Kissimmee Vacation Rentals

(257 rentals)
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Kissimmee Villa
6 BR | 5 BA | Sleeps 12 | Quick View
Sleeps 12, 6 Bedrooms, 5 Bathrooms

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

$27

avg/night

$27
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Welcome to our luxurious 6-bedroom, 9-bed, 3,200-square-foot villa. This stunning property features two en-suites, two living rooms, and a private screened-in pool with optional heating. Conveniently located near major attractions such as Disney, Universal, Seaworld, and golf courses, our villa can ...

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Property Type

Kissimmee Villa

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Kissimmee Villa
9 BR | 10 BA | Sleeps 26 | Quick View
Sleeps 26, 9 Bedrooms, 10 Bathrooms
15 reviews

$956

avg/night

$956
avg per night
View Details

Key Amenities

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

About this property

Imagine a vacation like no other spent in a 9 bedroom, 10 bath custom luxury lakefront pool villa. The Formosa Grand is located in the exclusive gated community of Formosa Gardens Estates and one of the closest communities to Disney (less than 10 minutes!!) No expense was spared in the gorgeous estate ...

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Property Type

Kissimmee Villa

Featured review

"Great Experience"

Had a great exerience. Owner was very pleasant to deal with throughout. I would definitely recommend this property to others.

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Kissimmee House
9 BR | 6 BA | Sleeps 23 | Quick View
Sleeps 23, 9 Bedrooms, 6 Bathrooms

$655

avg/night

$655
avg per night
View Details

Key Amenities

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

About this property

Embark on the ultimate Disney vacation at Jurassic Encanto! With elegantly designed thematic rooms, this spacious home provides ample room for larger groups and multiple families. Compete in the epic game room or take in the lake views while relaxing by the luxurious private pool and spa amidst world-class ...

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Kissimmee House

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Kissimmee Condo
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 Bedrooms, 2 Bathrooms
21 reviews

Distance to park: 2 miles to Disney World

$168

avg/night

$168
avg per night
View Details

Key Amenities

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

About this property

Welcome to Escape by KLMJ Sunshine! This is a completely renovated 3-bedroom condo in the beautiful gated community of Windsor Hills, just two miles from Disney. Enjoy the massive heated pool, brand new water park, large playground, tennis and basketball courts, mini-golf, arcade, movie theatre, fitness ...

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Property Type

Kissimmee Condo

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Kissimmee Townhome
4 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 4 Bedrooms, 3 Bathrooms

$187

avg/night

$187
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

Plush Pelican - Sleeps 10 at Storey Lake by Shine Villas! Gorgeous, beautifully appointed and high end designer decorated 4 bedroom, 3 bathroom townhome with private splash pool sleeping up to 10. Located in one of Orlando's newest resort communities: Storey Lake. Less than 10 minutes ...

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Property Type

Kissimmee Townhome

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Kissimmee Townhome
4 BR | 3 BA | Sleeps 11 | Quick View
Sleeps 11, 4 Bedrooms, 3 Bathrooms
1 review

$176

avg/night

$176
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

Happy Haven at Storey Lake Resort by Shine Villas – Sleeps up to 12 Welcome to your Holiday Home! Beautifully decorated 4 bedroom, 3 bathroom home inside the premium Storey Lake Community. Private Splash pool and space for up to 12 to stay. Storey Lake, Located in ...

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Property Type

Kissimmee Townhome

Featured review

"Beautiful house and location"

The house is in a resort complex and even we did not use they much for the weather cold. I want to say it is a very nice place for family vacation. House was clean and in excellent location. I would stay ...

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Kissimmee Villa
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 Bedrooms, 3 Bathrooms
27 reviews

$145

avg/night

$145
avg per night
View Details

Key Amenities

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

About this property

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

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Property Type

Kissimmee Villa

Featured review

"House rental on Santee Dr"

The house was very clean and well furnished. The location is perfect. I dealt with the homeowner Lisa who was professional and returned my text quickly. The pool and hot tub were also very clean. Quiet ...

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Kissimmee Villa
4 BR | 4 BA | Sleeps 10 | Quick View
Sleeps 10, 4 Bedrooms, 4 Bathrooms
2 reviews

$294

avg/night

$294
avg per night
View Details

Key Amenities

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

About this property

Name Of Home: Walking on Sunshine Villa Location: Windsor Hills Resort (24/7 guard gated community - Disney World only mins away!) Home Highlights: Recently Renovated Home - Incredible Air Conditioned 80s Game Room - Private South Facing Pool/Spa - Bunk Bedroom with PS5 Property Type: Single ...

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Property Type

Kissimmee Villa

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Kissimmee Townhome
3 BR | 2.5 BA | Sleeps 8 | Quick View
Sleeps 8, 3 Bedrooms, 2.5 Bathrooms

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Gorgeous 3 bedroom townhome in a gated resort community with many activities. The home is located right across the street from one of the pools and playground.

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Property Type

Kissimmee Townhome

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Kissimmee Villa
5 BR | 5 BA | Sleeps 12 | Quick View
Sleeps 12, 5 Bedrooms, 5 Bathrooms
16 reviews

Distance to park: 3 miles to Disney's Animal Kingdom

$325

avg/night

$325
avg per night
View Details

Key Amenities

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

About this property

☆☆ HIGHLIGHTS ☆☆ ✹ 5 spacious bedrooms w/ smart TVs: 2 kings, 1 queen, 1 full, 3 twins ✹ 5 full bathrooms ✹ Fully stocked kitchen w/ modern appliances ✹ Large living room w/ flat-screen TV + DVD player ✹ Fun game room w/ basketball, Lego table, skee ball + more ✹ Heated pool ...

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Property Type

Kissimmee Villa

Featured review

"EXCELLENT"

This location was perfect for our family while staying close to the Disney Park. It had all the amenities for two families plus more. The pool and hot tub were a wonderful addition. The game room was a ...

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Kissimmee Townhome
4 BR | 3.5 BA | Sleeps 11 | Quick View
Sleeps 11, 4 Bedrooms, 3.5 Bathrooms

$283

avg/night

$283
avg per night
View Details

Key Amenities

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

About this property

Make lifelong memories with your family and experience the bliss of a private home away from home. With the kids’ Frozen- and Avatar-inspired bedrooms, you'll have them squealing in delight! Enjoy luxuries like a fully equipped kitchen, epic game room, an inviting lounge area, children's ...

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Property Type

Kissimmee Townhome

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Kissimmee House
7 BR | 6 BA | Sleeps 15 | Quick View
Sleeps 15, 7 Bedrooms, 6 Bathrooms

$299

avg/night

$299
avg per night
View Details

Key Amenities

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

About this property

Stunning, designer furnished 7th Heaven Villa! This home has everything that you, your family and friends will ever need and more! Walt Disney World Resort is only 2 traffic signals away. This luxury South facing pool home, completed in June 2004, has 7 bedrooms, 6 bathrooms and will accommodate 15 people ...

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Property Type

Kissimmee House

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Kissimmee Villa
9 BR | 5 BA | Sleeps 28 | Quick View
Sleeps 28, 9 Bedrooms, 5 Bathrooms

$345

avg/night

$345
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

Water Kingdom @! Sleeps up to 28! Resort Living In The Tropics! * South Facing Pool * * Water/Lake and Conservation View * * Hot Tub Heat Included at no extra cost * Walking Distance and access to the brand Second ‘Pirate’ Water Park at Storey Lake Resort* - Find Your Amazing ...

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Property Type

Kissimmee Villa

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Kissimmee House
6 BR | 5.5 BA | Sleeps 18 | Quick View
Sleeps 18, 6 Bedrooms, 5.5 Bathrooms
58 reviews

Distance to park: 4 miles to Animal Kingdom

$179

avg/night

$179
avg per night
View Details

Key Amenities

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

About this property

Some of the best features of this house from Guest Reviews • Beautiful Vinyl Plank Flooring in all bedrooms, halls and on the steps • Less than a 4-mile drive to Disney World’s Animal Kingdom Theme Park • Two leather couches and a recliner with a total of 5 power reclining seats • ...

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Property Type

Kissimmee House

Featured review

"Spacious, well-appointed house in a great location close to the Disney Parks."

The owner provided very detailed and helpful information regarding the house, the Orlando area and the Disney parks before we arrived. The house was very clean and tidy and all the rooms were as described. ...

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Kissimmee House
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 Bedrooms, 3 Bathrooms
16 reviews

Distance to park: 4 miles to Disney

$162

avg/night

$162
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Magical Dreams come true in our elegant private 4 bedroom villa, 3 bathroom, all located on one floor, Quiet upgraded comforts of home and luxuries of an exceptionally rated vacation resort/hotel. Newly resurfaced and freshly painted pool and spa is sure to impress. There will be no waiting in line ...

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Property Type

Kissimmee House

Featured review

"Perfect rental for all of our needs!"

This was a Christmas vacation never to be forgotten! We had the time of our lives! My children, grandchildren and I enjoyed the comforts and privacy of a home where we could take in all the theme parks ...

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Kissimmee House
15 BR | 12 BA | Sleeps 38 | Quick View
Sleeps 38, 15 Bedrooms, 12 Bathrooms

$1342

avg/night

$1,342
avg per night
View Details

Key Amenities

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

About this property

Experience a magical holiday by renting TWO homes across the street from each other to accommodate large groups, teams and reunions! Queen of Hearts is 8 bedrooms and Moana's Minecraft is 7 bedrooms, both in Windsor at Westside Resort. Enjoy private pools, & game rooms in these fabulously equipped ...

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Property Type

Kissimmee House

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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
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

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 Villa
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 Bedrooms, 3 Bathrooms
18 reviews

Distance to park: 3 miles to Mgm

$125

avg/night

$125
avg per night
View Details

Key Amenities

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

About this property

Beautiful 4 bedroom /3 bath private villa only 3 miles to Disney and other parks. Including heated pool/jacuzzi and game room. Free wifi and phone use in USA and Canada and PR. Fully furnished with all kitchen needs . Greatest location to shopping , all major restaurants and stores including supermarkets ...

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Property Type

Kissimmee Villa

Featured review

"Top class accommodation"

We couldn't fault our accommodation at all. Everything you needed was on hand. Lovely beds and a awesome view of the lakes in front of our pool.

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Kissimmee Villa
7 BR | 7 BA | Sleeps 18 | Quick View
Sleeps 18, 7 Bedrooms, 7 Bathrooms
1 review

$283

avg/night

$283
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

Just Wow - Monterey Bay at Solara by Shine Villas! 7 Bedrooms and 7 Bathroom - Sleep up to 18 when using the trundle beds. This home is exquisitely designed and has all you could want from your vacation home away from home. Private Pool with Spa, Media Loft Area, Air-Conditioned Avengers ...

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Property Type

Kissimmee Villa

Featured review

"Very beautiful home"

It’s a very beautiful home and real spacious and clean I will love to book again very professional and the host was very sweet and kind

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Kissimmee Condo
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 Bedrooms, 2 Bathrooms
3 reviews

Distance to park: 1 miles to Disney Animal Kingdom

$97

avg/night

$97
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

About this property

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

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Property Type

Kissimmee Condo

Featured review

"Great location, clean and comfortable."

We had everything we needed. Excellent communication. Perfect location. Close to the parks as well as restaurants, etc! We will be back.Thanks

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Kissimmee Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms
2 reviews

Distance to park: 2 miles to Disney

$132

avg/night

$132
avg per night
View Details

Key Amenities

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

About this property

Our exquisite, tastefully decorated and perfectly maintained 2-bedroom and 2 full bath condo is perfect for your family and friends up to 6 people. We are on the top floor, and you will hear no noise from above! There are two double beds in the Master Bedroom with a walk-in closet and ensuite. The ...

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Property Type

Kissimmee Condo

Featured review

"Fabulous Host and Fantastic Accomodations!"

We stayed at this gorgeous condo resort for a week with my family and had a most comfortable and peaceful stay. The bedrooms were perfect for our family and I loved the separate full master bedroom ensuite. ...

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Kissimmee House
9 BR | 7 BA | Sleeps 16 | Quick View
Sleeps 16, 9 Bedrooms, 7 Bathrooms

$344

avg/night

$344
avg per night
View Details

Key Amenities

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

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 Villa
6 BR | 4 BA | Sleeps 14 | Quick View
Sleeps 14, 6 Bedrooms, 4 Bathrooms

$284

avg/night

$284
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

Fantasia @ – Sleeps 14 Welcome to your Magical Place!! Beautifully designer decorated 6 bedroom, 4 bathroom home inside the premium Storey Lake Resort Community. Private pool AND Spa with more than enough space for up to 14 to stay in comfort. Storey Lake, Located in ...

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Property Type

Kissimmee Villa

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Kissimmee House
9 BR | 8 BA | Sleeps 18 | Quick View
Sleeps 18, 9 Bedrooms, 8 Bathrooms
11 reviews

Distance to park: 3 miles to Disney Animal Kingdom

$664

avg/night

$664
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Mickey's Oyster is a luxurious oasis designed to make your Disney World vacation unforgettable. Nestled in a prestigious, gated community just minutes away from the magic, this freshly remodeled and renovated home offers an enchanting escape with all the comforts of a five-star resort. Luxurious ...

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Property Type

Kissimmee House

Featured review

"Hartley House family gathering"

We have just returned from a great family holiday in Florida we took all our family away for our fiftieth wedding anniversary ,three years late .We stayed at Hartley House ,we have never stayed in a american ...

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Kissimmee Villa
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 Bedrooms, 2 Bathrooms
13 reviews

Distance to park: 12 miles to All Disney Theme Park

$109

avg/night

$109
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

If you will be visiting Orlando Florida for all of the great attractions including Walt Disney World, Universal Studios, Sea World theme parks, and all of the other major attractions? You can stay in our beautifully decorated 3 bedroom private villa, which boasts it's own private pool for less than ...

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Property Type

Kissimmee Villa

Featured review

"New Years Getaway"

Stayed month of January..Villa was very well equipped and very comfortable.Location was fantastic being so close to all attractions. Would highly recommend for anybody to stay..

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Kissimmee Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms

$138

avg/night

$138
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

Sweet Suite @ – Sleeps 6. (#903) Sleeps up to 6 Master Suite has a King Bed with large TV, fabulous en-suite and large walk in shower, double vanity bathroom and walk in closet space. Sleeps 2 Second bedroom, also with TV with custom wall art, has a full size over full size ...

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Property Type

Kissimmee Condo

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Kissimmee House
6 BR | 5.5 BA | Sleeps 13 | Quick View
Sleeps 13, 6 Bedrooms, 5.5 Bathrooms

$344

avg/night

$344
avg per night
View Details

Key Amenities

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

About this property

Newly renovated and professionally decorated with upscale furnishings, this luxury family vacation home is an ideal get-away to relax with family and friends following visits to busy theme parks and area attractions. As a large private manor, located on a quiet cul-de-sac, Emerald Escape is a modern ...

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Property Type

Kissimmee House

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Kissimmee Townhome
3 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 3 Bedrooms, 3 Bathrooms
4 reviews

$215

avg/night

$215
avg per night
View Details

Key Amenities

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

About this property

A fabulous home-base for your trip to Orlando! Just Minutes to Theme Parks. Home Features: * 3 Bedrooms * 1 King, 1 Queen, 2 Full, 1 Twin (Sleeps 7-8) * All New Mattresses * TV's in every bedroom * USBs & Outlets convenient for charging * 3 Bathrooms * All En-Suite * ...

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Property Type

Kissimmee Townhome

Featured review

"Loved it."

Beautiful House, and a wonderful experience from start to finish! Cant wait to go back! The home was spacious and beautifully decorated and Lisa was a Pleasure to work with, and very helpful.

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Kissimmee House
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 Bedrooms, 3 Bathrooms
9 reviews

Distance to park: 4 miles to Disney World

$159

avg/night

$159
avg per night
View Details

Key Amenities

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

About this property

Welcome to La Casita on the Island (The Little House on the Island) "Our house, our casita" If you want a place to relax and enjoy the beautiful weather of Florida, I invite you to see the "encanto" (charm) that you can experience during your stay at La Casita on the Island. Enjoy ...

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Property Type

Kissimmee House

Featured review

"Great Villa"

Had a fantastic stay in the villa. Would definitely stay again and highly recommend. It was extremely clean and in a great location near shops, resturaunts and 192 and Disney. Would highly recommend and ...

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Kissimmee Villa
4 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 4 Bedrooms, 2 Bathrooms
7 reviews

Distance to park: 7 miles to Walt Disney World

$206

avg/night

$206
avg per night
View Details

Key Amenities

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

About this property

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

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Property Type

Kissimmee Villa

Featured review

"Lake house villa"

Lovely villa,spotlessly clean & well equipped,management company are very helpful & quick to respond,Jane the owner was also very helpful & quick to respond to any enquiries we had,great location & the ...

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Kissimmee Villa
4 BR | 2.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 Bedrooms, 2.5 Bathrooms
1 review

Distance to park: 3 miles to Disneys Animal Kingdom

$171

avg/night

$171
avg per night
View Details

Key Amenities

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

About this property

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

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Property Type

Kissimmee Villa

Featured review

"Tolles Haus"

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

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Kissimmee Villa
9 BR | 7.5 BA | Sleeps 22 | Quick View
Sleeps 22, 9 Bedrooms, 7.5 Bathrooms

$330

avg/night

$330
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

Moana Castle at Solara Resort by Shine Villas! Your children will thank you for years to come after they arrive and run around exploring this home excitedly. It has absolutely everything. 9 Bedrooms, 7 bathrooms, sleeps up to 22. This home is exquisitely designed and has all you could want from ...

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Property Type

Kissimmee Villa

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Kissimmee House
8 BR | 6 BA | Sleeps 16 | Quick View
Sleeps 16, 8 Bedrooms, 6 Bathrooms
2 reviews
owner special
Owner special: Stay for 7 nights or more and get free pool/spa. Offer not valid with any other discount.

$260

avg/night

$260
avg per night
Owner special:
Stay for 7 nights or more and get free pool/spa. Offer not valid with any other discount.

View Details

Key Amenities

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

About this property

Enjoy a whimsical getaway when you book a stay at this sleek, refreshing, 8-bedroom, 6-bathroom vacation rental home. Take a dip in the private pool, fix up something tasty in the fully equipped kitchen, play a game of pool in the game room, or head to the community fitness center for a quick workout. ...

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Property Type

Kissimmee House

Featured review

"Kissimmee Home/Windsor"

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

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Kissimmee Villa
6 BR | 5 BA | Sleeps 12 | Quick View
Sleeps 12, 6 Bedrooms, 5 Bathrooms
1 review

$258

avg/night

$258
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

Stars Align @ – Sleeps 12 Welcome to your Cosmic Place!! You have found your vacation home here – Congratulations! Beautifully designer decorated 6 bedroom, 6 bathroom home inside the premium Storey Lake Resort Community. Play Planet Pinball in the games area, hideaway in one of ...

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Property Type

Kissimmee Villa

Featured review

"Excellent"

This home was well taken care of. The moment we arrived the house was clean and even more beautiful than the pictures. The cleaning crew did an amazing job. The owner was so polite and made us feel welcomed. ...

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Kissimmee Villa
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 Bedrooms, 3 Bathrooms
16 reviews

$145

avg/night

$145
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

This Disney Villa is a fully furnished home and is one of the best kept turnkey properties you will find in Indian Creek ! Has an airy open floor plan, lots of light. Enjoy the crystal clear South facing pool and the covered lanai on your sunny and warm Florida holidays. This luxurious private home ...

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Property Type

Kissimmee Villa

Featured review

"Excellent villa"

We have been so pleased with this villa. Very clean, has everything we need and more. Very close to Disney and easy to get to Univerdal Studios and SeaWorld as well as easy commute from the airport. Would ...

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Kissimmee House
7 BR | 4.5 BA | Sleeps 14 | Quick View
Sleeps 14, 7 Bedrooms, 4.5 Bathrooms

$460

avg/night

$460
avg per night
View Details

Key Amenities

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

About this property

Perfect Family Destination Best lania/pool Minutes to Disney/Attractions/Conveniences Fun/Clean/Comfortable This is a fantastic house for family getaways! Enjoy the Food and Wine Festivals. Mickey's Not So Scary Halloween Party, Unforgettable Disney Christmas celebration, and everything else ...

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Property Type

Kissimmee House

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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
  • Kitchen
  • Pet friendly
  • Pool

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 Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms

$133

avg/night

$133
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

Storey Lake Resort, 2bd Condo Overlooking Water #703 Stunning, Top Floor, brand new (August 2021) 2 Bed, 2 bath Condo, overlooking the huge blue skies of Orlando and the canals of Storey Lake Resort. Sleeps a family of up to 6! Here is your piece of Magic: Luxuriously Furnished ...

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Property Type

Kissimmee Condo

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Kissimmee House
8 BR | 6 BA | Sleeps 22 | Quick View
Sleeps 22, 8 Bedrooms, 6 Bathrooms

$514

avg/night

$514
avg per night
View Details

Key Amenities

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

About this property

Experience the popular "Queen of Hearts" villa in the Windsor at Westside Resort! This home boasts a private heated pool & hot tub, fire pit and outdoor TV. The themed bedrooms are loaded with amazing details. All guests have free access to resort amenities. Your host Vacation Alchemy provides ...

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Property Type

Kissimmee House

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Kissimmee House
11 BR | 9 BA | Sleeps 30 | Quick View
Sleeps 30, 11 Bedrooms, 9 Bathrooms

$862

avg/night

$862
avg per night
View Details

Key Amenities

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

About this property

BRAND NEW 2023 remodeled 10+ bedroom luxurious home in the Encore/Reunion community. "The Great Escape" is designed for large groups and families who want their vacation home to be part of the adventure! Is this home already booked? Check out our Profile and chose from over a dozen magical ...

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Property Type

Kissimmee House

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Kissimmee Villa
9 BR | 6 BA | Sleeps 24 | Quick View
Sleeps 24, 9 Bedrooms, 6 Bathrooms
14 reviews

Distance to park: 2 miles to Sunday's Grill

$319

avg/night

$319
avg per night
View Details

Key Amenities

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

About this property

For last minute rentals or longer extended rentals, please inquiry about our discounted rates. This luxury vacation home is located in the Windsor at Westside upscale resort community - A perfect destination for DISNEY WORLD (10 minutes away), golf, and relaxing and celebrating with family and friends. ...

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Property Type

Kissimmee Villa

Featured review

"Excellent"

Thank You Ann great service. Me and my family will be renting from you again in the future

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Kissimmee House
4 BR | 2.5 BA | Sleeps 9 | Quick View
Sleeps 9, 4 Bedrooms, 2.5 Bathrooms
10 reviews

Distance to park: 10 miles to Disneyworld

$126

avg/night

$126
avg per night
View Details

Key Amenities

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

About this property

Our villa is modern style furnished, has everything you would expect in a holiday home, 4 bedrooms, 2 with king-size beds, 1 with single bed´s, 1 with triple bunk bed all with private TV. 2 bathrooms, 1 guest toilet, fully equipped kitchen, etc. with ceran stove, fridge, oven, microwave, coffee ...

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Property Type

Kissimmee House

Featured review

"Looking for a great vacation rental for the kids? This is it!!"

What a nice house! It has everything you could want in a vacation home. A very nice pool, patio and attached BBQ area with gas grill, literally a ton of DVD's to keep everyone entertained in the evening, ...

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Kissimmee Condo
2 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 2 Bedrooms, 2 Bathrooms

$134

avg/night

$134
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

Catch the Disney and Epcot Fireworks at Night from your top floor private balcony, Resort Living by Day! Sleeps up to 8 when using the bunk room trundle and the pull out sofa bed. Master Suite has a King Bed with fabulous en-suite, large walk in shower, double vanity bathroom and walk in closet ...

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Property Type

Kissimmee Condo

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Kissimmee House
3 BR | 2 BA | Sleeps 10 | Quick View
Sleeps 10, 3 Bedrooms, 2 Bathrooms
19 reviews

$187

avg/night

$187
avg per night
View Details

Key Amenities

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

About this property

Sunset Lakes is ideally situated, just 4 miles from Disney World and a short drive from other popular attractions like Universal Studios, Sea World, and more. The proximity to Orlando and other destinations makes it a prime choice for travelers. The gated community offers various amenities such as a community ...

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Property Type

Kissimmee House

Featured review

"Vacation retreat/$15 Uber to Disney/ HGTV looking retreat"

We are completing our stay in the morning at this beautiful vacation retreat! We brought the family all seven of us ranging from age in two years old to 60 years old. The pool and patio is incredibly maintained, ...

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Kissimmee House
4 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 4 Bedrooms, 3 Bathrooms
15 reviews

$118

avg/night

$118
avg per night
View Details

Key Amenities

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

About this property

Close to the Attractions but away from the crowds. 4 bedroom/3 bath single story home on "lake". Ducks, Sandhill Cranes, sometimes a falcon, turtles. King, king, and 4 twin beds, TV in all bedrooms, WiFi, FREE US, Canada and US Territory phone calls. Fully furnished. Not suitable for ...

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Property Type

Kissimmee House

Featured review

"Great Location for your stay."

The home was very comfortable and dealing with the owner was a breeze. Check in was very easy and the location is ideal for Disney and Universal visitors. Nice lake view and several chairs for outdoor seating. ...

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Kissimmee Villa
7 BR | 6 BA | Sleeps 14 | Quick View
Sleeps 14, 7 Bedrooms, 6 Bathrooms
3 reviews

$333

avg/night

$333
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

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

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Property Type

Kissimmee Villa

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Kissimmee House
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 Bedrooms, 3 Bathrooms
3 reviews

$170

avg/night

$170
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

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 Apartment
1 BR | 1 BA | Sleeps 3 | Quick View
Sleeps 3, 1 Bedroom, 1 Bathroom

$98

avg/night

$98
avg per night
View Details

Key Amenities

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

About this property

A newly constructed one-bedroom, one-bathroom luxury apartment situated in the charming area of Kissimmee, conveniently located from theme parks, attractions, restaurants, and shopping. This upscale apartment is equipped with all the amenities to ensure comfort, security, and an exceptional experience ...

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Property Type

Kissimmee Apartment

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Kissimmee House
4 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 4 Bedrooms, 2 Bathrooms

$119

avg/night

$119
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Whether you are looking for a place to relax and unwind, or a place to call home while you are making memories and enjoying fun-filled days at Orlando's many attractions, you will want to bring your entire family to Indiana J's Attraction! This spacious, newly refurbished and decorated home ...

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Property Type

Kissimmee House

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Kissimmee Condo
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 Bedrooms, 2 Bathrooms
1 review

$127

avg/night

$127
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool

About this property

This wonderful resort home is a three-bedroom, 2-bath town gem that sleeps 8. A short hop to Orlando’s world class theme parks this incredible location is just 6 miles to Disney, 25 minutes from Orlando Airport, West Lucaya Village Resort is an upscale gated resort community that is perfectly ...

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Property Type

Kissimmee Condo

Featured review

"My New Home Away from Home!"

I almost didn't want to write this review so that I can keep this home to myself, My family of 5 plus an infant stayed in this condo for 10 days and It was amazing, it looked just like the pictures, everything ...

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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 257 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 $180.

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