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Kissimmee Vacation Rentals

(219 rentals)
Kissimmee Villa
Sleeps 12, 6 bedrooms, 5 bathrooms
1 review

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

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to your elegant vacation retreat in Emerald Island Resort, Orlando, FL! This spacious 6-bedroom, 5-bathroom home has been recently upgraded and is located just 3 miles from Walt Disney World and only minutes from top attractions like Universal Studios, SeaWorld, and Old Town Kissimmee. With plenty...

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Featured review

"Wonderful stay"

We rented this property for the month of February 2025. As a family of 9 with Grandparents, parents and 2 young grandchildren, we found the villa to be spacious without feeling cavernous. It was well...

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$250
avg per night
Kissimmee House
Sleeps 10, 4 bedrooms, 3 bathrooms
5 reviews

Key Amenities

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

About this property

POOL SAFETY FENCE!!!! - Florida law requires that doors leading out to the pool have an alarm. THAT IS NOT ENOUGH!. If you are traveling with children please make sure the house you are renting has a pool safety fence.WE HAVE A NO PET POLICY FOR ALERGY REASONSThis Beautiful home is well situated,...

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Featured review

"Fabulous home"

The home was comfortable for our big group. The kitchen was well stocked with utensils, cookie sheets, and bowls. We were able to make our Christmas brunch! The game room was fun for the teens. The location...

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$167
avg per night
Kissimmee House
Sleeps 10, 4 bedrooms, 4 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

If you’re searching for Orlando vacation rentals and want something unique, this home fits the bill! As soon as you pull up, you’ll notice the incredible Mediterranean design, which makes this house stand out from all the others on the block. Inside, you’ll have access to all kinds of...

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$241
avg per night
Kissimmee Villa
Sleeps 8, 4 bedrooms, 3 bathrooms
19 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

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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Featured review

"Excellent Place to stay"

We had a wonderful stay! The place was very comfortable, well-equipped with all the amenities we needed, and perfectly located. It’s close to Disneyland and other major attractions, with Walmart and gas...

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$139
avg per night
Kissimmee Condo
Sleeps 8, 3 bedrooms, 2 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Situated in Orlando, within 8 km of Disney's Hollywood Studios and 9 km of Disney's Boardwalk, Windsor Hills Apartment By A3G offers accommodation with free WiFi, air conditioning, a fitness centre and a shared lounge. This property offers access to a patio and free private parking.The apartment...

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Featured review

"Vacation"

We stayed there in 2024 and it was amazing to stay there and experience all that fun. We will definitely be back again. Thanks again

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$146
avg per night

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Kissimmee House
Sleeps 14, 7 bedrooms, 4.5 bathrooms
16 reviews

Distance to park: 3 miles to Disney World Parks

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Spacious 7-Bedroom Orlando Vacation Home – Perfect for Families & Large Groups! Bring the whole family to this huge 7-bedroom, 4.5-bath vacation rental just minutes from Orlando’s world-famous attractions! Comfortably accommodating up to 14 guests, this home is ideal for family reunions,...

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Featured review

"Kissimmee Stay"

My husband and I were able to stay the month of January and February at a home in Windsor Palms that is managed by Epic FloridaRentals. We had an amazing stay and we’re so impressed with how prompt the...

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$249
avg per night
Kissimmee House
Sleeps 9, 4 bedrooms, 2.5 bathrooms
12 reviews

Distance to park: 6 miles to Disneyworld

Key Amenities

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

About this property

Our villa is modern style furnished, has everything you would expect in a holiday home, 4 bedrooms, 2 with king-size beds, 1 with single bed´s, 1 with triple bunk bed all with private TV. 2 bathrooms, 1 guest toilet, fully equipped kitchen, etc. with ceran stove, fridge, oven, microwave, coffee...

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Featured review

"The way to go"

Very nice house. Pool heat price could be about 10 $ The extra cost hurts. Always need hangers.towels and a extra fridge in garage would be handy. Location close to shopping and restaurants Not good...

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$139
avg per night
Kissimmee Villa
Sleeps 14, 7 bedrooms, 6 bathrooms
4 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Introducing 101 Happy Memories Florida Villa, your gateway to unforgettable vacations in the heart of Formosa Gardens, just minutes from the enchantment of Disney World!Step into luxury with our private heated pool and spa, perfect for unwinding after a day of adventure. Thrill-seekers will love our...

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Featured review

"2nd time still a charm"

We enjoyed a stay here 3 years ago and we lucky enough to find it available again in 2024. We can't say enough except that the property was somehow even an improvement over the 1st time. This is a great...

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$312
avg per night
Kissimmee House
Sleeps 10, 5 bedrooms, 4 bathrooms
12 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to our stunning spacious 5 bedroom, 4 bath home located in the much sought after community of Tuscan Hills near DisneyThis beautiful home offers 2 masters en-suite bedrooms and 3 sitting rooms.Full air con and hi-speed WiFi throughout.The villa uniquely has 3 sitting rooms, two of...

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Featured review

"Amazing villa"

My family and I stayed at this wonderful villa for 5 nights. The house is very spacious,.clean and in a secured gated community. Watersong community is the best area for villa rentals close to Disney. We...

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$165
avg per night
Special Offer
Kissimmee House
Sleeps 16, 8 bedrooms, 6 bathrooms
2 reviews

Key Amenities

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

About this property

Enjoy a whimsical getaway when you book a stay at this sleek, refreshing, 8-bedroom, 6-bathroom vacation rental home. Take a dip in the private pool, fix up something tasty in the fully equipped kitchen, play a game of pool in the game room, or head to the community fitness center for a quick workout....

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Featured review

"Kissimmee Home/Windsor"

My family & I enjoyed our stay at this lovely home during the summer time. This house gave us an enjoyable experience that we will all remember. We didnt have any problems with the house and we hope to...

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$328
avg per night
Kissimmee Villa
Sleeps 8, 4 bedrooms, 3 bathrooms
6 reviews

Distance to park: 3 miles to Disney World

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Sample the Florida lifestyle in our four-bedroom, three-bathroom spacious air-conditioned villa with 26ft x 13ft privately screened, heated, south-facing swimming pool and spa.Located on the peaceful Indian Creek community, our holiday home is comfortably furnished throughout, only 3 miles away from...

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Featured review

"Will come back whenever in area"

Very spacious Villa in excellent location with quiet neighbourhoud. Next Walmart and restaurants only a few minutes away. Check-In easy. Good communication with hosts and fast answers. We loved the atmosphere...

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$166
avg per night
Kissimmee Townhome
Sleeps 6, 3 bedrooms, 2.5 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Welcome to our beautiful townhome villa located at the luxurious 24-Hour Guard-Gated Emerald Island Resort in Kissimmee, Florida. Just 3 miles from Disney World's main gate.No cramped pool deck! No Shade from nearby houses blocking that fabulous Florida Sun! No shortage of pool chairs, tables...

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Featured review

"Outstanding rental!"

We spent three weeks in this rental and had a wonderful stay. Location is terrific. Very close to the pool, yet very quiet. Owner was great to work with and fast with communication. Home is clean and well...

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$117
avg per night
Kissimmee House
Sleeps 6, 3 bedrooms, 3 bathrooms
1 review

Distance to park: 4 miles to Disney

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

You will love it here in our Boutique styled Condos featuring contemporary interiors, located in Magic Village gated community only 5 minutes away from Disney’s Animal Kingdom. Step into your private villa and discover a chic and contemporary yet invitingly cozy sanctuary. All three bedrooms are...

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Featured review

"Best vacation rental ever!"

This property was absolutely gorgeous, spacious, private and quiet! We stayed for 11 days and wish we could've stayed for 11 more. The amenities are just like being in your own home - we did go to Walmart...

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$216
avg per night
Kissimmee House
Sleeps 14, 7 bedrooms, 5.5 bathrooms
2 reviews

Distance to park: 5 miles to Disney World

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Excellent Private Detached Family Vacation home/Villa located in the Prestigious Man Gated Vacation Resort of EMERALD ISLAND RESORTS. SPECIAL DISCOUNTS FOR LONGER STAYS !!! . Monthly bookings during January to April at special rates._________________________________________________________________ This...

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Featured review

"Amazing 7 Bed rooms Villa Near Disney"

Our stay with Family and friens were superb. Cost is just a fraction of what otherwise with any Hotels. VEry large House with 7 Bedrooms and 6 Wash rooms. Own private pool and lanai . Bbq grill was provided...

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$207
avg per night
Kissimmee House
Sleeps 10, 5 bedrooms, 4 bathrooms
9 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

*** For smaller groups we offer the opportunity to rent the main house. This area has 4 Bedrooms and 3 Bathrooms Please contact us and ask for a quote ***Newly painted throughput New wood/plank flooring currently be fitted in the main house upper floor. This will make the main house carpet...

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Featured review

"Excitement Place at Christmas time was Incredible!"

Knowing at the beginning of 2024 that we were going to take a family vacation to Disney World with all of our children and grandchildren over the Christmas 2024 Holiday, we would need accommodations for...

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$222
avg per night
Kissimmee Villa
Sleeps 12, 5 bedrooms, 4 bathrooms
2 reviews

Distance to park: 3 miles to Disney World

Key Amenities

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

About this property

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

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Featured review

"Excellent vacation & house"

we were a family of 10 staying in this beautiful house was well equipt with everything we needed room was a big hit ..The heated pool was sure a big catcher the 4 children loved it so did the adults.....

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$249
avg per night
Kissimmee Villa
Sleeps 12, 6 bedrooms, 5 bathrooms

Distance to park: 7 miles to Disney's Animal Kingdom Theme Park

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Experience Luxury and Comfort at Our 6-Bedroom, 3,200 sq. ft. Villa – Perfect for Families and Groups!Escape to our stunning luxury villa, featuring 6 spacious bedrooms (9 beds) and 3,200 sq. ft. of beautifully appointed living space. With 2 luxurious en-suites, 3 king-sized beds, 2 cozy living...

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$190
avg per night
Kissimmee House
Sleeps 10, 3 bedrooms, 2 bathrooms
25 reviews

Key Amenities

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

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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Featured review

"Vacation retreat/$15 Uber to Disney/ HGTV looking retreat"

We are completing our stay in the morning at this beautiful vacation retreat! We brought the family all seven of us ranging from age in two years old to 60 years old. The pool and patio is incredibly maintained,...

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$187
avg per night
Kissimmee House
Sleeps 16, 7 bedrooms, 4 bathrooms
68 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

A tropical oasis in Central Florida. Come experience all the details this home away from home has to offer, with the added benefit of being centrally-located to the best attractions in Orlando.Discover magic and family fun at this elegant Emerald Island Resort escape. Perfect for a group getaway,...

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$464
avg per night
Kissimmee Villa
Sleeps 24, 9 bedrooms, 6 bathrooms
14 reviews

Distance to park: 2 miles to Sunday's Grill

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

For last minute rentals or longer extended rentals, please inquiry about our discounted rates.This luxury vacation home is located in the Windsor at Westside upscale resort community - A perfect destination for DISNEY WORLD (10 minutes away), golf, and relaxing and celebrating with family and friends....

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Featured review

"Excellent"

Thank You Ann great service. Me and my family will be renting from you again in the future

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Kissimmee House
Sleeps 14, 7 bedrooms, 4.5 bathrooms
1 review

Key Amenities

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

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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Featured review

"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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$448
avg per night
Kissimmee Villa
Sleeps 10, 4 bedrooms, 4 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Name Of Home: Walking on Sunshine VillaLocation: Windsor Hills Resort (24/7 guard gated community - Disney World only mins away!)Home Highlights: Recently Renovated Home - Incredible Air Conditioned 80s Game Room - Private South Facing Pool/Spa - Bunk Bedroom with PS5Property Type: Single...

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$295
avg per night
Kissimmee House
Sleeps 16, 9 bedrooms, 7 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Located in the exclusive Encore community. This beautiful and luxurious vacation home is a 2-story home with 9 bedrooms, 7 bathrooms, a laundry room, game room, and a pool with hotube. It is completely fenced. The house has a capacity for 18 guests. This stylish place to stay is perfect for group trips. Charming...

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$382
avg per night
Kissimmee Villa
Sleeps 8, 4 bedrooms, 3 bathrooms
18 reviews

Distance to park: 3 miles to Mgm

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

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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Featured review

"Nice place"

Great place and great location . Close to the parks.. !!)!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!

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$125
avg per night
Kissimmee Villa
Sleeps 8, 4 bedrooms, 3 bathrooms
29 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Indian Creek Disney Retreat is a beautiful 1800SF, well maintained home in the Indian Creek subdivision which is literally on Disney's doorstep and your home away from home. Indian Creek is not a gated community but has a lot of community amenities.In the 1st section of Indian Creek you will...

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Featured review

"Beautiful rental on Santee Drive"

It is our 2nd time staying in this rental home. It does not disappoint. The home is very clean and well equipped. The owner is quick to respond and always pleasant. The outdoor space ( pool and hot tub)...

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$141
avg per night
Kissimmee House
Sleeps 14, 7 bedrooms, 5.5 bathrooms
1 review

Distance to park: 5 miles to Animal Kingdom

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Peaceful Private Getaway – Private Pool and Hot Tub - (6) NIGHT MINIMUMWelcome to Islands of Magic @ , a spacious and family-friendly vacation home just 5 miles from Walt Disney World! Perfect for large families, group getaways, or multi-family trips, this beautifully designed home offers...

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Featured review

"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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$227
avg per night
Kissimmee Villa
Sleeps 12, 6 bedrooms, 3.5 bathrooms
1 review

Key Amenities

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

About this property

Bring your family to this stunning 6BR 3.5BA in the luxurious gated community just minutes from the world-famous Disney World. Have hours of fun in the game room and scenic pool backyard, or set out to explore local theme parks, golf clubs, restaurants, shops, and more!6 Comfy Bedrooms (2 Themed) ...

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Featured review

"Wonderful Stay!"

The house was lovely and had everything we needed for my family of 6 week long stay. Kitchen was well stocked with everything we needed, house and pool were clean, and the beds were comfortable. The 80s...

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$261
avg per night
Kissimmee Villa
Sleeps 8, 4 bedrooms, 2 bathrooms
8 reviews

Distance to park: 7 miles to Walt Disney World

Key Amenities

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

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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Featured review

"A Gem"

Second visit to the Lake House. Clean, well stocked, nice hot pool and beautiful views of the lake. The owners and the management company responsive to every need.Thanks so much Carole & Brian

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$210
avg per night
Kissimmee House
Sleeps 12, 5 bedrooms, 4 bathrooms
8 reviews

Distance to park: 6 miles to Disney Animal Kingdom

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

***FREE WIRELESS INTERNET JUST BRING YOUR MOBILE DEVICES**. (Please note - there is no landline in the home). Your relaxing home from home. 15 minutes to Disney. Located on a gated community.Sleeps a maximum 12 guests, with a maximum of 8 guests over the age of 14 years old.As you enter our...

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Featured review

"Great Location"

The house was very nice. We enjoyed the pool, spa and game room. Very close to Disney. Great place to stay on vacation. Highly recommended.

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$206
avg per night
Special Offer
Kissimmee Condo
Sleeps 6, 3 bedrooms, 2 bathrooms
4 reviews

Distance to park: 1 miles to Disney Animal Kingdom

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

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...

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Featured review

"Great place"

We love the place. Close to everything we needed. The place is spacious. Will rent again in the future. Frank was an awesome host.Gregory and Ghyslaine From Aruba

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$97
avg per night
Kissimmee Villa
Sleeps 8, 4 bedrooms, 2.5 bathrooms
1 review

Distance to park: 3 miles to Disneys Animal Kingdom

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Our Home Features are 4 bedrooms consisting of 1 Master suit with en-suite bathroom located on the main level. 1 Queen and 2 twin rooms,1 twin room is themed Winnie the Poo,on the upper level, these bedrooms share the upper bathroom all bedrooms are equipped with TV and DVD player. There is a further...

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Featured review

"Tolles Haus"

Hallo, Wir haben hier mit der Familie Urlaub gemacht. Das Haus ist groß genug für acht Personen. Es ist super ausgestattet mit tollem Blick und schönem Pool. Der Vermieter ist sehr um eine tolle Atmosphäre...

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$208
avg per night
New
Special Offer
Kissimmee House
Sleeps 12, 6 bedrooms, 5 bathrooms
4 reviews

Distance to park: 5 miles to Disney

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Whether you are planning a family vacation, reunion with friends and family, or couples' retreat, Paradise Cove offers everything you need for an unforgettable stay!! Book your stay today and start making memories....This 6BR/5B spacious home is located in a secure gated family friendly resort...

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$307
avg per night
Kissimmee Condo
Sleeps 4, 1 bedroom, 1 bathroom

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Beautiful and clean unit with two queen size beds upstairs, it is part of a recently renovated condo-hotel furnished with modern design and great taste, with fenced pool, playground, gym, and indoor and outdoor dining/resting/seating areasTouristic area, super close to the parks, located on the main 192...

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$91
avg per night
Kissimmee Villa
Sleeps 14, 7 bedrooms, 5 bathrooms
6 reviews

Distance to park: 7 miles to Disney Magic Kingdom

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

* Gated and Guarded Resort 7 -10 minutes to Disney * Stunning Lake Views from Enclosed Pool Deck * Pool with 24 Hour Spa on Over ride - Handrails * Lots of Baby Equipment - Free to Use * 2 Lounges - Leather sofas * Game Room Disney Themed -Air conditioned - Slate Bed Pool Table *New Gaming Station...

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Featured review

"Great place to stay"

Our family of 10 rented this property. The host was unbelievable and assisted us every step of the way. The property is clean and neat with everything you could need. Its location is excellent for the parks....

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$264
avg per night
Kissimmee Bungalow
Sleeps 9, 4 bedrooms, 3 bathrooms
6 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Amazing Villa near Universal Studios and 15 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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Featured review

"The house was fantastic and a great location."

The house was very easy to find, quiet neighborhood and Walmart was 2 minutes away. The was neat and tidy with all kitchen amenities needed to prepare a home cook meal. The Air conditioner was the best,...

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$122
avg per night
Kissimmee Villa
Sleeps 9, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Immerse yourself in luxury at our Kissimmee villa, perfectly located minutes from Disney and Universal. Nestled in a secure gated community, our home boasts a private pool and spa, a fully-equipped modern kitchen, and comfortable bedrooms including a master suite with a king bed. Exclusive amenities include...

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$200
avg per night
Kissimmee Villa
Sleeps 8, 4 bedrooms, 3 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to M&M Dream Villa – Just 3 Miles from Disney! Experience peace, play, and pure comfort at this quiet and relaxing 4-bedroom retreat, perfect for families and Disney lovers alike.M&M Dream Villa – 4BR Family Retreat Just Minutes from DisneyWelcome to M&M Dream...

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Featured review

"We had a great holiday at Crushes Crash Pad."

We had a great holiday at Crushes Crash Pad.The villa is very well equipped and has everything you could possibly need (and more) to make your stay enjoyable. The location couldn’t be better, being...

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$277
avg per night
Kissimmee Townhome
Sleeps 8, 3 bedrooms, 2.5 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

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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Featured review

"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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$105
avg per night
Last Minute Deal
Kissimmee House
Sleeps 12, 5 bedrooms, 4 bathrooms
5 reviews

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

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Imagine coming home at the end of an exhilarating day at the parks... You grab a refreshing drink, relax in the poolside living area and reminisce about all you did that day.Memories made, job done!Serendipity offers all the comforts you dreamed of putting on your wish List:★ Private...

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Featured review

"Complete PRIVACY & The WARMEST Pool ️"

️BOOKED May 21-25️️This was our 10th VACA home rental (Cali, TN & FL) and without a doubt, Sarah is 1 of our FAVS as she is an exceptional host and it was our pleasure working with her. Her level...

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$298
avg per night
New
Kissimmee House
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

About this property

***FULLY FURNISHED*** 3 bedroom, 2 bathroom house in Kissimmee. Amenities included: central air, central heat, dishwasher, hardwood floors, pool, stainless steel appliance, updated kitchen, washer dryer, and yard. Utilities included: internet. Is pet friendly. Date Available: Oct 8th 2025. $3,000/month...

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$100
avg per night
Kissimmee House
Sleeps 15, 5 bedrooms, 4.5 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Welcome to our luxurious and spacious vacation home situated in the stunning gated community of Windsor at Westside. This magnificent 5-bedroom, 4.5-bathroom villa boasts everything you need for an unforgettable vacation with your family and friends, Close to theme parks, shopping mall outlets, restaurants...

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Featured review

"CLEAN & COMFORTABLE, PERFECT RENTAL!"

The location is perfect! It's situated in a sweet little area thats quiet and clean. Yet it's not far from anywhere to drive. Walmart and target are just around the corner as well as a gas station and other...

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$208
avg per night
Kissimmee Villa
Sleeps 8, 3 bedrooms, 2 bathrooms
15 reviews

Distance to park: 12 miles to All Disney Theme Park

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

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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Featured review

"Wonderful Vacation"

We enjoyed a lot during our stay. Everything was perfect! Thank you Mariana for making our stay excellent.

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$136
avg per night
Special Offer
Kissimmee House
Sleeps 14, 6 bedrooms, 4 bathrooms
4 reviews

Key Amenities

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

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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Featured review

"Amazing"

This was an amazing experience for my kids and I. I would definitely choose again!!!!!!!!!!!!!!!!!!!

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$327
avg per night
Kissimmee House
Sleeps 12, 6 bedrooms, 3 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Situated on the very popular well maintained and long-established peaceful golfing Highlands Reserve community on the US27 in Davenport is this beautiful, well-presented villa with 6 bedrooms and 3 bathrooms. It can accommodate up to 12 guests very comfortably.The spacious open-plan villa is a great...

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Featured review

"Great location"

We very much enjoyed our stay. Villa was clean, well equipped and close to Disney. Management company was quick to respond to any questions.

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$195
avg per night
New
Kissimmee Villa
Sleeps 14, 6 bedrooms, 4 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Just 10 minutes from Disney, this 6BR home has it all—Minions, Avatar, and Guardians of the Galaxy-themed kids' rooms, a hidden Mario game room, and luxe king suites. Outside, enjoy a private screened pool and spa with free heat, a full outdoor kitchen, firepit lounge, movie screen, sauna,...

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Kissimmee Apartment
Sleeps 4, 1 bedroom, 1 bathroom

Distance to park: 7 miles to Disney World

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

1/1 Condo. Queen sofabed in living room. Queen bed in master with desk and chair. Full kitchen. Just 7 miles from Disney, centrally located. Gated community , Complex has 2 pools, gym, tennis courts. Laundry room with full size washer/dryer in unit. Free wifi and streaming. Second floor unit.No elevators. No...

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$81
avg per night
Kissimmee House
Sleeps 8, 4 bedrooms, 4 bathrooms

Distance to park: 4 miles to Disney

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

"Boutique style very spacious Town house, ideally located in Magic Village community……right next to Disney’s parks like Magic Kingdom. All Units have unique furnishings, complete kitchens with gas range, living, and dining rooms with vaulted ceilings. Full size laundry room, extra...

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$222
avg per night
Kissimmee Condo
Sleeps 8, 3 bedrooms, 2 bathrooms
3 reviews

Distance to park: 5 miles to Disneyworld and Disney Springs

Key Amenities

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

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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Featured review

"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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$102
avg per night
Kissimmee Villa
Sleeps 8, 4 bedrooms, 4.5 bathrooms

Distance to park: 4 miles to Disney Theme Parks

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Welcome to Magic Village Views, part of Trademark Collection by Wyndham. This 4 Bedroom 4.5 Bath Luxury Townhouse Villas is a must stay. located in an ideally located gated community……right next to Disney’s parks. All Units are En-Suites with unique furnishings, complete kitchens,...

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$245
avg per night
Kissimmee Condo
Sleeps 7, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

This condo is one of our most highly sought-after Orlando vacation rentals, and for a good reason. This beautiful property is equipped for up to seven guests between its three bedrooms and two bathrooms. Those who stay in this rental will be able to take full advantage of every amenity and feature that...

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$144
avg per night
Full map
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Kissimmee Weather

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

FAQ

Proximity to Attractions

How close are Kissimmee rentals to the main entrance of Walt Disney World versus Orlando rentals?

Some Kissimmee vacation rentals are only 12 miles from Walt Disney World. Orlando rentals are a little further away from the amusement park at around 20 miles.

What is the average drive time from Kissimmee to Universal Studios or SeaWorld?

The average drive time from Kissimmee to Universal Studios is 23 minutes, while the average drive to SeaWorld takes 25 minutes.

Are there Kissimmee communities that offer shuttle services to the theme parks?

Yes. Encore Resort Condo, Wyndham Bonnet Creek Resort Condo, and Champions Gate Condo are some of Kissimmee’s vacation rentals offering shuttle service to Walt Disney World, Universal Studios, SeaWorld, and other attractions.

How bad is the traffic on US-192 or I-4 when driving from Kissimmee to the parks?

Both US-192 and I-4 are busy roadways leading to the parks. Traffic is heavier or lighter depending on the day of the week and the time of day. Weekday mornings, early evenings, and Saturdays are especially crowded.

Property Type & Communities

What are the most popular resort communities in Kissimmee (e.g., Reunion, ChampionsGate, Windsor Hills)?

Champions Gate, Reunion, Emerald Island, Windsor Hills, and Indian Creek are all popular resort communities in Kissimmee.

What kind of exclusive amenities do these large resort communities offer?

Some exclusive amenities include a clubhouse, tennis courts, a fitness center, a movie theater, a sauna, and a marketplace to purchase food.

Is it better to stay in a large resort or a smaller, non-gated community in Kissimmee?

The answer depends on your preferences. A smaller, non-gated community in Kissimmee offers fewer amenities than a large resort but still has a collection of fun activities nearby.

What are the main differences between staying in Kissimmee versus staying in Orlando?

Orlando is a large, bustling city full of restaurants, shops, and attractions, while Kissimmee is less crowded with a more family-friendly atmosphere. Though both cities are close to the major parks, Kissimmee is closer to Disney World, whereas Orlando is closer to Universal Studios.

Amenities & Features

What size homes are typically available for rent in Kissimmee?

The typical Kissimmee vacation home has four bedrooms and ranges from 1,980 to 2,000 square feet.

Do most house rentals come with a private, screened-in pool and lanai?

Though most house rentals come with a private, screened-in swimming pool, not all of them have a lanai.

Are multi-generational homes with multiple master suites common?

Yes, multiple master suites are common in Kissimmee vacation homes for rent.

What are some unique amenities to look for in Kissimmee homes, like private movie theaters or elaborate game rooms?

Check listings for unique amenities in Kissimmee house rentals such as EV chargers, gardens, balconies, ping pong tables, pool tables, game rooms, and heated pools.

Booking & Cost

Is it generally more affordable to rent a large house in Kissimmee compared to a similar one in Orlando?

Yes, when comparing similar homes in these two Florida cities, Kissimmee house rentals are the more affordable option.

What are the typical resort fees or community access fees I should budget for?

The typical resort fee is around $40 per day.

Are there any "hidden costs" associated with Kissimmee rentals, like pool heating or BBQ grill rental?

Studying the “Fees” section of a Kissimmee rental’s listing can help you avoid any surprise costs. Some owners list fees for services like pool heating, damage protection, and pets.

What is the best time of year to find deals on Kissimmee vacation homes?

September and October are the best times to find deals on Kissimmee vacation homes because fewer people are booking rentals.

Kissimmee Specifics

What attractions are there to see in Kissimmee itself, outside of the major theme parks?

Boggy Creek Airboat Adventures, Gatorland, Shingle Creek Regional Park, Congo River Golf, and Lake Tohopekaliga (Lake Taho) are all unique attractions in Kissimmee.

What are the best places for shopping and dining in the Kissimmee area?

The Promenade at Sunset Walk, The Crosslands, and Universal CityWalk are some of the best places for shopping, dining, or both.

How does the vibe of Kissimmee differ from the International Drive area in Orlando?

Orlando’s International Drive has a high-energy vibe with dozens of shops, restaurants, shows, spas, and other attractions. While Kissimmee has its own collection of shops, eateries, and attractions, the city’s vibe is more laid-back.

Are there any good nature-based activities, like airboat tours, that are easily accessible from Kissimmee?

Yes. Wild Florida Adventure Park, Gatorland Bird Rookery, and horseback riding sessions at Lazy H Ranch give visitors the opportunity to admire Kissimmee’s natural environment.