Kissimmee Vacation Rentals

(310 rentals)
❤️ Make Your Memories Magical ❤️ Family Friendly ❤️ 4 Miles to Disney

5 BR | 4 BA | Sleeps 12 | Quick View

2

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

$350

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool
  • Rentals by Owner

About this property

Imagine coming home at the end of an exhilarating day at the theme parks...You grab a refreshing drink from the fridge, flake out on the sofa in the outdoor living area right by the pool and reminisce about all the amazing things you did that day.The kids are splashing around in the pool, you ...

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Property Type

Kissimmee House

"Family Birthday Vacation"
Reviewed August 25, 2020

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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Luxury 10 Suite villa, man-guarded, amazing clubhouse at Reunion Encore Club

$443

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Pool
  • Private Pool

About this property

** Please kindly send us an inquiry before you book. ** The Encore Club at Reunion offers an excellent choice of luxury vacation rental homes for guests to relax and enjoy a dream visit to Kissimmee! With Walt Disney World, just 6 minutes drive away from your own front door, this new, luxury gated community ...

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Property Type

Kissimmee Villa

"The most awesome vacation"
Reviewed January 18, 2020

First experience! Totally AMAZING ! The house was fabulous, the staff superb, the amenities were above expectations. Already planning next visit!! Plan your trip you will NOT be disappointed. :)

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Champions Estate

8 BR | 5 BA | Sleeps 16 | Quick View

$384

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Located in one of the most sought-after resorts in the Orlando area, welcome to Champions Estate. The newly built 8 bedroom, 5 bath pool home is the perfect destination for your family getaway. The home was designed to fit every need that you could have when visiting the area. This villa accommodates ...

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Property Type

Kissimmee Villa

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MAKING HAPPY MEMORIES

4 BR | 2 BA | Sleeps 6 | Quick View

$104

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

LARGEST POOL IN THE COMMUNITY! HUGE POOL AND DECK. ENJOY BREAKFAST AND MEALS IN THE SUNSHINE . TERRIFIC SOUTH FACING POOL AND BACKS TO CONSERVATION SO YOU ARE NOT OVERLOOKED. SPLIT PLAN BEDROOMS, KING AND 2TWINS IN BACK BY THE POOL, AND QUEEN AND 2TWINS IN FRONT. EAT-IN KITCHEN, BREAKFAST BAR, Q-LED ...

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Property Type

Kissimmee House

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Refinished/Painted S. Facing Pool/Spa, Updated Decor, Near Disney, Sleeps 8

4 BR | 3 BA | Sleeps 8 | Quick View

9

Distance to park: 4 miles to Disney

$140

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • 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

"Family Vacay 2020"
Reviewed July 7, 2020

We enjoyed our family vacay 2020. A great getaway family was able to relax and enjoy themselves on the beach

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Luxury 5 bed villa with south-facing pool

5 BR | 4 BA | Sleeps 12 | Quick View

1

Distance to park: 3 miles to Disney World

$179

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool
  • Rentals by Owner

About this property

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

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Property Type

Kissimmee Villa

"Tigger's Magic"
Reviewed January 6, 2019

It was a pleasure renting this house in Emerald Island Resort, Florida. It was exactly what posted on the website and surpassed our expectations once we got there. The house was very spacious, clean, ...

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Storey Lake-3120-306CEPCILCO

2 BR | 2 BA | Sleeps 4 | Quick View

$120

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Storey Lake - Kissimmee is a brand new vacation community located just 4 miles from the magical world of Disney and just minutes to Universal, Sea World and the many water parks in the area. Central Florida is also home to some of the nation's top-rated golf courses and many are within a 10-minute drive ...

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Property Type

Kissimmee Condo

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Westside Deluxe | New in Windsor at Westside

$341

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to Westside Deluxe. You and your family will immediately love this wonderful vacation home from the moment you take a step inside. The great room has a large plush sofa and chairs for everyone to gather around and watch TV together. The decor is modern and accented with glass coffee and end tables. ...

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Property Type

Kissimmee House

"Need cleaning"
Reviewed October 16, 2020

When we arrive to the home the first we notice was the house was not cleaned properly so before we would allow the children to go in my family and i did a major cleaning and sanitizing in fear of corvid19 ...

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Sunny Luxury Legends Villa only 6 miles to Disney

$377

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

This beautiful home has everything you need to create your dream stay in Reunion Resort - 6 Miles to Disney!Legends Villa includes a large pool with a spillover spa, luxurious decor that creates an elegant ambiance, over 5,000 sq.ft of spacious living areas & large inviting bedrooms, a cinema, ...

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Property Type

Kissimmee Villa

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Westside Charm | 7 Bed Private Pool Home

$256

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Windsor at Westside is a gated vacation rental community close to Disney featuring an 8,000 sq.ft. clubhouse with the Tu Casa Bar & lounge, market & deli, video arcade, sundries shop & fitness center. Other fantastic amenities such as a playground, volleyball court & multi-purpose sports ...

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Property Type

Kissimmee House

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Palm Tree Villa Florida, 5 Star Review Rating with Pool Lift & Wheel in Shower

$142

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool
  • Rentals by Owner

About this property

Palm Tree Villa Florida, is tucked away in the much sought after location of Doral Woods. This large 4 Bedroom, 3 Bathroom villa, is ideal for making the perfect vacation.This is our own holiday home, so the furnishings are to a high standard, as you can see from the pictures and video. Fully Air ...

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Property Type

Kissimmee Villa

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Four Bedroom Family Vacation Home Close to Disney!

4 BR | 2.5 BA | Sleeps 8 | Quick View

3

Distance to park: 4 miles to Disney World

$140

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool

About this property

Great vacation home just three miles from the gates of Disney! Flat screen TV's in living room and all 4 bedrooms. Free wireless hi-speed internet and cable TV. HD TV in living room and all bedrooms. King bedroom has a flat screen 50" TV and 2 additional bedrooms have a built in DVD player in the ...

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Property Type

Kissimmee House

"Excellent Stay"
Reviewed August 15, 2019

Kay’s Retreat was the perfect destination for our recent vacation! Everything was perfect. She thought of everything we might need during our stay. The house was clean and comfortable. Will absolutely ...

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Discover newly refurbished 4 BR Windsor Palms Resort

4 BR | 3 BA | Sleeps 9 | Quick View

Distance to park: 10 miles to Walt Disney World

$169

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

Enjoy Windsor Palms, featuring gated resort style living at its finest! This beautiful, Orlando vacation resort is just 3 miles (4.5 km) from the gates of Walt Disney World. The perfect location for families to enjoy Disney Magical Gatherings. Our totally remodeled and renovated home provides lots of ...

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Property Type

Kissimmee House

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New Waterpark-Windsor Hill Luxury 6B/4B/Pool house

$234

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool
  • Rentals by Owner

About this property

Large 6 Bedroom Executive Vacation Home With 2 Themed Kids Rooms, Sleeps 14 Disney Dream Vacation Villa is located in the #1 rated upscale five-stars Windsor Hills Resort at the doorstep of Disney world.This property was newly thoroughly renovated. Web photos here won't be able to show all the beautiful ...

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Property Type

Kissimmee House

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Champions Breeze | 5 Bed Townhome in Champions Gate

$189

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Enjoy these amenities and more at The Retreat, only 12 miles to the gates of Disney World® and 6 miles from Reunion

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Property Type

Kissimmee Townhome

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Windsor Palms Resort-2334CISPDITHP

$111

avg/night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

Windsor Palms Resort- Kissimmee, Florida is an upscale gated community located just 2 miles from Walt Disney World. This luxury resort sits nestled just off Hwy 192 in Kissimmee, Florida and is one of the most desired resorts in the Orlando area. During your stay, you will enjoy this well-appointed home ...

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Property Type

Kissimmee Townhome

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6 bedroom Luxury Pool Home at Windsor Hills 2 miles from Disney

$307

avg/night

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Key Amenities

  • Air Conditioning
  • Kid Friendly
  • Pool
  • Private Pool

About this property

Just 2 miles to Disney, in Orlando's favorite resort community, Windsor Hills.When only the best will do, our luxurious 6 bed/4 bath sleeps up to 14 and covers more than 3500 sq ft with every comfort that you would expect from a 5* resort.South-facing private pool with spillover spa!Games ...

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Property Type

Kissimmee Villa

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Storey Lake-4797CEKCCJGIL

5 BR | 5 BA | Sleeps 10 | Quick View

1

$176

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Storey Lake - Kissimmee is a brand new vacation community located just 4 miles from the magical world of Disney and just minutes to Universal, Sea World and the many water parks in the area. Central Florida is also home to some of the nation's top-rated golf courses and many are within a 10-minute drive ...

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Property Type

Kissimmee Townhome

"Summer Vacation"
Reviewed July 28, 2020

The house was beautiful.... very clean.... excellent location!!!! My children really enjoyed the resorts pool and lazy river!!!! Will definitely visit again!

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Sweetwater Club Villas (FV91KV)

$95

avg/night

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Key Amenities

  • Air Conditioning

About this property

Floors: GROUND Floor Condo. We have multiple condos ground and upper level, please request your preference when inquiring. Pets: THIS HOME IS NOT PET FRIENDLY Rooms: 3 Bed rooms, 2 Bath rooms. En-suite in Master bedroom. Bed Configuration: King bed (1) Queen bed (1), Two Twin Beds (2). Sleeps 6. Flooring: ...

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Property Type

Kissimmee Condo

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Luxury Villa On 5 Star Bella Vida Resort, private pool and close to Disney

$140

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

A stunning, larger than average, 5-Bed 4-Bath villa with a beautiful view of the conservation area at the rear as backdrop to our private pool.The villa is furnished and maintained to a very high standard and all rooms in the villa are spacious.The villa is split over two floors which makes it ...

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Property Type

Kissimmee Villa

"Excellent rental"
Reviewed January 6, 2020

Great house for 10 people to stay in Disney area. It was our 6th time visiting the area and this was the best house we have ever rented. Kitchen is fully equipped, we found everything we needed, and we ...

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Luxury Villa with own private pool on gated Resort. Close to Disney

$104

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • 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

"Espectacular ubicación"
Reviewed February 3, 2020

Todo en perfecto orden . Muy buena ubicación . Perfecta para 6 personas Muy cómoda . Volveremos, sin duda .

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Modern Serenity Vacation Home | Private and Screened Pool | Home Theater |

$384

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

THIS HOME IS LOCATED IN THE RETREAT AT CHAMPIONS GATE, WHICH IS 6 MILES FROM REUNION RESORTThis home has everything you need for your next vacation. This brand new home with 8 beds and 5 baths can accommodate up to 16 guests with a spacious living area, fully equipped kitchen, private and screened ...

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Property Type

Kissimmee House

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One mile from Disney, Celabration, family condo, gated, Free WI-FI

3 BR | 2 BA | Sleeps 6 | Quick View

1

Distance to park: 1 miles to Disney Animal Kingdom

$94

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Rentals by Owner

About this property

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

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Property Type

Kissimmee Condo

"Nice place to stay for Disney trip"
Reviewed September 14, 2020

Close to Disney and nice and clean. We enjoyed our visit and would stay here again. No problems with our stay.

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4 BEDROOM IN Terra Verde Resort WITH PRIVATE POOL & Free Wi Fi

$130

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool

About this property

4 Bedroom / 3 Bathroom (1,940 sqft) Single Story Gated Community North Facing Private Pool and SPA Electric Pool Heat is an additional cost.Living Room 1: TV / DVD / Stereo Living Room 2: Seating Area Dining Area - Seats 6 Breakfast Table - Seats 4 Breakfast Bar - Seats 2Master Bedroom ...

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Property Type

Kissimmee Villa

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Family Fun | Games Room & No Rear Neighbors

$287

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

This expansive 3,909sq. ft home can also sleep 18 comfortably, set within a luxury resort. With 9 bedrooms and 5 bathrooms, this is a perfect home for a large family or group vacation. Your family will love relaxing in the Florida sun by the pool!The living area has an open floor plan, you will find ...

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Property Type

Kissimmee Villa

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3BR 1st Floor Condo Near Disney, Steps from Pool, Loaded with Amenities

$82

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Rentals by Owner

About this property

Built in 2002, Windsor Palms Resort is a gated community approximately five miles from Disney. This luxury complex has a 7500 square foot clubhouse, basket ball courts, volleyball courts, children's play area, olympic-size swimming pool, toddler pool, hot tub, picnic and barbecue area, outdoor bar, convenience ...

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Property Type

Kissimmee Condo

"Disney trip"
Reviewed January 5, 2020

Our stay was wonderful! Clean, close to Disney, beautiful pool! Loved it!! Check-in was easy and quick. Everyone was very polite and helpful.

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The Lake House at Sunset Lakes - Upscale Lakeside Villa Near Disney

4 BR | 2 BA | Sleeps 8 | Quick View

Distance to park: 7 miles to Walt Disney World

$194

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool
  • Rentals by Owner

About this property

WE NOW HAVE AVAILABILITY FOR FAMILIES OVER CHRISTMAS 2020 (18-27 DECEMBER, MINIMUM 7 DAY STAY). FAMILY GROUPS ONLY (2 ADULTS 2 CHILDREN), DON'T HESITATE. THIS WONT LAST LONG!!Welcome to our Florida villa, the Lake House at Sunset Lakes. The Lake House at Sunset Lakes is an upscale rental villa in ...

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Property Type

Kissimmee Villa

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Tranquil Sunshine | Walk to the Solara Resort Clubhouse!

$292

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

Located just minutes from Orlando’s theme parks, shopping, dining, and other area attractions, this luxury villa is located in Solara Resort. Solara Resort isEnjoy unlimited access to all the 8 acre resort has plenty to offer with a state of the art 13,000 sq.ft clubhouse, resort pool, FlowRider® ...

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Property Type

Kissimmee House

"Amazing!!!"
Reviewed March 17, 2020

This was our first family trip and we could not be happier with this house!!! We loved the resort too!

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Luxury Windsor Hills 3/2 Condo

3 BR | 2 BA | Sleeps 6 | Quick View

5

Distance to park: 2 miles to Disney

$112

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

Windsor Hills is one of the greatest gated community located within the heart of Orlando’s premier tourist attractions. Windsor Hills boasts the closest proximity to Central Florida's theme parks. Windsor Hills has all the amenities of a Five Star Hotel or Resort.Our 3 bed/2 bath (1 king, 1 ...

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Property Type

Kissimmee Apartment

"Excellent resort facilities"
Reviewed March 24, 2020

Resort was excellent with all the Disney attractions. Plus all the restaurants nearby and the Walmart store just one half mile away. The pool area was very large and accommodated all the guests. Very well ...

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Westside Extravaganza

8 BR | 6 BA | Sleeps 16 | Quick View

$330

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Windsor at Westside is a gated vacation rental community close to Disney featuring an 8,000 sq.ft. clubhouse with the Tu Casa Bar & lounge, market & deli, video arcade, sundries shop & fitness center. Other fantastic amenities such as a playground, volleyball court & multi-purpose sports ...

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Property Type

Kissimmee House

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Formosa Gardens Paradise | Fantastic Lake Views

$336

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

This magnificent 7 bedroom estate vacation home is located in Formosa Gardens, a gated community just 3 miles from the magic of Disney!Featuring a breathtaking lake view, this vacation home features 5 king bedroom/bathroom suites, a very large screened private pool and spa, 2 kids’ bedroom, ...

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Property Type

Kissimmee House

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Holiday Rest

3 BR | 2 BA | Sleeps 8 | Quick View

1

$100

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool
  • Rentals by Owner

About this property

Thinking about taking a Florida Vacation? Why not stay at our wonderful 1950 Sq ft property with three spacious bedrooms two bathrooms. Feature a fantastic floor plan with ceramic Tiles throughout. Master bedroom has a King sized bed, TV, Jacuzzi, stand up shower, his /her sink and a walk in closet. ...

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Property Type

Kissimmee House

"Our vacation house"
Reviewed February 19, 2018

Found the property very nice, close to all our vacation needs, owner and property manager attentive and friendly, on a personal note the pool did not get warm enough for my taste, good experience

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My Disney Castle

6 BR | 4 BA | Sleeps 12 | Quick View

$267

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool
  • Rentals by Owner

About this property

* LOCATED 3 miles from the Disney World Theme Parks*KEY-LESS entry with personalized access code is provided to each guest for enhanced security. Home Security Alarm with 24/7 monitoring for added security.* FREE Welcome starter items provided, including 1 roll of Paper Towels, Toilet Paper in ...

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Property Type

Kissimmee Villa

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Toy Story Tower

6 BR | 4 BA | Sleeps 14 | Quick View

Distance to park: 5 miles to Disney World

$255

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

Toy Story Tower is an imposing, six bedroom vacation home located within the prestigious gated community of Windsor Hills Resort. Here, you can enjoy the very best in luxurious accommodation all while being located just minutes from Walt Disney World Resort as well as many other great attractions. As ...

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Property Type

Kissimmee House

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Casa Bonita -- near Disney!

4 BR | 3 BA | Sleeps 8 | Quick View

25

Distance to park: 4 miles to Walt Disney World

$130

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool
  • Rentals by Owner

About this property

Florida License DWE5916118'Casa Bonita' which means 'Beautiful Home' is a beautifully furnished four bedroom, three bathroom home with a 26 ft x 14 ft swimming pool and covered lanai and is just a 3.5 mile drive to Walt Disney World Resort.This wonderfully located property backs onto natural Floridian ...

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Property Type

Kissimmee House

"Excellent"
Reviewed July 30, 2020

Because of Covid-19 we did not venture far from the rented home but the game room and the pool provided entertainment for the four children that were visiting with us. We were able to drive to St. John ...

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Disney Vacation Rental/heated pool - call for Specials now

4 BR | 3 BA | Sleeps 8 | Quick View

4

Distance to park: 3 miles to Mgm

$119

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • 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

"Hope I could stay here."
Reviewed August 30, 2020

Hi. My family and I was planned to stay this place fo our vacation in the beginning of august. It would have been good. Nevertheless because of the Covid 19 pandemic we could fly and our vacation was cancelled. ...

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Reunion Manor | Luxury 8 Bed Home, Custom Kids Bedrooms, Balcony w/ great views

$875

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Private Pool

About this property

Truly one of a kind custom, luxury home situated inside of the world famous Reunion Resort. The home is located within the well established Homestead community boasting spectacular views of the Independence golf course.Stepping into the grand entrance of the exquisitely designed home, you will be ...

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Property Type

Kissimmee House

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The Floridian Oasis - Relaxing 5 bedroom, 5 bath pool home

5 BR | 5 BA | Sleeps 12 | Quick View

Distance to park: 2 miles to Walt Disney World

$213

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

Terrific 5-bedroom/5-bathroom rental home 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 floor making this home ideal ...

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Property Type

Kissimmee House

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Beautiful & Spacious Family Villa in Rolling Hills, Kissimmee 4BR / 2BA

$127

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool

About this property

***NO PETS***4 Bedroom / 2 Bathroom (1,822 sqft) Single Story South Facing Private Pool Electric Pool Heat is an additional cost.Living Room: TV / DVD Dining Area - Seats 6 Breakfast Table - Seats 4Master Bedroom 1: Queen/ TV / Garden Tub Bedroom 2: Double Bedroom 3: Twins Bedroom ...

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Property Type

Kissimmee Villa

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Rachael Ray Recommend Vacation Home Near Disney, Free Wi-Fi

$94

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Rentals by Owner

About this property

'Every Day with Rachael Ray' magazine recommended vacation home, page 162, Dec.2010/Jan.2011 combined issue!!! Minutes from parks, affordable luxury & free wireless high speed Internet. Charming four-bedroom townhouses in the heart of Kissimmee, Florida. Minutes from Disney World, Sea World and Universal ...

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Property Type

Kissimmee Townhome

"Florida home away from home"
Reviewed December 3, 2018

We enjoyed our stay in this comfortable town home. It was close to everything we were interested in, especially Disney World. Very affordable. The only complaint was the hours the pool was available. ...

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The perfect Disney vacation home rental property! Only Weekly/Monthly Rentals

3 BR | 2 BA | Sleeps 8 | Quick View

2

Distance to park: 12 miles to All Disney Theme Park

$100

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool

About this property

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

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Property Type

Kissimmee Villa

"This Is a comfortable family friendly home with a wonderful screened in pool area with great privacy and a heated pool."
Reviewed May 25, 2020

I have rented this home for six years and have usually stayed for three months. I obviously love it or I would not return each year. The pool area is quiet and screened in so there is no problem with insects ...

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308SPD Windsor Palms Condo 3 bedrooms and 2 bathrooms in Kissimmee, FL

$109

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

***NO PETS***3 Bed / 2 Bath (1,268 sqft) CONDO (3rd Floor) Community Pool (Heated from October until May) Small Movie Theatre GymLiving Room : TV Dining Area - Seats 4 Breakfast Bar - Seats 2Master Bedroom 1 : Queen / TV Bedroom 2 : Full Bedroom 3 : Twins Free Wi-FI access

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Property Type

Kissimmee Condo

"Great place"
Reviewed July 5, 2019

This house was spotless it felt warm and cozy I’d recommend it too everyone thanks for the greatest vacation ever:)

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Your private oasis a step away from Disney is awaiting for your arrival !!!

$200

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Private Pool

About this property

Disney on your Doorstep is just a charming, relaxing, and feel at home, kind of home... you know when you're sitting by the pool and the kids are having a ball, that you've picked the right spot.... our, wonderful 5 bedroom, 4 bathroom vacation home with private pool, spa & Game room in the exclusive ...

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Property Type

Kissimmee House

"Home away from Home"
Reviewed March 25, 2020

This was our second year staying at this home. The owner and management - Karen - are fantastic to work with. Lots of linens and pool towels, exceptionally clean, a an immediate feeling of home!!! ...

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The Floridian : Ultra Luxuary 5BR Pool Home, 2 Master Suites, Sleeps 12!

$272

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool

About this property

Enjoy our three-thousand square foot, custom luxury pool home, less than four miles from Disney World. We offer two master suites with king-size beds (one with Jacuzzi), two queen-bedrooms, one twin-bedroom, and queen size pullout-couch, all on one floor. This is not your typical Rolling Hills house. ...

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Property Type

Kissimmee House

"Our Dream Vacation"
Reviewed July 30, 2018

This home was PERFECT for my family! It was very spacious and had everything we needed to make us comfortable. Very close to Disney and close to a lot of nice eating places we could not have chosen a ...

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Gorgeous Modern Luxurious W/ pool, hot tub, fitness centre mins away from Disney

$162

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

Welcome to 7558 Sunville Avenue, your home away from home. This luxurious townhome at Summerville Resort features 3-bedroom, (plus a bonus room) and 3.5 bathrooms easily accommodating up to 8 guests comfortably. This brand new luxury townhome is perfect for a family or a big group who are coming to enjoy ...

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Property Type

Kissimmee Townhome

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Lakeview Retreat, luxury villa, large pool, game room and cookout area

6 BR | 5 BA | Sleeps 14 | Quick View

Distance to park: 4 miles to Disney Animal kingdom

$280

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool

About this property

Luxury 6 bed 5 bath Villa with large south west facing pool, just 4 miles from Disney! Our wonderful villa can sleep up to 14 guests. Situated in the prestigious gated upscale community of Formossa Gardens, where properties enjoy spacious garden plots giving privacy, your wonderful pool home has a ...

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Property Type

Kissimmee House

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MICKEY'S VILLA near Disney!

5 BR | 4 BA | Sleeps 11 | Quick View

12

Distance to park: 4 miles to Disney World

$142

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly

About this property

Florida State License DWE5910390 )COME SWIM WITH MICKEY! This beautiful 5-Bed 4-Bath home located in the very popular community of Indian Creek is one of only three homes in the development with a Mickey Pool. Featuring two en-suites with private baths and three other bedrooms and two other baths ...

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Property Type

Kissimmee House

"A great vacation destination."
Reviewed April 26, 2020

There were five adults in our group and each one of us had a great time at Mickey's Villa. When we needed extra lounge chairs for the pool area, Bob came right away with the extra chairs. The house is ...

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Homestead Paradise - Rare Extended Pool Deck

$524

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

This luxury Mediterranean inspired custom home is on an oversized corner lot. Located on the beautiful Tom Watson Independence Reunion Resort golf course and just 6 miles to the gates of Disney.Enjoy Florida sun on the rare extended pool deck that sets this home apart from most in Reunion. Featuring ...

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Property Type

Kissimmee House

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Dory's Magic - Luxury villa with theater room, lake view and south-facing pool

7 BR | 5.5 BA | Sleeps 16 | Quick View

Distance to park: 3 miles to Disney World

$368

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

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

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Property Type

Kissimmee Villa

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Lakeside pool villa, kissimmee 3 miles disney

$182

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Private Pool

About this property

Location, Location, Location, situated just 3 miles from Disneys Animal Kingdom and less than a mile from the Formosa gardens shopping area and restaurants on the US192 you are perfectly placed to hit the parks before the rush, come home to cool down by the pool for dinner and hit the parks again for ...

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Property Type

Kissimmee Villa

"Lovely Villa, Great Location"
Reviewed June 14, 2019

Really nice villa. Plenty of living space. Sleeps up to 12 but there were 7 of us so it was really roomy.Pool area is so nice, with a view over a lake with lots of wildlife to see. Pool also has a colour ...

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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

Find your ideal Kissimmee vacation rental today
 
Aiming to take an incredible vacation to this year? Ditch the traditional hotel and opt for one of our Kissimmee vacation rentals instead. We have plenty of condos available in Kissimmee on FloridaRentals.com. Whether you’re looking for luxury Kissimmee villa rentals or kid-friendly mansions with an arcade, you can find it on our site.
 
Kissimmee, Florida travel advice
 
A short drive south of Orlando finds you in sunny, friendly Kissimmee. Here you’ll be near all the theme parks, but you’ll be away from the bustling crowds. Rentals will cost less than a stay in Orlando, so you’ll have extra cash to spend on park tickets and meals. This area also offers activities for those who love outdoor exploration, with exotic plants and animals in the local nature preserves.
 
Top attractions
 
The Florida theme parks are the major draw for visitors to the area. Walt Disney World, Universal Studios, SeaWorld, and the Wizarding World of Harry Potter draw millions of families every year. 
 
The fun doesn’t stop as kids and adults alike can mingle with their favorite characters, feel the chills and thrills of amusement rides, and cool off in the area’s water parks. If the theme parks don’t meet your need for speed, spend an afternoon at Fun Spot America. With two unique go-kart tracks and 18 rides you’ll be dizzy with delight. 
 
The Museum of Military History offers exhibits that highlight the bravery and humanity of the men and women who have served in the armed forces. Genuine artifacts, military relics, photographs and memorable accounts by former soldiers are on display here.
 
For some Florida history, stop in to Osceola County Pioneer Village and Museum. This museum features many exhibits depicting life in the 19th century. The Pioneer Village has a general store, blacksmith shop, one room schoolhouse, and nature preserve.
 
Family-friendly activities
 
Strap on your hiking boots and take off on the Shingle Creek Regional Trail. The trail offers a beautiful, natural environment for cyclists, pedestrians, canoeists/kayakers, bird watchers and other nature lovers.  A wide variety of habitats on the trail include Lake Tohopekaliga waterfront and islands, a pristine cypress swamp, an orange grove and wild grasslands.
 
For a more cuddly experience, Green Meadows Petting Farm has over 50 acres of animals to greet and family rides. If you’re visiting during spring training, stop in to see the Houston Astros practice as Osceola County Stadium. 
 
Of course, the options for fun aren’t limited to the parks. For golfers, Central Florida is a veritable paradise. With dozens of award-winning courses within a few square miles, you should definitely pack your clubs when visiting. If your family prefers mini-golf you have plenty of options, too. 
 
Kissimmee Lakefront Park features a playground and splash park for kids, BBQ grills for a cookout, and fishing piers. For more along these lines, nearby St. Cloud Lakefront Park and Beach offers a family picnic area and volleyball court. Located along the breathtaking Lake Tohopekaliga, these parks are great options to spend a relaxing afternoon.
 
Spend your evenings in Old Town Kissimmee, where every Saturday night there is a classic car cruise through the city streets, accompanied by a live band. In Old Town you’ll also find everything from high end retailers to souvenir shops. There is live music playing almost every night, and restaurants offering pizza, Tex-Mex, or anything in between. 
 
Annual events
 
Osceola Heritage Park has a variety of world-class shows and sporting events. You'll find the Silver Spurs Rodeo here, too. It's a real crowd pleaser, offering a taste of the Wild West and reflective of the area's ranching heritage. You can watch bull riding, bronco bucking, barrel racing, steer wrestling, team roping, and even those funny rodeo clowns.
 
Kissimmee vacation home rentals on FloridaRentals.com
 
Booking one of our vacation homes in Kissimmee on FloridaRentals.com can save you 20% over our competitors. Plus, we have a wide array of inventory appealing to any group size or traveler tastes. Book today!