Kissimmee Vacation Rentals

(263 rentals)
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Kissimmee House
4 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 4 Bedrooms, 2 Bathrooms

$109

avg/night

$109
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 House
5 BR | 4 BA | Sleeps 10 | Quick View
Sleeps 10, 5 Bedrooms, 4 Bathrooms
10 reviews

$165

avg/night

$165
avg per night
View Details

Key Amenities

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

About this property

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

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Property Type

Kissimmee House

Featured review

"Great Home… Great location"

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

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Kissimmee 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

$159

avg/night

$159
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 House
5 BR | 4 BA | Sleeps 10 | Quick View
Sleeps 10, 5 Bedrooms, 4 Bathrooms
1 review

Distance to park: 7 miles to Disney Hollywood Studio

$147

avg/night

$147
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Beautiful, clean and spacious 5 bedroom and 4 bath house in the most sought after community near Disney! 10 minutes drive to Disney and you can hear the Disney fireworks at night. Close to stores, restaurants and tons of shops. The house was renovated and professionally designed recently. The house has ...

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Property Type

Kissimmee House

Featured review

"Very good"

The trip was great me and my family really had fun and enjoyed ourselves we will be coming back soon.

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Kissimmee House
5 BR | 5 BA | Sleeps 12 | Quick View
Sleeps 12, 5 Bedrooms, 5 Bathrooms
2 reviews

$436

avg/night

$436
avg per night
View Details

Key Amenities

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

About this property

Booking is available from the website in Owner info. Modern architecture, state-of-the-art furnishings, and hip-to-the-minute décor make this 5 bedroom, 5 bath getaway in Storey Lake a bonafide safe haven for luxury and comfort. This home is brimming with amenities, from an action-packed game ...

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Property Type

Kissimmee House

Featured review

"Great place, nice price!"

The themed kids' rooms and game room are topping on this rental a club house with so much going on for everyone, including pickup/drop off service to and from the club house. Heated pool and gas grill. ...

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

$814

avg/night

$814
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 House
4 BR | 3.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 Bedrooms, 3.5 Bathrooms
1 review

$150

avg/night

$150
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Beautiful south facing Villa with private pool and hot tub overlooking a peaceful lake. This private gated community is 20 minutes to Disney’s Magic Kingdom and 20 minutes to Universal Studio and 45minutes to the gorgeous Daytona beach where you can actually drive your car onto this huge beach. A ...

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Property Type

Kissimmee House

Featured review

"This property is very nice I worked out very fine for us and would recommend it"

The area is very fun with lots of things to do We like the area there is plenty of restaurants in the area feels very safe

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Kissimmee House
5 BR | 4 BA | Sleeps 10 | Quick View
Sleeps 10, 5 Bedrooms, 4 Bathrooms
7 reviews

$221

avg/night

$221
avg per night
View Details

Key Amenities

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

About this property

*** For smaller groups we offer the opportunity to rent the main house. This area has 4 Bedrooms and 3 Bathrooms Please contact us and ask for a quote *** Our beautiful 3000sq 5 Bed, 4 Bathroom home is located on a generous corner plot. With a south facing Pool and stunning views over the second ...

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Property Type

Kissimmee House

Featured review

"Amazing accommodation and location"

Spacious, well equipped home in an amazing golf resort. Master suite was stunning with huge bathroom and balcony overlooking the second tee. Very well situated for Disney and Universal studios. Nice pool ...

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Kissimmee House
9 BR | 5 BA | Sleeps 22 | Quick View
Sleeps 22, 9 Bedrooms, 5 Bathrooms
1 review

$307

avg/night

$307
avg per night
View Details

Key Amenities

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

About this property

Brand new, very spacious, modern 9-Bed 5-Bath pool home in an exclusive, private gated golf resort. You'll love the feeling of luxury and space throughout the house, the 2 King en-suite master bedrooms, 4 kids themed bedrooms, 3 additional King bedrooms, the games room, the private pool and spa, ...

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Property Type

Kissimmee House

Featured review

"Florida Holiday"

Hi there! We enjoyed our stay quite a bit. However, there were a few things that could have improved our stay. The one lounger was damaged and the one chair was damaged. There was not a bottle opener ...

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

$222

avg/night

$222
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
7 BR | 6 BA | Sleeps 15 | Quick View
Sleeps 15, 7 Bedrooms, 6 Bathrooms

$277

avg/night

$277
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 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 House
7 BR | 5.5 BA | Sleeps 14 | Quick View
Sleeps 14, 7 Bedrooms, 5.5 Bathrooms
2 reviews

Distance to park: 5 miles to Disney World

$244

avg/night

$244
avg per night
View Details

Key Amenities

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

About this property

Excellent Private Detached Family Vacation home/Villa located in the Prestigious Man Gated Vacation Resort of EMERALD ISLAND RESORTS. SPECIAL DISCOUNTS FOR LONGER STAYS !!! . Monthly bookings during January to April at special rates. _________________________________________________________________ This ...

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Property Type

Kissimmee House

Featured review

"Amazing 7 Bed rooms Villa Near Disney"

Our stay with Family and friens were superb. Cost is just a fraction of what otherwise with any Hotels. VEry large House with 7 Bedrooms and 6 Wash rooms. Own private pool and lanai . Bbq grill was provided ...

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Kissimmee Townhome
4 BR | 4.5 BA | Sleeps 10 | Quick View
Sleeps 10, 4 Bedrooms, 4.5 Bathrooms
14 reviews

$218

avg/night

$218
avg per night
View Details

Key Amenities

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

About this property

Stay in our magical residence! This modern 4 bedroom and 4.5 bath villa is filled with high-end finishes & amenities and is just 5 miles from the entrance to Walt Disney World! Every room has its own ensuite bathroom. No need to wait in line. Enjoy the resort style amenities that include a community ...

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Property Type

Kissimmee Townhome

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

Distance to park: 3 miles to Disney World Parks

$240

avg/night

$240
avg per night
View Details

Key Amenities

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

About this property

This is a spacious vacation rental home located in Orlando, perfect for large families of up to 14 guests. The house has 7 bedrooms and 4.5 bathrooms, including two King Master Suites, one on each floor. The first-floor suite features a walk-in shower and a separate garden tub. Bedroom 3 and 4 have King ...

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Property Type

Kissimmee House

Featured review

"Brilliant villa and location"

What a lovely place Be Our Guest is, weve just come back and are depressed now..... The villa was well kept, equiped, clean & pleasant. The owner and the management company couldnt do enough for us. The ...

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

$275

avg/night

$275
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 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 BA | Sleeps 6 | Quick View
Sleeps 6, 4 Bedrooms, 2 Bathrooms
9 reviews

$107

avg/night

$107
avg per night
View Details

Key Amenities

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

About this property

CHEERY AND BRIGHT. Just what a vacation home should be. 4 bedrooms, 2 bathrooms, great views and just minutes from all the fun. Fully furnished , just bring personal items or things you cannot live without. Located in Eagle Pointe, a well sought-after vacation home community. Just minutes from what ...

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Property Type

Kissimmee House

Featured review

"Wonderful stay"

Traveled from the UK. Villa was a little dated but was very clean and the beds comfortable. Pool was a great hit with our teenagers. Parks were easy to get to from the villa. We had a great stay and ...

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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

$164

avg/night

$164
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 Villa
5 BR | 3 BA | Sleeps 12 | Quick View
Sleeps 12, 5 Bedrooms, 3 Bathrooms
4 reviews

$165

avg/night

$165
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen

About this property

Welcome to this stunning lake view vacation home close to Disney. This 5 bed 3 bath home is the perfect place to unwind after a busy day visiting many of the local attractions. The home has 5 bedrooms, 3 bathrooms and sleeps 12. Hi speed WiFi and air con throughout the villa. Our 5 Bed, 3 Bath ...

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Property Type

Kissimmee Villa

Featured review

"Fantastic Stay"

We have been coming to Florida and resting villas for the last 30 years and this is without a doubt one of my favourites. You are always a bit nervous when you open the door but as soon as entering hearing ...

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

$461

avg/night

$461
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
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 Bedrooms, 3 Bathrooms
12 reviews

$165

avg/night

$165
avg per night
View Details

Key Amenities

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

About this property

We invite you to stay at our villa which is a 4 Bedroom 3 Bathroom luxury vacation home, however there is a sofa bed in the sitting room so the villa can sleep 10 guests. The villa is fully equipped with everything you will need including air con throughout, private pool, WiFi, fully equipped kitchen, ...

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Property Type

Kissimmee Villa

Featured review

"Lovely villa in a great location"

Villa is lovely and well organised in a great location in a gated community near all the attractions and restaurants. The villa is well proportioned spacious and clean with new flat screen tv’s in all ...

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

$298

avg/night

$298
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
7 BR | 4.5 BA | Sleeps 14 | Quick View
Sleeps 14, 7 Bedrooms, 4.5 Bathrooms
1 review

$461

avg/night

$461
avg per night
View Details

Key Amenities

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

About this property

5 star property! Reviews say it all! You will be delighted by the great combination of lux comfort and Disney theming for the whole family! Located in the upscale Emerald Island Resort gated community, our newly remodeled home is a welcome oasis to return to after a long day enjoying the parks. Relax ...

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Property Type

Kissimmee House

Featured review

"Where to even start!!!"

Whenever we travel, I read reviews. Some reviews you wonder about because no two people seem to see it the same way. However with this house everyone seemed to love it and after staying there I can see ...

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Kissimmee Villa
5 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 5 Bedrooms, 3 Bathrooms
13 reviews

$150

avg/night

$150
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
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
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 Bedrooms, 2 Bathrooms
20 reviews

$150

avg/night

$150
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Beautiful south facing lakeside villa with electrically heated pool option. Great location for all the theme parks, Disney 20 mins, Seaworld 15mins, Universal 30 mins and Cocoa Beach/Kennedy Space Centre 45 mins. Local English management contact and fully inspected/licensed by the Florida Hotels Board. ...

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Property Type

Kissimmee Villa

Featured review

"Had a great stay"

Angie's was clean and cozy with lots of space. Location was very good and the pool was great for families and adults.

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Kissimmee Condo
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 Bedroom, 1 Bathroom

$95

avg/night

$95
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Pool

About this property

Beautiful and clean unit with two queen size beds upstairs, it is part of a recently renovated condo-hotel furnished with modern design and great taste, with fenced pool, playground, gym, and indoor and outdoor dining/resting/seating areasTouristic area, super close to the parks, located on the main 192 ...

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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
18 reviews

$175

avg/night

$175
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
5 BR | 4.5 BA | Sleeps 15 | Quick View
Sleeps 15, 5 Bedrooms, 4.5 Bathrooms

$219

avg/night

$219
avg per night
View Details

Key Amenities

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

About this property

Welcome to our luxurious and spacious vacation home situated in the stunning gated community of Windsor at Westside. This magnificent 5-bedroom, 4.5-bathroom villa boasts everything you need for an unforgettable vacation with your family and friends, Close to theme parks, shopping mall outlets, restaurants ...

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Property Type

Kissimmee House

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Kissimmee Townhome
3 BR | 3 BA | Sleeps 9 | Quick View
Sleeps 9, 3 Bedrooms, 3 Bathrooms
11 reviews

Distance to park: 5 miles to Animal Kingdom Lodge

$145

avg/night

$145
avg per night
View Details

Key Amenities

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

About this property

**The private pool is not heated unless requested by the guest. Pool heating is available for an additional fee of $10.00 per day. Pool heating must be arranged and paid for prior to arrival.** *No long-term rentals - 14 nights maximum *Minimum rental age is 25 years old (exception for married couples ...

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Property Type

Kissimmee Townhome

Featured review

"FANTASTIC property!"

This is the place to stay! This rental truly felt like a home away from home. It was a short drive to countless restaurants and shopping...location is perfect! If you're going to Disney, you'll only ...

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Kissimmee House
6 BR | 4 BA | Sleeps 14 | Quick View
Sleeps 14, 6 Bedrooms, 4 Bathrooms
3 reviews

$314

avg/night

$314
avg per night
View Details

Key Amenities

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

About this property

Welcome to your ultimate themed vacation experience in the heart of Kissimmee, Florida! Prepare to embark on an extraordinary journey as you step into this spectacular 6-bedroom, 4-bathroom house in the prestigious Windsor Hills community. This newly listed paradise has been meticulously designed to immerse ...

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Property Type

Kissimmee House

Featured review

"Two week stay"

We stayed for two weeks in August/September. Great house and location to the parks. Kids enjoyed the pool table and game systems. Would book again.

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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

$205

avg/night

$205
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 House
8 BR | 6 BA | Sleeps 22 | Quick View
Sleeps 22, 8 Bedrooms, 6 Bathrooms

$461

avg/night

$461
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
5 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 5 Bedrooms, 3 Bathrooms

Inquire for rates

Inquire for rates

View Details

Key Amenities

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

About this property

NO Party’s but Our mission is to provide excellent service and guest relations for every guest that comes to stay in our home. we wish to provide a fabulous experence of relaxation and comfort thoughout your time with us. But above all, we want to give you the chance to create the great memories ...

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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
2 reviews

$239

avg/night

$239
avg per night
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 Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms
2 reviews

Distance to park: 2 miles to Disney

$133

avg/night

$133
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
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
5 BR | 5.5 BA | Sleeps 13 | Quick View
Sleeps 13, 5 Bedrooms, 5.5 Bathrooms
4 reviews

Distance to park: 12 miles to Disney's Magic Kingdom Park

$335

avg/night

$335
avg per night
View Details

Key Amenities

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

About this property

Welcome to Westside Villa! -20 minute drive to all Disney Parks -Private, heated pool; gas grill; EV charger on-site -Modern arcade: racing simulators, virtual reality, vintage games -3 king size suites with smart TVs -2 uniquely themed bunk rooms (Star Wars and Fairy Tale) -All bedrooms have ensuite ...

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Property Type

Kissimmee House

Featured review

"Amazing"

The house was simply amazing. The family could not believe what I had rented when we arrived, so spacious. So many things games/entertainment in the house. The house was very clean, the beds were really ...

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

$953

avg/night

$953
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 Villa
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 Bedrooms, 2 Bathrooms
17 reviews

$135

avg/night

$135
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

This is a beautiful professionally decorated and furnished 3 Bed, 2 Bath Villa located at Lake Berkley Resort. Have your vacation here in comfort and relaxation with air conditioning throughout. The spacious sitting room has a Queen sofa sleeper bed so the villa can easily accommodate 8 persons. This ...

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Property Type

Kissimmee Villa

Featured review

"Lake Berkley Resort"

Luxury Villa 3 bedroom with own pool on Lake Berkley Resort. Close to all Disney parks, Kissimmee. The property was clean and well equipped. The resort property was also well maintained with walking trails, ...

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

Distance to park: 3 miles to Walt Disney World

$172

avg/night

$172
avg per night
View Details

Key Amenities

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

About this property

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

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Property Type

Kissimmee House

Featured review

"Fantastic Villa"

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

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Kissimmee House
6 BR | 5 BA | Sleeps 14 | Quick View
Sleeps 14, 6 Bedrooms, 5 Bathrooms

$214

avg/night

$214
avg per night
View Details

Key Amenities

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

About this property

Brand new 6 bedroom resort home located in Champions Gate.This home is brand new and has been finished to a very high standard by an interior designer.From the minute you walk in this home does not dissapoint with modern furnishings and fittings throughout the home.The home features 6 bedrooms , 5 bathrooms, ...

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Property Type

Kissimmee House

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Kissimmee Villa
Studio | 4.5 BA | Sleeps 14 | Quick View
Sleeps 14, 0 Bedrooms, 4.5 Bathrooms

$331

avg/night

$331
avg per night
View Details

Key Amenities

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

About this property

7 bedroom 4.5 bath waterfront home located in the highly desired Emerald Island resort close to Disney and Universal Studios. The ground floor of this villa is an open concept with a living area featuring a 65" Smart 4k tv. The granite countertop kitchen boasts all new 2022 stainless appliances. ...

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Property Type

Kissimmee Villa

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Kissimmee House
7 BR | 6.5 BA | Sleeps 16 | Quick View
Sleeps 16, 7 Bedrooms, 6.5 Bathrooms
1 review

$432

avg/night

$432
avg per night
View Details

Key Amenities

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

About this property

This gorgeous home was completely redesigned in 2023! Experience unforgettable moments with your family at Solara Resort. The kids will delight in our thoughtfully designed themed bedrooms, while others can unwind on the inviting custom patio or enjoy a refreshing swim in the private heated pool. Is ...

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Property Type

Kissimmee House

Featured review

"AMAZING customer service"

I was skeptical of booking online with a company I wasn't familiar with, however they ended up being so responsive to any concerns or questions I had, including when me and my kids were in the house. It ...

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

$156

avg/night

$156
avg per night
View Details

Key Amenities

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

About this property

POOL SAFETY FENCE!!!! - Florida law requires that doors leading out to the pool have an alarm. THAT IS NOT ENOUGH!. If you are traveling with children please make sure the house you are renting has a pool safety fence. WE HAVE A NO PET POLICY FOR ALERGY REASONS This Beautiful home is well situated, ...

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Property Type

Kissimmee House

Featured review

"Florida 2024"

This was a nice peaceful place just didn't like the holes outside screen for the pool n no baking dishes..we like to bake

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

$160

avg/night

$160
avg per night
View Details

Key Amenities

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

About this property

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

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Property Type

Kissimmee Villa

Featured review

"Summer trip"

We love it had a great time in the pool and hot tub very clean nice place for a family was our first trip as a family all the people working there was very nice played Putt putt the game room was very nice ...

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Kissimmee House
8 BR | 6 BA | Sleeps 18 | Quick View
Sleeps 18, 8 Bedrooms, 6 Bathrooms
4 reviews

$504

avg/night

$504
avg per night
View Details

Key Amenities

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

About this property

Check out this amazing home! The sparkling pool basks in sunlight all day, while the lanai offers refreshing shade. It's the perfect setting for complete relaxation and enjoyment. This spacious family retreat comfortably accommodates up to 16 adults. If there is a mix of children and adults, the ...

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Property Type

Kissimmee House

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Kissimmee Vacation Rentals

Kissimmee Weather

 | 

7222°  489°
JANUARY
7323°  499°
FEBRUARY
7725°  5312°
MARCH
8228°  5814°
APRIL
8731°  6418°
MAY
9032°  7021°
JUNE
9233°  7222°
JULY
9233°  7222°
AUGUST
9032°  7122°
SEPTEMBER
8429°  6518°
OCTOBER
7926°  5714°
NOVEMBER
7323°  5010°
DECEMBER

Soak up the Sun on Your Next Trip to Kissimmee Vacation Rentals


There’s nothing quite like a vacation to sunny Florida, a unique and inviting state with a huge variety of distinctive cities and natural areas to explore. One popular vacation destination in Florida is Kissimmee, a charming city with plenty to see and do just south of the Orlando metropolitan area. 

Kissimmee has a lot more to offer visitors than just excellent weather year-round. With a huge variety of scenic nature, shopping opportunities, and outdoor activities, Kissimmee itself has lots to offer every member of the family, not to mention its extremely close proximity to some of Orlando’s biggest amusement parks. 

You could stay in a busy hotel during your trip to Kissimmee, but then you wouldn’t be able to get a truly immersive experience of local city life. Kissimmee vacation rentals allow you to enjoy Kissimmee from inside its authentic residential neighborhoods. Additionally, having your own home to live in rather than a jam-packed hotel will provide some much-needed peace and quiet during your vacation. It will also offer plenty of space for the whole family to spread out.  

Top Tips for Traveling to Kissimmee Rentals


Like most other Florida cities, Kissimmee enjoys sunshine and clear skies throughout the majority of the year. However, the tropical climate of the state means that bouts of rain can occur throughout the seasons, particularly during the summer months, peaking in August. 

In addition to a higher likelihood of rain, the summer season in Kissimmee tends to be the most humid time of year. That’s why most vacationers choose mid to late spring or early autumn to make their trip to the city. At those times of the year, vacationers can enjoy great weather and lots of outdoor activities. 

Though the Kissimmee Gateway Airport is located centrally within the city, most vacationers taking commercial flights will fly into Orlando International Airport. It is located roughly 17 miles northeast of the city center, about halfway between Kissimmee and Orlando. Vacationers coming in from elsewhere in Florida can access Kissimmee by road using U.S. Route 192 and U.S. Route 441.

Things to Do Nearby Kissimmee House Rentals


Some of the most popular natural areas around Kissimmee are the swamps, which are located in major local bodies of water like Lake Tohopekaliga (known around town as Lake Toho). At Boggy Creek Airboat Adventures, you can experience the swamps from the water and get the thrill of a lifetime on an airboat driven by a local wetlands expert. Get up-close views of gator ponds, discover precious gemstones, and then grab a delicious lunch with the family at Boggy Bottom BBQ! 

Looking to explore a piece of history during your trip to Kissimmee? Medieval Times Dinner & Tournament allows visitors to step into the 11th century for an evening of authentic feasting, jousting, and sword fighting in true medieval style! Enjoy a delicious four-course meal, incredible performances, and a truly unforgettable experience for the entire family.
 
Any vacation to Kissimmee isn’t complete without a trip or two to Old Town, a popular outdoor attraction with opportunities for shopping, dining, and family fun. Old Town is made up of an 18-acre stretch of classic city attractions, including the Old Town Ferris Wheel, the Great Magic Hall, and Mortem Manor, a year-round haunted house that is open for visitors to explore.

Kissimmee Annual Events


Kissimmee is a vibrant area with lots of annual festivals and events to enjoy in and around the city throughout the year. Kissimmee locals and visitors alike flock to the Ford Cuban Sandwich Festival each May near downtown Kissimmee, which celebrates the colorful history of Cuban cuisine in the area. Watch as local dining professionals attempt to build the world’s biggest Cuban sandwich during the event!
 
The Ford Taste of Latino Festival is another local opportunity to celebrate and experience the best in authentic Latin cuisines in Kissimmee. The event features a contest to find the Top Latino Chef as well as plenty of live music and dance performances to enjoy as you taste a variety of Latin dishes. 

Not sure if you’ll be in town for any of Kissimmee’s larger annual events? You can enjoy Show Car Saturday Nights every Saturday night in the city on Margaritaville Boulevard. Check out the city’s best classic cars from a variety of eras and enjoy the plethora of delicious eateries and exciting shops located along the boulevard.

Wining and Dining in Kissimmee  


Between your outdoor activities and trips to local amusement parks while in Kissimmee, you’re sure to need some satisfying food and refreshing drinks to complete your perfect day. Luckily, Kissimmee is home to some of the best restaurants that Florida has to offer, combining authentic local flavors with worldly cuisine. 

To start your day off right with a delicious and hearty breakfast, look no further than Woodsby’s Countryside Café. This spot has authentic, cozy diner vibes to spare, not to mention a stacked menu of classic breakfast favorites, coffee bar items, and unique dishes you won’t want to miss out on. 

Tarantino’s Italian Restaurant is a great choice for a vacation date night or simply a nice dinner out with the family. A hearty Italian meal is a great way to finish a fun day of activities, and you’re sure to get that and more at Tarantino’s. If you bring the family along, you can take advantage of the takeout dinner special, which feeds four and includes a massive entrée, salad, and garlic bread.


FAQ

How many vacation rentals are there in/around Kissimmee?

There are 263 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 $176.

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