Kissimmee Vacation Rentals

(339 rentals)
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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

Our beautiful 3 bedroom, 2 bathroom pool home is ideally located in the quiet residential community of Liberty Village, Kissimmee. Conveniently situated close to Disney and the other major theme parks. There are several restaurants, shopping and World-Class Golf is nearby.Hi speed WiFi and air ...

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Property Type

Kissimmee Villa

"Loved this villa"

We go to Disney every December and this is one of the best we ever stayed in. Very comfortable and clean. Amazing value for money. Rent this villa and you will be delighted. We already booked for Dec ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

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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Property Type

Kissimmee Villa

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Key Amenities

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

About this property

Popular Dates in July & August AvailableWe also offer the opportunity to rent just the main house which is a 4 Bedroom 3 Bathroom. Please contact us and ask for a quote.Our beautiful 3000sq 5 Bed, 4 Bathroom home is located on a generous corner plot. With a south facing Pool and stunning ...

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Property Type

Kissimmee House

"Amazing accommodation and location"

Spacious, well equipped home in an amazing golf resort. Master suite was stunning with huge bathroom and balcony overlooking the second tee. Very well situated for Disney and Universal studios. Nice pool ...

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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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5 BR | 5 BA | Sleeps 12 | Quick View

2

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

$269

avg/night

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Key Amenities

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

About this property

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

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Property Type

Kissimmee Villa

"Fantastic Stay"

We loved staying at this house it was truly amazing. There were 9 of us altogether, 6 adults and 3 children aged 10,8 & 4. The kids loved the games room and the pool, everything you could wish for in ...

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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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Key Amenities

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

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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Property Type

Kissimmee House

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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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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

"Great Experience. Great Location"

Love the location for this house. Only a few miles (on back roads) from the Disney parks, so we go in the morning and return to the house for lunch and a swim then return to the parks in the evening. ...

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5 BR | 4 BA | Sleeps 12 | Quick View

2

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

$321

avg/night

View Details

Key Amenities

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

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:★ Pool & ...

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Property Type

Kissimmee House

"Family Birthday Vacation"

Everything was great! The house was very spacious. The back area a bit small but still great! We had a blast!

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4 BR | 2 BA | Sleeps 7 | Quick View

4

$124

avg/night

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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

Welcome to Minnie's Mansion! A 5 bd/ 5 bth pool home located in the closest community to Disney World-Windsor Hills Resort!This resort features, $2.1 mil Lagoon Style pool with Zero Depth Entry and Water Slides. Also, with a Water Park for the littles! Clubhouse has Sundry Shop /Deli, Games Room, ...

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Property Type

Kissimmee Villa

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

This stunning Disney area pool villa offers your family comfortable and convenient accommodations that will make your next Florida vacation a memorable one.Ideal for your next family vacation, this attractive 4 bedroom, 2 bath Disney area vacation home is conveniently located just 10 minutes to the ...

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Property Type

Kissimmee House

"wonderful stay at this villa"

Villa has everything you will need, very spacious and great pool. Nice quiet Resort. We loved it and hopefully one day we can go back....need to start saving.

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6 BR | 5.5 BA | Sleeps 18 | Quick View

56

Distance to park: 4 miles to Animal Kingdom

$145

avg/night

View Details

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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3 BR | 2 BA | Sleeps 6 | Quick View

$150

avg/night

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Key Amenities

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

About this property

Booking Protection Guarantee In the unlikely event that a Host needs to cancel your booking within 30 days of check-in, we’ll find you a similar or better home or we’ll refund you.Check-In Guarantee If you can’t check into your home and the Host cannot resolve the issue, we’ll ...

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Property Type

Kissimmee Apartment

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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
  • 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

"Royal Palms Mansion"

This was the first time we had stayed in this house, we are regular visitors to Orlando and we know the area well. This house is located in our favourite area and is minutes away from Walmart which is a ...

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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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$124

avg/night

View Details

Key Amenities

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

About this property

$70/NIGHT JANUARY SPECIAL DUE TO CANCELLATION. FOR 2 ; ADD $5 EACH EXTRA TO MAXIMUM $90/NGHTCHEERY AND BRIGHT. Just what a vacation home should be. 4 bedrooms, 2 bathrooms, great views and just minutes from all the fun. Fully furnished , just bring personal items or things you cannot live ...

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Property Type

Kissimmee House

"Lovely stay"

Really enjoyed our stay, hope to book again! Very clean & great pool which was lovely & warm & well equipped

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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

"Wonderful place"

Omg we loved the house and how nice everything was it really felted like we were back home I definitely will be booking again with this company we really enjoyed our stay such lovely place

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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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Key Amenities

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

About this property

This home has everything that you, your family and friends will ever need and more! Walt Disney World Resort is only 2 traffic signals away. This luxury South facing pool home, completed in June 2004, has 7 bedrooms, 6 bathrooms and will accommodate 15 people plus infants comfortably. The private pool ...

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Property Type

Kissimmee House

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3 BR | 2 BA | Sleeps 6 | Quick View

3

Distance to park: 1 miles to Disney Animal Kingdom

$97

avg/night

View Details

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 ...

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Property Type

Kissimmee Condo

"Great location, clean and comfortable."

We had everything we needed. Excellent communication. Perfect location. Close to the parks as well as restaurants, etc! We will be back.Thanks

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Key Amenities

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

About this property

Welcome to our stunning, larger than average, 5 Bed 4 Bathroom villa with a beautiful view of the conservation area at the rear as background of our private pool. All rooms in the villa are spacious. The villa is furnished and maintained to a very high standard.The villa is located just off US 192 ...

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Property Type

Kissimmee Villa

"Great Place!"

This house was absolutely beautiful! It was clean, close to Disney, and the pool kept our children entertained for hours! I highly recommend this place!

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Key Amenities

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

About this property

Property Reference EMI_1700RA perfect size vacation home for families who wish to stay close to Disney and come home to their own private pool to cool off after a long day at the parks. The decor was professionally updated in June 2022 aand again with further updates such as new flooring, new beds ...

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Property Type

Kissimmee House

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Key Amenities

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

"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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Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner

About this property

Excellent location pool community gimnasio walking through complex

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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

A fabulous home-base for your trip to Orlando! Just Minutes to Theme Parks.Home Features:* 3 Bedrooms* 1 King, 1 Queen, 2 Full, 1 Twin (Sleeps 7-8) * All New Mattresses * TV's in every bedroom * USBs & Outlets convenient for charging* 3 Bathrooms* All En-Suite * ...

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Property Type

Kissimmee Townhome

"Loved it."

Beautiful House, and a wonderful experience from start to finish! Cant wait to go back! The home was spacious and beautifully decorated and Lisa was a Pleasure to work with, and very helpful.

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2 BR | 2 BA | Sleeps 6 | Quick View

Distance to park: 2 miles to Disney

$138

avg/night

View Details

Key Amenities

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

About this property

This 2 bedroom, 2 bathroom condo is on the top floor with comfortable furnishings and is quiet for sleeping. An elevator on site. Lots of free parking available for your vehicles. Great value vacation condo sleeps up to 6. The condo includes a fully equipped kitchen with all appliances and utensils. There ...

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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_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

About this property

2bd/2ba with the Best View in the amazing community of Storey Lake. Located 10 minutes from Disney Come in and enjoy a unique experience. There is a beautiful waterpark in the community center for you to enjoy. It is the perfect place to relax, have a good time and enjoy all that Orlando has to offer. This ...

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Property Type

Kissimmee Apartment

"2024 vacation"

The house was lovely.. lots of room, clean, bright The resort pool was absolutely beautiful.. my grandson loved his time in the pool .. lot of room to sit around and food at the pool area was really good

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Key Amenities

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

About this property

Perfect Family Destination Best lania/pool Minutes to Disney/Attractions/Conveniences Fun/Clean/ComfortableThis is a fantastic house for family getaways! Enjoy the Food and Wine Festivals. Mickey's Not So Scary Halloween Party, Unforgettable Disney Christmas celebration, and everything else ...

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Property Type

Kissimmee House

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4 BR | 3 BA | Sleeps 10 | Quick View

3

Distance to park: 7 miles to Disney World, Animal Kingdom is 7 miles, HS is 8.5

$156

avg/night

View Details

Key Amenities

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

About this property

June 29-July 5 last minute rates available! NEW! Clubhouse will now offer a coffee bar serving Starbucks coffee and also a Hershey ice cream counter!Let the sense of excitement fill the air. Nestled in the gated and secure community of Paradise Palms, CR Getaway awaits its adventurous guests. ...

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Property Type

Kissimmee Townhome

"Great home!"

This is the second time we have stayed at Duane and Tina's place. They're always so friendly and helpful, and the place is clean, organized and a convenient location to the parks.We had a great stay!

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Key Amenities

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

About this property

Our 6 Bedrooms 6 Bathroom, luxury villa ideal for you and your families / friend’s vacation.As you enter the home you are greeted with a large living room area. Towards the back of the villa there is an open plan living/dining/kitchen area. There are tri-sliding doors to the pool area where ...

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Property Type

Kissimmee Villa

"Nice villa"

We went down for a football tourney this four bedroom villa was great. We were concerned about being stuck in a hotel room for the week so this was perfect plenty of room and very clean. If the weather ...

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9 BR | 8 BA | Sleeps 18 | Quick View

9

Distance to park: 3 miles to Disney Animal Kingdom

$615

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Luxurious Southeast Facing - 9 Bedroom and 8 Bathroom in a Prestigious Secure Gated Community • Freshly remodeled and renovated • Sleeps up to a total of 18 • 9 bedrooms, 5 x Master’s and 3 x Themed and ideal for kids • Amazing location 2 miles to (5 minutes) from Disney World ...

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Property Type

Kissimmee House

"Hartley House family gathering"

We have just returned from a great family holiday in Florida we took all our family away for our fiftieth wedding anniversary ,three years late .We stayed at Hartley House ,we have never stayed in a american ...

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Key Amenities

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

About this property

Imagine a vacation like no other spent in a 9 bedroom, 10 bath custom luxury lakefront pool villa. The Formosa Grand is located in the exclusive gated community of Formosa Gardens Estates and one of the closest communities to Disney (less than 10 minutes!!) No expense was spared in the gorgeous estate ...

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Property Type

Kissimmee Villa

"West Family Reunion"

We had a great time at the mansion. Only a few things I would change. The hot tub price should have been included in the rental agreement.

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3 BR | 2 BA | Sleeps 7 | Quick View

3

Distance to park: 6 miles to Disney - Animal Kingdom

$116

avg/night

View Details

Key Amenities

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

About this property

The "Sweet Retreat" is just 6 miles to Disney! This "Sweet" Villa has 3 Bedrooms, 2 Baths and sparkling Sunny private pool... Perfect for families & "Sweet" on your feet with all tile in the main rooms & carpet in the bedrooms.The living room feels bright and ...

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Property Type

Kissimmee House

"SWEET RETREAT"

We enjoyed the home very much. The price was right neighborhood is a quiet residential area near everything. The kitchen well equipped with everything one would need! Furniture clean & comfy. Pool ...

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Key Amenities

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

About this property

Huge South Facing Rear Deck The Most Exclusive Home in Reunion ResortThis unique, one of a kind, beautiful, private custom Estate Home features over 8,200 sq/ft of luxury accommodation and balconies. This 'WOW!' factor home is private, quiet and not overlooked.Soak up the Florida sun ...

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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_1021RBalconies, patios, and lanais are not accessible. During 2023 - 2024 there may be construction occurring on the exterior of the building by the homeowners association; contact us for updates Welcome to Seven Eagles Joy. This 3 bed, 3 bath townhome is located in the heart ...

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Property Type

Kissimmee Townhome

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Key Amenities

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

About this property

This gorgeous home was completely redesigned in 2023! Experience unforgettable moments with your family at Solara Resort. The kids will delight in our thoughtfully designed themed bedrooms, while others can unwind on the inviting custom patio or enjoy a refreshing swim in the private heated pool.Is ...

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Property Type

Kissimmee House

"AMAZING customer service"

I was skeptical of booking online with a company I wasn't familiar with, however they ended up being so responsive to any concerns or questions I had, including when me and my kids were in the house. It ...

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Key Amenities

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

About this property

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

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Property Type

Kissimmee House

"Beautiful"

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

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4 BR | 3 BA | Sleeps 8 | Quick View

27

$145

avg/night

View Details

Key Amenities

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

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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Property Type

Kissimmee Villa

"House rental on Santee Dr"

The house was very clean and well furnished. The location is perfect. I dealt with the homeowner Lisa who was professional and returned my text quickly. The pool and hot tub were also very clean. Quiet ...

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4 BR | 3.5 BA | Sleeps 10 | Quick View

12

Distance to park: 5 miles to Animal Kingdom

$120

avg/night

View Details

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

"Cozy stay at townhouse"

My wife, son and I stayed for the month of April. The resort property is well maintained. Garbage is picked up daily and each home has a bin right in front of the home.The condo was very clean upon ...

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6 BR | 5 BA | Sleeps 12 | Quick View

3

Distance to park: 5 miles to Old Town, food,shops and rides

$224

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Spacious air conditioned home on large plot and not overlooked! Living area with 3 sofas and huge TV with cable triple play included and doors to pool deck. Dining tables and chairs enough for all guests and seating at breakfast bar. Refurbished kitchen with granite work tops, stove, microwave, dishwasher, ...

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Property Type

Kissimmee House

"Lovely villa"

We had a wonderful holiday at this villa, the location is perfect both for the setting and for the convenience for access to the attractions and restaurants. Cumbrian Lakes is very peaceful and quiet, perfect ...

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4 BR | 3 BA | Sleeps 8 | Quick View

9

Distance to park: 4 miles to Disney World

$151

avg/night

View Details

Key Amenities

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

About this property

Welcome to La Casita on the Island (The Little House on the Island) "Our house, our casita" If you want a place to relax and enjoy the beautiful weather of Florida, I invite you to see the "encanto" (charm) that you can experience during your stay at La Casita on the Island.Enjoy ...

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Property Type

Kissimmee House

"Great Villa"

Had a fantastic stay in the villa. Would definitely stay again and highly recommend. It was extremely clean and in a great location near shops, resturaunts and 192 and Disney. Would highly recommend and ...

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Key Amenities

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

About this property

Experience the popular "Queen of Hearts" villa in the Windsor at Westside Resort! This home boasts a private heated pool & hot tub, fire pit and outdoor TV. The themed bedrooms are loaded with amazing details. All guests have free access to resort amenities. Your host Vacation Alchemy provides ...

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Property Type

Kissimmee House

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5 BR | 4 BA | Sleeps 10 | Quick View

1

Distance to park: 7 miles to Disney Hollywood Studio

$144

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Beautiful, clean and spacious 5 bedroom and 4 bath house in the most sought after community near Disney! 10 minutes drive to Disney and you can hear the Disney fireworks at night. Close to stores, restaurants and tons of shops. The house was renovated and professionally designed recently. The house has ...

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Property Type

Kissimmee House

"Very good"

The trip was great me and my family really had fun and enjoyed ourselves we will be coming back soon.

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Key Amenities

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

About this property

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

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Property Type

Kissimmee Villa

"a perfect house for a family group. CLEAN, good location, nice resort"

stayed for my daughter's wedding. had family and friends stay in house. house had everything needed, but not cluttered. people on second floor could not hear the main room, so they could avoid if desired. ...

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Key Amenities

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

About this property

Experience a magical holiday at this luxe 7-bedroom home! Nestled in Windsor at Westside Resort, you and your loved ones will be a short drive to many attractions. Stretch out into sprawling living areas where comfort awaits you before heading outside for an exciting time - enjoy a dip in your private ...

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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 339 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 $55 per night with an average price per night of $180.

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