Kissimmee Vacation Rentals

(338 rentals)
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Key Amenities

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

About this property

A stunning, larger than average 4 Bed 3 Bathroom villa that had a major refurbishment in 2017There are 2 sitting rooms both with lots of comfortable seating. Both rooms have large screen TVs, ideal for when the adults want to watch the latest sports programme whilst the kids enjoy the latest Disney ...

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Property Type

Kissimmee Villa

"Highly recommend"

We recently stayed at this very nice villa in Lake Berkley Resort for 6 weeks.The villa was very well presented when we arrived and clean. It has everything you need to enjoy your stay in Florida. The management ...

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9 BR | 6 BA | Sleeps 18 | Quick View

5

Distance to park: 8 miles to Disney World

$401

avg/night

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Key Amenities

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

About this property

Windsor at Westside Resort is one of the newest and most luxurious resort communities in the Orlando/Kissimmee,Developed by one of the nation's largest developer , the Pulte Homes. Just 8 miles from Disney, and within easy reach to all the attractions, shopping, and dining in the Disney area, this ...

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Property Type

Kissimmee House

"Fantastic Stay"

This was a perfect location, close to everything and away from the congestion. The property was everything that was advertised, clean, spacious and great amenities, both on property and in the community. ...

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7 BR | 6.5 BA | Sleeps 14 | Quick View

$325

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

Wow – Sea Shore at Solara by Shine Villas!7 Bedrooms and 6.5 Bathrooms – Sleeps 14 in comfort.This home is exquisitely designed and has all you could want from your vacation home away from home.Private Pool with Spa, Media Loft Area, Air-Conditioned ‘Starcade’ ...

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Property Type

Kissimmee Villa

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Key Amenities

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

About this property

Ideal for your next family vacation, this striking 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

"Fantastic Host"

We had the best time on our trip to Florida this year. I had a few changes in the dates chosen because of certain circumstances and the host was very understanding and willing to help out. I took my son ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

3 Bedroom Townhome close to Disney WorldThe spacePROPERTY: Welcome to your perfect vacation rental close to Disney. This 3 bed 2.5 bath town home is the perfect place to unwind after a busy day visiting many of the local attractions. The home has 3 bedrooms, 2.5 bathrooms and sleeps 8. The home ...

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Property Type

Kissimmee House

"Great"

A great family vacation rental.booking was easy and check in process was flawless. We had an issue with the internet but the manager resolved it as soon as possible.The rental was safe clean and convenient ...

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3 BR | 2 BA | Sleeps 6 | Quick View

$129

avg/night

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Key Amenities

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

About this property

This is a NON SMOKING condo *Community: Sweetwater Club VillasFloors: First Floor CondoPets: THIS IS NOT A PET FRIENDLY CONDORooms: 3 Bedrooms, 2 Bath rooms. En-suite in Master bedroom.Bed Configuration: King bed (1) Queen bed (1), Full Bed (1). Sleeps 6.Flooring: Tile throughout ...

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Property Type

Kissimmee Condo

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5 BR | 3 BA | Sleeps 10 | Quick View

7

Distance to park: 8 miles to Disney

$150

avg/night

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Key Amenities

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

About this property

Come stay in our spacious one story single family home that features 5 bedrooms, 3 bathrooms fully kitchen and a private pool (can be heated for additional fee)Our home is very well located in Lake Berkley Resort with short walking distance to the lake berkley, where you may walking or fishing. ...

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Property Type

Kissimmee House

"Excellent villa in great location"

Family trip here in July 23 for 10 days. Villa is excellent, very modern and well furnished. Great pool area, many happy days by the pool. Grealt location, everything is close by. Highly recommend, ...

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Key Amenities

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

About this property

Welcome to our stunning 7 Bed 4 Bath villa, located on the secures and gated Aviana Resort, just a few minutes from Disney..The villa has been furnished to a very high standard, is modern and very spacious. Ideal for a large family or 2/3 families sharing. Fully airconditioned throughout and free ...

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Property Type

Kissimmee Villa

"Briliant 5 nights stay"

5 night stay at this villa in Dec 2023, had a brilliant time. Villa more then met our expectations, it is really nice and very well located. We highly recommend. Easy booking process with just $150 deposit. ...

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Key Amenities

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

About this property

Dreams really do come true when you treat your family to our Mickey-themed villa, “Wish Upon A Splash”! Custom-designed with elevated, modern furniture and decor, tasteful, Mickey-themed artwork, and soft, relaxing colors, you’ll be just a few minutes from the most magical place on Earth! ...

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Property Type

Kissimmee Townhome

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$288

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

Welcome to WellerDen at Reunion Resort! Just 12 Miles from Walt Disney World Resort.This Two story home has 6 bedrooms, 5.5 bathrooms South East facing pool and much more to enjoy your Florida vacation in the Resort community of Reunion Resort and Spa!SPECIAL FEATURES * Air Conditioned throughout * ...

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Property Type

Kissimmee Villa

"Not Bad"

The villa was not bad just a little hick up with the pool not clean and the wifi did not connect to the tv in theatre room. The house was clean and the area was nice. We going back in August

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5 BR | 3 BA | Sleeps 10 | Quick View

2

Distance to park: 6 miles to Disney kingdom

$139

avg/night

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Key Amenities

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

About this property

Welcome to Coral Cay Resort! Coral Cay resort Situated 6 miles from Disney World, 1 mile to Walmart and target. 0.5 mile off highway 192.Seaworld and Convention Center are 8 miles away.Just minutes from Orlando's vast array of theme parks, fabulous dining options and world-class shopping.Our ...

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Property Type

Kissimmee Townhome

"Vacation was beautiful!"

We had an awesome week in Florida! The house was amazing! The owners were awesome!!!!’ 6 stars! My family and myself will book again very soon!!

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4 BR | 3 BA | Sleeps 8 | Quick View

1

Distance to park: 2 miles to Disney’s Animal Kingdom Park

$121

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

This huge 1650 sqft condo has 4 bedrooms and 3 full bathrooms. It is located at Sun Lake Resort, just 2 Miles to Disney world Florida.sleeping accommodations for 8.* King-size Master bedroom with bathroom* One queen size sofa bed in family room for extra guests* One 40" HDTV(free ...

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Property Type

Kissimmee Condo

"Nice Vacation Condo Rental"

Located near Disney, shopping, restaurants. Everything on 1st floor was wonderful for a group of oldsters!

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Key Amenities

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

About this property

Amazing 2BD / 2BA in the beautiful community of Storey Lake Resort Style, perfect stay to relax, have a good time with family/friends, and of course, enjoy the parks and many attractions that Orlando offers.Two comfortable rooms accommodate 6 guests: one king bed in Master Suite with smartTV and private ...

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Property Type

Kissimmee Apartment

"wonderful stay"

We recently had the pleasure of staying at an Airbnb that exceeded our expectations in every way. the location of storeylake resort is just minutes away from disney world, provided the perfect blend of ...

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4 BR | 3 BA | Sleeps 8 | Quick View

3

Distance to park: 12 miles to Disney World

$175

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Beautiful lakeside home with a private south facing pool in a gated community 12 miles from Disney. Enjoy fishing in the lake behind the house. Game room with pool table, skeet ball, foosball table and a gaming system with hundreds of old favorites like Pac Man and Mario Brothers. 4 bedrooms and 3 bathrooms. ...

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Property Type

Kissimmee House

"Wonderful home"

This is a beautiful home to stay in. It had all the comforts of your own home, incredible view from the huge pool, lots of wildlife and friendly neighbors. The owners are super nice and so easy to work ...

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4 BR | 3 BA | Sleeps 8 | Quick View

8

Distance to park: 2 miles to Disney’s Animal Kingdom Park

$121

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Welcome to the Sun Lake Resort. We have 4 identical 1650 sqft units with 4 bedrooms and 3 bathrooms. The beautiful condo faces to sun lake and it has a spacious screened patio. It only takes 1 minute walk to a plaza for shopping and restaurants which is very convenient! More importantly, you are only ...

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Property Type

Kissimmee Condo

"Awesome stay"

Beautiful resort and room was great. Great location and staff was very helpful. Would highly recommend this property.

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Key Amenities

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

About this property

Fairway Retreat is a home that truly lives up to its name and more. This five-bedroom custom-designed vacation home offer sweeping Fairway views and tons of fun and excitement all under one roof. This home is sure to set the bar of expectations much higher for future getaways for you and your family.When ...

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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

One of the closest communities to Walt Disney World (less than 3 miles away), Emerald Island Resort is a quiet oasis in which to spend your vacation. Emerald Island is an exclusive man gated resort community less than a mile from the world famous US Highway 192 where you will find shops, restaurants, ...

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Property Type

Kissimmee Villa

"a nice stay"

We have 16 people from Ma. Maine N H and North Carolina coming he for the last 15 years. We enjoy staying at Emerald Isle resort as it close to the courses that we play. The house that we rented was very ...

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6 BR | 5 BA | Sleeps 12 | Quick View

5

Distance to park: 4 miles to Disney

$429

avg/night

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Key Amenities

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

About this property

We are only 3.5 miles from Disney!! So close to all the fun, Hollywood Studios, Sea World, beaches, walks, restaurants and shopping!! We are in the middle of it all! You will enjoy our lovely villa by yourself or with a group. Our pool is one of the biggest among the rental communities. When comparing ...

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Property Type

Kissimmee Villa

"Wow!!!! Perfect 10 out of 10!!!!"

We stayed at the property for 6 nights during our recent family's Disney World vacation. Right from the start of the process, the owner was very courteous and prompt with her responses to our many questions. ...

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4 BR | 3 BA | Sleeps 12 | Quick View

Distance to park: 15 miles to Disney World

$173

avg/night

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Key Amenities

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

About this property

Experience this spacious 4 bed/3 bath Home and "Optional Private Heated Pool" with garage transformed into a sensational glow in the dark game room, where both kids and adults can revel in laughter and friendly competition. As if that's not enough, a dazzling LED screened-in pool tailor-made ...

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Property Type

Kissimmee House

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5 BR | 3 BA | Sleeps 10 | Quick View

5

Distance to park: 6 miles to Disney,Seworld

$134

avg/night

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Key Amenities

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

About this property

Welcome to the beautiful Coral Cay Resort. It is one of the most popular resort destinations in the Kissimmee/Orlando area for its proximity to theme parks and other major attractions. Situated 6 miles from Disney,1 mile to Walmart and target, 8 miles to Seaworld and Convention Center.This gorgeous ...

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Property Type

Kissimmee Townhome

"Thank you"

The property my children and I stayed at for 6 months was amazing. Would definitely recommend this rental again. Five stars.

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9 BR | 6 BA | Sleeps 18 | Quick View

4

Distance to park: 8 miles to Disney World

$383

avg/night

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Key Amenities

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

About this property

Windsor at Westside Resort is one of the newest and most luxurious resort communities in the Orlando/Kissimmee,Developed by one of the nation's largest developer , the Pulte Homes. Just 8 miles from Disney, and within easy reach to all the attractions, shopping, and dining in the Disney area, this ...

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Property Type

Kissimmee House

"Great for large family"

Very spacious, 9 bedrooms, for my family vacation of 12 people. Had some issues with the spa heat, but Iverson was very responsive.

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

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

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Property Type

Kissimmee Villa

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Key Amenities

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

About this property

Vacation in style with this luxurious family-friendly villa with your very own pool, spa and lake view. Family games room.The villa is located on the 5 Star safe gated Bella Vida Resort in the heart of Kissimmee, close to shops, restaurants and bars, and is only 15 minutes from Disney.Offering ...

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Property Type

Kissimmee House

"Beautiful"

Beautiful home and spacious with all the things you would need to enjoy your stay . After out all day come back and relax in the roomy and comfortable home.The weather did't pan out while we were there ...

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5 BR | 3 BA | Sleeps 10 | Quick View

3

Distance to park: 6 miles to Disney,Seaworld

$139

avg/night

View Details

Key Amenities

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

About this property

Welcome to the beautiful Coral Cay Resort. It is one of the most popular resort destinations in the Kissimmee/Orlando area for its proximity to the theme parks and other major attractions. Situated 6 miles from Disney World, 1 mile to Walmart and target. 8 miles to Seaworld and Convention center. Minutes ...

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Property Type

Kissimmee Townhome

"Comfortable place to stay....."

We stayed here while in Florida for my daughter's dance competition. It was so nice to come "home" after a long day of dance. I loved that the driveway was right up to the door. I also loved that it ...

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8 BR | 5 BA | Sleeps 16 | Quick View

7

Distance to park: 6 miles to Disney world

$248

avg/night

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Key Amenities

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

About this property

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

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Property Type

Kissimmee House

"Pleasant Stay in Crystal Cove"

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

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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-bathDisney area vacation home is conveniently located just 10 minutes to theWalt Disney World Resort, 15-20 minutes from Universal StudiosFlorida and SeaWorld Orlando. Florida’s famous beaches are just aquick 45 minutes ...

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Property Type

Kissimmee Villa

"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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Key Amenities

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

About this property

Welcome to VIPvilla Johanna and Stephen thank you for visiting our website of hand-picked 5 Star quality villas. We manage the bookings for 20 private villa owners at lake Berkley Resort and we can personally assure you that you will be delighted with any of the villas offered to you. We have many ...

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Property Type

Kissimmee Villa

"Fantastic-Excellent."

IWe visited Orlando a lots of time,We are familiar with Lake Berkley.We had always very good impresion of staying in Lake Berkley.This time we stayed in Lake berkley drive 929.We arrived at almost 03;00 ...

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4 BR | 2 BA | Sleeps 8 | Quick View

$210

avg/night

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Key Amenities

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

About this property

This is a NON SMOKING HOME *Community: Citrus RidgePets: NO Pets.Rooms: 4 Bedrooms, 2 Bath rooms. En-suite in Master bedroom. Sleeper 8 peopleBed Configuration: Bedroom 1: King size bed with en-suite, and walk in closet. Bedroom 2: Queen size bed. Bedroom 3: 2 Single beds. Bedroom ...

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

Treat Retreat @ – Sleeps 16Welcome to your awesome vacation spot by Shine Villas at Storey Lake.Beautifully decorated superior location, 7 bedroom, 6 bathroom home inside the premium Storey Lake Resort Community with full resort access included in the advertised rate. No resort fees ...

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Property Type

Kissimmee Villa

"Wonderful home"

We loved our stay. Large, clean, gated community. Pool was beautiful and hot tub was a hit during the cold front. Some negatives…. Not well stocked and about a 45 minute drive to Disney parks, due ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

This stunning 4-bedroom home boasts an expansive east-facing pool deck that overlooks a pristine natural area, all within the prestigious gated community named Sanctuary.Full air con and hi-speed WiFi throughout.The spacious living room features a three-seater sofa and two wing-backed chairs, ...

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Property Type

Kissimmee House

"Fantasic villa, lovely pool"

Family had a great stay at this lovely villa, it is even nicer than the photos. We would definitely stay here again. Easy booking process and check in. Pat

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5 BR | 3 BA | Sleeps 10 | Quick View

3

Distance to park: 6 miles to Disney World,Seaworld

$138

avg/night

View Details

Key Amenities

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

About this property

Welcome to the beautiful Coral Cay Resort. It is one of the most popular resort destinations in the Kissimmee/Orlando area for its proximity to theme parks and other major attractions. Situated 6 miles from Disney,1 mile to Walmart and target, 8 miles to Seaworld and Convention Center.This gorgeous ...

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Property Type

Kissimmee Townhome

"Always a pleasure to stay at Coral Cay, Liu was great!"

Everything was as stated. This is a nice, clean unit, with a ton of space. The hot tub in the screen room is awesome, and great for sore feet and muscles at the end of a Theme Park day. Beds are super ...

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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

"Exceptional Stay"

We had the pleasure of booking this villa during our family vacation to Disney World. The villa is beautiful inside and out. It is tucked away in a secluded area. I felt safe and welcomed by the gate attendants. ...

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9 BR | 6 BA | Sleeps 24 | Quick View

13

Distance to park: 2 miles to Sunday's Grill

$319

avg/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

"Great place for large family"

We were pleased with the size and location of the house. It was walking distance to the community amenities including the water park. The park is very well kept. We had heated pool heat and BBQ included ...

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3 BR | 2 BA | Sleeps 6 | Quick View

2

Distance to park: 2 miles to Disney's Animal Kingdom Theme Park

$115

avg/night

View Details

Key Amenities

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

About this property

Welcome to the Sun Lake Resort. This 1500 sqft 3bedroom/2bathroom unit is on 2nd floor. The beautiful condo faces to sun lake and it has a spacious screened patio with an amazing view. It only takes 1 minute walk to a plaza for shopping and restaurants which is very convenient ! More importantly, you ...

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Property Type

Kissimmee Condo

"Larry’s Villas, Kissimmee, Florida"

Loved the area! Easy access to restaurants and attractions! The condo was very clean! Needs some bathroom updates! There was a problem with the wifi and eventually was rectified!

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Key Amenities

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

About this property

Gorgeous 6-Bedrooms, 4 bathroom Resort Pool Home, just 3 miles from the Walt Disney World Resort! Located in the guard gated community of Emerald Island Resort, this nicely presented pool home has two master suites. This is one of the closest Resort to Disney.Uniquely the villa has twp master bedrooms ...

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Property Type

Kissimmee Villa

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Key Amenities

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

About this property

Property Reference WW_718ARWelcome 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 ...

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Property Type

Kissimmee House

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7 BR | 4.5 BA | Sleeps 16 | Quick View

10

Distance to park: 3 miles to Disney world

$166

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly
  • Pool

About this property

Newly furnished luxurious 2-story Villa home opens its door to welcome you! This villa is furnished with two master suite and one large bedroom with upscale King-size beds; two bedrooms with queen-size beds; and two bedrooms with two twin-beds each. All bedding and mattresses are Brand New with top quality ...

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Property Type

Kissimmee Villa

"Peaceful, quiet secured property"

Villa 2662 Emerald Island Blvd. large home with seven bedrooms and four and a half bathrooms. Game room with a pool table was a hit for my family. Gated, clean and safe. Kitchen equipped with all appliances, ...

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5 BR | 5 BA | Sleeps 12 | Quick View

1

Distance to park: 5 miles to Disney World/Animal Kingdom

$294

avg/night

View Details

Key Amenities

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

About this property

Our Disney vacation villa is furnished to the highest standard and offers your family the luxury of a Five star hotel combined with the relaxed atmosphere of a family vacation home. Soak up the Florida sun on our extended deck where you can relax in the pool and spa, or simply enjoy the shade of the lanai ...

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Property Type

Kissimmee Villa

"Wonderful home and resort"

This home was super clean and there was so much room. The two kids rooms upstairs are amazing. My kids were in heaven. The game room was so much fun. Always nice to be able to come back after a day at ...

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Key Amenities

  • Air conditioning
  • Kid friendly

About this property

This 7 bedroom/4½ bathroom private house features a huge 10' x 40' covered lanai, with ceiling fans, extra patio furniture and a large flatscreen TV (accessed only by Netflix/Hulu, etc). Nice pool area in general. Interior furnishings are nice (certainly not spectacular). This is ...

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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

If You're Looking For One Of The Best 5 Bedroom Vacation Homes In Solara Resort or Central Florida, Look No Further!Located just minutes from Orlando's theme parks, shopping, dining, and other area attractions, this luxury villa is located in Solara Resort. Solara Resort is just a 5-minute ...

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Property Type

Kissimmee House

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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
  • Kitchen
  • Pool
  • Private pool

About this property

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

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Property Type

Kissimmee Condo

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5 BR | 4 BA | Sleeps 12 | Quick View

3

Distance to park: 3 miles to Disney World

$229

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • 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

"Awesome house"

Our family of 10 spent a week at this awesome house..Lots of room for all of us was well was very clean ..heated pool was the hit ..Rails at spa and pool steps would have been nice as I am waiting hip surgery ...

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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

""

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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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

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

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Property Type

Kissimmee Villa

"Very beautiful home"

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

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Key Amenities

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

About this property

Property Reference SL_660RStep inside the enchanted doors of this magnificent abode and be transported to a world of wonder and delight. Nine luxurious bedchambers and five opulent bathrooms await your arrival for a family sojourn like no other.The heart of the home, the modern kitchen, is a place ...

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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

4 Bedroom villa with 4 ensuite bathrooms.This exquisite villa is an ideal destination for a family holiday, offering a prime location.Situated within walking distance of the resort clubhouse and pool.Hi speed WiFi and air con throughout the villa.Set against a backdrop of serene ...

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Property Type

Kissimmee Villa

"Amazing villa"

Amazing villa, very clean, well furnished, modern. Beds all comfortable, kitchen has everything you need. Pool and pool deck were wonderful, we had many happy hours there. Highly recommended. Very easy ...

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$145

avg/night

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Key Amenities

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

About this property

Community: Bella Piazza Floors: Second Floor Condo, Elevator Access. NO pets This is a NON SMOKING HOME * Rooms: 3 Bedrooms, 3 Bath rooms. En-suite in Master bedroom.Bed Configuration: King bed(1) King bed(1), Full plus 2 twins., Sleep 8.Flooring: tile throughout with Carpet in the bedrooms.General: ...

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Property Type

Kissimmee House

"Great Location"

Great location near all the major parks. The pool in the gated community was really nice, staff there was excellent. The condo was good. The living room floor was dirty with someone elses bobby pins on ...

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Key Amenities

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

About this property

One of the closest possible communities to Walt Disney World (less than 3 miles away), Emerald Island is a quiet oasis in which to spend your vacation. Emerald Island is an exclusive gated community less than a mile from the world famous US Highway 192 where you will find shops, restaurants, and entertainment. ...

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Property Type

Kissimmee Villa

"Family vacation"

Our family were there for 2 1/2 weeks and everyone loved it. Location very close to parks,restaurants and stores.Grandkids loved the time in the pool. House was big enough for the family and clean.Screens ...

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool

About this property

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

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Property Type

Kissimmee Condo

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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 338 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 $208.

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