Kissimmee Vacation Rentals

(260 rentals)
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Kissimmee Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
4 reviews

Distance to park: 5 miles to Disney World

$140

avg/night

$140
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

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

Featured review

"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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Kissimmee House
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms

$204

avg/night

$204
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

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

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Property Type

Kissimmee House

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Kissimmee House
8 BR | 6 BA | Sleeps 16 | Quick View
Sleeps 16, 8 bedrooms, 6 bathrooms
8 reviews

$356

avg/night

$356
avg per night
View Details

Key Amenities

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

About this property

5 star Property! Welcome to Sunset Magic Villa! Delightful Windsor at Westside Resort home villa 8 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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Kissimmee Condo
3 BR | 2 BA | Sleeps 7 | Quick View
Sleeps 7, 3 bedrooms, 2 bathrooms

$116

avg/night

$116
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

This condo is one of our most highly sought-after Orlando vacation rentals, and for a good reason. This beautiful property is equipped for up to seven guests between its three bedrooms and two bathrooms. Those who stay in this rental will be able to take full advantage of every amenity and feature that ...

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Property Type

Kissimmee Condo

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Kissimmee House
4 BR | 3.5 BA | Sleeps 9 | Quick View
Sleeps 9, 4 bedrooms, 3.5 bathrooms

$193

avg/night

$193
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Welcome to Your Luxurious Escape in Reunion Resort! Exquisite 4-Bedroom Pool Home Overlooking the Golf Course Discover the perfect blend of luxury and comfort in this fully remodeled 4-bedroom home within the exclusive Reunion Resort. Wake up to stunning views of the golf course and enjoy a freshly ...

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Property Type

Kissimmee House

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Kissimmee Villa
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

$160

avg/night

$160
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This newly remodeled pool Villa is the perfect getaway. From the new kitchen and bath to the newly resurfaced pool. Large pool deck with room to spread out. A covered area for dining and tons of pool deck for those who love the sun. The pool is south facing. Sunsets are spectacular. #3 bedrooms. ...

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Property Type

Kissimmee Villa

Featured review

"Awesome !!!"

Super Clean, Everything was excellent. Pool was amazing. Close enoogh tall many immendities for day trips. Had a very relaxing time very fun vacaton.

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Kissimmee Condo
3 BR | 2 BA | Sleeps 7 | Quick View
Sleeps 7, 3 bedrooms, 2 bathrooms
1 review

$207

avg/night

$207
avg per night
View Details

Key Amenities

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

About this property

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

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Property Type

Kissimmee Condo

Featured review

"Perfect Spot for a Peaceful Getaway"

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

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Kissimmee Apartment
2 BR | 2 BA | Sleeps 5 | Quick View
Sleeps 5, 2 bedrooms, 2 bathrooms
1 review

$165

avg/night

$165
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

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

Featured review

"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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Kissimmee House
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms

$166

avg/night

$166
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

It's hard to find much more luxurious Orlando vacation rentals than this! BellaVida Palms 390 is an excellent option for families of up to 8 people. You’ll not only find all kinds of convenient and luxurious amenities within the house itself, but you'll also have plenty of fun things to ...

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Property Type

Kissimmee House

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Kissimmee Villa
5 BR | 5 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 5 bathrooms

$191

avg/night

$191
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Embark on an enchanting journey with our exquisite 5-bedroom home nestled in the prestigious Windsor Hills community. Ideal for families or groups, this charming retreat promises a perfect blend of luxury and proximity to the magic. Key Features: Bedroom Retreats: 2 King Beds 1 Queen Bed 5 ...

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Property Type

Kissimmee Villa

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Kissimmee Condo
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms

$114

avg/night

$114
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Welcome to our charming condo in the heart of Kissimmee, Florida! Nestled in the sought-after Villa Island Club, our inviting three-bedroom, two-bathroom retreat is the perfect spot for your next vacation. Located just off HWY 192, you’ll be less than 15 minutes from the magical gates of Walt Disney ...

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Property Type

Kissimmee Condo

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Kissimmee House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms

$171

avg/night

$171
avg per night
View Details

Key Amenities

  • Air conditioning
  • WiFi

About this property

If you want to experience all the fun of Orlando while enjoying a bit of distance from the heart of the city, you might be interested in Kissimmee vacation rentals. This Amazing Vacation Home in Kissimmee, Florida, is one of the best! This home features 3 bedrooms and 2 bathrooms and is furnish with all ...

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Property Type

Kissimmee House

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Kissimmee House
6 BR | 4 BA | Sleeps 14 | Quick View
Sleeps 14, 6 bedrooms, 4 bathrooms

$276

avg/night

$276
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

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 6-bedroom Orlando vacation rental fits the bill! Windsor Hills Dream Private Screened Pool Home is an absolute dream come true ...

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Property Type

Kissimmee House

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Kissimmee Townhome
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
3 reviews

Distance to park: 2 miles to Fun Spot America Theme Parks

$122

avg/night

$122
avg per night
View Details

Key Amenities

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

About this property

Your family will be close to everything when you stay at this centrally-located place. This property it is fully renovated; first-floor unit with a laminate floor, high ceiling in the living room, open floor plan. The kitchen and bathrooms have been upgraded. The whole community was recently replumbed. Nice ...

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Property Type

Kissimmee Townhome

Featured review

"Great Vacation Home"

We found the townhouse to be nicely decorated with cute little touches, updated, very clean and equipped with all the necessities for a fabulous experience. It's a very safe, quiet, peaceful location, ...

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Kissimmee House
6 BR | 5 BA | Sleeps 14 | Quick View
Sleeps 14, 6 bedrooms, 5 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Welcome to your Disney and Universal vacation dream home! This stunning 6-bedroom house is situated in the luxurious Storey Lake Resort, one of the best locations you could wish for in the entire resort! Just a short walk from the main clubhouse and waterpark, you'll have access to all the fantastic ...

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Property Type

Kissimmee House

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Kissimmee Apartment
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom

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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Property Type

Kissimmee Apartment

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Kissimmee House
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms
6 reviews

$165

avg/night

$165
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

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

Featured review

"Great stay at a lovely villa"

We are just back from 2 weeks here, we had a fabulous time making use of the games room and the pool. Thank you

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Kissimmee House
5 BR | 4 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 4 bathrooms
10 reviews

$165

avg/night

$165
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to our stunning spacious 5 bedroom, 4 bath home located in the much sought after community of Tuscan Hills near Disney This beautiful home offers 2 masters en-suite bedrooms and 3 sitting rooms. Full air con and hi-speed WiFi throughout. The villa uniquely has 3 sitting rooms, two of ...

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Property Type

Kissimmee House

Featured review

"Great Home… Great location"

My family and I just spent a week in this lovely home. It was nicely decorated, well-maintained, and had everything in a well stock kitchen that one would need for fixing meals. The pool/spa was great and ...

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Kissimmee Villa
4 BR | 4 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4 bathrooms
20 reviews

Distance to park: 2 miles to Disney

$293

avg/night

$293
avg per night
View Details

Key Amenities

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

About this property

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

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Property Type

Kissimmee Villa

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Kissimmee House
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms
3 reviews

$170

avg/night

$170
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Our luxury 4 bedroom home is located within the top rated community of Indian Creek. 2 of the bedrooms have ensuite bathrooms. The villa is furnished to a very high standard and is fully Air-conditioned throughout keeping the villa cool in the warm Florida weather. Full hi-speed WiFi throughout ...

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Property Type

Kissimmee House

Featured review

"Brilliant stay at this villa"

\We stayed here a week and all the family loved this villa. Pool is so nice. Highly recommneded, we will stay here again. Tim

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Kissimmee Townhome
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms
4 reviews

Distance to park: 6 miles to Disney,Seworld

$143

avg/night

$143
avg per night
View Details

Key Amenities

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

About this property

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

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Property Type

Kissimmee Townhome

Featured review

"Condo was the best part of our vacation!"

Condo was the best part of our vacation! From flights been delayed to car rental company being close when we landed and having to sort all of that out, arriving at the condo and it being everything we ...

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Kissimmee Villa
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms
19 reviews

$130

avg/night

$130
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

A stunning, larger than average 4 Bed 3 Bathroom villa. There are 2 sitting rooms both with lots of comfortable seating. Both rooms have large screen TVs, ideal for when the adults want to watch the latest sports programme whilst the kids enjoy the latest Disney film. Netflix subscription is also included ...

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Property Type

Kissimmee Villa

Featured review

"Very enjoyable stay"

Very enjoyable stay at this lovely villa, it is spacious and well maintained. Great pool area. Loved the Resort amenities, and we were close to shops and restaurants. Definitely stay there again. Sally

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Kissimmee Condo
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms

$250

avg/night

$250
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This is a NON SMOKING condo * Community: Sweetwater Club Villas Floors: First Floor Condo Pets: PLEASE ASK ABOUT OUR PET POLICY. Rooms: 3 Bedrooms, 2 Bath rooms. En-suite in Master bedroom. Bed Configuration: King bed (1) Queen bed (1), Two Twin Beds (2). Sleeps 6. Flooring: Ceramic ...

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Property Type

Kissimmee Condo

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Kissimmee Villa
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms
4 reviews

$100

avg/night

$100
avg per night
View Details

Key Amenities

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

About this property

Hello, Our vacation home is located in a gated community with a large swimming pool, playground for the children, shuffle board, pool table and a workout room. It’s a duplex with its own separate driveway. There are three bedrooms and two full baths. The kitchen was just fully remodeled in 2022 ...

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Property Type

Kissimmee Villa

Featured review

"family time"

THIS PLACE WAS AWESOME AND WE ENJOYED IT. QUIET AND PEACEFUL PLACE. I WILL RECOMMEND THIS RESORT TO ALL MY FRIENDS.

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Kissimmee Villa
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
5 reviews

$160

avg/night

$160
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Luxury Screened-In, Lake Front, Private Pool Home! This amazing 3 bedroom, 2 bathroom, Disney Area Vacation Rental Home is located in the family-friendly residential community of Eagle Pointe. Just a few short miles from Orlando's World-Renowned Theme Parks including the Walt Disney World Resort, ...

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Property Type

Kissimmee Villa

Featured review

"soaring eagle lane"

tidy villa nice views our small lake ducks will come up to be fed nice size pool overall good villa games room in garage

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Kissimmee Townhome
3 BR | 3 BA | Sleeps 7 | Quick View
Sleeps 7, 3 bedrooms, 3 bathrooms

$200

avg/night

$200
avg per night
View Details

Key Amenities

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

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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Kissimmee Villa
5 BR | 4 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 4 bathrooms
20 reviews

$160

avg/night

$160
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to our stunning, larger than average, 5 Bed 4 Bathroom villa with a beautiful view of the conservation area at the rear as background of our private pool. All rooms in the villa are spacious. The villa is furnished and maintained to a very high standard. The villa is located just off US 192 ...

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Property Type

Kissimmee Villa

Featured review

"Nice place to visit"

Comfortable rental with convenient access to places we needed to go. The house had nice features that provided a good place to relax and rest

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Kissimmee Apartment
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom

Distance to park: 11 miles to Castaway Cove Adventure Park

$105

avg/night

$105
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Welcome to this charming fully furnished one bedroom one bathroom apartment located in Heritage Key Villas, Kissimmee, Florida. This apartment is the epitome of convenience and comfort, offering a flexible lease term ranging from one month to twelve months, with a minimum stay of just 30 days, making ...

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Property Type

Kissimmee Apartment

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Kissimmee Villa
6 BR | 6 BA | Sleeps 12 | Quick View
Sleeps 12, 6 bedrooms, 6 bathrooms
6 reviews

$185

avg/night

$185
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Our 6 Bedrooms 6 Bathroom, luxury villa ideal for you and your families / friend’s vacation. As you enter the home you are greeted with a large living room area. Towards the back of the villa there is an open plan living/dining/kitchen area. There are tri-sliding doors to the pool area where ...

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Property Type

Kissimmee Villa

Featured review

"Nice villa"

We went down for a football tourney this four bedroom villa was great. We were concerned about being stuck in a hotel room for the week so this was perfect plenty of room and very clean. If the weather ...

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Kissimmee Villa
5 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 3 bathrooms
7 reviews

$160

avg/night

$160
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Your villa is located on the gated 5 Star Lake Berkley Resort in Kissimmee. 5 Beds, 3 Bath home that is beautifully furnished throughout (Big TV/Games Room/Heated Pool/Free Internet). Our villa is furnished to a very high standard and being all one level is ideal for one or two families. The villa ...

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Property Type

Kissimmee Villa

Featured review

"Excellent location"

Just returned from our holiday after 2 weeks at this lovely villa. Perfectly located 15mins from all the Disney parks and a stones throw from Walmart and our favourite Chick-a-fille. Set in a quiet, secure ...

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Kissimmee Villa
4 BR | 4 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4 bathrooms
7 reviews

$294

avg/night

$294
avg per night
View Details

Key Amenities

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

About this property

NEW TO MARKET!!! "Summer House" at Windsor Hills is an extra clean vacation home - recently upgraded with new floors, paint, decor, furniture and brand new Stearns & Foster mattresses in every room. The villa is a 4 Bedroom 4 Bathroom Ensuite property with an attached bathroom on every bedroom! ...

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Property Type

Kissimmee Villa

Featured review

"Best place to stay EVER!!!!"

This villa was perfect for our family of 8. Everything was extremely clean and Kim was so wonderful to work with. The heated pool and spa was so refreshing after a long days at the parks. The kitchen is ...

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Kissimmee Villa
6 BR | 5.5 BA | Sleeps 12 | Quick View
Sleeps 12, 6 bedrooms, 5.5 bathrooms
2 reviews

$165

avg/night

$165
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to our superb 6-bedroom 5.5-bathroom villa, located on the secure and safe gated Solana Resort. The villa is modern and very spacious with all the amenities you could want. Full air con and hi-speed WiFi throughout. The villa benefits from 2 sitting rooms, so is great when more than one ...

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Property Type

Kissimmee Villa

Featured review

"Great Location"

Wonderful villa in a quiet location. Villa was spotless on arrival. Close to all attractions and suoermarkets.

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Kissimmee House
5 BR | 4 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 4 bathrooms

Distance to park: 6 miles to Disney World

$245

avg/night

$245
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

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

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Property Type

Kissimmee House

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Kissimmee Condo
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms
1 review

Distance to park: 2 miles to Disney’s Animal Kingdom Park

$139

avg/night

$139
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

This huge 1650 sqft condo has 4 bedrooms and 3 full bathrooms. It is located at Sun Lake Resort, just 2 Miles to Disney world Florida. sleeping accommodations for 8. * King-size Master bedroom with bathroom * One queen size sofa bed in family room for extra guests * One 40" HDTV(free ...

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Property Type

Kissimmee Condo

Featured review

"Nice Vacation Condo Rental"

Located near Disney, shopping, restaurants. Everything on 1st floor was wonderful for a group of oldsters!

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Kissimmee Villa
6 BR | 4 BA | Sleeps 12 | Quick View
Sleeps 12, 6 bedrooms, 4 bathrooms
2 reviews

$200

avg/night

$200
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Beautiful two-story home with 6 bedrooms and 4 bathrooms. This home is situated on a quiet street within the Solterra Resort. It boasts modern open plan living. It has an additional outdoor balcony space along with a large private pool and spa, loungers, outdoor table and chairs with an optional BBQ ...

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Property Type

Kissimmee Villa

Featured review

"Amazing villa"

Totally overwhelmed, villa is amazing, very spacious. Highly recommended. We will book this villa again next family gathering. jim

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Kissimmee House
9 BR | 6 BA | Sleeps 18 | Quick View
Sleeps 18, 9 bedrooms, 6 bathrooms
8 reviews

$395

avg/night

$395
avg per night
View Details

Key Amenities

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

About this property

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

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Property Type

Kissimmee House

Featured review

"Great View"

Fantastic time. Pool overlooks the lake. We had an issue with a burner on the stove the first day and the owner had a brand new stove delivered the next day. The owner has similar properties also. We have ...

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Kissimmee Townhome
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms
1 review

Distance to park: 5 miles to Disney,Seworld

$139

avg/night

$139
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Welcome to our new opening 4 Bedroom/3 bathroom Townhouse in CLUB CORTILE,This gated-community is close to every major Orlando attraction: Disney's Magic Kingdom, Epcot, Animal Kingdom, Universal Studios (Harry Potter), Sea World, and many more. Club Cortile is also conveniently close to WalMart, ...

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Property Type

Kissimmee Townhome

Featured review

"Well located safe townhouse on a lake with good club facilities"

We are a pensioned couple from the Netherlands and in Florida to play golf in the sunshine. We have rented from the owner on several occasions over the last 15 years. This was our first time in the Club ...

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Kissimmee House
5 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 3 bathrooms

$230

avg/night

$230
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This is a NON SMOKING HOME * Community: Calabay Parc Floors: 2 Floor, 5 Bedrooms, master downstairs and 4 bedrooms up. Pets: Please ask about our pet policy Rooms: 5 Bedrooms, 3.5 Bath rooms. Bed Configuration: Bedroom 1: King size bed with En-suite Bedroom 2: Queen size bed with shared bathroom. Bedroom ...

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Property Type

Kissimmee House

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Kissimmee House
5 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 3 bathrooms
8 reviews

Distance to park: 8 miles to Disney

$150

avg/night

$150
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Come stay in our spacious one story single family home that features 5 bedrooms, 3 bathrooms fully kitchen and a private pool (can be heated for additional fee) Our home is very well located in Lake Berkley Resort with short walking distance to the lake berkley, where you may walking or fishing. ...

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Property Type

Kissimmee House

Featured review

"Fantastic Villa, exceeded our expectations"

The location was great, a very nice and super clean area. The Villa was great and exceeded our expectations. It had all amenities and then some and was super clean which was very much appreciated. Property ...

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Kissimmee Villa
4 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 2 bathrooms
15 reviews

$130

avg/night

$130
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to VIPvilla Johanna and Stephen thank you for visiting our website of hand-picked 5 Star quality villas. We manage the bookings for 20 private villa owners at lake Berkley Resort and we can personally assure you that you will be delighted with any of the villas offered to you. We have many ...

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Property Type

Kissimmee Villa

Featured review

"Fantastic-Excellent."

IWe visited Orlando a lots of time,We are familiar with Lake Berkley.We had always very good impresion of staying in Lake Berkley.This time we stayed in Lake berkley drive 929.We arrived at almost 03;00 ...

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Kissimmee House
8 BR | 6 BA | Sleeps 16 | Quick View
Sleeps 16, 8 bedrooms, 6 bathrooms
4 reviews

Distance to park: 8 miles to Disney Animal Kingdom

$356

avg/night

$356
avg per night
View Details

Key Amenities

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

About this property

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

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Property Type

Kissimmee House

Featured review

"Quite and comfortable"

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

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Kissimmee Townhome
5 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 3 bathrooms
2 reviews

Distance to park: 6 miles to Disney kingdom

$152

avg/night

$152
avg per night
View Details

Key Amenities

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

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

Featured review

"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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Kissimmee House
6 BR | 6 BA | Sleeps 12 | Quick View
Sleeps 12, 6 bedrooms, 6 bathrooms
4 reviews

$260

avg/night

$260
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Vacation in style with this luxurious family-friendly villa with your very own pool, spa and lake view. Family games room. The villa is located on the 5 Star safe gated Bella Vida Resort in the heart of Kissimmee, close to shops, restaurants and bars, and is only 15 minutes from Disney. Offering ...

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Property Type

Kissimmee House

Featured review

"Beautiful"

Beautiful home and spacious with all the things you would need to enjoy your stay . After out all day come back and relax in the roomy and comfortable home.The weather did't pan out while we were there ...

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Kissimmee Villa
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms
2 reviews

$170

avg/night

$170
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Water View and Outdoor Spa! Stay close to just about everything and enjoy easy access to our world-renowned theme parks, exciting golf, mega shopping and exceptional dining. Ideal for your next family vacation, this attractive 4 bedroom, 3 bath Disney area vacation home is conveniently located just ...

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Property Type

Kissimmee Villa

Featured review

"Great Location, Close to Parks, Private Oasis"

So many great things to say about this private getaway! Plenty of room for a big family! The private pool wasn't heated (our choice not to) so it was a little cool, but definitely not so cold that we couldn't ...

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Kissimmee Villa
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms
4 reviews

$170

avg/night

$170
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Ideal for your next family vacation, this striking 4-bedroom, 3 bath Disney area vacation home is conveniently located just 10 minutes to the Walt Disney World Resort, 15-20 minutes from Universal Studios Florida and SeaWorld Orlando. Florida’s famous beaches are just a quick 45 minutes away. ...

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Property Type

Kissimmee Villa

Featured review

"Fantastic Host"

We had the best time on our trip to Florida this year. I had a few changes in the dates chosen because of certain circumstances and the host was very understanding and willing to help out. I took my son ...

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Kissimmee House
6 BR | 5 BA | Sleeps 12 | Quick View
Sleeps 12, 6 bedrooms, 5 bathrooms

$346

avg/night

$346
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

A Truly Luxurious Executive Retreat, Main Level Features: Quality Ceramic Tile Flooring throughout. Spacious Family Room with Vaulted Ceiling and Corner Leather Sofa.70″ TV with 5.1 surround sound with blue tooth capabilities. Formal Dining Room/ Sitting Area with table for six, Fabulous Kitchen ...

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Property Type

Kissimmee House

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Kissimmee House
8 BR | 6 BA | Sleeps 16 | Quick View
Sleeps 16, 8 bedrooms, 6 bathrooms
8 reviews

Distance to park: 8 miles to Disney World

$354

avg/night

$354
avg per night
View Details

Key Amenities

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

About this property

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

View all property information

Property Type

Kissimmee House

Featured review

"GREAT"

Great home for large family .. home is located close to shops … it’s a great location to be at! Very nice

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Kissimmee Villa
9 BR | 6 BA | Sleeps 18 | Quick View
Sleeps 18, 9 bedrooms, 6 bathrooms

$450

avg/night

$450
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

(AWAITING PROFESSIONAL PHOTOS) South-west facing private pool & spa Complimentary BBQ Recently upgraded with modern furnishings throughout All nine bedrooms throughout are immaculately furnished, each with a unique design Great themed bedrooms to appeal to younger family members Situated on ...

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Property Type

Kissimmee Villa

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Kissimmee Townhome
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms
3 reviews

Distance to park: 6 miles to Disney,Seworld

$143

avg/night

$143
avg per night
View Details

Key Amenities

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

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 1500 ...

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Property Type

Kissimmee Townhome

Featured review

"Wonderful location"

Very nice home, close to Disney and shopping places. Very quiet friendly neighborhood. Def will be booking again in the future

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Kissimmee House
4 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 3 bathrooms
5 reviews

$155

avg/night

$155
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This stunning 4-bedroom home boasts an expansive east-facing pool deck that overlooks a pristine natural area, all within the prestigious gated community named Sanctuary. Full air con and hi-speed WiFi throughout. The spacious living room features a three-seater sofa and two wing-backed chairs, ...

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Property Type

Kissimmee House

Featured review

"Perfect serene environment"

My family and I thoroughly enjoyed our stay at the villa. It’s truly one of the best private rental properties in Florida, and we would rate it over 100%!

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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 260 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 $27 per night with an average price per night of $184.

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