Kissimmee Vacation Rentals

(266 rentals)
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Kissimmee Townhome
3 BR | 3 BA | Sleeps 9 | Quick View
Sleeps 9, 3 bedrooms, 3 bathrooms
11 reviews

Distance to park: 5 miles to Animal Kingdom Lodge

$166

avg/night

$166
avg per night
View Details

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.** *No long-term rentals - 14 nights maximum *Minimum rental age is 25 years old (exception for married couples ...

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Property Type

Kissimmee Townhome

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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Kissimmee House
7 BR | 6.5 BA | Sleeps 16 | Quick View
Sleeps 16, 7 bedrooms, 6.5 bathrooms
1 review

$550

avg/night

$550
avg per night
View Details

Key Amenities

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

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

Featured review

"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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Kissimmee Townhome
4 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 3 bathrooms

$213

avg/night

$213
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Plush Pelican - Sleeps 10 at Storey Lake by Shine Villas! Gorgeous, beautifully appointed and high end designer decorated 4 bedroom, 3 bathroom townhome with private splash pool sleeping up to 10. Located in one of Orlando's newest resort communities: Storey Lake. Less than 10 minutes ...

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Property Type

Kissimmee Townhome

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Kissimmee Townhome
3 BR | 2.5 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2.5 bathrooms
1 review

$79

avg/night

$79
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

About this property

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

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Property Type

Kissimmee Townhome

Featured review

"Quite friendly"

Great property courteous prompt service and flexible payment options. Close to many attractions. All around a pleasant get away.

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Kissimmee House
7 BR | 4 BA | Sleeps 14 | Quick View
Sleeps 14, 7 bedrooms, 4 bathrooms

$224

avg/night

$224
avg per night
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Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

This 7 bedroom/4½ bathroom private house features a huge 10' x 40' covered lanai, with ceiling fans, extra patio furniture and a large flatscreen TV (accessed only by Netflix/Hulu, etc). Nice pool area in general. Interior furnishings are nice (certainly not spectacular). This is ...

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Property Type

Kissimmee House

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Kissimmee Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$153

avg/night

$153
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Sweet Suite @ – Sleeps 6. (#903) Sleeps up to 6 Master Suite has a King Bed with large TV, fabulous en-suite and large walk in shower, double vanity bathroom and walk in closet space. Sleeps 2 Second bedroom, also with TV with custom wall art, has a full size over full size ...

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Property Type

Kissimmee Condo

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Kissimmee Villa
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms
27 reviews

$144

avg/night

$144
avg per night
View Details

Key Amenities

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

About this property

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

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Property Type

Kissimmee Villa

Featured review

"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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Kissimmee House
5 BR | 5 BA | Sleeps 12 | Quick View
Sleeps 12, 5 bedrooms, 5 bathrooms
2 reviews

$435

avg/night

$435
avg per night
View Details

Key Amenities

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

About this property

Booking is available from the website in Owner info. Modern architecture, state-of-the-art furnishings, and hip-to-the-minute décor make this 5 bedroom, 5 bath getaway in Storey Lake a bonafide safe haven for luxury and comfort. This home is brimming with amenities, from an action-packed game ...

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Property Type

Kissimmee House

Featured review

"Great place, nice price!"

The themed kids' rooms and game room are topping on this rental a club house with so much going on for everyone, including pickup/drop off service to and from the club house. Heated pool and gas grill. ...

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Kissimmee Villa
6 BR | 4 BA | Sleeps 14 | Quick View
Sleeps 14, 6 bedrooms, 4 bathrooms

$311

avg/night

$311
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Fantasia @ – Sleeps 14 Welcome to your Magical Place!! Beautifully designer decorated 6 bedroom, 4 bathroom home inside the premium Storey Lake Resort Community. Private pool AND Spa with more than enough space for up to 14 to stay in comfort. Storey Lake, Located in ...

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Property Type

Kissimmee Villa

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Kissimmee Townhome
3 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 3 bathrooms
4 reviews

$248

avg/night

$248
avg per night
View Details

Key Amenities

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

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

Featured review

"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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Kissimmee Townhome
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms

$196

avg/night

$196
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Magic Lily Gorgeous and designer decorated 4 bedroom, 3 bathroom townhome with private splash pool sleeping up to 8. Brand New July 2021 Located in one of Orlando's newest and finest resort communities: Storey Lake. Less than 10 minutes from Walt Disney ...

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Property Type

Kissimmee Townhome

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Kissimmee Villa
7 BR | 6.5 BA | Sleeps 16 | Quick View
Sleeps 16, 7 bedrooms, 6.5 bathrooms

$336

avg/night

$336
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

WELCOME To “Rebel Flamingo” at Solara Resort by Shine Villas! Sleeps Up to 16 Adults and 1 Baby (Premium Wooden Crib in ‘Mom Haven’ in downstairs master). - PREMIUM Home Size - Premium Games Room with AC and Dual X Box Setup with Included Games Subscription! - Premium ...

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Property Type

Kissimmee Villa

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Kissimmee Villa | On the beach
4 BR | 3 BA | Sleeps 11 | Quick View
Sleeps 11, 4 bedrooms, 3 bathrooms
owner special
Owner special: Dec 1-14 special deal 30% off per night stay

$250

avg/night

$250
avg per night
Owner special:
Dec 1-14 special deal 30% off per night stay

View Details

Key Amenities

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

About this property

Magic Lake View Villa near Disney- Totally private (no neighbors looking in either side) heated PRIVATE South pool with hot tub facing a 14 acre natural fishing lake on a prestigious Lake Berkley Resort, 24/7 Security - gated territory, 100% SAFE! Just 7.8 miles to DISNEY! The villa has everything ...

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Property Type

Kissimmee Villa

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Kissimmee House
9 BR | 8 BA | Sleeps 18 | Quick View
Sleeps 18, 9 bedrooms, 8 bathrooms
11 reviews

Distance to park: 3 miles to Disney Animal Kingdom

$701

avg/night

$701
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Mickey's Oyster is a luxurious oasis designed to make your Disney World vacation unforgettable. Nestled in a prestigious, gated community just minutes away from the magic, this freshly remodeled and renovated home offers an enchanting escape with all the comforts of a five-star resort. Luxurious ...

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Property Type

Kissimmee House

Featured review

"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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Kissimmee Villa
6 BR | 4 BA | Sleeps 12 | Quick View
Sleeps 12, 6 bedrooms, 4 bathrooms
2 reviews

$200

avg/night

$200
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Beautiful two-story home with 6 bedrooms and 4 bathrooms. This home is situated on a quiet street within the Solterra Resort. It boasts modern open plan living. It has an additional outdoor balcony space along with a large private pool and spa, loungers, outdoor table and chairs with an optional BBQ ...

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Property Type

Kissimmee Villa

Featured review

"Amazing villa"

Totally overwhelmed, villa is amazing, very spacious. Highly recommended. We will book this villa again next family gathering. jim

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Kissimmee House
3 BR | 3.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3.5 bathrooms

$213

avg/night

$213
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Luxury vacation homes accommodations feature contemporary interiors, located in Magic Village gated community only 5 minutes away from Disney’s Animal Kingdom. Step into your private villa at Magic Village Yards and discover a chic and contemporary yet invitingly cozy sanctuary. All Bedrooms are ...

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Property Type

Kissimmee House

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Kissimmee Villa
3 BR | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2.5 bathrooms

$164

avg/night

$164
avg per night
View Details

Key Amenities

  • Air conditioning
  • WiFi

About this property

Surfstyle at Margaritaville by Shine Villas This 3 bedroom getaway is the Surfstyle Margaritaville Cottage home of your family dreams. Sitting outside overlooking the lake is what where you will find yourself drawn. Your decision is whether this will be with a coffee or a Margarita in hand! Margaritaville ...

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Property Type

Kissimmee Villa

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Kissimmee House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
2 reviews

$110

avg/night

$110
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This well maintained 3 bedroom 2 baths home located in the renowned Lindfields Estate. It is perfectly placed to maximize your family’s vacation fun here in the entertainment capital of Florida! You will not want to miss this lovely vacation home close to Disney and on the doorsteps of local ...

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Property Type

Kissimmee House

Featured review

"Great"

A great family vacation rental.booking was easy and check in process was flawless. We had an issue with the internet but the manager resolved it as soon as possible. The rental was safe clean and convenient ...

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Kissimmee House
9 BR | 6 BA | Sleeps 23 | Quick View
Sleeps 23, 9 bedrooms, 6 bathrooms

$721

avg/night

$721
avg per night
View Details

Key Amenities

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

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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Kissimmee House
4 BR | 4 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4 bathrooms

Distance to park: 4 miles to Disney

$225

avg/night

$225
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

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

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Property Type

Kissimmee House

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Kissimmee Villa
4 BR | 2 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 2 bathrooms

$165

avg/night

$165
avg per night
View Details

Key Amenities

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

About this property

The heart and soul of any Disney vacation is the centerpiece in this Mickey Mouse themed villa. Leading from the living/dining room is the upgraded and fully-equipped kitchen, which includes a ceramic top range, side by side refrigerator/freezer, dishwasher, garbage disposal, and microwave. Along with ...

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Property Type

Kissimmee Villa

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Kissimmee Villa
5 BR | 4 BA | Sleeps 12 | Quick View
Sleeps 12, 5 bedrooms, 4 bathrooms

$170

avg/night

$170
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

The spacious two storey 5 bed, 4 bath fully air-conditioned home has a south facing pool. There is an extended pool deck for all day sun and has a spacious covered lanai for alfresco dining and poolside entertaining. This well-equipped and newly furnished home caters for all your holiday needs with ...

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Property Type

Kissimmee Villa

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Kissimmee Villa
7 BR | 7 BA | Sleeps 18 | Quick View
Sleeps 18, 7 bedrooms, 7 bathrooms
1 review

$331

avg/night

$331
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Just Wow - Monterey Bay at Solara by Shine Villas! 7 Bedrooms and 7 Bathroom - Sleep up to 18 when using the trundle beds. This home is exquisitely designed and has all you could want from your vacation home away from home. Private Pool with Spa, Media Loft Area, Air-Conditioned Avengers ...

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Property Type

Kissimmee Villa

Featured review

"Very beautiful home"

It’s a very beautiful home and real spacious and clean I will love to book again very professional and the host was very sweet and kind

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Kissimmee Villa
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms
4 reviews

$189

avg/night

$189
avg per night
View Details

Key Amenities

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

About this property

Palm Tree Villa Florida, is tucked away in the much sought after location of Doral Woods. This large 4 Bedroom, 3 Bathroom villa, is ideal for making the perfect vacation. This is our own holiday home, so the furnishings are to a high standard, as you can see from the pictures and video. Fully Air ...

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Property Type

Kissimmee Villa

Featured review

"Lovely Villa with a lot of extras !"

Beautiful place for a relaxing holiday or just 15 minutes away from the Disney and Resorts area . The home was perfect and the welcome package was great. Andy was great and checked in on us during our stay. ...

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Kissimmee Villa
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms
3 reviews

$170

avg/night

$170
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Water View and Outdoor Spa! Stay close to just about everything and enjoy easy access to our world-renowned theme parks, exciting golf, mega shopping and exceptional dining. Ideal for your next family vacation, this attractive 4 bedroom, 3 bath Disney area vacation home is conveniently located just ...

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Property Type

Kissimmee Villa

Featured review

"Our Walt Disney World vacation"

The villa was absolutely wonderful as well as the pool and exactly as shown on the site picture. We were in Florida for 10 nights. The company which takes care of the site was also great, they responded ...

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Kissimmee Villa
8 BR | 6 BA | Sleeps 23 | Quick View
Sleeps 23, 8 bedrooms, 6 bathrooms

$358

avg/night

$358
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to Camp Mickey at Solara Resort by Shine Villas. This home has it All. Private Pool and Spa Overlooking Water, Media Loft Area with Arcade Machine, Air-Conditioned Pool Room. Camp Mickey Bunk Room and Star Wars bedroom is just the start! This beautiful property comfortably provides accommodation ...

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Property Type

Kissimmee Villa

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Kissimmee House
4 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 3 bathrooms

$218

avg/night

$218
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

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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Kissimmee Villa
4 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 3 bathrooms
2 reviews

$187

avg/night

$187
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

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

Featured review

"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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Kissimmee House
5 BR | 4 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 4 bathrooms
1 review

Distance to park: 7 miles to Disney Hollywood Studio

$146

avg/night

$146
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

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

Featured review

"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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Kissimmee House
4 BR | 2.5 BA | Sleeps 9 | Quick View
Sleeps 9, 4 bedrooms, 2.5 bathrooms
10 reviews

Distance to park: 10 miles to Disneyworld

$137

avg/night

$137
avg per night
View Details

Key Amenities

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

About this property

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

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Property Type

Kissimmee House

Featured review

"Looking for a great vacation rental for the kids? This is it!!"

What a nice house! It has everything you could want in a vacation home. A very nice pool, patio and attached BBQ area with gas grill, literally a ton of DVD's to keep everyone entertained in the evening, ...

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Kissimmee House
5 BR | 4 BA | Sleeps 12 | Quick View
Sleeps 12, 5 bedrooms, 4 bathrooms
3 reviews
last minute deal
LAST MINUTE DEAL 12/1 - 12/27: Christmas Cancellation! December dates reduced with FREE pool heat, messages for a quote :)

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

$283

avg/night

$283
avg per night
Offer for: Dec 1 - Dec 27:
Christmas Cancellation! December dates reduced with FREE pool heat, messages for a quote :)

View Details

Key Amenities

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

About this property

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

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Property Type

Kissimmee House

Featured review

"Our Very Magical Thanksgiving"

From the moment we inquired about booking until the day we checked out communication was extremely easy and quick responses. Upon arrival everything was so clean. Pictures don’t do it justice. We had ...

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DEAL
Kissimmee House
5 BR | 4.5 BA | Sleeps 15 | Quick View
Sleeps 15, 5 bedrooms, 4.5 bathrooms

$236

avg/night

$236
avg per night
View Details

Key Amenities

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

About this property

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

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Property Type

Kissimmee House

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Kissimmee House
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms
16 reviews

Distance to park: 4 miles to Disney

$155

avg/night

$155
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Magical Dreams come true in our elegant private 4 bedroom villa, 3 bathroom, all located on one floor, Quiet upgraded comforts of home and luxuries of an exceptionally rated vacation resort/hotel. Newly resurfaced and freshly painted pool and spa is sure to impress. There will be no waiting in line ...

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Property Type

Kissimmee House

Featured review

"Perfect rental for all of our needs!"

This was a Christmas vacation never to be forgotten! We had the time of our lives! My children, grandchildren and I enjoyed the comforts and privacy of a home where we could take in all the theme parks ...

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Kissimmee Condo
2 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 2 bedrooms, 2 bathrooms

$144

avg/night

$144
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Catch the Disney and Epcot Fireworks at Night from your top floor private balcony, Resort Living by Day! Sleeps up to 8 when using the bunk room trundle and the pull out sofa bed. Master Suite has a King Bed with fabulous en-suite, large walk in shower, double vanity bathroom and walk in closet ...

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Property Type

Kissimmee Condo

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Kissimmee House
9 BR | 5 BA | Sleeps 22 | Quick View
Sleeps 22, 9 bedrooms, 5 bathrooms
1 review

$277

avg/night

$277
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Brand new, very spacious, modern 9-Bed 5-Bath pool home in an exclusive, private gated golf resort. You'll love the feeling of luxury and space throughout the house, the 2 King en-suite master bedrooms, 4 kids themed bedrooms, 3 additional King bedrooms, the games room, the private pool and spa, ...

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Property Type

Kissimmee House

Featured review

"Florida Holiday"

Hi there! We enjoyed our stay quite a bit. However, there were a few things that could have improved our stay. The one lounger was damaged and the one chair was damaged. There was not a bottle opener ...

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Kissimmee Villa
Studio | 4.5 BA | Sleeps 14 | Quick View
Sleeps 14, 0 bedrooms, 4.5 bathrooms

$337

avg/night

$337
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

7 bedroom 4.5 bath waterfront home located in the highly desired Emerald Island resort close to Disney and Universal Studios. The ground floor of this villa is an open concept with a living area featuring a 65" Smart 4k tv. The granite countertop kitchen boasts all new 2022 stainless appliances. ...

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Property Type

Kissimmee Villa

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Kissimmee Villa
6 BR | 5 BA | Sleeps 12 | Quick View
Sleeps 12, 6 bedrooms, 5 bathrooms
1 review

$288

avg/night

$288
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Stars Align @ – Sleeps 12 Welcome to your Cosmic Place!! You have found your vacation home here – Congratulations! Beautifully designer decorated 6 bedroom, 6 bathroom home inside the premium Storey Lake Resort Community. Play Planet Pinball in the games area, hideaway in one of ...

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Property Type

Kissimmee Villa

Featured review

"Excellent"

This home was well taken care of. The moment we arrived the house was clean and even more beautiful than the pictures. The cleaning crew did an amazing job. The owner was so polite and made us feel welcomed. ...

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Kissimmee House
7 BR | 4.5 BA | Sleeps 14 | Quick View
Sleeps 14, 7 bedrooms, 4.5 bathrooms

$460

avg/night

$460
avg per night
View Details

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 else ...

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Property Type

Kissimmee House

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Kissimmee House
4 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 4 bedrooms, 3 bathrooms
15 reviews

$127

avg/night

$127
avg per night
View Details

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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Property Type

Kissimmee House

Featured review

"Great Location for your stay."

The home was very comfortable and dealing with the owner was a breeze. Check in was very easy and the location is ideal for Disney and Universal visitors. Nice lake view and several chairs for outdoor seating. ...

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Kissimmee House
5 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 3 bathrooms
8 reviews

Distance to park: 8 miles to Disney

$150

avg/night

$150
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Come stay in our spacious one story single family home that features 5 bedrooms, 3 bathrooms fully kitchen and a private pool (can be heated for additional fee) Our home is very well located in Lake Berkley Resort with short walking distance to the lake berkley, where you may walking or fishing. ...

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Property Type

Kissimmee House

Featured review

"Fantastic Villa, exceeded our expectations"

The location was great, a very nice and super clean area. The Villa was great and exceeded our expectations. It had all amenities and then some and was super clean which was very much appreciated. Property ...

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Kissimmee Villa
4 BR | 4 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 4 bathrooms
2 reviews

$325

avg/night

$325
avg per night
View Details

Key Amenities

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

About this property

Name Of Home: Walking on Sunshine Villa Location: 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 PS5 Property Type: Single ...

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Property Type

Kissimmee Villa

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Kissimmee Villa
4 BR | 2.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 2.5 bathrooms
1 review

Distance to park: 3 miles to Disneys Animal Kingdom

$202

avg/night

$202
avg per night
View Details

Key Amenities

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

About this property

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

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Property Type

Kissimmee Villa

Featured review

"Tolles Haus"

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

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Kissimmee Townhome
4 BR | 3 BA | Sleeps 11 | Quick View
Sleeps 11, 4 bedrooms, 3 bathrooms
1 review

$198

avg/night

$198
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Happy Haven at Storey Lake Resort by Shine Villas – Sleeps up to 12 Welcome to your Holiday Home! Beautifully decorated 4 bedroom, 3 bathroom home inside the premium Storey Lake Community. Private Splash pool and space for up to 12 to stay. Storey Lake, Located in ...

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Property Type

Kissimmee Townhome

Featured review

"Beautiful house and location"

The house is in a resort complex and even we did not use they much for the weather cold. I want to say it is a very nice place for family vacation. House was clean and in excellent location. I would stay ...

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Kissimmee Villa
9 BR | 7.5 BA | Sleeps 22 | Quick View
Sleeps 22, 9 bedrooms, 7.5 bathrooms

$366

avg/night

$366
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Moana Castle at Solara Resort by Shine Villas! Your children will thank you for years to come after they arrive and run around exploring this home excitedly. It has absolutely everything. 9 Bedrooms, 7 bathrooms, sleeps up to 22. This home is exquisitely designed and has all you could want from ...

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Property Type

Kissimmee Villa

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Kissimmee House
5 BR | 4 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 4 bathrooms
8 reviews

$233

avg/night

$233
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

*** For smaller groups we offer the opportunity to rent the main house. This area has 4 Bedrooms and 3 Bathrooms Please contact us and ask for a quote *** Our beautiful 3000sq 5 Bed, 4 Bathroom home is located on a generous corner plot. With a south facing Pool and stunning views over the second ...

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Property Type

Kissimmee House

Featured review

"A Memorable Vacation"

We are delighted with the care and wonderful hospitality that Jackie and Vicky provided to us during our stay. Their attention to any needs were met promptly and respectfully. We are so fortunate of their ...

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Kissimmee Villa
7 BR | 6 BA | Sleeps 14 | Quick View
Sleeps 14, 7 bedrooms, 6 bathrooms
4 reviews

$376

avg/night

$376
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

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

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Property Type

Kissimmee Villa

Featured review

"2nd time still a charm"

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

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Kissimmee House
8 BR | 6 BA | Sleeps 22 | Quick View
Sleeps 22, 8 bedrooms, 6 bathrooms

$548

avg/night

$548
avg per night
View Details

Key Amenities

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

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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Kissimmee House
3 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3 bathrooms

Distance to park: 4 miles to Disney

$216

avg/night

$216
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

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

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Property Type

Kissimmee House

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Kissimmee Villa
9 BR | 10 BA | Sleeps 26 | Quick View
Sleeps 26, 9 bedrooms, 10 bathrooms
16 reviews

$965

avg/night

$965
avg per night
View Details

Key Amenities

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

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

Featured review

"50th birthday celebration"

We booked this for my husbands 50th birthday getaway and it was all we imagined! The place was very spacious and the owner was easy to communicate with. The pool and the outdoor living areas are spectacular. ...

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Kissimmee Townhome
4 BR | 3.5 BA | Sleeps 11 | Quick View
Sleeps 11, 4 bedrooms, 3.5 bathrooms

$330

avg/night

$330
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Make lifelong memories with your family and experience the bliss of a private home away from home. With the kids’ Frozen- and Avatar-inspired bedrooms, you'll have them squealing in delight! Enjoy luxuries like a fully equipped kitchen, epic game room, an inviting lounge area, children's ...

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Property Type

Kissimmee Townhome

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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 266 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 $65 per night with an average price per night of $188.

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