Kissimmee Vacation Rentals

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

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 Townhome
4 BR | 3 BA | Sleeps 11 | Quick View
Sleeps 11, 4 bedrooms, 3 bathrooms
1 review

$171

avg/night

$171
avg per night
View Details

Key Amenities

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

About this property

New 4-bedroom, 3-baths townhouse with a private pool. Nestled in the peaceful Preserve Area of Storey Lake Resort, this property can accommodate up to 11 guests.It's totally equipped: - Kitchen has everything you need to cook - Towels & linen - Wifi - Basic cable and TVs - Enough free ...

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Property Type

Kissimmee Townhome

Featured review

"Excelente lugar para vacacional y pasar un tiempo en familia."

Nuestra estancia fue excelente desde la reservacion, el host muy atento, accesible y comunicador. La propiedad la encontramos en excelentes condiciones como así la vimos en las imágenes. Todo muy bonito, ...

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

$155

avg/night

$155
avg per night
View Details

Key Amenities

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

About this property

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

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Property Type

Kissimmee Townhome

Featured review

"Great place"

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

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

$202

avg/night

$202
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

Featured review

"Nice"

The house was real nice.I’ll rent it again The pool was great epic answered any questions I had and the weather was great

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Kissimmee House
9 BR | 7 BA | Sleeps 16 | Quick View
Sleeps 16, 9 bedrooms, 7 bathrooms

$323

avg/night

$323
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

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

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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

$366

avg/night

$366
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 villa8 bedrooms (2 Downstairs/6 Upstairs) and 6 full bathrooms. Space for up to 16 guests, (stretch out and relax with all the comforts of home) WEST facing private pool ensuring stunning sunset ...

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Property Type

Kissimmee House

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

$186

avg/night

$186
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 Apartment
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom

Distance to park: 7 miles to Disney World

$81

avg/night

$81
avg per night
View Details

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

$139

avg/night

$139
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
3 BR | 2 BA | Sleeps 7 | Quick View
Sleeps 7, 3 bedrooms, 2 bathrooms
12 reviews

Distance to park: 6 miles to Disney - Animal Kingdom

$125

avg/night

$125
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

This private, lakefront with nature reserve, pool home offers a fusion of luxury, comfort, and convenience. This spacious 3 bedroom and 2 bath home has cathedral ceilings and an open floorplan, with a living room, breakfast nook, and formal dining area. The kitchen is fully outfitted with all the appliances ...

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Property Type

Kissimmee House

Featured review

"Great Area"

Location was quiet. Home was beautiful and well maintained. My only comment would be to have a casserole dish to be able to bake something in the oven. Also a pizza pan. Besides these items it is well stocked. ...

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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

$114

avg/night

$114
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 Apartment
2 BR | 2 BA | Sleeps 5 | Quick View
Sleeps 5, 2 bedrooms, 2 bathrooms
1 review

$147

avg/night

$147
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
7 BR | 4 BA | Sleeps 14 | Quick View
Sleeps 14, 7 bedrooms, 4 bathrooms

$303

avg/night

$303
avg per night
View Details

Key Amenities

  • Air conditioning
  • WiFi

About this property

When it comes to finding Orlando vacation rentals that are conveniently located and fully equipped, Terra Verde 137 is a great option. This 7-bed, 4-bath house is suited for up to 14 guests and is situated in one of the best locations in the incredible Terra Verde Resort community. This home offers all ...

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Property Type

Kissimmee House

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Kissimmee House
6 BR | 3 BA | Sleeps 14 | Quick View
Sleeps 14, 6 bedrooms, 3 bathrooms
1 review

Distance to park: 5 miles to Disney World

$180

avg/night

$180
avg per night
View Details

Key Amenities

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

About this property

Experience a relaxing & unforgettable vacation in this stunning Tiffany Blue-colored villa, nestled in a peaceful & safe residential neighborhood. Enjoy easy access to theme parks, golf, restaurants, and supermarkets, all just a short drive away. Don't miss out - contact me with any questions!...

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Property Type

Kissimmee House

Featured review

"Amazing family-friendly home w/ a stunning pool"

Excellent location very close to Disney World. Beautiful and clean home. Host is very welcoming and helpful. The pool is stunning. The pictures do not do it justice. Wish we would have stayed longer!

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

Distance to park: 4 miles to Animal Kingdom

$250

avg/night

$250
avg per night
View Details

Key Amenities

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

About this property

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

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Property Type

Kissimmee Villa

Featured review

"Very well maintained home"

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

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

$200

avg/night

$200
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 CourseDiscover 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

Featured review

"Great stay! Highly recommend"

This house has everything a family needs for a short or long stay. The house was clean and decorated very nicely. The beds were comfortable and the furniture was well kept, almost new. We loved sitting ...

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

$132

avg/night

$132
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

If you're searching for Orlando vacation rentals near Disney, the name of this unit simply says it all: This unique condo with a newly remodel kitchen with all new appliances is set up to accommodate six guests between its three bedrooms and two bathrooms. Not only will you be able to benefit from ...

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Property Type

Kissimmee Condo

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Kissimmee House
3 BR | 2 BA | Sleeps 7 | Quick View
Sleeps 7, 3 bedrooms, 2 bathrooms
5 reviews

Distance to park: 6 miles to Disney - Animal Kingdom

$125

avg/night

$125
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

The "Sweet Retreat" is just 6 miles to Disney! This "Sweet" Villa has 3 Bedrooms, 2 Baths and sparkling Sunny private pool... Perfect for families & "Sweet" on your feet with all tile in the main rooms & carpet in the bedrooms.The living room feels bright and ...

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Property Type

Kissimmee House

Featured review

"Very nice villa"

Had a 2 week stay at this very nice villa. Clean, comfortable and great pool area. Good locaction. We highly recommend.

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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

$115

avg/night

$115
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
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 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

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

"Wonderful vacation spot"

The home is beautiful and cozy. Although we only used part of the house it was perfect. Everything was clean and in good shape. We spent almost everyday in the pool and jacuzzi . The pond was right behind ...

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Kissimmee Villa
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms
17 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

"Highly recommend this villa"

We have just returned home after spending two great weeks at this amazing villa.It was spacious,spotlessly clean, with very comfortable beds and all the amenities you need for a relaxing, enjoyable holiday. The ...

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

Distance to park: 2 miles to Disney

$315

avg/night

$315
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 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

$122

avg/night

$122
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
7 BR | 5.5 BA | Sleeps 16 | Quick View
Sleeps 16, 7 bedrooms, 5.5 bathrooms
1 review

Distance to park: 3 miles to Disney World

$309

avg/night

$309
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

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

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Property Type

Kissimmee Villa

Featured review

"7 bedroom house 8460 Secret Key Cove"

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

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Kissimmee Villa
5 BR | 4 BA | Sleeps 12 | Quick View
Sleeps 12, 5 bedrooms, 4 bathrooms
2 reviews

Distance to park: 3 miles to Disney World

$259

avg/night

$259
avg per night
View Details

Key Amenities

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

About this property

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

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Property Type

Kissimmee Villa

Featured review

"Excellent vacation & house"

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

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Kissimmee House
6 BR | 6 BA | Sleeps 12 | Quick View
Sleeps 12, 6 bedrooms, 6 bathrooms
3 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 Condo
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms

Distance to park: 3 miles to Disney World

$129

avg/night

$129
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Welcome to Surrounded in Magic! Please check your spam for any quotes.For current 2025 availability, see calendar in photos: Email us for a quote.Kids of all ages will love this magical, bright and spacious Disney & Universal Studios themed (1400 sq ft), 3-bedroom, 2-bath, 1st floor condo. ...

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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

$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

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Kissimmee Villa
5 BR | 3 BA | Sleeps 12 | Quick View
Sleeps 12, 5 bedrooms, 3 bathrooms
14 reviews

$145

avg/night

$145
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This villa is a stunning 5 Bed 3 Bath villa that can comfortably sleep 12 guests.A stunning, larger than average, 5 Bed 3 Bathroom villa with a fantastic private pool. All rooms in the villa are spacious. The villa is furnished and maintained to a very high standard.The villa is spaciously arranged ...

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Property Type

Kissimmee Villa

Featured review

"Quiet homely villa in a great location"

The villa is in a great location, in a good position to access WDW and Universal, but in a secluded gated community, which means it quiet in the evenings. It really feels like home, not impersonal like ...

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Kissimmee House
3 BR | 2 BA | Sleeps 7 | Quick View
Sleeps 7, 3 bedrooms, 2 bathrooms
7 reviews

Distance to park: 12 miles to Disney

Key Amenities

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

About this property

Heavenly Retreat, a designated rental vacation home, was just remodeled in a casual and comfortable style. It is a complete turn key ready vacation home with a full equipped kitchen, three bedrooms, and two bathrooms for up to 6 guests. The pool offers lots of privacy and relaxing atmosphere.This ...

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Property Type

Kissimmee House

Featured review

"Everything was good"

House was very clean and in a nice community. I guess the best review I can give is everything was as advertised.

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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
4 reviews

$155

avg/night

$155
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Luxury villa right on lake edge. Free fishing on 3 lakes. Gated 5 Star Resort.FREE Gas BBQ.Hi speed WiFi and air con throughout the villa.Our 4 Bed, 2 Bath villa is furnished to a very high standard and benefits from a perfect lake view position.Free fishing on 3 well stocked lakes. The ...

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Property Type

Kissimmee Villa

Featured review

"Great Stay"

My family and I chose to do Disney for the holiday. We stayed at one of your florida rentals. I must say that we had a pleasant stay. Very nice and quiet community. I would definitely return as a frequent ...

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

Distance to park: 7 miles to Disney World, Animal Kingdom is 7 miles, HS is 8.5

$160

avg/night

$160
avg per night
View Details

Key Amenities

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

About this property

Our home is currently blocked from May 7-21, 2025 due to pool resurfacing. But if would like a great deal and are willing to use the resort pool during your stay, reach out now!Welcome to CR Getaway—a beautiful 4-bedroom, 3-bathroom, townhome on Candy Palm Road in the exclusive Paradise Palms ...

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Property Type

Kissimmee Townhome

Featured review

"Great home!"

This is the second time we have stayed at Duane and Tina's place. They're always so friendly and helpful, and the place is clean, organized and a convenient location to the parks.We had a great stay!

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

$155

avg/night

$155
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Our luxury 4 bedroom home is located within the top rated community of Hamiltons near DisneyThe villa is furnished to a very high standard and is fully Air-conditioned throughout keeping the villa cool in the warm Florida weather.The tastefully furnished lounge has two large comfortable sofas ...

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Property Type

Kissimmee Villa

Featured review

"Lovely stay at this villa"

Booking process very easy. Had lovely stay here with family. Villa is great location, is clean modern and well furnished/equipped. We will stay here again next visit to Micky. Stan

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Kissimmee Villa
4 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 3 bathrooms

$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

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

$290

avg/night

$290
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
4 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 2 bathrooms
6 reviews

$155

avg/night

$155
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Lake front property with stunning sunsets.Newly renovated this spacious home has been completely refurbished as the perfect rental getaway for families seeking a modern villa.Nestled alongside a picturesque lake, this property features a generous pool surrounded by ample deck space, offering the ...

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

Distance to park: 12 miles to Disney World

$180

avg/night

$180
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 lovely home, in a lovely neighborhood. The house had everything needed to make your stay enjoyable and have the same comforts of your own home. The pool is huge and you have a beautiful view with ...

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

$165

avg/night

$165
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

About this property

This newly refurbished 5 bed, 4 bath villa can be found on the resort of Hampton Lakes, with direct access to Highway 27 and is ideally located for all the attractions!This home is a haven of modern living, offering both comfort and style for your Florida vacation.You can sleep up to 10 guests ...

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Property Type

Kissimmee House

Featured review

"Emerald Island Resort"

Enjoy my 12 days stay with family kids had a blast at the theme parks. There were some minor problems but they were very responsive and was dealt with in a timely manner.

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

$120

avg/night

$120
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

About this property

This is a NON SMOKING condo *Community: Secret LakeFloors: Ground Floor Condo.Pets: Pets OK.Rooms: 2 Bed rooms, 2 Bath rooms. En-suite in Master bedroom.Bed Configuration: King (1), Two Queen Beds (2). Sleeps 6Flooring: Carpet throughout with tile in bath and kitchen.General: ...

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Property Type

Kissimmee Condo

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

$120

avg/night

$120
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

This is a NON SMOKING condo *Community: Sweetwater Club VillasFloors: Second Floor Condo.Pets: NOT PET FRIENDLY.Rooms: 3 Bed rooms, 2 Bath rooms. En-suite in Master bedroom.Bed Configuration: King bed (1) Queen bed (1), Full Bed (2). Sleeps 6.Flooring: Hard wood throughout with ...

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Property Type

Kissimmee Villa

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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

$370

avg/night

$370
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 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

"Wild life"

This Villa is Located in the Country gated community. Quiet area for walking and 25 minutes to Disney by taking the local roads. close to Publix and some fast food . the House is big from front door to ...

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

Distance to park: 6 miles to Disney world

$286

avg/night

$286
avg per night
View Details

Key Amenities

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

About this property

Welcome to our luxury finished 3600 Sq ft pool home at beautiful Crystal Cove Resort. It is conveniently located close to shopping and dining (less than 1 mile away). Disney is only 6 miles away. Just minutes from major attractions like Sea World, Universal Studios, Aquatica and the Convention Center ...

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Property Type

Kissimmee House

Featured review

"Pleasant Stay in Crystal Cove"

Large and spacious home in Kissimmee. Close to many attractions and restaurants. Bedrooms, kitchen and bathrooms. Pleasant and easy to maintain for extended stay. Washer and Dryer on site make vacation ...

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

$360

avg/night

$360
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

$185

avg/night

$185
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to our beautiful villa situated in Veranda Palms, ideally located close to US-192 and only a 10-minute drive from I-4Our home boasts peaceful water views at the back with no rear neighbours plus the front is situated across from open countryside.The villa has also been professionally decorated ...

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Property Type

Kissimmee Villa

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

$146

avg/night

$146
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

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

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Property Type

Kissimmee Condo

Featured review

"Great Escape"

I visited to watch softball. The house was a perfect location and has everything I needed. Would stay again.

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

$205

avg/night

$205
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

This fantastic 5 bedroom, 4 bath Vacation Villa offers all of the conveniences of home and everything you need for a fun family vacation including a Private Screened-In Pool, Outdoor Spa, Games Room, Fully Equipped Kitchen, Free Wireless High-Speed Internet, Full Size Washer/Dryer, Coffee Maker and Microwave. ...

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Property Type

Kissimmee Villa

Featured review

"Perfect house for our group"

House was perfect for what we were looking for! It was very clean and comfortable. Pool and hot tub were fantastic! This place was awesome!

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Kissimmee Vacation Rentals

Kissimmee Weather

F° | C°

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 222 Kissimmee vacation rentals available on FloridaRentals.com. From villa rentals to house 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 $58 per night with an average price per night of $173.

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