choose a room! Escape to a world of sports-themed luxury with this stunning vacation villa in Veranda Palms, just ...

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Property Type

Kissimmee House

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$174

avg/night

View Details

Key Amenities

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

About this property

Charming brand new 4 br, 3 bath townhouse with pool. Located in the desirable Storey Lake Resort, in the new quiet Preserve Area, It has capacity for 12 guests. Storey Lake has a resort-style clubhouse full of amenities and fun for families, including a business center, basketball court, ping pong table, ...

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Property Type

Kissimmee House

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6 BR | 4.5 BA | Sleeps 12 | Quick View

9

$205

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

The Villa is fully air conditioned, pool has solar heating, all rooms have cable tv, Free WIFI, local calls are free, Safe and baby equipment also available for use at no extra cost.The villa has a 30ft South West facing solar heated Pool/Spa with a large patio area with table chairs and sun loungers,Also ...

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Property Type

Kissimmee Villa

"Extremely Satisfied"

My family and I enjoyed our stay at Brendas home. It was clean and very comfortable. It felt just like “home”. Though it was too cold that week in Florida, we weren’t able to enjoy the pool and jacuzzi ...

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10 BR | 8 BA | Sleeps 20 | Quick View

owner special
Owner special: Check out the Spring deals

$641

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Sonoma Resort - Kissimmee, Florida is only 15 minutes to the area's main attraction... Walt Disney World. This brand new resort community sits nestled just outside of Orlando, between W. Osceola and W. Irlo Bronson Memorial Hwy and conveniently located next to "The Loop", a premier shopping ...

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Property Type

Kissimmee House

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7 BR | 5.5 BA | Sleeps 16 | Quick View

5

Distance to park: 8 miles to Disney World

$325

avg/night

View Details

Key Amenities

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

About this property

Waiting to welcome you is this 7 bedroom, 5.5 bathroom, 3300 sq/ft villa - perfect for large families or multigenerational gatherings comfortably sleeping up to 16 people.With Star Wars, Spiderman, Harry Potter, Avengers, and Mickey & Minnie theming, everyone is bound to find somthing they'll ...

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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

2bd/2ba with the Best View in the amazing community of Storey Lake. Located 10 minutes from Disney Come in and enjoy a unique experience. There is a beautiful waterpark in the community center for you to enjoy. It is the perfect place to relax, have a good time and enjoy all that Orlando has to offer. This ...

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Property Type

Kissimmee Apartment

"2024 vacation"

The house was lovely.. lots of room, clean, bright The resort pool was absolutely beautiful.. my grandson loved his time in the pool .. lot of room to sit around and food at the pool area was really good

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$166

avg/night

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Key Amenities

  • Air conditioning

About this property

Are you looking for a private home in Kissimmee for your next Florida vacation? Rolling Hills 7965 is just the place! This home is suited for up to 8 guests and features 4 bedrooms and 3 bathrooms. When you step inside, you’ll notice that the décor is upscale and tasteful to suit the style ...

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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

Name Of Home: Walking on Sunshine VillaLocation: Windsor Hills Resort (24/7 guard gated community - Disney World only mins away!)Home Highlights: Recently Renovated Home - Incredible Air Conditioned 80s Game Room - Private South Facing Pool/Spa - Bunk Bedroom with PS5Property Type: Single ...

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Property Type

Kissimmee Villa

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4 BR | 2 BA | Sleeps 8 | Quick View

1

Distance to park: 3 miles to Walt Disney World

$185

avg/night

View Details

Key Amenities

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

About this property

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

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Property Type

Kissimmee House

"Fantastic Villa"

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

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Key Amenities

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

About this property

Find total relaxation at this luxurious four-bedroom, two-bath villa that sleeps 10 with your own private, screened-in pool and patio area. Beyond the patio area, find a grassy, tree-lined backyard that provides quiet seclusion.Inside, you’ll find enough room for everyone with the spacious living ...

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Property Type

Kissimmee Villa

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Key Amenities

  • Air conditioning
  • Pool

About this property

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

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Property Type

Kissimmee House

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7 BR | 4.5 BA | Sleeps 14 | Quick View

3

Distance to park: 4 miles to Animal Kingdom

$250

avg/night

View Details

Key Amenities

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

About this property

Conveniently located on the Exclusive Emerald Island Resort. With 7 Bedrooms and 4.5 bathrooms, Berni’s Home from Home can easily accommodate two families travelling together or will give one family plenty of space.Enjoy relaxing by your very own private extended south facing pool or spend some ...

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Property Type

Kissimmee Villa

"Very well maintained home"

This home was lovely and very well kept. Would rent again if the occasion arose that we needed a home this big again.

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Key Amenities

  • Air conditioning
  • Pool

About this property

Epic Florida Rentals is proud to offer this Beautiful 6-bedroom 4-bathroom home for your enjoyment. Renovated in 2020, now includes: AC and heated game room, allergy free no carpet. It truly is a home away from home from the moment you drive up to the guarded and gated entrance, you realize you are ...

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Pool

About this property

This may be one of the most upgraded and modern feeling townhome which is 5 miles to get to Disney World! This 4-bedroom Disney vacation rental can sleep up to 8 people and is located within the beautiful Emerald Island Resort, a gated community just minutes away from the most popular attractions of Orlando.You’ll ...

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Property Type

Kissimmee Townhome

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$107

avg/night

View Details

Key Amenities

  • Air conditioning
  • Pool

About this property

If you're searching for Orlando vacation rentals near Disney, the name of this unit simply says it all: 3 BD Condo with Minutes from Disney! This unique condo is set up to accommodate six guests between its three bedrooms and two bathrooms.This 3-bedroom Orlando vacation rental offers everything ...

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Property Type

Kissimmee Condo

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

Now taking bookings for 2025. Sorry no pets. Smoking is not permitted. Welcome to “Hibiscus on the Lake” with a true south facing pool/spa. The villa has stunning, uninterrupted views of the largest lake with an island in the middle full of beautiful birds on Lake Berkley resort in Kissimmee. ...

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Property Type

Kissimmee Villa

"Great location"

Stayed here in April for 2 weeks as a family of 6 adults. Villa is in a great location with easy access to the parks. It is on the main lake with beautiful views. Lots of wildlife. Saw a family of otters ...

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4 BR | 2.5 BA | Sleeps 8 | Quick View

1

Distance to park: 3 miles to Disneys Animal Kingdom

$165

avg/night

View Details

Key Amenities

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

About this property

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

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Property Type

Kissimmee Villa

"Tolles Haus"

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

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Key Amenities

  • Air conditioning
  • Pool

About this property

If you're bringing a big group with you on your next trip to Florida, you're probably looking for a luxurious vacation rental with plenty of room for everyone. This 5-bedroom Orlando vacation rental fits the bill! This Reunion home with Main Street USA game room is an absolute dream come true ...

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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

$306

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
  • Rentals by owner

About this property

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

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Property Type

Kissimmee House

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4 BR | 3 BA | Sleeps 8 | Quick View

1

Distance to park: 3 miles to Disney Animal Kingdom

$149

avg/night

View Details

Key Amenities

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

About this property

Great location - fabulous pool area

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Property Type

Kissimmee Villa

"Great Experience"

Rented a house through Florida Rentals. Great experience, nice home in a convenient location. House was clean, had all the essentials and a large pool

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$458

avg/night

View Details

Key Amenities

  • Air conditioning
  • Pool

About this property

If you're bringing a big group with you on your next trip to Orlando, Florida, you have found an amazing and luxurious vacation rental with plenty of room for everyone. The entire home is newly professionally decorated, fully furnished and theme rooms throughout!!! If you have a favorite Disney or ...

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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 336 Kissimmee vacation rentals available on FloridaRentals.com. From house rentals to villa rentals and beyond, find a unique vacation rental for you to enjoy a memorable vacation in Florida.

How much does it cost to rent a vacation rental in Kissimmee?

There are vacation rentals available in Kissimmee for as low as $46 per night with an average price per night of $200.

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