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Kissimmee Vacation Rentals

(211 rentals)
New
Kissimmee House
Sleeps 11, 5 bedrooms, 5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Calling all sun seekers & splash lovers! This Storey Lake gem boasts 5 bedrooms & 5 bathrooms, making it the perfect escape for your squad (sleeps 11). Dive into the sparkling pool, whip up culinary masterpieces in the fully-equipped kitchen. After a day of adventures, gather for movie nights...

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$389
avg per night
New
Kissimmee House
Sleeps 28, 9 bedrooms, 5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

The ultimate group getaway! This massive 9BR/5BA Storey Lake estate sleeps 28 and is packed with entertainment. Just 10 miles to Disney & 12 to Universal. Kids will be amazed by the Harry Potter, Minions, and Tangled themed rooms! Host movie nights in your private cinema or challenge friends in the...

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$514
avg per night
Kissimmee Villa
Sleeps 12, 5 bedrooms, 5 bathrooms

Key Amenities

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

About this property

Welcome to Whimsical Mouse Manor! This 5BR/5BA Disney-themed villa sleeps 12 and features a private pool, Dumbo arcade, and magical bedrooms. Located in Windsor Hills Resort, just 5 minutes to Disney. Free pool heat, crib, smart TVs, and resort waterpark access included. Family fun awaits! Make sure...

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$420
avg per night
Kissimmee House
Sleeps 10, 5 bedrooms, 4 bathrooms
10 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

You can also view our 5 stars reviews on Airbnb Please ask for details. Free Spa Heat For Remaining Dates in 2026 Reunion Resort is the home to many multiple custom million dollar homes. It is not your standard rental community. This is home to many residents. Our beautiful 3000sq 5 Bed, 4...

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Featured review

"Lovely home"

My family enjoyed staying in this lovely home while visiting Disney. While it was a bit of a drive away from all the parks, it was in a quiet, gated community with an on site pool and small hot tub. There...

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$224
avg per night
Kissimmee House
Sleeps 17, 8 bedrooms, 6 bathrooms
10 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

YOUR FLORIDA OASIS AWAITS! This gorgeous villa is NEWLY UPDATED for your Kissimmee Disney Vacation Rental. Located in the gated Windsor at Westside Resort, with 8 bedrooms, 6 bathrooms there is plenty of room to sleep 17 guests! Enjoy your own private pool with privacy curtains (a rare feature in this...

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Featured review

"Five star all the way!"

LOVE THIS HOUSE! This villa was exactly as described - private, luxurious and with all the amenities you could ask for. I was one of the first renters with the new owners and I can’t wait to get back!...

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$455
avg per night

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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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$96
avg per night
Kissimmee Bungalow
Sleeps 9, 4 bedrooms, 3 bathrooms
8 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

"Suited our needs"

We had 2 weeks here with our daughter, it suited our needs well It was clean and bright, with everything we needed, my husband and myself had an en suite and so did our daughter, we were delighted with...

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$130
avg per night
Last Minute Deal
Kissimmee Villa
Sleeps 10, 5 bedrooms, 5 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

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! WE HAVE ALL 5 STAR REVIEWS ON VRBO #3553563 This resort features, $2.1 mil Lagoon Style pool with Zero Depth Entry and Water Slides. Also, with a Water Park for the littles!...

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Featured review

"Place is fantastic"

Stayed for a week in April. Had everything we needed, felt at home, and close to all of the major attractions. Was a great quiet area, kids swam in the pool everyday, and hot tub was a needed amenity...

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$245
avg per night
Kissimmee House
Sleeps 16, 7 bedrooms, 4 bathrooms
87 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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$331
avg per night
Kissimmee Townhome
Sleeps 9, 3 bedrooms, 3 bathrooms
16 reviews

Distance to park: 5 miles to Animal Kingdom

Key Amenities

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

About this property

**The private pool is not heated unless requested by the guest. Pool heating is available for an additional fee of $10.00 per day. Pool heating must be arranged and paid for prior to arrival.** *Minimum rental age is 25 years old (exception for married couples and active duty military) *Pets are not...

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Featured review

"FANTASTIC property!"

This is the place to stay! This rental truly felt like a home away from home. It was a short drive to countless restaurants and shopping...location is perfect! If you're going to Disney, you'll only...

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$163
avg per night
Kissimmee House
Sleeps 14, 7 bedrooms, 4.5 bathrooms
18 reviews

Distance to park: 3 miles to Disney World Parks

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Margaritavilla | 7 Bedrooms, Private Pool & Spa Near Disney Make room for everyone—and time to relax. Located in Emerald Island Resort, Margaritavilla welcomes up to 14 guests with seven bedrooms, 4.5 bathrooms, and inviting spaces to gather or enjoy a quiet moment. It’s a comfortable...

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Featured review

"Best home away from home rental"

This was truly a Dream Come True Rental. Very clean , no surprises every thing just advertised. I'm setting up another stay now and hopefully yearly stays going forward.

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$259
avg per night
New
Kissimmee Villa
Sleeps 14, 7 bedrooms, 4 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Disney Dream | 7-Bedroom Lakeview Villa with Private Pool & Hot Tub To Book please go to Bring the whole family to Disney Dream, our spacious seven-bedroom villa in Terra Verde Resort, a gated community in Kissimmee near Orlando's world-famous theme parks. With room for up to 14 guests,...

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$163
avg per night
Kissimmee House
Sleeps 10, 3 bedrooms, 2 bathrooms
34 reviews

Key Amenities

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

About this property

Escape to our modern coastal home, a private oasis just 4 miles from Disney World! Perfect for families, this spacious retreat comfortably accommodates 4 adults and 6 kids. Enjoy a private pool for relaxing after long park days, a fully equipped kitchen for family meals, and a dedicated workspace if you...

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Featured review

"Perfect stay"

Went there for a girls weekend and this home was perfect! Had everything we needed, clean and decorated so nice! Loved the pool with lights above. Furniture was so comfortable. Not far from anywhere you...

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$157
avg per night
New
Kissimmee House
Sleeps 12, 6 bedrooms, 4 bathrooms

Key Amenities

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

About this property

Stay near Disney in this family-friendly six-bedroom home in Veranda Palms, Kissimmee, with space for up to 12 guests. Enjoy a private screened pool and hot tub/spa, BBQ grill, outdoor dining, and comfortable shared living spaces. SLEEPING ARRANGEMENTS Bedroom 1: King bed and crib Bedroom 2: Two...

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$479
avg per night
Kissimmee House
Sleeps 8, 4 bedrooms, 3 bathrooms
4 reviews

Distance to park: 3 miles to Disney Parks

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

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

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Featured review

"Family of 5, 3 adults 2 children"

I would highly recommend Palm Breeze in Emerald Island. The villa is in a perfect location for a Disney holiday and has the large benefit of being in a locked community. We felt very safe during our holiday....

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$142
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 10 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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$190
avg per night
Kissimmee Villa
Sleeps 8, 4 bedrooms, 3 bathrooms
3 reviews

Distance to park: 3 miles to Disney Animal Kingdom

Key Amenities

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

About this property

Welcome to Honeypot Villa, a comfortable four-bedroom, three-bathroom vacation home in Kissimmee, sleeping up to eight guests. With approximately 1,800 square feet of living space, it offers a relaxing base for families and groups visiting Walt Disney World and Central Florida. Spend time together...

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Featured review

"Total Relaxation"

Exactly what I was looking for. Great location.Definitely not 1 of those show homes that you are afraid to do anything in. This villa is so Homely and Comfortable with Everything you'll need throughout...

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$152
avg per night
Kissimmee Villa
Sleeps 8, 4 bedrooms, 3 bathrooms
20 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

"Home from home"

Myself and my husband made a last minute decision to come to Florida from Scotland Uk. I had previously seen Kim’s villa and made contact earlier in the year but plans didn’t allow the visit at that...

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$144
avg per night
New
Kissimmee House
Sleeps 11, 5 bedrooms, 5 bathrooms

Distance to park: 4 miles to Disney Animal Kingdom (to the gate)

Key Amenities

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

About this property

Family-owned and operated by Beautiful Life Villas Bella Vita Villa is a recently remodeled luxury vacation home in Kissimmee, Florida, located inside the prestigious gated community of Windsor Hills — just 2 miles from Walt Disney World. Designed for unforgettable family vacations, this private...

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$305
avg per night
Kissimmee House
Sleeps 16, 8 bedrooms, 6 bathrooms
3 reviews

Key Amenities

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

About this property

Welcome to Your Family’s Kissimmee Retreat — Space, Comfort & Resort Luxury Minutes From Disney Step into a 4,000 sq ft haven designed for families and groups who want to spread out, relax, and create unforgettable memories together. With a private heated pool + spa, multiple king suites,...

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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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$346
avg per night
Kissimmee House
Sleeps 8, 4 bedrooms, 3 bathrooms
17 reviews

Distance to park: 3 miles to Disney

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Magical Dreams come true in this newly renovated home. Beach and Coastal themed Villa, throughout with something for everyone. We recently renovated the entire home with paint, inside and out, landscaping and decor. Come relax and unwind and enjoy our slice of paradise. The property offers a south...

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Featured review

"Kissimmee Villa (Sept - Oct 2025 = 3 Weeks)"

Overall - perfect location, lovely villa / home, great pool and jacuzzi, everything we wanted and needed! A+ A shaky start on arrival with an air conditioning issue, but sorted within a few hours and...

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$139
avg per night
Kissimmee House
Sleeps 24, 9 bedrooms, 6.5 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to your unforgettable Orlando vacation home in Solara Resort, where peaceful lake views, private entertainment, themed bedrooms, and resort-style amenities come together for an amazing Central Florida getaway. Located approximately 9 miles from Walt Disney World, this spacious 9-bedroom villa...

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$562
avg per night
Kissimmee Villa
Sleeps 20, 9 bedrooms, 5 bathrooms
114 reviews

Distance to park: 7 miles to Disneyworld

Key Amenities

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

About this property

SCAN QR CODE for a VIRTUAL TOUR. WE ARE A TOP 5 STAR LUXURY VILLA AND INVITED TO FEATURE ON THE EMMY AWARD WINNING SHOW STAYCATION ON THE DESTINATION CHANNEL. Experience luxury and entertainment in this 9-bedroom villa that has 7 different themed rooms, a private pool/hot tub, and unobstructed...

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$662
avg per night
Kissimmee Townhome
Sleeps 10, 4 bedrooms, 3.5 bathrooms
17 reviews

Distance to park: 5 miles to Animal Kingdom

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

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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Featured review

"Great!"

We love staying here. Close to everything, clean, spacious and reasonable priced. The area is quite and we have never had a problem. We have stayed here twice now and will cont when we visit Florida.

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$118
avg per night
Kissimmee Villa
Sleeps 14, 6 bedrooms, 4 bathrooms
39 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to Crush's Crash Pad – Where Legacy Vacations Begin Welcome to Crush's Crash Pad WDW – the crown jewel of Windsor Hills and the only villa your family will ever want to book again. We're not just owners; we're vacationers just like you. Having stayed at Windsor...

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Featured review

"Perfect family vacation home"

Great location close to shopping and entertainment. All restaurants within minutes. House is amazing with everything we could have needed. Pool and Hot Tub area perfect for the family and the kids loved...

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$399
avg per night
Kissimmee Townhome
Sleeps 8, 3 bedrooms, 2.5 bathrooms
2 reviews

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

"Awsome!"

Very nice quiet area. The location was very near to all of the attractions (Disney, Old Town, universal and the World food truck etc) The villa was beautiful clean and well kept. Mr Barry was very...

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$103
avg per night
Kissimmee Villa
Sleeps 16, 8 bedrooms, 6 bathrooms
1 review

Distance to park: 7 miles to Disney World

Key Amenities

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

About this property

We have had some dates open up in October! Contact us for a great weekly and monthly rate! October is one of the best times to visit Central Florida. Spooktacular events at all the parks! Some wonder what makes your Disney vacation memorable? We can help you have the best vacation in Central Florida....

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Featured review

"Amazing for our family!!"

My girlfriend, daughter and I stayed with 4 other family members during our time there, 7 of us total! One of our party members is in a wheelchair and the accessibility options Monica has worked into the...

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$261
avg per night
Kissimmee House
Sleeps 32, 12 bedrooms, 11 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Create unforgettable memories at this newly renovated luxury vacation home inside the gated Bella Vida Resort in Kissimmee. Featuring 12 bedrooms, 19 beds and space for up to 32 guests, this one-of-a-kind villa is designed for large families, multiple families, reunions, group vacations and special celebrations...

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$669
avg per night
New
Kissimmee House
Sleeps 9, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Private screened pool with lake views and no rear neighbors, inside gated Storey Lake Resort. Sleeps 10 in 4 bedrooms (king suite, ground-floor queen, two rooms with two full beds each). Free lazy river, mini-golf, and fitness center access Fully equipped kitchen Fast Wi-Fi Washer/dryer Free...

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$253
avg per night
Kissimmee Villa
Sleeps 8, 4 bedrooms, 2 bathrooms
10 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

"Excellent"

Comfortable well-equipped villa in a convenient location. Our second visit and hope to return in the future. Most enjoyable.

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$204
avg per night
New
Kissimmee House
Sleeps 22, 8 bedrooms, 6 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Step into this fully renovated ultimate Disney vacation home, designed to impress. All-new furniture and stylish finishes make it one of the most sought-after stays in the area. Featuring 5 king bedrooms plus 3 fun bunk-bed rooms, it’s perfect for large groups. Enjoy a fully immersive movie theater,...

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$558
avg per night
Kissimmee House
Sleeps 26, 9 bedrooms, 6 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to your unforgettable Orlando vacation home in Storey Lake Resort, Kissimmee, Florida. Designed for large families, multiple families traveling together, family reunions, sports groups, and group vacations, this spacious 9-bedroom, 6-bathroom home sleeps up to 26 guests and combines the privacy...

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$496
avg per night
New
Kissimmee House
Sleeps 28, 12 bedrooms, 8 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Group getaways: the weekend after Thanksgiving (Nov 27–Dec 1), December before Christmas and much of January and February are still open. Two side-by-side themed homes with two private pools and spas, a neon arcade and a superhero game room, and room for up to 28 guests, all in gated Windsor Hills...

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$831
avg per night
Kissimmee House
Sleeps 14, 7 bedrooms, 4.5 bathrooms
1 review

Key Amenities

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

About this property

⭐Perfect Family Destination ⭐Best lania/pool ⭐Minutes to Disney/Attractions/Conveniences ⭐ Fun/Clean/Comfortable This 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...

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Featured review

"Amazing holiday stay"

This villa was absolutely fantastic, we had a brilliant time staying here on our holiday. The location was ideal for frequent trips to Disney as well as close to many shops and restaurants. The host Jeanne...

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$413
avg per night
New
Kissimmee Villa
Sleeps 8, 4 bedrooms, 2 bathrooms

Key Amenities

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

About this property

Palm Ever After – Where Disney Magic Meets Your Dream Florida Vacation! Welcome to Palm Ever After, a beautifully renovated 4-bedroom, 2-bathroom private villa nestled in the wonderful gated community of Windsor Palms Resort in Kissimmee, less than 10 minutes from Walt Disney World! Designed...

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$189
avg per night
Kissimmee House
Sleeps 18, 6 bedrooms, 5.5 bathrooms
62 reviews

Distance to park: 4 miles to Animal Kingdom

Key Amenities

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

About this property

Some of the best features of this house from more than 300 5-star 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 with a total of 4 power reclining...

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Featured review

"Wow! Amazing house!!!"

I am a frequent visitor to Florida. I have gone 10 years in a row with my husband and boys, and now the past two years with my mother. I have not found anywhere to stay that compares to the beauty and excellence...

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$179
avg per night
Kissimmee Villa
Sleeps 8, 4 bedrooms, 2 bathrooms
11 reviews

Distance to park: 5 miles to Walt Disney World

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Located in the 5 star gated (guarded) resort of Windsor Palms, this 4 bedroom home is minutes away from Disney World, Universal Studios, and other major attractions. Keyless entry for easy access. You'll find all the comforts of home including a private pool, flat screen HDTVs, XBOX 360 and N64,...

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Featured review

"Amazing Owner/Host"

Don was an outstanding host! He responded to every question I had extremely fast. Don was so kind to send a list of "things to do", restaurants entertainment, etc. I felt he genuinely wants all guests to...

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$225
avg per night
New
Kissimmee House
Sleeps 14, 6 bedrooms, 4 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Holiday dates in November and early December are still open. Spend your days on Disney's holiday magic, then come home to your own neon arcade, racing simulators and a private screened pool and spa (pool and spa heat available on request). Welcome to the Magical Themed Home, a themed 6-bedroom,...

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$327
avg per night
New
Kissimmee House
Sleeps 20, 9 bedrooms, 9 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Enjoy the Epitome of Luxury living in Sonoma Resort! This 9-bedroom/10-bathroom mansion sleeps 22 guests with modern state-of-the-art perks. The chef’s kitchen, pool, hot tub, theater, and arcade are magical enough to charm anyone! Conveniently located near restaurants, shops, Disney Parks, Universal...

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$495
avg per night
New
Kissimmee Villa
Sleeps 28, 10 bedrooms, 5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This 10-bedroom | 5-Bathroom luxury villa is the perfect escape for large groups, just minutes from Walt Disney World and Universal Studios. With sleeping for up to 28 guests, this home features a private backyard pool & spa and a fun game room. Experience the magic of your own themed bedrooms,...

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$561
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

Family dream getaway: a stunning 6-bedroom, 3.5-bathroom villa in a luxurious Kissimmee gated community. Minutes from Walt Disney World, it features a private heated pool, game room, and exceptional community amenities. Comfortably fits large families or groups seeking relaxation and adventure near Central...

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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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$226
avg per night
Kissimmee House
Sleeps 6, 4 bedrooms, 2 bathrooms
15 reviews

Key Amenities

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

About this property

CHEERY 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 without. Located in Eagle Pointe, a well sought-after vacation home community. Just minutes from what...

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Featured review

"Absolutely Fantastic"

Just everything about the house was .brilliant could not fault anything clean well kept really well maintained

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$124
avg per night
Kissimmee House
Sleeps 10, 5 bedrooms, 5 bathrooms
2 reviews

Distance to park: 2 miles to Walt Disney World

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

The Floridian Oasis is a terrific 5-bedroom/5-bathroom rental home located in Windsor Hills Resort. This beautiful villa includes upstairs and downstairs King Bedroom suites. It also has a Queen Bedroom and Twin Bedroom on the first floor. And there is an another Twin Bedroom on second floor making this...

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Featured review

"Disney get away"

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

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$238
avg per night
Kissimmee House
Sleeps 6, 4 bedrooms, 3 bathrooms
19 reviews

Key Amenities

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

About this property

Close to the Attractions but away from the crowds. 4 bedroom/3 bath single story home on "lake". Ducks, Sandhill Cranes, sometimes a falcon, turtles. King, king, and 4 twin beds, TV in all bedrooms, WiFi, FREE US, Canada and US Territory phone calls. Fully furnished. Not suitable for...

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Featured review

"Home Away from Home"

The name says it all! This was the perfect house for my family and I. It was in close proximity to most of the stores and restaurants we visited. Mrs. Diane was a most accomodating, gracious and caring...

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$123
avg per night
Kissimmee Villa
Sleeps 14, 7 bedrooms, 5.5 bathrooms

Distance to park: 11 miles to Disney's Magic Kingdom

Key Amenities

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

About this property

Saleda at Windsor – 7BR/5BA Luxury Villa w/ Private Pool + Spa | Steps From Clubhouse Welcome to Saleda at Windsor, a beautifully updated 7-bedroom, 5-bath resort home located in the highly desirable Windsor at Westside, one of Orlando’s newest premium vacation communities. Perfectly positioned...

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$320
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 near Disney and Universal. Nestled in a secure gated community, our home boasts a private pool and hot tub, a fully-equipped kitchen, and comfortable bedrooms including a master suite with a king bed. Exclusive amenities include access...

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$180
avg per night
Kissimmee House
Sleeps 30, 12 bedrooms, 11.5 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to your unforgettable 12-bedroom Orlando vacation home near Walt Disney World, thoughtfully designed for large families, multiple families traveling together, family reunions, sports groups, celebrations, and once-in-a-lifetime Central Florida getaways. This spacious luxury villa offers the...

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$754
avg per night
Kissimmee House
Sleeps 33, 12 bedrooms, 11.5 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to your unforgettable Orlando vacation retreat at Veranda Palms Resort in Kissimmee, Florida. This spacious 12-bedroom, 11.5-bathroom luxury vacation home near Walt Disney World was designed for large families, multiple families traveling together, family reunions, sports groups, celebration trips,...

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$683
avg per night
New
Kissimmee Townhome
Sleeps 10, 5 bedrooms, 4.5 bathrooms

Distance to park: 9 miles to Disney’s Animal Kingdom

Key Amenities

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

About this property

Ideal for families and groups, this newly renovated Solara villa features themed bedrooms and a gaming loft, keeping kids entertained while adults unwind by the screened heated private pool and stylish living spaces. Designer interiors, fast Wi-Fi, keypad check-in, and family-friendly amenities make every...

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$200
avg per night
New
Kissimmee House
Sleeps 14, 6 bedrooms, 5 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

I would like to personally invite you to the #1 Luxury Vacation Rental Villa near Disney at the Encore Reunion Resort. Welcome to 384 Southfield, a 3,203 sq. ft., 6-bedroom, 5-bathroom luxury resort home in the gated Encore Resort at Reunion, thoughtfully designed to host up to 14 guests. Located less...

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$489
avg per night
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Kissimmee Weather

F° | C°

7222°  489°
JANUARY
7423°  5111°
FEBRUARY
7826°  5412°
MARCH
8328°  6016°
APRIL
8731°  6619°
MAY
9032°  7222°
JUNE
9233°  7423°
JULY
9133°  7423°
AUGUST
9032°  7323°
SEPTEMBER
8529°  6619°
OCTOBER
7926°  5714°
NOVEMBER
7423°  5211°
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.