Kissimmee Vacation Rentals

(371 rentals)
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5 BR | 4 BA | Sleeps 10 | Quick View

$284

avg/night

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About this property

Be sure to visit our website to check availability on all our homes! Save our page for future vacations to the Orlando area!Visit us at lostinthemagic . comSolara Resort - Kissimmee, Florida is an upscale community currently under development just 7 miles from Walt Disney World. This gated resort ...

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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

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

"Excellent villa"

Very clean and central to all theme parks, it was well cleaned for our arrival and the pool was cleaned twice a week during our stay. Would highly recommend this villa

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Key Amenities

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

About this property

"This home is so much fun and is the best we have ever stayed in! The 2 theaters were a hit, and my kids could not get enough of the game room. So much to do in there- play pool, foosball, air hockey, shuffleboard, arcade style video games and PS4 games. We also spent so much time enjoying the private ...

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Property Type

Kissimmee House

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7 BR | 4.5 BA | Sleeps 14 | Quick View

9

Distance to park: 3 miles to Disney World Parks

$245

avg/night

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Key Amenities

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

About this property

Huge Orlando vacation rental home has 7 bedrooms and 4.5 bathrooms. Great for a large Family with up to 14 guests! There are two King Master Suites, one on each floor. The master bathroom on the first floor has a walk-in shower and separate garden tub. Bedroom 3 & 4 King beds and Bedroom 5 One Queen ...

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Property Type

Kissimmee House

"Excellent"

Great place. So much room to spread out. Great decor. Large kitchen. We cooked breakfast, lunch and dinner daily. Bunk room huge hit w the kids.Thanks for everything. We’ll be rebooking

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3 BR | 2 BA | Sleeps 7 | Quick View

5

Distance to park: 12 miles to Disney

$136

avg/night

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Key Amenities

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

About this property

Heavenly Retreat, a designated rental vacation home, was just remodeled in a casual and comfortable style. It is a complete turn key ready vacation home with a full equipped kitchen, three bedrooms, and two bathrooms for up to 6 guests. The pool offers lots of privacy and relaxing atmosphere.This ...

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Property Type

Kissimmee House

"Clean the pool Nice"

Nice could use some updates. Pool was dirty could use a good cleaning will return someday to check out updates

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9 BR | 5 BA | Sleeps 20 | Quick View

3

Distance to park: 4 miles to Disney

$552

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

9 Bedrooms 5 Bathrooms Immaculate Designer furnishings throughout Family Room with large HD Cable TV Minions themed designer Upstairs TV Loft Incredible Simpsons themed Indoor Air conditioned Game Room with Pool Table, Air Hockey, Arcade Games, Game Consoles, Dart Board All bedrooms with Flat Screen ...

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Property Type

Kissimmee House

"Sons wedding"

Excellent place for our family. Everyone enjoyed very much, lots of room, pool and game room were a hit. They could have gave a starter kit, kitchen not enough stuff, NO paper towels, dish soap, dishwasher ...

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

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

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Property Type

Kissimmee Condo

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

Private Pool, Spa and Premium Resort Amenities Included! Blissful haven @You have found your bliss!Comfortably sleeping up to 12, this professionally redecorated (February 2022) 5-bedroom, 4 bathroom, gated resort community home has all you could possibly want:Private Pool and Spa / (Hot ...

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Property Type

Kissimmee Villa

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

The spacious two storey 5 bed, 4 bath fully air-conditioned home has a south facing pool. There is an extended pool deck for all day sun and has a spacious covered lanai for alfresco dining and poolside entertaining.This well-equipped and newly furnished home caters for all your holiday needs with ...

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Property Type

Kissimmee Villa

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Key Amenities

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

About this property

Get ready to experience the vacation of a lifetime at Big Top Family Vacation Villa, situated in the heart of Solara Resort. This stunning villa boasts 9 spacious bedrooms and 6.5 luxurious bathrooms, providing ample space for up to 22 guests. Perfectly located just 8 miles away from Walt Disney World ...

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Property Type

Kissimmee Villa

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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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Key Amenities

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

About this property

Property Reference #RVH_030RThis luxury Mediterranean inspired custom home is on a rare oversized corner lot. This home boasts one of the largest vacation home spillover spas in the whole of central Florida, up to 10 people can relax in the hot jets. Located on the beautiful Tom Watson Independence ...

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Property Type

Kissimmee House

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9 BR | 6 BA | Sleeps 18 | Quick View

1

Distance to park: 6 miles to Disney

$552

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

9 Bedrooms 6 Bathrooms Family Room with large HD Cable TV Huge Upstairs TV Loft with HD Cable TV. A great teen/tween or adult hang out space with game / card table and fridge All bedrooms with Flat Screen TVs Fully Equipped Chefs Gourmet Kitchen with Granite Counters and Stainless Steel Appliances Formal ...

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Property Type

Kissimmee House

"Sun Ridge Villia"

. This was our second year of our family staying here. Very quite area. Our grandson likes the flow Rider. They have towels and bedding so you do not have to take your own. Two levels so lots of room ...

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4 BR | 3 BA | Sleeps 8 | Quick View

17

Distance to park: 10 miles to Disney Theme Parks

$120

avg/night

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Key Amenities

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

About this property

A brilliant family home for a Florida holidayQuiet and peaceful, Stylishly furnished with granite countertops in kitchen and bathrooms, the open-plan accommodation offers both formal and informal dining inside, as well as al fresco dining in the lanai by the sparkling, South-facing private pool. The ...

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Property Type

Kissimmee Villa

"Excellent"

Great house with all needed for a great stay. The is house is located close to all parks and amenities.

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9 BR | 5 BA | Sleeps 22 | Quick View

Distance to park: 8 miles to Disney

$552

avg/night

View Details

Key Amenities

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

About this property

9 Bedrooms 5 Bathrooms Designer furnishings throughout Family Room with large HD Cable TV All bedrooms with Flat Screen TVs Upstairs 2nd TV loft / Den Fully Equipped Chefs Gourmet Kitchen with Granite Counters and Stainless Steel Appliances Formal Dining Room seating 12 plus breakfast bar seating ...

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Property Type

Kissimmee House

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4 BR | 3 BA | Sleeps 8 | Quick View

2

Distance to park: 8 miles to Disney

$228

avg/night

View Details

Key Amenities

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

About this property

Welcome home to Bellavida Resort, a GATED community, conveniently located approximately 8 miles from Walt Disney World! Enjoy nearby golf, restaurants, shopping, attractions, & much more!Remodeled including carpet, bedding, curtains, beach & bath towels, face cloths, silverware, leather recliner ...

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Property Type

Kissimmee Townhome

"Florida Vacation"

Nice home but could use a few updates. The cushions on the outside furniture should be replaced. They are faded, moldy and smelly. The house is also short on silverware. There were sheets covering the ...

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2 BR | 2 BA | Sleeps 4 | Quick View

1

$263

avg/night

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Key Amenities

  • Air conditioning
  • 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 ...

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Property Type

Kissimmee Condo

"Perfect spot for a get-away with your family."

My expectations were exceeded. Actually, my wife and my children keep asking me to go back. I am looking forward to booking again in April 2021.

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

Private Pool, Spa and Premium Resort Amenities Included! Treat Retreat @ – Sleeps 16 Welcome 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 ...

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Property Type

Kissimmee Villa

"Spring break"

The house was great we had 15 in our party. Pool was a big hit for us (heated) and the beds were very comfy. Plenty of kitchen supplies (cookware). The only thing I noticed with a lot of these homes ...

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9 BR | 6 BA | Sleeps 18 | Quick View

Distance to park: 8 miles to Disney

$427

avg/night

View Details

Key Amenities

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

About this property

9 Bedrooms 6 Bathrooms Family Room with large HD Cable TV Adjacent billiard room Upstairs Loft with HD Cable TV All bedrooms with Flat Screen TVs Fully Equipped Chefs Gourmet Kitchen with Granite Counters and Stainless Steel Appliances Formal Dining Room seating 10 plus breakfast bar seating 5 ...

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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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Key Amenities

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

About this property

Located in popular Sonoma Resort, our home is the perfect place to stay for a care and stress-free holiday away. Whether you are looking to spend long days lounging by the pool, exploring the parks or stretching your legs on one of the surrounding golf courses, this is the perfect location. Guests benefit ...

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Property Type

Kissimmee Villa

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$125

avg/night

View Details

Key Amenities

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

About this property

Your dates don't match? no worries! Check our profile for similar homes that might suit your needs.WE HAVE 24/7 CUSTOMER SERVICE!Disney is only 10 miles awayBeautiful themed home with a private pool, and a fully equipped kitchen. Located at Champions gate Resort, a quiet and family-friendly ...

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Property Type

Kissimmee House

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3 BR | 2 BA | Sleeps 8 | Quick View

12

Distance to park: 12 miles to All Disney Theme Park

$111

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

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

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Property Type

Kissimmee Villa

"Lovely villa close to parks"

Great location close to the airport, Disney parks and outlets. Spacious villa that was really comfortable with a lovely pool. So many 'extras' provided such as pool toys, on demand family friendly films ...

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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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4 BR | 3 BA | Sleeps 8 | Quick View

Distance to park: 3 miles to Disney Parks

$142

avg/night

View Details

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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7 BR | 5 BA | Sleeps 14 | Quick View

2

Distance to park: 6 miles to Disney

$359

avg/night

View Details

Key Amenities

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

About this property

GUARANTEED BEST RATES! DISCOUNTS FOR LONG STAYS. Welcome to our stunning Florida holiday home where you'll find everything you could ever wish for, from our large south facing private heatable swimming pool and spa to the purpose built and well-appointed games room. Easy walking distance to the ...

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Property Type

Kissimmee House

"Amazing villa and great service"

Visited in May 2019, villa was exactly like the photos. Impeccably clean and finished to an exceptionally high standard. Everything you need for a fabulous holiday. Alison was extremely helpful and responsive. ...

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5 BR | 4 BA | Sleeps 12 | Quick View

7

Distance to park: 6 miles to Disney Animal Kingdom

$238

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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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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5 BR | 4.5 BA | Sleeps 10 | Quick View

Distance to park: 8 miles to Disney

$262

avg/night

View Details

Key Amenities

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

About this property

5 Bedrooms 4.5 Bathrooms Family Room with large HD Cable TVAll bedrooms with Flat Screen TVs Fully Equipped Chefs Gourmet Kitchen with Granite Counters and Stainless Steel Appliances Formal Dining Room seating 6 plus breakfast bar seating 4 outdoor dining for 6 Private screened Pool Patio with ...

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Property Type

Kissimmee Townhome

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Key Amenities

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

About this property

Property Reference RVH_1018RMajor Excitement is situated in the Liberty Bluff neighborhood of Reunion Resort, this luxurious 6-bedroom, 6 bath home offers a private pool and much more!With an open-planned floor plan, the living area is bright and spacious with an "L-Shaped" sofa before ...

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Property Type

Kissimmee House

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6 BR | 5.5 BA | Sleeps 12 | Quick View

5

Distance to park: 8 miles to Disney

$359

avg/night

View Details

Key Amenities

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

About this property

6 Bedrooms 5.5 Bathrooms Family Room with large HD Cable TV Upstairs Hang out Den / TV Loft with large HD Cable TV Screen All bedrooms with Flat Screen TVs Fully Equipped Chefs Gourmet Kitchen with Granite Counters and Stainless Steel Appliances Formal Dining Room seating 8 plus breakfast bar and ...

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Property Type

Kissimmee House

"Girls Vacation 2023"

Excellent service. Any issues were addressed immediately! Close to everything. Excellent location. Beautiful pool area. Lots of room very spacious.

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5 BR | 5 BA | Sleeps 10 | Quick View

1

$284

avg/night

View Details

Key Amenities

  • Air conditioning
  • Private pool

About this property

Be sure to visit our website to check availability on all our homes! Save our page for future vacations to the Orlando area!Visit us at lostinthemagic . comStorey Lake - Kissimmee is a brand new vacation community located just 4 miles from the magical world of Disney and just minutes to Universal, ...

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Property Type

Kissimmee House

"Summer Vacation"

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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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

Private Pool, Spa and Premium Resort Amenities Included! Summer Solstice @Welcome to The Summer Solstice, your haven home at . Sleeps up to 14. With your own private pool and spa (can be heated – see details and optional costs below), you never need to leave your Oasis inside this luxury ...

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Property Type

Kissimmee Villa

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Key Amenities

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

About this property

This newly renovated 4 bedroom, 2 bathroom open concept home has a private screened in pool with a covered porch for poolside dining and lounging.Less than 20 minutes to all major theme parks and a short distance from major highways, shopping, and restaurants.Professionally designed, the house ...

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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

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

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Property Type

Kissimmee Villa

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9 BR | 5 BA | Sleeps 18 | Quick View

1

$488

avg/night

View Details

About this property

Be sure to visit our website to check availability on all our homes! Save our page for future vacations to the Orlando area!Visit us at lostinthemagic . comStorey Lake - Kissimmee is a brand new vacation community located just 4 miles from the magical world of Disney and just minutes to Universal, ...

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Property Type

Kissimmee House

"Nice Place to Stay! Enjoyed Family Time"

Overall, we had an amazing time. It is so spacious, which is just what I wanted. The hot tub (even though we were too busy to utilize it) was warm even though we had cold days and nights. The rooms are ...

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6 BR | 5 BA | Sleeps 13 | Quick View

Distance to park: 4 miles to Disney

$273

avg/night

View Details

Key Amenities

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

About this property

6 Bedrooms 5 Bathrooms Family Room with large HD Cable TV Second upstairs TV Loft All bedrooms with Flat Screen TVs Fully Equipped Chefs Gourmet Kitchen with Granite Counters and Stainless Steel Appliances Formal Dining Room seating 8 plus breakfast bar seating 4 and outdoor dining Private screened ...

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Property Type

Kissimmee House

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6 BR | 4 BA | Sleeps 14 | Quick View

last minute deal
LAST MINUTE DEAL 11/25 - 12/31: Discounted rates for December and January!

$386

avg/night

View Details

Key Amenities

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

About this property

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

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Property Type

Kissimmee House

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DEAL

$314

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

Golf Course Views, Grand 6 Bedroom Home in Reunion 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 ...

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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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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

Magnificent Views over Water, Private Pool, Spa - First Class Home! 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’ ...

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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

Come stay in our luxury family villa that features 5 bedrooms, 3 bathrooms, full kitchen and private pool and spa. Sleeps 12 guests.Full air con and hi speed WiFi throughout the villa.Strictly no smoking and no petsOur home is very well located in Lake Berkley Resort with short walking distance ...

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Property Type

Kissimmee Villa

"Very convenient and lovely Villa"

Villa easy to book and no issues on arrival all ready and as described. Villa location brilliant for all the Disney Parks within 15 mins drive at most. 3 supermarkets near by would recommend the Target ...

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

Pool View, Top Floor, Oversized Balcony, Premium Resort Amenities Included. Storey Lake Resort, 2bd Condo Overlooking Pool #825Stunning, brand new in 2021 2 Bed, 2 bath Condo, overlooking one of the heated resort pools.Furnished and designer-decorated to a high standard, stone kitchen and ...

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Property Type

Kissimmee Condo

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5 BR | 5 BA | Sleeps 13 | Quick View

3

Distance to park: 4 miles to Disney

$359

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

GUARANTEED BEST RATES. DISCOUNTS FOR LONG STAYS. 5 Bedrooms 5 Bathrooms Family Room with large HD Cable TV Upstairs Loft with large HD Cable TV All bedrooms with Flat Screen TVs Fully Equipped Chefs Gourmet Kitchen with Granite Counters and Stainless Steel Appliances Formal Dining Room seating ...

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Property Type

Kissimmee House

"5 bed 4 bath house"

Just home after 2 weeks staying in your house at Storey Lakes the perfect location for all the parks,

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5 BR | 4.5 BA | Sleeps 12 | Quick View

Distance to park: 8 miles to Disney

$248

avg/night

View Details

Key Amenities

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

About this property

5 Bedrooms 4.5 Bathrooms Family Room with large HD Cable TV Upstairs Loft with large HD cable TV All bedrooms with Flat Screen TVs Fully Equipped Chefs Gourmet Kitchen with Granite Counters and Stainless Steel Appliances Formal Dining Room seating 6 plus breakfast bar seating 4 and outdoor dining ...

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Property Type

Kissimmee Townhome

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4 BR | 2 BA | Sleeps 10 | Quick View

$165

avg/night

View Details

Key Amenities

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

About this property

The heart and soul of any Disney vacation is the centerpiece in this Mickey Mouse themed villa.Leading from the living/dining room is the upgraded and fully-equipped kitchen, which includes a ceramic top range, side by side refrigerator/freezer, dishwasher, garbage disposal, and microwave. Along with ...

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Property Type

Kissimmee Villa

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8 BR | 6 BA | Sleeps 20 | Quick View

$250

avg/night

View Details

Key Amenities

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

About this property

Experience a dreamy getaway in "Queen of Hearts" villa in the Windsor at Westside Resort! Relax in luxury and revel in themed bedrooms loved by all, sprawling living areas fit for winding down, an exciting games room for good times, not to mention your own private pool. With free resort amenities ...

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Property Type

Kissimmee Villa

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

10 Bedrooms 8 Bathrooms Family Room with large HD Cable TV Large upstairs Cinema Screen Loft Loft with Pool Table All bedrooms with Flat Screen TVs Fully Equipped Chefs Gourmet Kitchen with Granite Counters and Stainless Steel Appliances Formal Dining Room seating 16 plus breakfast bar and outdoor ...

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Property Type

Kissimmee House

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9 BR | 6 BA | Sleeps 19 | Quick View

2

Distance to park: 8 miles to Disney

$529

avg/night

View Details

Key Amenities

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

About this property

9 Bedrooms 6 Bathrooms Family Room with large HD Cable TV Large Upstairs Loft HD Cable TV and play area All bedrooms with Flat Screen TVs Fully Equipped Chefs Gourmet Kitchen with Granite Counters and Stainless Steel Appliances Formal Dining Room seating 8 plus breakfast bar and outdoor dining Private ...

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Property Type

Kissimmee House

"Great family and friends vacation rental!!"

Had a great time In central Florida while staying at this rental property. April was a great host, quick at replying on any question, issue, or concern. The Windsor facilities were nice and clean staff ...

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5 BR | 3.5 BA | Sleeps 12 | Quick View

$300

avg/night

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Key Amenities

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

About this property

This newly remodeled 5bd/3.5bath gated community home is waiting for you to visit! Saltwater pool, game room IN the house, all new flooring, granite countertops in kitchen, new pool furniture, new decorations, community playground and SO much more! This home is located only 5 miles from Disney World and ...

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Property Type

Kissimmee Villa

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3 BR | 2 BA | Sleeps 6 | Quick View

2

Distance to park: 8 miles to Disney

$175

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

3 Bedrooms 2 Bathrooms Family Room with large HD Cable TV All bedrooms with Flat Screen TVs Fully Equipped Chefs Kitchen Formal Dining Room seating 6 plus breakfast bar Master Bedroom with BalconyWasher/DryerCentral Air Towels and Bed Linens provided Wireless Internet Telephone with ...

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Property Type

Kissimmee Townhome

"Awesome"

I really enjoyed the stay. We stsy there all the time. Kids friendly and very quite. I recommend to anybody that has kids.

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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 371 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 $64 per night with an average price per night of $238.

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