Kissimmee Vacation Rentals

(335 rentals)
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6 BR | 5 BA | Sleeps 12 | Quick View

2

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

$215

avg/night

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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

"This was an outstanding Florida vacation experience for our family!"

This house easily accommodated 11 of us which was ourselves, our two sons and their families - 6 adults and 5 grandchildren (including a set of 20 month old twins). The location was perfect to access all ...

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8 BR | 6 BA | Sleeps 16 | Quick View

owner special
Owner special: Check out the Spring deals

$371

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen

About this property

Be sure to visit our website to check availability on all our homes! Save our page for future vacations to the Orlando area!Visit us at lostinthemagic . comWindsor at Westside - Kissimmee, Florida is an upscale gated community located just 10 minutes from Walt Disney World. This luxury home sits ...

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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

$159

avg/night

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Key Amenities

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

About this property

Four nights, March 19-22 now available for $1050.00 includes taxes and cleaning fee! Three nights may be allowed, please reach out if interested.8+ amazing golf courses within 30 minutes of the townhome! Including Orange Lake, Legends, Celebration, Panther Lake, Crooked Cat and, of course, the Walt ...

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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
  • Rentals by owner

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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Property Type

Kissimmee Villa

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5 BR | 5 BA | Sleeps 12 | Quick View

11

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

$218

avg/night

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Key Amenities

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

About this property

☆☆ HIGHLIGHTS ☆☆ ✹ 5 spacious bedrooms w/ smart TVs: 2 kings, 1 queen, 1 full, 3 twins ✹ 5 full bathrooms ✹ Fully stocked kitchen w/ modern appliances ✹ Large living room w/ flat-screen TV + DVD player ✹ Fun game room w/ basketball, Lego table, skee ball + more ✹ Heated pool ...

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Property Type

Kissimmee Villa

"EXCELLENT"

This location was perfect for our family while staying close to the Disney Park. It had all the amenities for two families plus more. The pool and hot tub were a wonderful addition. The game room was a ...

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5 BR | 5.5 BA | Sleeps 13 | Quick View

4

Distance to park: 12 miles to Disney's Magic Kingdom Park

$359

avg/night

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Key Amenities

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

About this property

Welcome to Westside Villa! -20 minute drive to all Disney Parks -Private, heated pool; gas grill; EV charger on-site -Modern arcade: racing simulators, virtual reality, arcade deck -3 king size suites with smart TVs -2 uniquely themed bunk rooms (Star Wars and Fairy Tale) -All bedrooms have ensuite ...

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Property Type

Kissimmee House

"Amazing"

The house was simply amazing. The family could not believe what I had rented when we arrived, so spacious. So many things games/entertainment in the house. The house was very clean, the beds were really ...

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

Now taking bookings for 2025. Sorry no pets. Smoking is not permitted. Welcome to “Hibiscus on the Lake” with a true south facing pool/spa. The villa has stunning, uninterrupted views of the largest lake with an island in the middle full of beautiful birds on Lake Berkley resort in Kissimmee. ...

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Property Type

Kissimmee Villa

"Great location"

Stayed here in April for 2 weeks as a family of 6 adults. Villa is in a great location with easy access to the parks. It is on the main lake with beautiful views. Lots of wildlife. Saw a family of otters ...

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6 BR | 6 BA | Sleeps 12 | Quick View

owner special
Owner special: Check out the Spring deals

$310

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Be sure to visit our website to check availability on all our homes! Save our page for future vacations to the Orlando area!Visit us at lostinthemagic . comThe Retreat at Champions Gate - Kissimmee, Florida is a new upscale gated resort community located just 12 miles from Walt Disney World. ...

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Property Type

Kissimmee House

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9 BR | 5 BA | Sleeps 20 | Quick View

22

Distance to park: 7 miles to Disneyworld

$522

avg/night

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Key Amenities

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

About this property

SCAN QR CODE for a VIRTUAL TOUR. Experience luxury and entertainment in this 9-bedroom villa that has 7 different themed rooms, a private pool/hot tub, and unobstructed lake views. Enjoy our Avengers movie room, Star Wars game room, Harry Potter, Frozen, Toy Story, Moana, Mickey bedrooms and 2 exclusive ...

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Property Type

Kissimmee Villa

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7 BR | 6 BA | Sleeps 14 | Quick View

1
owner special
Owner special: Great Spring Savings. Up to 20% off stays arriving in the next 45 days

$296

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Solara Resort - Kissimmee, Florida is an upscale community currently under development just 7 miles from Walt Disney World. This gated resort community sits nestled just outside of Orlando, Florida. During your stay, you will enjoy this well-appointed home that has been designed and decorated to provide ...

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Property Type

Kissimmee House

"Awesome Stay"

This house was the perfect holiday stay, lots of space and no problem at all.Only thing missing was a game table, we love game nights.

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Key Amenities

  • Air conditioning

About this property

Are you looking for a massive 7-bedroom Orlando vacation rental to keep your entire family comfortable? Emerald Island 8538 is the one! This home features two master suites, five additional bedrooms, four full bathrooms, and one half-bathroom. Up to 14 guests can sleep here comfortably! Plus, you’ll ...

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Property Type

Kissimmee House

"Beautiful vrbo"

Beautiful home with lots of room for friends or family. Just minutes to everything.. we already booked for next February.

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10 BR | 8 BA | Sleeps 20 | Quick View

owner special
Owner special: Check out the Spring deals

$643

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Sonoma Resort - Kissimmee, Florida is only 15 minutes to the area's main attraction... Walt Disney World. This brand new resort community sits nestled just outside of Orlando, between W. Osceola and W. Irlo Bronson Memorial Hwy and conveniently located next to "The Loop", a premier shopping ...

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Pool

About this property

If you're bringing a big group with you on your next trip to Florida, you're probably looking for a luxurious vacation rental with plenty of room for everyone. This 5-bedroom Orlando vacation rental fits the bill! This Reunion home with Main Street USA game room is an absolute dream come true ...

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Property Type

Kissimmee House

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3 BR | 2 BA | Sleeps 6 | Quick View

20

Distance to park: 2 miles to Disney World

$173

avg/night

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Key Amenities

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

About this property

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

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Property Type

Kissimmee Condo

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Key Amenities

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

About this property

5 star Property!Welcome to Sunset Magic Villa!Delightful Windsor at Westside Resort home villa8 bedrooms (2 Downstairs/6 Upstairs) and 6 full bathrooms. Space for up to 16 guests, (stretch out and relax with all the comforts of home) WEST facing private pool ensuring stunning sunset ...

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Pool

About this property

If you're searching for Orlando vacation rentals near Disney, the name of this unit simply says it all: Three-bedroom 2nd Floor condo within minutes from Disney! This unique condo is set up to accommodate six guests between its three bedrooms and two bathrooms. Not only will you be able to benefit ...

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Property Type

Kissimmee Condo

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4 BR | 3 BA | Sleeps 10 | Quick View

2

$172

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Our villa is beautifully furnished and airconditioned and has a heated swimming pool and spa for that morning swim and for you family’s personal enjoyment there is a security fence to protect the young ones. A covered lanai on an extended pool deck includes a large table with seating for four plus ...

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Property Type

Kissimmee Villa

"Excellent Villa"

Well equiped, excellent location, friendly and helpful estate. The villa was one of the best we have hired over the past 20 years. The gated estate was first class, helpful and friendly clubhouse. Close ...

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Key Amenities

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

About this property

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

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Pool

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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Property Type

Kissimmee Condo

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6 BR | 6 BA | Sleeps 12 | Quick View

owner special
Owner special: Check out the Spring deals

$481

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Be sure to visit our website to check availability on all our homes! Save our page for future vacations to the Orlando area!Visit us at lostinthemagic . comThe Retreat at Champions Gate - Kissimmee, Florida is a new upscale gated resort community located just 12 miles from Walt Disney World. ...

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Property Type

Kissimmee House

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5 BR | 4 BA | Sleeps 10 | Quick View

1
owner special
Owner special: Great Spring Savings. Up to 20% off stays arriving in the next 45 days

$157

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Solara Resort - Kissimmee, Florida is an upscale community currently under development just 7 miles from Walt Disney World. This gated resort community sits nestled just outside of Orlando, Florida. During your stay, you will enjoy this well-appointed home that has been designed and decorated to provide ...

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Property Type

Kissimmee House

"Great stay"

Home was just right. Pool , lawn was beautiful the yard well kept garbage was collected on time We enjoy every moment of our stay .We are looking forward to return again in the new year.

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3 BR | 2 BA | Sleeps 7 | Quick View

2
last minute deal
LAST MINUTE DEAL 4/21 - 6/2: $100 OFF any week in May or June ... "Super Spring early Summer Specials"

Distance to park: 6 miles to Disney - Animal Kingdom

$120

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

"This was everything we were looking for all in one place. Five stars!"

The neighborhood was quiet, which was really nice. The layout of the house was perfect for the 5 of us. (All adults). The pool was perfect! It was the ideal size and offered plenty of sun and fun. We ...

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DEAL

4 BR | 3 BA | Sleeps 8 | Quick View

1

Distance to park: 3 miles to Disney Animal Kingdom

$149

avg/night

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Key Amenities

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

About this property

Great location - fabulous pool area

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Property Type

Kissimmee Villa

"Great Experience"

Rented a house through Florida Rentals. Great experience, nice home in a convenient location. House was clean, had all the essentials and a large pool

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Key Amenities

  • Air conditioning
  • Pool

About this property

Embark on an enchanting journey with our exquisite 5-bedroom home with theme bedrooms and themed out game room that is nestled in the prestigious Windsor Hills community. Ideal for families or groups, this charming retreat promises a perfect blend of luxury and proximity to the magic.? Key Features:?? ...

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Property Type

Kissimmee Villa

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Key Amenities

  • Air conditioning
  • Pool

About this property

Epic Florida Rentals is proud to offer this Beautiful 6-bedroom 4-bathroom home for your enjoyment. Renovated in 2020, now includes: AC and heated game room, allergy free no carpet. It truly is a home away from home from the moment you drive up to the guarded and gated entrance, you realize you are ...

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning

About this property

If you’re searching for Orlando vacation rentals that will have plenty of room for your entire family, look no further than Windsor Palms with private pool. This incredible home can fit up to 10 guests between its 4 bedrooms and 3 bathrooms. You’ll find another incredible amenity around every ...

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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

Your family will be close to everything when you stay at this centrally-located place. Welcome to the perfect vacation place at Encore Resort. Luxurious, 2 story house, 8 bedroom, 7 bathroom with Pool, Perfect place to vacation near Disney. A great destination for family and friend reunions. Minutes ...

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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

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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3 BR | 2 BA | Sleeps 6 | Quick View

Distance to park: 7 miles to ESPN WIde World of Sports

$125

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Rentals by owner

About this property

Welcome to your dream vacation destination! This recently renovated condominium is perfectly situated just minutes away from the magical world of Disney. Located in a prime location close to renowned attractions such as ESPN Wide World of Sports Complex, Epcot center, Disney's Blizzard Beach Water ...

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Property Type

Kissimmee Apartment

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7 BR | 5.5 BA | Sleeps 16 | Quick View

5

Distance to park: 8 miles to Disney World

$329

avg/night

View Details

Key Amenities

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

About this property

Waiting to welcome you is this 7 bedroom, 5.5 bathroom, 3300 sq/ft villa - perfect for large families or multigenerational gatherings comfortably sleeping up to 16 people.With Star Wars, Spiderman, Harry Potter, Avengers, and Mickey & Minnie theming, everyone is bound to find somthing they'll ...

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

After. *** Location Location Location*** It’s all about. ‘The View’The uninterrupted view of the 14 acre lake and bird island, takes unwinding by the pool to a new level! Relax on a sun bed, or perhaps get wrinkly in the spa whilst ...

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Property Type

Kissimmee Villa

"What a view"

In July 2023 we stayed at Winter Haven a fantastic villa in Lake Berkley which had enough room for 8 of us comfortably. The guys partially liked the games room/pool room, and we all loved to pool and jacuzzi, ...

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Key Amenities

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

About this property

Find total relaxation at this luxurious four-bedroom, two-bath villa that sleeps 10 with your own private, screened-in pool and patio area. Beyond the patio area, find a grassy, tree-lined backyard that provides quiet seclusion.Inside, you’ll find enough room for everyone with the spacious living ...

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Property Type

Kissimmee Villa

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$108

avg/night

View Details

Key Amenities

  • Air conditioning
  • Pool

About this property

If you're searching for Orlando vacation rentals near Disney, the name of this unit simply says it all: 3 BD Condo with Minutes from Disney! This unique condo is set up to accommodate six guests between its three bedrooms and two bathrooms.This 3-bedroom Orlando vacation rental offers everything ...

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Property Type

Kissimmee Condo

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Name Of Home: Live Your Adventure Family VillaLocation: Encore Resort (Gated community - Disney World only mins away!)Home Highlights: XBox, Private Pool, Marvel Themed Games RoomProperty Type: Single Family Home, Two Story (2,570 SF)Bedrooms: 5 Total - 2 w/ King Beds, 1 w/ Queen Bed, ...

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Property Type

Kissimmee Villa

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Key Amenities

  • Air conditioning
  • Pool

About this property

Embark on an enchanting journey with our exquisite 5-bedroom home nestled in the prestigious Windsor Hills community. Ideal for families or groups, this charming retreat promises a perfect blend of luxury and proximity to the magic.? Key Features:?? Bedroom Retreats:2 King Beds 1 Queen Bed 5 ...

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Property Type

Kissimmee Villa

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$174

avg/night

View Details

Key Amenities

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

About this property

Charming brand new 4 br, 3 bath townhouse with pool. Located in the desirable Storey Lake Resort, in the new quiet Preserve Area, It has capacity for 12 guests. Storey Lake has a resort-style clubhouse full of amenities and fun for families, including a business center, basketball court, ping pong table, ...

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Property Type

Kissimmee House

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6 BR | 3 BA | Sleeps 14 | Quick View

1

Distance to park: 5 miles to Disney World

$180

avg/night

View Details

Key Amenities

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

About this property

Experience a relaxing & unforgettable vacation in this stunning Tiffany Blue-colored villa, nestled in a peaceful & safe residential neighborhood. Enjoy easy access to theme parks, golf, restaurants, and supermarkets, all just a short drive away. Don't miss out - contact me with any questions!...

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Property Type

Kissimmee House

"Amazing family-friendly home w/ a stunning pool"

Excellent location very close to Disney World. Beautiful and clean home. Host is very welcoming and helpful. The pool is stunning. The pictures do not do it justice. Wish we would have stayed longer!

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5 BR | 4 BA | Sleeps 10 | Quick View

Distance to park: 6 miles to Disney World

$203

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

This beautiful 5 bedroom house is located in Crystal cove gated community. Perfect vacation home for families with small children or large groups. This vacation villa offers a sunny private pool, relaxing spa overlooking the lake. There are 2 master suites, private pool, community pool / gym. Pool ...

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Property Type

Kissimmee House

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2 BR | 2 BA | Sleeps 6 | Quick View

4
owner special
Owner special: 4 bedroom condo, also at Legacy Dunes, is available between 4/30 & 5/9 @ $95 per night + 13.5% tax

Distance to park: 5 miles to Disney World

$97

avg/night

View Details

Key Amenities

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

About this property

Our lakeside condo is on the ground floor and has a screened lanai seating area for your enjoyment. The living room is quite spacious and has a flat screen television, a DVD player, a queen sleeper sofa bed, and has seating for up to six guests. The dining area also has seating for six. Save money by ...

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Property Type

Kissimmee Condo

"Very Comfortable and Quiet Long Term Stay"

We spent 6 weeks in Mary's Ground Floor 4 Bedroom Condo at Legacy Dunes. The condo is spacious and tastefully decorated, it is very clean and well equipped with all we needed for a comfortable long term ...

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3 BR | 2 BA | Sleeps 6 | Quick View

3

Distance to park: 2 miles to Fun Spot America Theme Parks

$116

avg/night

View Details

Key Amenities

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

About this property

Your family will be close to everything when you stay at this centrally-located place.This property it is fully renovated; first-floor unit with a laminate floor, high ceiling in the living room, open floor plan. The kitchen and bathrooms have been upgraded. The whole community was recently replumbed.Nice ...

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Property Type

Kissimmee Townhome

"Great Vacation Home"

We found the townhouse to be nicely decorated with cute little touches, updated, very clean and equipped with all the necessities for a fabulous experience. It's a very safe, quiet, peaceful location, ...

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$167

avg/night

View Details

Key Amenities

  • Air conditioning

About this property

Are you looking for a private home in Kissimmee for your next Florida vacation? Rolling Hills 7965 is just the place! This home is suited for up to 8 guests and features 4 bedrooms and 3 bathrooms. When you step inside, you’ll notice that the décor is upscale and tasteful to suit the style ...

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Pool

About this property

When you’re searching for Orlando vacation rentals, you want a property that’s spacious, luxurious, and full of all the creature comforts of home. This 6 bedroom villa delivers all that and more! Within your home, you’ll have a fully equipped kitchen to whip up some delicious meals, ...

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Pool

About this property

Welcome to your ultimate vacation destination at the ChampionsGate Resort 9-bedroom home! Located in the heart of excitement, this luxurious retreat offers the perfect blend of relaxation, entertainment, and proximity to both golfing paradise and Disney magic.As you step into this vacation dream, ...

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner

About this property

RECENTLY REFURBISHEDLuxurious Windsor Palms with an extra wide cul de sac lot and with a pool that is not overlooked. Our guests enjoy terrific privacy in one of the premier resorts in the Disney vicinity. We have a south facing pool with kiddy pool and stand alone hot tub. Numerous child friendly ...

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Property Type

Kissimmee Villa

"Awesome vacation"

Everything was perfect from start to finish. House was better than we expected, owner was great to deal with and will for sure book this house again and have already referred friends to book this property ...

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Key Amenities

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

About this property

Moran Disney Rentals would love to welcome you to our Luxury 6 bedroom house which is perfectly located on the exclusive Emerald Island Resort community less than 3 miles from the Walt Disney a world Parks in Florida. This property has 6 bedrooms two of which are master bedrooms with a further two and ...

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Property Type

Kissimmee House

"Family spring break"

We had a wonderful time! Everything was clean and fun enough room for the whole family. There are a couple things that need updated but nothing your ordinary house don’t need to! We recommend this house!

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

Treat Retreat @ – Sleeps 16Welcome to your awesome vacation spot by Shine Villas at Storey Lake.Beautifully decorated superior location, 7 bedroom, 6 bathroom home inside the premium Storey Lake Resort Community with full resort access included in the advertised rate. No resort fees ...

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Property Type

Kissimmee Villa

"Wonderful home"

We loved our stay. Large, clean, gated community. Pool was beautiful and hot tub was a hit during the cold front. Some negatives…. Not well stocked and about a 45 minute drive to Disney parks, due ...

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Key Amenities

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

About this property

Just 5 minutes away from Disney World, this Cozy, Lux, themed townhouse will be your perfect getaway from Disney while being your neural operation center to Disney, Golf and Orlando itself. Equipped with everything you need to have unforgettable vacations, from a fully equipped Kitchen to cook the best ...

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Property Type

Kissimmee Townhome

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$450

avg/night

View Details

Key Amenities

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

About this property

This home is located in Storey Lake Resort. This community offers a resort-style clubhouse with a gym and day spa, tiki bar, beautiful pool, lazy river, waterslides, beach volleyball court, kayaks, and children's play area. This warm and spacious two-story single-family home will immediately make ...

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

About this property

Water Kingdom @! Sleeps up to 28!Resort Living In The Tropics!* South Facing Pool * * Water/Lake and Conservation View * * Hot Tub Heat Included at no extra cost *Walking Distance and access to the brand Second ‘Pirate’ Water Park at Storey Lake Resort* - Find Your Amazing ...

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Property Type

Kissimmee Villa

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3 BR | 2 BA | Sleeps 7 | Quick View

6

Distance to park: 12 miles to Disney

Key Amenities

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

About this property

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

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Property Type

Kissimmee House

"Everything was good"

House was very clean and in a nice community. I guess the best review I can give is everything was as advertised.

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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 $69 per night with an average price per night of $201.

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