Kissimmee Vacation Rentals

(259 rentals)
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Kissimmee Villa
4 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 3 bathrooms
2 reviews

$165

avg/night

$165
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Our gorgeous 4 bedroom detached single storey villa is perfect for families sleeping a maximum of 10 guests. Located in the gated community of Tuscan Hills, you can enjoy a private south facing pool deck and a fully stocked home of comfort. The single floor living makes it easy and safe for all your families’ ...

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Property Type

Kissimmee Villa

Featured review

"Brilliant villa"

Had awesome 10 night stay at this villa. Just brilliant. Book this villa, you will not be disappointed.

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

Distance to park: 8 miles to Disney World

$406

avg/night

$406
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • 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 property!!"

What a great property! It was perfect for our family. Very spacious and clean. Definitely staying there again on our next stay in Florida.

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Kissimmee House
4 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 2 bathrooms
5 reviews

$170

avg/night

$170
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

This stunning Disney area pool villa offers your family comfortable and convenient accommodations that will make your next Florida vacation a memorable one. Ideal for your next family vacation, this attractive 4 bedroom, 2 bath Disney area vacation home is conveniently located just 10 minutes to the ...

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Property Type

Kissimmee House

Featured review

"wonderful stay at this villa"

Villa has everything you will need, very spacious and great pool. Nice quiet Resort. We loved it and hopefully one day we can go back....need to start saving.

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

Distance to park: 12 miles to Disney World

$179

avg/night

$179
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Beautiful lakeside home with a private south facing pool in a gated community 12 miles from Disney. Enjoy fishing in the lake behind the house. Game room with pool table, skeet ball, foosball table and a gaming system with hundreds of old favorites like Pac Man and Mario Brothers. 4 bedrooms and 3 bathrooms. ...

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Property Type

Kissimmee House

Featured review

"Wonderful home"

This is a beautiful home to stay in. It had all the comforts of your own home, incredible view from the huge pool, lots of wildlife and friendly neighbors. The owners are super nice and so easy to work ...

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Kissimmee House | On the beach
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
2 reviews

$189

avg/night

$189
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Pet friendly
  • 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 House

Featured review

"Magical Stay"

We recently had the pleasure of staying at an Airbnb that exceeded our expectations in every way. stay at this united that is located just minutes away from the Disney world , provided the perfect blend ...

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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 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 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
4 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 2 bathrooms
11 reviews

$140

avg/night

$140
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This fabulous 4 Bed Villa is located in secure gated Lake Berkley Resort This fabulous 4 Bed Villa is located in a peaceful corner of Lake Berkley Resort with beautiful views to the Conservation Area and one on the lakes at Lake Berkley. The villa is fully equipped with everything you will need ...

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Property Type

Kissimmee Villa

Featured review

"2 week family vacation"

Our family had an amazing trip. It was as comfortable as being at home. Great communications with owner and management group if we had an issues or questions. Thank you.

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

$170

avg/night

$170
avg per night
View Details

Key Amenities

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

About this property

Ideal for your next family vacation, this attractive 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 ...

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Property Type

Kissimmee Villa

Featured review

"Very nice house"

We had an amazing stay at this very nice house. Everything was perfect. We enjoyed the pool very much. House is in great loaction. Hope we can stay again in couple of years. Pam

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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
9 BR | 6 BA | Sleeps 18 | Quick View
Sleeps 18, 9 bedrooms, 6 bathrooms
4 reviews

Distance to park: 8 miles to Disney World

$369

avg/night

$369
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

"Great for large family"

Very spacious, 9 bedrooms, for my family vacation of 12 people. Had some issues with the spa heat, but Iverson was very responsive.

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

$160

avg/night

$160
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to this beautiful luxury villa on the gated 5 Star Resort of Lake Berkley. This villa has 5 bedrooms, 2 of which are on the ground floor and 3 are on the first floor. It can sleep up to 10 comfortably. This is a perfect location for fishing on 3 well stocked lakes. Fish all day long whilst ...

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Property Type

Kissimmee Villa

Featured review

""

Booked to stay in our favourite place Lake Berkley through VIP Villas again for our Florida holiday. Stayed here many times. Cannot fault Stephen and Joanna, always there to help and promptly sort out ...

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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
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 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 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 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 Villa
8 BR | 4.5 BA | Sleeps 18 | Quick View
Sleeps 18, 8 bedrooms, 4.5 bathrooms
16 reviews

$186

avg/night

$186
avg per night
View Details

Key Amenities

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

About this property

One of the closest communities to Walt Disney World (less than 3 miles away), Emerald Island Resort is a quiet oasis in which to spend your vacation. Emerald Island is an exclusive man gated resort community less than a mile from the world famous US Highway 192 where you will find shops, restaurants, ...

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Property Type

Kissimmee Villa

Featured review

"a perfect house for a family group. CLEAN, good location, nice resort"

stayed for my daughter's wedding. had family and friends stay in house. house had everything needed, but not cluttered. people on second floor could not hear the main room, so they could avoid if desired. ...

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

$125

avg/night

$125
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to our stunning 3 bed, 2 bath villa perfectly located just off Highway 27 in Davenport and is only 15 minutes from Disney main gate. Full air con and hi-speed Wi-Fi throughout. It has an open, inviting floorplan with its own pool and gorgeous private pool, deck and spa; as well as a games ...

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Property Type

Kissimmee Villa

Featured review

"Great place to stay."

The villa is very convenient for shops and eating places - Walmart, Aldi and a large number of restaurants are less than 10 minutes away. The villa is also easily accessible to all the theme parks and shopping ...

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

$140

avg/night

$140
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This stunning 4 Bed 2 Bath Villa enjoys one of the premier positions on Lake Berkley Resort with an unspoilt beautiful view over the lake. Enjoy breakfast, lunch or dinner on the pool patio whilst watching the wildlife on the lake. If you enjoy fishing then you only need to walk a few yards to fish in ...

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Property Type

Kissimmee Villa

Featured review

"Excellent House and stay"

We had such a lovely house it was even nicer in person when we arrived. Great communication all the way through the booking and during the stay also. Would highly recommend and will Definatly stay ...

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

$136

avg/night

$136
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

One of the closest possible communities to Walt Disney World (less than 3 miles away), Emerald Island is a quiet oasis in which to spend your vacation. Emerald Island is an exclusive gated community less than a mile from the world famous US Highway 192 where you will find shops, restaurants, and entertainment. ...

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Property Type

Kissimmee Villa

Featured review

"Family vacation"

Our family were there for 2 1/2 weeks and everyone loved it. Location very close to parks,restaurants and stores. Grandkids loved the time in the pool. House was big enough for the family and clean. Screens ...

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

$357

avg/night

$357
avg per night
View Details

Key Amenities

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

About this property

Fantastic 2 KING bed EnSuite Villa w heated pool HOT TUB Mins to Disney Family-friendly Kissimmee vacation home in Four Corners with water park Contactless one time access code check in! All white linen! Private pool heat up to 104 degree. It’s like a 5 star hotel but better! Pet Friendly ...

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Property Type

Kissimmee House

Featured review

"Great place"

The owners were very easy to work with. The house was in perfect condition, very clean and well maintained. We had 9 people and plenty of room for everyone. Definitely would recommend the house.

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

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

$136

avg/night

$136
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Welcome to the Sun Lake Resort. We have 4 identical 1650 sqft units with 4 bedrooms and 3 bathrooms. The beautiful condo faces to sun lake and it has a spacious screened patio. It only takes 1 minute walk to a plaza for shopping and restaurants which is very convenient! More importantly, you are only ...

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Property Type

Kissimmee Condo

Featured review

"Awesome stay"

Beautiful resort and room was great. Great location and staff was very helpful. Would highly recommend this property.

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

$110

avg/night

$110
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This well maintained 3 bedroom 2 baths home located in the renowned Lindfields Estate. It is perfectly placed to maximize your family’s vacation fun here in the entertainment capital of Florida! You will not want to miss this lovely vacation home close to Disney and on the doorsteps of local ...

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Property Type

Kissimmee House

Featured review

"Great"

A great family vacation rental.booking was easy and check in process was flawless. We had an issue with the internet but the manager resolved it as soon as possible. The rental was safe clean and convenient ...

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

$160

avg/night

$160
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Our gorgeous, newly refurbished 4 bedroom 3 bathrooms detached single storey villa is perfect for families sleeping a maximum of 8 guests. Located at Tuscan Ridge it enjoys a prestigious resort style community in a beautiful countryside setting. You can enjoy a private south-east facing pool and spa. ...

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Property Type

Kissimmee Villa

Featured review

"great stay with family"

Had a week here with family and it was great. Villa is well kept, has everything we needed. Highly recommended and we will stay here again. Percy

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

Distance to park: 6 miles to Disney,Seaworld

$148

avg/night

$148
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 the theme parks and other major attractions. Situated 6 miles from Disney World, 1 mile to Walmart and target. 8 miles to Seaworld and Convention center. Minutes ...

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Property Type

Kissimmee Townhome

Featured review

"Comfortable place to stay....."

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

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

$111

avg/night

$111
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Our vibrant 3 bedrooms condo is perfect for your families and Work professional friends up to 7 people. Enjoy a spacious living room to hang out and a full-size pullout sofa.The designer master bedroom, Disney Princess bedroom&Superhero Marvel bedroom each feature a large 4KTV. Unwind in our home ...

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Property Type

Kissimmee Condo

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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 Villa
7 BR | 4.5 BA | Sleeps 14 | Quick View
Sleeps 14, 7 bedrooms, 4.5 bathrooms
15 reviews

$172

avg/night

$172
avg per night
View Details

Key Amenities

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

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

Featured review

"Sibling Weekend Getaway"

The home was spacious and clean. This was our second visit. The first visit being 10 years ago. The owner is kind and accommodating with our needs. Looking forward to next year. Same time, same place

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

$217

avg/night

$217
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner

About this property

RECENTLY REFURBISHED Luxurious Windsor Palms with an extra wide cul de sac lot and with a pool that is not overlooked. Our guests enjoy terrific privacy in one of the premier resorts in the Disney vicinity. We have a south facing pool with kiddy pool and stand alone hot tub. Numerous child friendly ...

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Property Type

Kissimmee Villa

Featured review

"Awesome vacation"

Everything was perfect from start to finish. House was better than we expected, owner was great to deal with and will for sure book this house again and have already referred friends to book this property ...

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Kissimmee Villa
7 BR | 4.5 BA | Sleeps 16 | Quick View
Sleeps 16, 7 bedrooms, 4.5 bathrooms
11 reviews

Distance to park: 3 miles to Disney world

$166

avg/night

$166
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Pool
  • WiFi

About this property

Newly furnished luxurious 2-story Villa home opens its door to welcome you! This villa is furnished with two master suite and one large bedroom with upscale King-size beds; two bedrooms with queen-size beds; and two bedrooms with two twin-beds each. All bedding and mattresses are Brand New with top quality ...

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Property Type

Kissimmee Villa

Featured review

"Wonderful Vacation Home"

Our family of 12 spent 2 weeks at 2662 Emerald Island Blvd. Everyone had a wonderful time and hated to leave when our vacation was over. The house has very comfortable furniture and everyone said their ...

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Kissimmee House
9 BR | 6 BA | Sleeps 20 | Quick View
Sleeps 20, 9 bedrooms, 6 bathrooms
4 reviews

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

$400

avg/night

$400
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. Just 8 miles from Disney, and within easy reach to all the attractions, shopping, and dining in the Disney area, This 24 hour guard gated ...

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Property Type

Kissimmee House

Featured review

"Very comfortable"

I went with my family, very comfortable. Beds 6 out of 10. Pool 7 out of 10. Rest of amenities 10 out of 10.

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

Distance to park: 8 miles to Disney World

$356

avg/night

$356
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • 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

"Very nice"

We really enjoyed our stay. Community was really nice and house was huge. Had some good amenities and was a real easy drive to all the parks. Pool was nice… wish we paid for heat but we didn’t. ...

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

$135

avg/night

$135
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This is a beautiful professionally decorated and furnished 3 Bed, 2 Bath Villa located at Lake Berkley Resort. Have your vacation here in comfort and relaxation with air conditioning throughout. Full air con and hi-speed WiFi throughout. The spacious sitting room has a Queen sofa sleeper bed so ...

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Property Type

Kissimmee Villa

Featured review

"Three week home from home stay"

We found this company following the cancellation of a booking made elsewhere. After sending out enquiries, Stephen and Johanna were the first people to contact us personally by phone to offer their help. ...

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

$155

avg/night

$155
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

4 Bedroom villa with 4 ensuite bathrooms. This exquisite villa is an ideal destination for a family holiday, offering a prime location. Situated within walking distance of the resort clubhouse and pool. Hi speed WiFi and air con throughout the villa. Set against a backdrop of serene ...

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Property Type

Kissimmee Villa

Featured review

"Modern and clean villa"

We had a wonderful time in this villa. We always love coming to the Bellavida resort. Our favorite location near the Disney parks. The villa is modern and was clean and has lots of privacy. We had a problem ...

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

Distance to park: 4 miles to Disney

$429

avg/night

$429
avg per night
View Details

Key Amenities

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

About this property

We are only 3.5 miles from Disney!! So close to all the fun, Hollywood Studios, Sea World, beaches, walks, restaurants and shopping!! We are in the middle of it all! You will enjoy our lovely villa by yourself or with a group. Our pool is one of the biggest among the rental communities. When comparing ...

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Property Type

Kissimmee Villa

Featured review

"Wow!!!! Perfect 10 out of 10!!!!"

We stayed at the property for 6 nights during our recent family's Disney World vacation. Right from the start of the process, the owner was very courteous and prompt with her responses to our many questions. ...

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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!