Kissimmee Vacation Rentals

(335 rentals)
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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

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

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Property Type

Kissimmee House

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3 BR | 2 BA | Sleeps 8 | Quick View

13

Distance to park: 12 miles to All Disney Theme Park

$109

avg/night

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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

"New Years Getaway"

Stayed month of January..Villa was very well equipped and very comfortable.Location was fantastic being so close to all attractions. Would highly recommend for anybody to stay..

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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
  • Pet friendly
  • Pool
  • Private pool

About this property

Embark on the ultimate Disney vacation at Jurassic Encanto! With elegantly designed thematic rooms, this spacious home provides ample room for larger groups and multiple families. Compete in the epic game room or take in the lake views while relaxing by the luxurious private pool and spa amidst world-class ...

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Property Type

Kissimmee House

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4 BR | 2.5 BA | Sleeps 8 | Quick View

$154

avg/night

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Key Amenities

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

About this property

Bedroom 1 queen bedBedroom 2 King bedBedroom 3 double bedBedroom 4 2 single bedsUse of clubhouse, pool, gym, pool table, cinema room wi-fi

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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_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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Key Amenities

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

About this property

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

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Property Type

Kissimmee Villa

"Family Christmas Vacation"

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

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5 BR | 5 BA | Sleeps 12 | Quick View

2

Distance to park: 2 miles to Walt Disney World

$305

avg/night

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Key Amenities

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

About this property

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

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Property Type

Kissimmee House

"Disney get away"

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

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Key Amenities

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

About this property

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

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

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

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Property Type

Kissimmee House

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4 BR | 3 BA | Sleeps 8 | Quick View

16

Distance to park: 4 miles to Disney

$143

avg/night

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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
  • Private pool

About this property

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

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Property Type

Kissimmee Bungalow

"Hidden gem"

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

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8 BR | 5 BA | Sleeps 20 | Quick View

2

$383

avg/night

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Key Amenities

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

About this property

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

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Property Type

Kissimmee House

"Emerald Island Resort"

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

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Key Amenities

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

About this property

Welcome to our magical Disney-themed retreat! Nestled in the heart of the Westside at Windsor Resort, our cozy and charming home is the perfect place for you and your loved ones to experience all the wonders of the happiest place on earth. Whether you're planning a family vacation or a romantic getaway, ...

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Property Type

Kissimmee Villa

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6 BR | 5.5 BA | Sleeps 18 | Quick View

56

Distance to park: 4 miles to Animal Kingdom

$159

avg/night

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Key Amenities

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

About this property

Some of the best features of this house from Guest Reviews • Beautiful Vinyl Plank Flooring in all bedrooms, halls and on the steps • Less than a 4-mile drive to Disney World’s Animal Kingdom Theme Park • Two leather couches and a recliner with a total of 5 power reclining seats • ...

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Property Type

Kissimmee House

"Wonderful Disney family home"

This is the second time my family and I have rented this lovely home and will do so again. At one time there were 12 of us, all adults, and nobody felt cramped. The covered lanai around the beautiful pool ...

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Key Amenities

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

About this property

Come to Livin' Large at Windsor Westside with 100% Free Resort amenities!* Private Heated Pool & Spa * FREE Arcade! Yes, play all you want for Free! * Poolside Tiki Bar & Grill * FREE Resort w/ Heated Lazy River * Kids water playground & slides * FREE 400MB Wifi * Roku: 11 ...

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Property Type

Kissimmee House

"Exceptional Service and Stay!"

Our family of 18 had an amazing week in "Livin' Large"! The hosts thought of everything and provided so much more than other places normally do - a thoughtful welcome bucket filled with goodies, laundry ...

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Key Amenities

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

About this property

GroovyMouseHouse, 8-bedroom luxury villa with private pool and spa, located at The Encore Resort in Reunion, is perfect for families wanting an unforgettable stay in Orlando.Conveniently located close to Disney theme parks, restaurants, supermarkets and golf courses, it benefits from all the amazing ...

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Property Type

Kissimmee Villa

"Johnson trip of a lifetime"

This home was awesome and perfect for our large family. The 16 of us were very comfortable in this beautiful home. The grandkids loved the pool, game room and PS game console. The proximity to the Disney ...

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4 BR | 3 BA | Sleeps 8 | Quick View

Distance to park: 3 miles to Disney Parks

$124

avg/night

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Key Amenities

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

About this property

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

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Property Type

Kissimmee House

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Key Amenities

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

About this property

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

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Property Type

Kissimmee Villa

"Love our Stay"

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

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3 BR | 2 BA | Sleeps 7 | Quick View

Distance to park: 6 miles to Disney World

$159

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

Sophisticated, stylish, and serene surroundings await at this cozy home in North Kissimmee. Relax in the spacious living room, enjoy gourmet meals in the executive dining room or bask in the Florida sunshine as you work, rest, and play! After a busy day, enjoy your downtime with an immersive experience ...

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Property Type

Kissimmee House

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Key Amenities

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

About this property

5 star property! Reviews say it all!You will be delighted by the great combination of lux comfort and Disney theming for the whole family! Located in the upscale Emerald Island Resort gated community, our newly remodeled home is a welcome oasis to return to after a long day enjoying the parks. Relax ...

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Property Type

Kissimmee House

"Where to even start!!!"

Whenever we travel, I read reviews. Some reviews you wonder about because no two people seem to see it the same way. However with this house everyone seemed to love it and after staying there I can see ...

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9 BR | 6 BA | Sleeps 18 | Quick View

3

Distance to park: 8 miles to Disney's Animal Kingdom Theme Park

$507

avg/night

View Details

Key Amenities

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

About this property

Welcome to Magic Moments, a perfect retreat only 8 miles from Disney for large gatherings with friends, family, work groups, or sports teams. Our spacious 9-bedroom villa, located just 20 minutes from Disney, offers an unforgettable experience. With a private pool, hot tub, BBQ, and themed bedrooms, including ...

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Property Type

Kissimmee Villa

"Amazing family oriented home with everything we needed and more!"

We rented this house for a family vacation and everyone was so impressed with the size of the home and everything it had to offer. The pool area was perfect for kids and the adults. The ensuite was off ...

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4 BR | 3 BA | Sleeps 8 | Quick View

15

Distance to park: 3 miles to Mgm

$125

avg/night

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Key Amenities

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

About this property

Beautiful 4 bedroom /3 bath private villa only 3 miles to Disney and other parks. Including heated pool/jacuzzi and game room. Free wifi and phone use in USA and Canada and PR. Fully furnished with all kitchen needs . Greatest location to shopping , all major restaurants and stores including supermarkets ...

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Property Type

Kissimmee Villa

"Great Location!"

This location is great! A few minutes drive to good restaurants (Carrabbas, Olive Garden, Outback, Bonefish Grill, Texas Road House, Red Lobster) and all the usual fast food places. This house is well ...

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Key Amenities

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

About this property

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

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Property Type

Kissimmee House

"Disney Escape"

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

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7 BR | 4.5 BA | Sleeps 14 | Quick View

10

Distance to park: 3 miles to Disney World Parks

$236

avg/night

View Details

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

"Roomy comfy place"

Marisela and Kevin are very engaged owners. Very responsive in communicating. Everything we needed was in the house. Plenty of space and seating inside and out. Clean and comfortable. Or second time staying ...

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Key Amenities

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

About this property

Disney Wood Wonderland*** 7 miles from Disney popular attractions Disney's Animal Kingdom Theme Park and Epcot. Walt Disney World and Magic Kingdom Park.

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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

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

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Property Type

Kissimmee House

"Nice home, spacious and clea"

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

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Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

This Disney Villa is a fully furnished home and is one of the best kept turnkey properties you will find in Indian Creek ! Has an airy open floor plan, lots of light. Enjoy the crystal clear South facing pool and the covered lanai on your sunny and warm Florida holidays.This luxurious private home ...

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Property Type

Kissimmee Villa

"Awesome place to stay!"

We are currently on vacation at this home. We have rented this many times through the years. Kim the owner will do anything to ensure you have the best vacation. House is clean, the pool is beautiful ...

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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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Key Amenities

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

About this property

Take the whole family to this fantastic place with many areas to have fun.

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Property Type

Kissimmee House

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Key Amenities

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

About this property

Property Reference #RVH_1009RWelcome to Radiant View! This gorgeous 5 bedroom, 5 bath pool home is located in Reunion Resort in the Homestead neighborhood of the exclusive Reunion Resort. A truly beautiful place with world-class amenities such as infinity pools, a full-service spa, scenic walking ...

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Property Type

Kissimmee House

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3 BR | 2.5 BA | Sleeps 8 | Quick View

1

$123

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

About this property

You have arrived in the "Vacation Capital of the World" and you're going to love staying in our luxury, 3 bedroom, 2.5 bath, fully equipped vacation townhouse rental situated near DisneyWorld and all other theme park attractions. The property rental is located within the resort community ...

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Property Type

Kissimmee Townhome

"Beautiful Condo! Exactly as shown!"

We are a retired couple who stayed for 3 months from Jan to March. Beautiful Condo, exactly as pictured. Furniture is very comfy. Close to all attractions. We felt very safe. Publix and Walmart are ...

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Key Amenities

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

About this property

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

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Property Type

Kissimmee Villa

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Key Amenities

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

About this property

ASK ABOUT SPECIAL REDUCED NIGHTLY RATE FOR REMAINING SUMMER 2024 DATES!Luxury 4 BR / 3 Bath Villa with Private Pool in Gated Resort Close to DisneyWelcome to the Disney Getaway Villa, located in the beautiful and luxurious Emerald Island Resort! This villa is “the one” for your magical ...

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Property Type

Kissimmee House

"March 2024 Family Vacation"

We enjoyed 3 wonderful weeks at Disney Getaway Villa. The villa was very clean, well maintained and equipped with everything you need. It is close to all amenities such as groceries, dining ,Disney , shopping ...

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4 BR | 2 BA | Sleeps 8 | Quick View

6

Distance to park: 7 miles to Walt Disney World

$205

avg/night

View Details

Key Amenities

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

About this property

Welcome to our Florida villa, the Lake House at Sunset Lakes. The Lake House at Sunset Lakes is an upscale rental villa in the greater Orlando Florida area, minutes away from Disney’s Magic Kingdom and theme parks, your choice of fine golf courses and many other attractions. This four bedroom house ...

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Property Type

Kissimmee Villa

"Perfect vila"

The lake house is a very spacious villa All the amenities you could ever need It's in the perfect location 10mins to Disney parks supermarkets very close We did not have any problems so no need to contact ...

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Key Amenities

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

About this property

More info can be found at property website www. dolphinvillas-orlando dot com or directly click the links at end of this page.For over 15 years, Dolphin Villa - Doral Woods has been listed with Holiday Lettings/Trip Advisor, receiving 5-star reviews. If you're interested, we can provide you ...

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Property Type

Kissimmee Villa

"Recommend!!"

Great experience during our recent stay at Dolphin House! Clean, spacious and everything you need to have a relaxing time. The welcome gift basket was such a thoughtful and helpful idea. Much appreciated! ...

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Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Beautiful south facing lakeside villa with electrically heated pool option. Great location for all the theme parks, Disney 20 mins, Seaworld 15mins, Universal 30 mins and Cocoa Beach/Kennedy Space Centre 45 mins. Local English management contact and fully inspected/licensed by the Florida Hotels Board. ...

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Property Type

Kissimmee Villa

"Had a great stay"

Angie's was clean and cozy with lots of space. Location was very good and the pool was great for families and adults.

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8 BR | 4 BA | Sleeps 16 | Quick View

12

Distance to park: 6 miles to Disney

$382

avg/night

View Details

Key Amenities

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

About this property

AMAZING Pool Deck Extension cira 2023! Its the BIGGEST pool deck at the resort! Plus JAW DROPPING, Fancy, Fun, Fountain Jets w/ LED lighting, high-end glass tile & a Mickey Mosaic giving you an ULTIMATE luxury pool experience. This SALT WATER POOL/SPA will leave your skin feeling soft w/ no eye-sting ...

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Property Type

Kissimmee Villa

"Amazing house"

We had an amazing time and the house had everything we needed and wanted for our vacation in Florida. If you are going to Florida we recommend this house. It's has a great pool and patio and can accommodate ...

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4 BR | 3 BA | Sleeps 10 | Quick View

9

Distance to park: 3 miles to Disney World

$147

avg/night

View Details

Key Amenities

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

About this property

4 Bedroom (2 master suites) 3 full baths, separate living and family rooms, will sleep up to 10 people. Decor in this house is Timeless!!The game room includes an 8 foot pool table, foosball table, poker table. The private pool deck provides a distant view of the nightly DisneyWorld fireworks display ...

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Property Type

Kissimmee House

"Wonderful home!"

My family and I stayed here for a week and would definitely return. The home was spacious and clean. because it sat high, the back was private and did not look into another yard. The owner was very responsive ...

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3 BR | 2 BA | Sleeps 8 | Quick View

3

Distance to park: 5 miles to Disneyworld and Disney Springs

$97

avg/night

View Details

Key Amenities

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

About this property

You have arrived in the "Vacation Capital of the World" and you're going to love staying in our luxury, three bedroom, two bath, fully equipped vacation condo rental situated near DisneyWorld and all other theme park attractions. The property rental is located within the resort community ...

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Property Type

Kissimmee Condo

"Holiday season in Kisimmee"

Excellent vacation in Florida Sunsations. Condo is close to main attractions , restaurants and airport. Excellent communication with owner Barry Paulus. Will return next year.

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8 BR | 4.5 BA | Sleeps 16 | Quick View

21

Distance to park: 3 miles to Disney's Animal Kingdom

$286

avg/night

View Details

Key Amenities

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

About this property

Thanks for stopping by to check out Mickey's Mansion, an 8 bedroom, 4.5 bath home in the heart of all the action, yet quiet and peaceful. In fact, Emerald Island is one of the closest resorts to the Disney parks! There's nothing better than being in the Florida sunshine to relax but have fun ...

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Property Type

Kissimmee House

"Awesome stay at Mickey's Mansion"

First let me start out by saying, as a family we do Florida for approximately 5 weeks at a time every year. With that being said our hosts were the most accommodating that we had ever had. The house was ...

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Key Amenities

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

About this property

Property Reference # RVH_1085RWelcome to Magical Moments, the luxurious vacation home that awaits you on your next visit to the Central Florida area. This highly sought-after estate boasts seven spacious bedrooms and over 6600 square feet of air-conditioned living space, offering ample room for everyone ...

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Property Type

Kissimmee House

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4 BR | 3 BA | Sleeps 10 | Quick View

Distance to park: 2 miles to Walt Disney World

$193

avg/night

View Details

Key Amenities

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

About this property

Our luxury villa is perfectly located, just 2.5 miles away from Walt Disney World's front door. This amazing four bedroom/three bath/fully furnished villa has room for 10 to sleep, dine, and relax in comfort. After the parks or dinner, retreat to your own private pool for a refreshing swim, or the ...

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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

Experience the magic of Disney World, Universal Studios, and the very best of Orlando from the comfort of this luxury private resort! Conveniently located in Storey Lake Resort, enjoy the the resort style amenities or explore the world class attractions in Orlando and Kissimmee. Minutes from Disney World, ...

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Property Reference # RVH_1049RWelcome to Whisper Way Paradise! This beautiful 3 bedroom, 3 bathroom condo is located in The Villas South neighborhood of Reunion Resort (near the center of Reunion Resort). This condo is just steps away from one of Reunion's many playgrounds.The spacious living ...

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Property Type

Kissimmee Condo

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Key Amenities

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

About this property

Property Reference #RVH_1069RFor those looking to find a home loaded with luxury, fun, and great views, look no further than Fairway Ridge Joy. This perfectly planned five-bedroom golf view home has everything to offer under one roof, perfect for a great getaway or vacation!From the moment you ...

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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

Escape to a magical 8-bed 6-bath retreat for up to 16 guests at the Windsor at the Westside resort community. This is an entire home rental. Super Mario game room, Beauty and the Beast dining, Paris-themed kitchen, Guardians of the Galaxy primary bedroom. Upstairs: Hollywood, Pirates, Mickey Mouse, Princesses, ...

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Property Type

Kissimmee Villa

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Key Amenities

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

About this property

Nestled over at the Bella Vida Resort, just a measly 8 miles away from the magical kingdom of Walt Disney World (yeah, we're basically neighbors!), this 12-bedroom vacation home has room for your whole crew. It can host up to 30 guests at a time, so bring the whole fam!Let's kick things ...

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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

Beautiful 4 bedroom/3 bathroom house in the luxurious Emerald Island Resort - Only ~ 4 miles from Disney & close to other major attractions! This home is equipped with a heated private pool, spa & game room. There is a large SMART TV in the living room & in each bedroom. There are queen beds ...

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Property Type

Kissimmee House

"Clean, comfortable and aesthetically pleasing"

We stayed for about 2 weeks. Home is extremely comfortable with enough of everything we needed. The owners are easy to work with and the property management very responsive. The location is superb for all ...

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Key Amenities

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

About this property

This vacation home isn't just a place to stay; it's your own personal wonderland. Step outside, and you'll be greeted by a backyard oasis that dreams are made of – a sparkling swimming pool with a spillover jacuzzi hot tub and a sun-soaked sundeck, complete with lounging chairs that ...

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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 335 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 $46 per night with an average price per night of $200.

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