Kissimmee Vacation Rentals

(406 rentals)
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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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$144

avg/night

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Key Amenities

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

About this property

Enjoy a magical vacation just 3 miles from all the Disney parks at the Pineapple Vacation Villa situated in the elegant Windsor Palms Resort. -Our holiday home offers all of the latest features in vacation rentals. With four bedrooms including two master-en-suites with private bathrooms plus two twin ...

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Property Type

Kissimmee Villa

"Home away home."

We enjoyed 10 nights here late July. Karen is amazing to work with. Communication is number 1. Very safe and quiet within a gated community. This was just the kind of place we were looking for, cozy, ...

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Key Amenities

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

About this property

This fantastic 5 bedroom, 4 bath Vacation Villa offers all of the conveniences of home and everything you need for a fun family vacation including a Private Screened-In Pool, Outdoor Spa, Games Room, Fully Equipped Kitchen, Free Wireless High-Speed Internet, Full Size Washer/Dryer, Coffee Maker and Microwave. ...

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Property Type

Kissimmee Villa

"Safe, Clean and Quiet"

We stayed at this beautiful home in March, 2023. Within days of returning home I reserved it for next year. It was extremely clean - I felt very safe in this quiet community. Pool was lovely and worth ...

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4 BR | 3 BA | Sleeps 8 | Quick View

1

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

$200

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

4 Bedroom /3 Bath / Pool & Spa Vacation HomeCONTACT US AND REQUEST A DETAILED QUOTE !! No Booking Fees - Book Direct with the HomeownerCheck our Reviews on VRBO - Property #284051

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Property Type

Kissimmee House

"Awesome"

Thank you Awesome Would do again Very close to everything Great pool sand hot tub Felt safe Thank you again

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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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3 BR | 2.5 BA | Sleeps 6 | Quick View

1

Distance to park: 5 miles to Disney Animal Kingdom

$142

avg/night

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Key Amenities

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

About this property

Our Disney World themed townhome is located in the beautiful Emerald Island Resort. It is a gated community minutes from Disney and all of the main attractions in Kissimmee and Orlando. You will see we have decorated the home with Mickey Mouse and Animal Kingdom (we even have the same carpet upstairs ...

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Property Type

Kissimmee Townhome

"Great stay!"

We had a great stay at this home. Great location, beds were comfortable, and everything was well stocked to make this our home for the week.

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Key Amenities

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

About this property

"Kids and adults love the game room. Really cool. Movie theater in the converted garage is incredible - better than being at a regular movie theater. And, maybe your biggest treat will be the poolside theater. Very pretty and comfortable home and full of fun." Keith C.LOOKING for an incredibly ...

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Property Type

Kissimmee House

"Great spot! Exactly as described!"

Terrific house. Has everything you need. All the electronics were working as they should. The theatre room and the outdoor pool/tub were the highlights. When I had question about the place while I was there, ...

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Key Amenities

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

About this property

Our beautiful 3000sq 5 Bed, 4 Bathroom home is located on a generous corner plot. With a south facing Pool and stunning views over the second tee of the Arnold Palmer Golf Course on Reunion ResortThe open plan living area is comfortably furnished and has a wood look tiled floor. Flat screen tv. ...

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Property Type

Kissimmee House

"Loved this place"

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

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Key Amenities

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

About this property

Ready for an ultra-special Disney area vacation? You’ll have everything you dreamed of in this luxury villa with 12 bedrooms! The large screened lanai with a built-in pool and hot tub will fast become one of everyone’s favorite gathering spaces, along with the dedicated theater room with seating ...

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Property Type

Kissimmee Villa

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6 BR | 4 BA | Sleeps 14 | Quick View

4.9 rating on other travel sites

$358

avg/night

View Details

Key Amenities

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

About this property

"When you walk through the front door, you immediately walk into fun with the adult area's pool table and large TV. And that's just the beginning. There's an awesome game room, 3 themed bedrooms, and in the pool area are a poolside theater and bar counter with TV. You will be totally entertained ...

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Property Type

Kissimmee House

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Key Amenities

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

About this property

This stylish place to stay is perfect for group trips. It is fully stocked Kitchen, Private pool and only 3 minutes walk to the club house amenities. This open air townhouse has two master bedroom with very comfortable beds. The house has a Master bedroom on the first floor with a King size bed, 1 Master ...

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Property Type

Kissimmee Townhome

"Perfect Stay"

Great location! Did several day trips to fun towns/attractions. Solara Resort was a bonus - nice gym and pool. Handy to have a restaurant/bar - Staff was super friendly. Would stay here again!

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7 BR | 4.5 BA | Sleeps 14 | Quick View

9

Distance to park: 3 miles to Disney World Parks

$243

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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6 BR | 4 BA | Sleeps 14 | Quick View

4.9 rating on other travel sites

$338

avg/night

View Details

Key Amenities

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

About this property

ARE YOU LOOKING for a just renovated beautiful vacation home that is full of fun? This is it . . . Avenger theme game room - South facing (plenty of sun) private saltwater pool and spa - Poolside movie theater - Themed kids bedrooms - And much more. Also, it's located in Windsor Hills Resort - the closest ...

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Property Type

Kissimmee House

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6 BR | 4 BA | Sleeps 14 | Quick View

LAST MINUTE DEAL 9/19 - 10/31: Discounted Rates for Fall Season check out our calendar!

$309

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

3 BR | 2 BA | Sleeps 6 | Quick View

13

Distance to park: 2 miles to Disney World

$138

avg/night

View Details

Key Amenities

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

About this property

Welcome to Escape by KLMJ Sunshine! This is a completely renovated 3-bedroom condo in the beautiful gated community of Windsor Hills, just two miles from Disney. Enjoy the massive heated pool, brand new water park, large playground, tennis and basketball courts, mini-golf, arcade, movie theatre, fitness ...

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Property Type

Kissimmee Condo

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Key Amenities

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

About this property

Immerse yourself in this much-beloved world and find the hidden easter eggs in the room as you open the door to Potter's Place. This charming open-concept themed home is ready to make you feel revitalized. From a cleaned, well-maintained space to a fully equipped kitchen to cozy beds and pillows, your ...

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Property Type

Kissimmee Townhome

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4 BR | 3.5 BA | Sleeps 10 | Quick View

11

Distance to park: 5 miles to Animal Kingdom

$105

avg/night

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Key Amenities

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

About this property

Enjoy Orlando, Florida, home to Disney World, Sea World, Universal Studios, and Islands of Adventure, in style. Our home is within minutes of all the Orlando attractions, golf courses, shopping, and exciting night life. Our richly appointed vacation Townhouse will give you luxurious living and a vacation ...

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Property Type

Kissimmee Townhome

"All together"

Great place to stay. Near to the parks. My family enjoyed a lot. Comfortable place for large families

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Key Amenities

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

About this property

Welcome to a magnificent 5-bedroom, 5-bathroom in the prestigious Storey Lake community. As you step into this stunning home, prepare to be captivated by its elegant design and exceptional features, promising an unforgettable vacation experience.The ground floor invites you into a spacious bedroom ...

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Property Reference FG_800ER Sunset Mansion This home has been fully renovated in May 2023. With all new flooring and paint throughout the home, all new furniture, mattresses, pillows, bedding, dinnerware and kitchenware.This magnificent 9 bedroom estate home is located in Formosa Gardens Estates ...

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Property Type

Kissimmee House

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Key Amenities

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

About this property

Guests have private access to the entire home including all outdoor areas, the private, sparkling heated pool and spa as well as the in house laundry and fun game room. Also included with your stay is full use of the amazing Veranda Palms Resort amenities on offer including: Gated entrance with 24-hour ...

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Property Type

Kissimmee Villa

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Key Amenities

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

About this property

The Hidden Mickey BnB is the perfect spot for your Florida vacation! Located just 5 miles from the Walt Disney World Resort in a beautiful resort community.The house has EVERYTHING you need for your dream vacation:* Private Pool * Private Hot Tub (Heat Included) * Covered and Screened in Patio * ...

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Private pool

About this property

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

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Property Type

Kissimmee House

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6 BR | 4 BA | Sleeps 14 | Quick View

4.9 rating on other travel sites

$273

avg/night

View Details

Key Amenities

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

About this property

"This was an ideal spot to relax and enjoy what Florida has to offer. The bedrooms were comfortable and clean. The theater room was great for adults and kids to enjoy movies and video games. Would definitely stay here again!! " Cynthia TARE YOU LOOKING for a beautiful totally renovated ...

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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

Recently renovated luxury property now available for your next Orlando adventure. Two themed kids bedrooms each sleep 4 kids (or adults), five oversized bedrooms each with king size beds. All bedrooms feature en-suite bathrooms. Two bedrooms downstairs, 5 bedrooms upstairs (including the two themed bedrooms). ...

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Property Type

Kissimmee House

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8 BR | 6 BA | Sleeps 16 | Quick View

4.8 rating on other travel sites

$416

avg/night

View Details

Key Amenities

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

About this property

"Great house, even better than the listing indicated. Great pool and hot tub, huge living area and plenty of space for a group of 14. The movie room was great, with a highlight of watching Space X launch a rocket on the big screen, then walking to back yard to watch it in the sky. The upstairs is ...

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Property Type

Kissimmee House

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Key Amenities

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

About this property

Welcome to Islands of Magic at Emerald Island Resort - only 5 miles to Walt Disney World theme parks!FORMAL SEATING & DINING AREASWhen you enter the house, you will see the formal seating area and a formal dining area to your right. The formal seating area has a sectional sofa with views of ...

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Property Type

Kissimmee House

"Best Vacation Home"

Renting this beautiful house was a breeze!! We were very happy that after checking out at least a dozen houses, we all agreed on this one!! We wanted a big house with lots of bedrooms/bathrooms! We got ...

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3 BR | 2 BA | Sleeps 6 | Quick View

2

Distance to park: 1 miles to Disney Animal Kingdom

$97

avg/night

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Key Amenities

  • Air conditioning
  • 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

"Recommended"

This is a beautiful property to stay in. Very clean and neat. I truly recommend it to anyone who wants to be near the main attractions. Everything is very close. You have gift shops, souvenirs shops, target ...

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5 BR | 5 BA | Sleeps 10 | Quick View

4.8 rating on other travel sites

$345

avg/night

View Details

Key Amenities

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

About this property

"We loved staying at this house, it is in a convenient location to the parks, and groceries are nearby. The house was clean and well-equipped. Our grandkids really enjoyed the themed rooms, the game room, and of course the pool! The gated resort community is awesome, and the water park/big pool were ...

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Property Type

Kissimmee House

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6 BR | 6 BA | Sleeps 12 | Quick View

1

$450

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

The Classic Disney Villa in the prestigious Encore Resort at Reunion awaits you and your family for the ultimate vacation. Step inside this uniquely themed villa located minutes from Disney World & create lifelong memories! This fully equipped villa boasts 2,831 sq. ft., 6 bedrooms and 6 bathrooms ...

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Property Type

Kissimmee Villa

"A Vintage Disneyland Classic"

Love how everyone had their own bathroom. The themeing is spot on. Details, Details, Details The kids loved the Peter Pan room with arcade games. And us adults love the Adventureland movie lounge. And ...

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Key Amenities

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

About this property

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

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Property Type

Kissimmee House

"Great place, nice price!"

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

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

The main spaces of the home:- 3 BEDROOMS & 2 BATHROOMS to accommodate 8 guests as such: (All bedrooms have flat-screen SMART TVs.)BEDROOM 1: 1 King bed (master suite 1st floor) BEDROOM 2: 1 King bed (2nd floor) BEDROOM 3: 2 Full beds (2nd floor)- MAIN LIVING ROOM features plush ...

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Property Type

Kissimmee Townhome

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Key Amenities

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

About this property

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

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Property Type

Kissimmee Villa

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4 BR | 4 BA | Sleeps 8 | Quick View

10

Distance to park: 2 miles to Disney

$258

avg/night

View Details

Key Amenities

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

About this property

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

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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

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

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Property Type

Kissimmee House

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5 BR | 5 BA | Sleeps 12 | Quick View

5.0 rating on other travel sites

$372

avg/night

View Details

Key Amenities

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

About this property

"We just got home from our 1 week stay and are already wishing we were back! The home was beautiful and looked just as pictured in the listing. We were very close to the parks and shopping but yet felt like we were secluded. The neighborhood is wonderful and was great for walks. The pool and game ...

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Property Type

Kissimmee House

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6 BR | 5.5 BA | Sleeps 18 | Quick View

1

Distance to park: 4 miles to Animal Kingdom

$324

avg/night

View Details

Key Amenities

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

About this property

Pack your bags for an unforgettable trip to the happiest place on Earth at 'Minnie's Maingate Manor'! Minnie’s Maingate Manor is a 6-bedroom, 5.5-bathroom vacation rental home with themed bedrooms, sleeping accommodations for 16, and a private screened-in pool and spa. This Florida escape is perfect ...

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Property Type

Kissimmee House

"Amazing"

Such an amazing home! You want for nothing. My grandkids were in awe of the dress up clothes.They loved the games room. It was very clean. The pool was warm and they had so many beach towels and pool toys. ...

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4 BR | 2 BA | Sleeps 7 | Quick View

4

$117

avg/night

View Details

Key Amenities

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

About this property

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

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Property Type

Kissimmee House

"Best vacation ever"

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

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • 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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Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Beautiful Lagoon Style Pool with water view! Stay close to the excitement and discover amazing things to do in Orlando! Just 10 minutes away, visit the world's most visited attraction, the Walt Disney World® Resort. Literally, ride the movies at Universal Studios Florida® or take your family on ...

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Property Type

Kissimmee Villa

"Great place to stay."

The villa is very convenient for shops and eating places - Walmart, Aldi and a large number of restaurants are less than 10 minutes away. The villa is also easily accessible to all the theme parks and shopping ...

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Key Amenities

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

About this property

Sunset Lakes is ideally situated, just 4 miles from Disney World and a short drive from other popular attractions like Universal Studios, Sea World, and more. The proximity to Orlando and other destinations makes it a prime choice for travelers. The gated community offers various amenities such as a community ...

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Property Type

Kissimmee House

"Home away from home!"

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

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3 BR | 3 BA | Sleeps 9 | Quick View

2

Distance to park: 5 miles to Animal Kingdom Lodge

$145

avg/night

View Details

Key Amenities

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

About this property

**The private pool is not heated unless requested by the guest. Pool heating is available for an additional fee of $10.00 per day.**Create unforgettable memories in this beautifully decorated townhouse, located in the lovely Windsor Palms Resort, just minutes from Disney parks and Universal. This ...

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Property Type

Kissimmee Townhome

"Perfect place to stay and close to the theme parks"

The unit was super clean and the kitchen was supplied with everything you need to prepare meals when dining in. It is great location to Disney as well as our go-to restaurant – Bahama Breeze! There ...

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4 BR | 3 BA | Sleeps 8 | Quick View

16

Distance to park: 4 miles to Disney

$149

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Magical Dreams come true in our elegant private 4 bedroom villa, 3 bathroom, all located on one floor, Quiet upgraded comforts of home and luxuries of an exceptionally rated vacation resort/hotel. Newly resurfaced and freshly painted pool and spa is sure to impress. There will be no waiting in line ...

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Property Type

Kissimmee House

"Perfect rental for all of our needs!"

This was a Christmas vacation never to be forgotten! We had the time of our lives! My children, grandchildren and I enjoyed the comforts and privacy of a home where we could take in all the theme parks ...

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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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$302

avg/night

View Details

Key Amenities

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

About this property

Luxury vacation 5 bedroom home with a private pool. Wi-Fi, Swimming Pool . Relax in your resort-style vacation home in Windsor at Westside Mediterranean-themed community and enjoy resort-style amenities such as outside fireplace, resort-style pool, cover patio, lazy river, water playground, private cabanas, ...

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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

"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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8 BR | 6 BA | Sleeps 16 | Quick View

6
LAST MINUTE DEAL 9/15 - 10/27: Do Not Miss this Amazing Deal - 15-35% Off this Gorgeous 8 Bed Pool Home - Book Now!

$273

avg/night

View Details

Key Amenities

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

About this property

Windsor at Westside - Kissimmee, Florida is an upscale gated community located just 10 minutes from Walt Disney World. This luxury home sits nestled just outside of Orlando, Florida and has quickly become one of the most desired locations in the Orlando area. During your stay you will enjoy this well ...

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Property Type

Kissimmee House

"Awsome family vacation home"

The owner Jane was easy to work with. House was everything described. Totally furnished and great for the 7 kids we had with us ages 15,8,7,6,6,5 and 3. Pool was warm Beds were comfy, property manager ...

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DEAL

8 BR | 6 BA | Sleeps 16 | Quick View

4
LAST MINUTE DEAL 9/19 - 10/31: Special Discount 15-35% Off this Gorgeous 8 Bed Pool Home in Windsor at Westside - Don't Miss Out!

$302

avg/night

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Key Amenities

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

About this property

Windsor at Westside - Kissimmee, Florida is an upscale gated community located just 10 minutes from Walt Disney World. This luxury home sits nestled just outside of Orlando, Florida, and has quickly become one of the most desired locations in the Orlando area. During your stay, you will enjoy this well-appointed ...

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Property Type

Kissimmee House

"Champion gates"

Beautiful house, nice and spacious Clean, private, easy to book. Had 13 people there, 3 families, could have stayed longer

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DEAL

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

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

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Property Type

Kissimmee Townhome

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$389

avg/night

View Details

Key Amenities

  • Private pool

About this property

Bring the whole family to this great place with lots of room for fun. You will love it

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Property Reference RVH_088RRThe Legends Villa at Reunion Vacation HomesSpend your next vacation in comfort at Villa Tuscana. This five-bedroom, Tuscany-inspired home, provides guests with some of the best views in Reunion Resort. As soon as you exit your car in the driveway, you are greeted with ...

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Property Type

Kissimmee House

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Kissimmee Vacation Rentals

Kissimmee Weather

 | 

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

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


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

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

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

Top Tips for Traveling to Kissimmee Rentals


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

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

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

Things to Do Nearby Kissimmee House Rentals


Some of the most popular natural areas around Kissimmee are the swamps, which are located in major local bodies of water like Lake Tohopekaliga (known around town as Lake Toho). At Boggy Creek Airboat Adventures, you can experience the swamps from the water and get the thrill of a lifetime on an airboat driven by a local wetlands expert. Get up-close views of gator ponds, discover precious gemstones, and then grab a delicious lunch with the family at Boggy Bottom BBQ! 
Looking to explore a piece of history during your trip to Kissimmee? Medieval Times Dinner & Tournament allows visitors to step into the 11th century for an evening of authentic feasting, jousting, and sword fighting in true medieval style! Enjoy a delicious four-course meal, incredible performances, and a truly unforgettable experience for the entire family. 
Any vacation to Kissimmee isn’t complete without a trip or two to Old Town, a popular outdoor attraction with opportunities for shopping, dining, and family fun. Old Town is made up of an 18-acre stretch of classic city attractions, including the Old Town Ferris Wheel, the Great Magic Hall, and Mortem Manor, a year-round haunted house that is open for visitors to explore.

Kissimmee Annual Events


Kissimmee is a vibrant area with lots of annual festivals and events to enjoy in and around the city throughout the year. Kissimmee locals and visitors alike flock to the Ford Cuban Sandwich Festival each May near downtown Kissimmee, which celebrates the colorful history of Cuban cuisine in the area. Watch as local dining professionals attempt to build the world’s biggest Cuban sandwich during the event! 
The Ford Taste of Latino Festival is another local opportunity to celebrate and experience the best in authentic Latin cuisines in Kissimmee. The event features a contest to find the Top Latino Chef as well as plenty of live music and dance performances to enjoy as you taste a variety of Latin dishes. 
Not sure if you’ll be in town for any of Kissimmee’s larger annual events? You can enjoy Show Car Saturday Nights every Saturday night in the city on Margaritaville Boulevard. Check out the city’s best classic cars from a variety of eras and enjoy the plethora of delicious eateries and exciting shops located along the boulevard.

Wining and Dining in Kissimmee  


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

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

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


FAQ

How many vacation rentals are there in/around Kissimmee?

There are 406 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 $86 per night with an average price per night of $228.

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