Kissimmee Vacation Rentals

(339 rentals)
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6 BR | 5.5 BA | Sleeps 18 | Quick View

55

Distance to park: 4 miles to Animal Kingdom

$175

avg/night

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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

"Great Family Vacation"

We took our 4 kids and their kids to Orlando and this was the perfect location for what we wanted. We were looking for something where we could relax at the facility grounds in a nice pool, be able to ...

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Key Amenities

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

About this property

KEY FEATURES 7 Spacious, themed bedrooms; 4 kings, 2 queens, 2 doubles + 2 sofa beds 4.5 Large bathrooms; 3 full ensuites, 1 shared full, 1 half Modern kitchen; dining area and kitchen island seating Two separate lounge areas, each with a Smart TV and comfortable seating High-speed WiFi throughout ...

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Property Type

Kissimmee House

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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

"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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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Princess Hideaway is a 7 Bedroom, 6 Bathroom home located in Formosa Gardens Estates. You'll love the 4 master en-suite bedrooms, the 3 themed kids bedrooms, the large pool with spa, the games room, the peace and tranquility of the neighborhood which is just 2 miles from Disney.After an enchanting ...

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Property Type

Kissimmee House

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Key Amenities

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

About this property

Property Reference EMI_1700RA perfect size vacation home for families who wish to stay close to Disney and come home to their own private pool to cool off after a long day at the parks. The decor was professionally updated in June 2022 aand again with further updates such as new flooring, new beds ...

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Property Type

Kissimmee House

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$322

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly
  • Private pool

About this property

This 6 bds 6 bathrooms by Disney Villa is made to impress. 5 en-suite bedrooms and 1 bedroom with a full bathroom right outside the door makes it all perfect. Relax in our themed rooms and with pool and hot tub. All bedrooms are equipped with Smart TVs and enjoy home cooked meals in this nice full kitchen. ...

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Property Type

Kissimmee Villa

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4 BR | 3 BA | Sleeps 8 | Quick View

Distance to park: 3 miles to Disney Parks

$117

avg/night

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Key Amenities

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

About this property

This home is thoughtfully furnished. Recently upgraded with a Tempur-Pedic contour supreme king size mattress, LED TV in every bedroom, Frozen themed and Mickey themed twin rooms. This four bedroom luxury home is specifically set up for vacationing guests. The house, just three miles from Disney, is located ...

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Property Type

Kissimmee House

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8 BR | 5 BA | Sleeps 20 | Quick View

2

$378

avg/night

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Key Amenities

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

About this property

Welcome To The Emerald Island Resort, Orlando's Premier Gated Community *** ***Fantasmic Location***closest Resort To Disney*** ***free Wireless Internet Just Bring Your Laptop*** Our 7/bedroom 5.5/bath villa (with 4 Master Bedrooms, all King bed with full private bath!) 3 bedroom each have 2 ...

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Property Type

Kissimmee House

"Emerald Island Resort"

My family and I highly recommend this home for your vacation rental. It contained everything we needed and much more. Its space, cleanliness, and comfort was exactly what we were looking for. Its location ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Luxury Villa near Universal Studios and 12 Minutes from Disney with Large Private Pool, Game Room and Free Wifi. LCD TVs and Game Room in the villa complement the upscale furnishings and large pool included in the villa. There is plenty of space to spread out with 4 bedrooms and 3 bathrooms.Welcome ...

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Property Type

Kissimmee Bungalow

"Hidden gem"

Absolutely idyllic villa so close to Disney and shops and restaurants yet far enough away for the peace and quiet. Has everything needed for an amazing holiday even down to private pool which is not overlooked ...

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Key Amenities

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

About this property

Property Reference RVH_1029RExperience luxury and elegance at Bear's Den Delight, a nine-bedroom custom-built retreat located in the highly sought-after Bear's Den neighborhood of Reunion Resort. This spacious and peaceful end lot boasts an extended patio and yard, perfect for a large family ...

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Property Type

Kissimmee House

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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

"Home away from home!"

We are regular Airbnb travelers and would rate this stay one of the nicest, best located, and real value of all the places we have stayed. The place was very clean, modern, had everything we needed to feel ...

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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

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Key Amenities

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

About this property

Experience a magical holiday at this luxe 7-bedroom home! Nestled in Windsor at Westside Resort, you and your loved ones will be a short drive to many attractions. Stretch out into sprawling living areas where comfort awaits you before heading outside for an exciting time - enjoy a dip in your private ...

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Property Type

Kissimmee House

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5 BR | 5 BA | Sleeps 12 | Quick View

2

Distance to park: 2 miles to Walt Disney World

$299

avg/night

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Key Amenities

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

About this property

Terrific 5-bedroom/5-bathroom rental home owned by firefighters and located in Windsor Hills Resort. This beautiful villa includes upstairs and downstairs King Bedroom suites. It also has a Queen Bedroom, Twin Bedroom and sleeper sofa on the first floor. And there is an another Twin Bedroom on second ...

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Property Type

Kissimmee House

"Disney get away"

Had a great time at this property love location definitely recommend.The clubhouse at this resort was really well-maintained and we had a great time

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Key Amenities

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

About this property

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

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Property Type

Kissimmee Villa

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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/ComfortableThis 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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Key Amenities

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

About this property

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

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Property Type

Kissimmee Villa

"Love our Stay"

I have been a vacation renter at this property for 10 plus years now. We absolutely love our stay and we love all the new updates on the home my foster loved that her room was Mickey themed and her bathroom ...

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4 BR | 3 BA | Sleeps 10 | Quick View

$184

avg/night

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Key Amenities

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

About this property

Beautifully renovated, decorated corner Townhome. Perfect size for a family to have a getaway. Terra verde Resort has many amenities to enjoy and relax. This townhome has a private pool. The resort has many amenities to enjoy at no extra cost. Please send me an email at infovacationhome101@

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Property Type

Kissimmee Townhome

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Key Amenities

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

About this property

☆☆ HIGHLIGHTS ☆☆️ 3 Fun Kids Bedrooms: Pirate room, Choo-Choo Train room & Enchanted Fortress Room 2 Master Suites Total 8 beds; 3 Kings, 1 Queen + 4 Twins 5 Full Bathrooms: all essential toiletries provided Full Kitchen w/ Island with seating for 4 ️ Coffee bar ️ ...

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Property Type

Kissimmee House

"Nice home, spacious and clea"

The clubhouse was nice as well. Very good experience. Close to restaurants and close to the attractions.

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5 BR | 4 BA | Sleeps 12 | Quick View

7

Distance to park: 6 miles to Disney Animal Kingdom

$233

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

***FREE WIRELESS INTERNET JUST BRING YOUR MOBILE DEVICES**. (Please note - there is no landline in the home)Sleeps a maximum 12 guests, with a maximum of 8 guests over the age of 14 years old.As you enter our lovely home, you will be impressed with the soaring 17ft high ceilings in the spacious ...

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Property Type

Kissimmee House

"Wonderful place to stay !!!"

House was located as stated ,15 minute access to all of our Disney visits,shopping and dining . Pool was great for relaxing afterwards,plenty of bedrooms was very nice that they had things set up for ...

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7 BR | 5.5 BA | Sleeps 14 | Quick View

2

Distance to park: 5 miles to Disney World

$244

avg/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

"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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Key Amenities

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

About this property

Discover the perfect blend of luxury and convenience at our Kissimmee villa, a stone's throw away from Disney and Universal. Situated in a gated community, this oasis offers a private pool and spa, a modern kitchen, and plush bedrooms, including a master suite with a king bed. Experience exclusive ...

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Property Type

Kissimmee Villa

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Key Amenities

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

About this property

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

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Property Type

Kissimmee Townhome

"Great place"

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

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Key Amenities

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

About this property

3 bedroom 3 bathroom homeOpen plan living room, dining, and kitchen downstairsBonus den to relax or work from homeLiving/Dining Room: - 58” 4K Smart TV (Log into your favorite streaming service, Live and On demand TV shows) - 4 seater dining setDen: - Work/study space - Comfy ...

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Property Type

Kissimmee Townhome

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$177

avg/night

View Details

Key Amenities

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

About this property

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

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Property Type

Kissimmee Townhome

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Key Amenities

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

About this property

12 Min Drive to Disney World20 Min Drive to SeaWorld26 Min Drive to Universal StudiosLocated in the gated Storey Lakes resort, this modern 8 bedroom, 5 bathroom home is the perfect place for large groups looking to stay near all the action of central Florida. Aside from an amazing location, ...

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Property Type

Kissimmee Villa

"Excellent stay in the magical mansion!"

Great place, very clean and comfortable. Kids had a blast in the game room and cars room. The movie theater was perfect! Loved the modern and contemporary style of the home with tons of space for everyone ...

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5 BR | 4 BA | Sleeps 12 | Quick View

2
last minute deal
LAST MINUTE DEAL 3/23 - 4/5: Discounted Easter Rates - message for a quote!

Distance to park: 5 miles to Disney's Animal Kingdom

$400

avg/night

View Details

Key Amenities

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

About this property

Imagine coming home at the end of an exhilarating day at the parks... You grab a refreshing drink, relax in the poolside living area and reminisce about all you did that day.Memories made, job done!Serendipity offers all the comforts you dreamed of putting on your wish List:★ Pool & ...

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Property Type

Kissimmee House

"Family Birthday Vacation"

Everything was great! The house was very spacious. The back area a bit small but still great! We had a blast!

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DEAL

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

After. *** Location Location Location*** It’s all about. ‘The View’The uninterrupted view of the 14 acre lake and bird island, takes unwinding by the pool to a new level! Relax on a sun bed, or perhaps get wrinkly in the spa whilst ...

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Property Type

Kissimmee Villa

"What a view"

In July 2023 we stayed at Winter Haven a fantastic villa in Lake Berkley which had enough room for 8 of us comfortably. The guys partially liked the games room/pool room, and we all loved to pool and jacuzzi, ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

Property Reference RVH_1021RBalconies, patios, and lanais are not accessible. During 2023 there may be construction occurring on the exterior of the building by the home owners association.Welcome to Seven Eagles Joy. This 3 bed, 3 bath townhome is located in the heart of Reunion Resort - Seven ...

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Property Type

Kissimmee Townhome

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8 BR | 6 BA | Sleeps 16 | Quick View

1
owner special
Owner special: Book 7 nights or more and get free pool/spa heat. Offer not valid with any other discounts.

$337

avg/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

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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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Property Type

Kissimmee House

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Key Amenities

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

About this property

Popular Dates in July & August AvailableOur 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 tee of the Arnold Palmer Golf Course on Reunion ResortThe open plan living area is comfortably furnished and ...

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Property Type

Kissimmee House

"Loved this place"

This place fit our requirements to a tee. Great location, beautiful home, wonderful contact person. Cannot complain about anything. Hated to leave, missing it , I want to return someday. Thank you for ...

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Key Amenities

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

About this property

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 plus infants comfortably. The private pool ...

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Property Type

Kissimmee House

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$105

avg/night

View Details

Key Amenities

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

About this property

Unit 1 is a nice three bedroom homes personally decorated, furnished and maintained well. It is located in Crestwynd Bay a gated community which is peaceful and safe as well as closest to shopping, Disney and restaurants.The home consists of 1 KING bed with attached bathroom 1 QUEEN bedroom with ...

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Property Type

Kissimmee House

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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

"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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8 BR | 6 BA | Sleeps 20 | Quick View

3

Distance to park: 3 miles to Disney World Animal Kingdom

$433

avg/night

View Details

Key Amenities

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

About this property

You and your family can have the vacation of a lifetime in this exquisite home in a quiet neighborhood that has all the extras you could imagine and one of the largest pools in the entire area. It's in the best location - super close to all attractions as well as restaurants, shopping, golf courses, ...

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Property Type

Kissimmee House

"Wonderful, Beautiful, Clean, and Convenient to the Parks!"

My children and grandchildren stayed at this beautiful home for our Disney World trip. This home was so beautiful and clean and set the tone of our trip. Seeing the excitement on my 5-year-old granddaughter's ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Property Reference FG_800BR Sunset Mansion This home has been fully renovated in May 2023. With all new flooring and paint throughout the home, all new furniture, mattresses, pillows, bedding, dinnerware and kitchenware.This magnificent 9 bedroom estate home is located in Formosa Gardens Estates ...

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Property Type

Kissimmee House

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4 BR | 3 BA | Sleeps 8 | Quick View

14

Distance to park: 3 miles to Mgm

$125

avg/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

"Relaxation"

We rented this vacation home for the first time. My husband and I needed a little time away. Love the location as to being just a few miles from shopping, restaurants and very close to the Disney attractions. ...

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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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Key Amenities

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

About this property

Property Reference #RVH_1008RWelcome to Fairway Dream! This beautiful property is located at Reunion Resort in the Fairway Ridge neighborhood, close to Orlando's world-class attractions.Through the foyer, you have access to the second floor and the game room, before it leads you into the ...

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Property Type

Kissimmee House

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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

"Disney Escape"

The house was clean when we entered it. There was an issue and there was someone there within a day to fix it for us (other than the issue we had it was great). Each room is true to the theme it was great ...

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Key Amenities

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

About this property

Our luxury Kissimmee vacation villa will comfortably sleep 10 people. It is fully air-conditioned for your comfort, and has a very roomy and spacious floor plan. It has 2 lounge areas (one with 2 full sofas, and a ceiling fan, the other with a love seat and a sofa bed), both have cable T.V. The kitchen ...

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Property Type

Kissimmee Villa

"Family Christmas Vacation"

The home was a perfect fit for our family. Plenty of room. Well equipped. Had a small issue with a faucet in the bathroom, but was fixed promptly when reported. Nice pool and was heated as requested. ...

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4 BR | 4 BA | Sleeps 8 | Quick View

11

Distance to park: 2 miles to Disney

$298

avg/night

View Details

Key Amenities

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

About this property

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

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Property Type

Kissimmee Villa

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Key Amenities

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

About this property

FLAT SCREEN TV in Living Room! NEW MATTRESSES in all bed rooms NEW LAMINATE FLOORS in all bed rooms! Bed Room Configuration: 1 QUEEN Master Suite with balcony overlooking conservation area and private bath 1 bedroom with a double bed 1 bedroom with two twin beds. TV's in all Rooms! This ...

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Property Type

Kissimmee Townhome

"Perfect location near attractions"

Loved our stay close to Disney and other attractions.Townhome was clean and had everything we needed for our stay. The owner was quick to respond to any questions. We would definitely stay here again.

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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

"West Family Reunion"

We had a great time at the mansion. Only a few things I would change. The hot tub price should have been included in the rental agreement.

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Key Amenities

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

About this property

Moran Disney Rentals would love to welcome you to our Luxury 6 bedroom house which is perfectly located on the exclusive Emerald Island Resort community less than 3 miles from the Walt Disney a world Parks in Florida. This property has 6 bedrooms two of which are master bedrooms with a further two and ...

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Property Type

Kissimmee House

"FAMILY VACATION 2022 all the way from the Virgin Islands St Croix"

The best Airbnb I've stayed in Well kept Nicely decorated Close to everything Karina was the best I'll recommended this house to anyone It is beautiful

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4 BR | 2 BA | Sleeps 7 | Quick View

4

$137

avg/night

View Details

Key Amenities

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

About this property

WELL CARED FOR HOME IN LOVELY COMMUNITY. HOME BACKS TO CONSERVATION SO YOU ARE NOT OVERLOOKED AND IS A FEW STEPS FROM RETENTION POND WITH POND VIEWS FROM THE POOL DECK. SHADED PATIO WITH TABLE AND CHAIRS .KING, KING AND 4 TWIN BEDS WITH THEMED TWIN BEDROOMS - LITTLE MERMAID AND DORY. TV IN ALL ...

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Property Type

Kissimmee House

"Best vacation ever"

This house has it all! I definitely recommend this villa and it also has a huge swimming pool with hot tub. Villa is beautiful and so convenient to all Disney Parks and shopping. Diane is the best on ...

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Key Amenities

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

About this property

A beautiful vacation condo located in a prestigious gated and guarded community, for you to relax and spend time with your family and friends. With the prime location in Kissimmee near Disney World, major parks and restaurants, shops and so much more, this 3BD/2BA condo unit is designed for your best ...

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Property Type

Kissimmee Condo

"Great family time"

Our family went to florida for a Disney vacation. House was excellent with all the amenities. Clean and pool was great. Greatly recommend

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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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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 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 339 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 $72 per night with an average price per night of $209.

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