Kissimmee Vacation Rentals

(260 rentals)
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Kissimmee House
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms
4 reviews

$156

avg/night

$156
avg per night
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Key Amenities

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

About this property

Beautiful 4 bedroom/3 bathroom house in the luxurious Emerald Island Resort - Only ~ 4 miles from Disney & close to other major attractions! This home is equipped with a heated private pool, spa & game room. There is a large SMART TV in the living room & in each bedroom. There are queen beds ...

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Property Type

Kissimmee House

Featured review

"Fantastic gem"

Just spent two weeks in this beautiful villa. Definitely a home from home and everything you need for a holiday near to all the parks . Plenty of shops and restaurants nearby and we definitely sampled ...

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Kissimmee House
12 BR | 11.5 BA | Sleeps 24 | Quick View
Sleeps 24, 12 bedrooms, 11.5 bathrooms

$419

avg/night

$419
avg per night
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Key Amenities

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

About this property

Nestled over at the Bella Vida Resort, just a measly 5 miles away from the magical kingdom of Walt Disney World (yeah, we're basically neighbors!), this 12 bedroom mansion is big enough to host 24 of your favourite people. Let's kick things off with the amazing back deck. Picture this: a ...

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Kissimmee House

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Kissimmee Villa
4 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 2 bathrooms
2 reviews

Distance to park: 5 miles to Walt Disney World

$200

avg/night

$200
avg per night
View Details

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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Property Type

Kissimmee Villa

Featured review

"Great place to stay!!"

Don and Sarah's home is very nice. We appreciated how clean and well kept it was. We were very impressed with the variety of kitchen appliances that were available. We had hamburgers on the George Foreman ...

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Kissimmee House
10 BR | 8 BA | Sleeps 20 | Quick View
Sleeps 20, 10 bedrooms, 8 bathrooms

$180

avg/night

$180
avg per night
View Details

Key Amenities

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

About this property

Home Features: · 10 bedrooms, 8 bathrooms · Smart TVs in every bedroom and both the living room and upstairs lounge · Modern, fully equipped chef's kitchen with new stainless steel appliances · Granite countertop island with bar-stool seating · In-home Washer ...

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Property Type

Kissimmee House

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Kissimmee Villa
5 BR | 5 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 5 bathrooms
owner special
Owner special: HURRY! Some dates still open in December/January!! Inquire with owner for details

$249

avg/night

$249
avg per night
Owner special:
HURRY! Some dates still open in December/January!! Inquire with owner for details

View Details

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! This resort features, $2.1 mil Lagoon Style pool with Zero Depth Entry and Water Slides. Also, with a Water Park for the littles! Clubhouse has Sundry Shop /Deli, Games Room, ...

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Property Type

Kissimmee Villa

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

Distance to park: 4 miles to Disney's Animal Kingdom

$163

avg/night

$163
avg per night
View Details

Key Amenities

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

About this property

This home sleeps 8 with two master king suites and two twin rooms with two twin beds in each. All bedding is quality, clean, and comfortable with European duvets and covers. Mattress and pillow protectors on all beds. A private swimming pool and a stand-alone hot tub are yours to enjoy throughout your ...

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Property Type

Kissimmee Villa

Featured review

"Great and affordable"

Rented this place to go to Halloween horror nights. The place was clean and actually had all the equipment and everything for the game room which I’ve rented more luxurious homes to have pool sticks with ...

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Kissimmee House
8 BR | 6 BA | Sleeps 18 | Quick View
Sleeps 18, 8 bedrooms, 6 bathrooms
4 reviews

$485

avg/night

$485
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Check out this amazing home! The sparkling pool basks in sunlight all day, while the lanai offers refreshing shade. It's the perfect setting for complete relaxation and enjoyment. This spacious family retreat comfortably accommodates up to 16 adults. If there is a mix of children and adults, the ...

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Property Type

Kissimmee House

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

Distance to park: 3 miles to Disney World

$156

avg/night

$156
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

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

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Property Type

Kissimmee Villa

Featured review

"Great location and a lovely accommodation"

Perfect location for the Disney theme parks as well as SeaWorld and Universal Studios. Very modern interior decor, and fresh and vibrant linens and accessories. Would highly recommend and will visit again.

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Kissimmee House
12 BR | 11 BA | Sleeps 26 | Quick View
Sleeps 26, 12 bedrooms, 11 bathrooms

$390

avg/night

$390
avg per night
View Details

Key Amenities

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

About this property

From the minute you pull through the gated entry you will be lost in your dream vacation. Located at the beautiful Veranda Palms Resort, this 26 guest capacity vacation home has everything you could possibly need for a fantastic stay. Let's start with the gorgeous sundeck patio at the back of ...

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Property Type

Kissimmee House

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Kissimmee Villa
5 BR | 4 BA | Sleeps 15 | Quick View
Sleeps 15, 5 bedrooms, 4 bathrooms
5 reviews

$379

avg/night

$379
avg per night
View Details

Key Amenities

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

About this property

Villa Overview No extra charges! 5 bedrooms, 4 full bathrooms Sleeps 15 guests ~440 square foot Star Wars theme room upstairs with two full over full bunk beds between a 3D TIE Fighter and swirly slide Twin bunk bed with a trundle in the Lego-themed room, complete with multi-color ...

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Property Type

Kissimmee Villa

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Kissimmee Villa
5 BR | 3 BA | Sleeps 12 | Quick View
Sleeps 12, 5 bedrooms, 3 bathrooms
10 reviews

Distance to park: 3 miles to Disney

$188

avg/night

$188
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

5 bedrooms, 3 bathrooms, sleeps 10 - 12. Spacious, 5 bed, 3 bath, luxury villa with Private Pool, Spa +Games Room (pool, air hockey and football tables) Guests have full use of all facilities of the Prestigious Emerald Island Resort, including Club House with pool, spa & licensed Tiki Hut Bar, ...

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Property Type

Kissimmee Villa

Featured review

"Very Comfortable"

Very comfortable stay! We had a group of 4 adults and 3 kiddos, and each of us enjoyed our stay. House was very clean and well appointed. Owner was a pleasure to deal with, and VERY responsive to our needs. ...

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Kissimmee Townhome
3 BR | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2.5 bathrooms
4 reviews
last minute deal
LAST MINUTE DEAL 11/17 - 12/13: 15% off for rental on Nov and Dec.

$119

avg/night

$119
avg per night
Offer for: Nov 17 - Dec 13:
15% off for rental on Nov and Dec.

View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

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

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Property Type

Kissimmee Townhome

Featured review

"Outstanding rental!"

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

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DEAL
Kissimmee House
15 BR | 15 BA | Sleeps 36 | Quick View
Sleeps 36, 15 bedrooms, 15 bathrooms

$876

avg/night

$876
avg per night
View Details

Key Amenities

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

About this property

This vacation home isn't just a place to stay; it's your own personal wonderland. Step outside, and you'll be greeted by a backyard oasis that dreams are made of – a sparkling swimming pool with a spillover jacuzzi hot tub and a sun-soaked sundeck, complete with lounging chairs that ...

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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
1 review

Distance to park: 2 miles to Disney's Animal Kingdom

$200

avg/night

$200
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

4 Bedroom /3 Bath / Pool & Spa Vacation Home CONTACT US AND REQUEST A DETAILED QUOTE !! No Booking Fees - Book Direct with the Homeowner Check our Reviews on VRBO - Property #284051

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Property Type

Kissimmee House

Featured review

"Awesome"

Thank you Awesome Would do again Very close to everything Great pool sand hot tub Felt safe Thank you again

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Kissimmee House
4 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 2 bathrooms
1 review

Distance to park: 3 miles to Walt Disney World

$177

avg/night

$177
avg per night
View Details

Key Amenities

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

About this property

4 Bedrooms| 2 Baths| Sleeps 8|Private Pool|Games Room|Disney-Themed Kids Rooms| Updated Decor| If you’re looking for the perfect home away from home for your family’s perfect Disney vacation, look no further. Our bright, airy house in the desirable 5-star Emerald Island Resort means that ...

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Property Type

Kissimmee House

Featured review

"Fantastic Villa"

We have recently returned from a fantastic stay at Joanna’s villa and couldn’t recommend highly enough. After a long day of travel the immediate comfort we felt opening the door of what would be our ...

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Kissimmee Villa
7 BR | 5 BA | Sleeps 14 | Quick View
Sleeps 14, 7 bedrooms, 5 bathrooms
5 reviews

Distance to park: 7 miles to Disney Magic Kingdom

$258

avg/night

$258
avg per night
View Details

Key Amenities

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

About this property

* Gated and Guarded Resort 7 -10 minutes to Disney * Stunning Lake Views from Pool Deck * Pool with 24 Hour Spa on Over ride - Handrails * Lots of Baby Equipment - Free to Use * 2 Lounges - Leather sofas * Game Room Disney Themed -Air conditioned - Slate Bed Pool Table *New Gaming Station PS4, ...

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Property Type

Kissimmee Villa

Featured review

"Fabulous home and perfect location"

The home is absolutely beautiful, very clean and has everything you could possibly need or want in a rental home. The only thing we had to add was our own food and toiletries. The location was perfect, ...

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Kissimmee House
5 BR | 2 BA | Sleeps 11 | Quick View
Sleeps 11, 5 bedrooms, 2 bathrooms

$147

avg/night

$147
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

The 5 Bedrooms-2 Bathrooms non-smoking house offers free private parking, free Wifi, 5 smart TVs, game room, fence gated private pool, a full equipped kitchen & Washer & Dryer. THIS HOUSE IS SELF-CATERING. Please stop by your nearest supermarket to purchase personal toiletries and desired meals. ...

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Property Type

Kissimmee House

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

Distance to park: 3 miles to Disney Animal Kingdom

$141

avg/night

$141
avg per night
View Details

Key Amenities

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

About this property

Great location - fabulous pool area South West Facing - Fully Fenced Area

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Property Type

Kissimmee Villa

Featured review

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

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

$315

avg/night

$315
avg per night
View Details

Key Amenities

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

About this property

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

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Property Type

Kissimmee Villa

Featured review

"Fantastic Stay"

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

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Kissimmee House
15 BR | 16 BA | Sleeps 33 | Quick View
Sleeps 33, 15 bedrooms, 16 bathrooms

$330

avg/night

$330
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

The whole crew will love the swimming pool. It has a spill-over jacuzzi hot tub and a spacious sundeck with lounge chairs. After a swim, why not enjoy a poolside BBQ meal? There's space for 12 guest to dine al fresco. Bring out your inner Gordon Ramsey while cooking on your private grill! Had ...

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Property Type

Kissimmee House

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Kissimmee House
12 BR | 11.5 BA | Sleeps 30 | Quick View
Sleeps 30, 12 bedrooms, 11.5 bathrooms

$468

avg/night

$468
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

At this 30-guest capacity, 12-bedroom mansion, bedtime will be a blast because these kids bedrooms have some of the coolest beds we've ever seen! For all the Star Wars fans, if you've ever wanted to sleep under an AT-AT, this is your time to shine. Whether storming the battle of Hoth or getting ...

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Property Type

Kissimmee House

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

Distance to park: 6 miles to Walt Disney World

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Name Of Home: Ohana Mouse House Location: Windsor Hills Resort (24/7 guard gated community - Disney World only mins away!) Home Highlights: Recently Renovated Home - Private Pool - Bunk Bedroom with PS4 Property Type: Townhouse, Two Stories (1,437 SF) Bedrooms: 3 Total - 1 Master w/ King Bed, ...

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Property Type

Kissimmee Townhome

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Kissimmee Villa
8 BR | 7 BA | Sleeps 16 | Quick View
Sleeps 16, 8 bedrooms, 7 bathrooms

$350

avg/night

$350
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to the perfect vacation place at Encore Resort. beautiful 2 story house, 8 bedroom, 7 bathroom, game room, fenced-in backyard and pool. Perfect place to a family meeting/vacation near Disney. Minutes from Orlando's world-famous excitements. Totally equipped kitchen, towels & linen, Wifi, ...

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Property Type

Kissimmee Villa

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Kissimmee House
8 BR | 6 BA | Sleeps 16 | Quick View
Sleeps 16, 8 bedrooms, 6 bathrooms
8 reviews

$356

avg/night

$356
avg per night
View Details

Key Amenities

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

About this property

5 star Property! Welcome to Sunset Magic Villa! Delightful Windsor at Westside Resort home villa 8 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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Kissimmee Villa
4 BR | 2 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 2 bathrooms

$162

avg/night

$162
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

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

$204

avg/night

$204
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Welcome to your dream vacation home! Nestled in the heart of the exclusive Storey Lake resort, this modern 4-bedroom townhouse is the perfect retreat for your Disney World or Universal Orlando getaway. With its unbeatable location, luxurious amenities, and a private pool, your vacation experience will ...

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Property Type

Kissimmee House

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Kissimmee Townhome
3 BR | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2.5 bathrooms
5 reviews

$83

avg/night

$83
avg per night
View Details

Key Amenities

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

About this property

FLAT SCREEN TV in Living Room! NEW MATTRESSES in all bed rooms NEW LAMINATE FLOORS in all bed rooms! Bed Room Configuration: 1 QUEEN Master Suite with balcony overlooking conservation area and private bath 1 bedroom with a double bed 1 bedroom with two twin beds. TV's in all Rooms! This ...

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Property Type

Kissimmee Townhome

Featured review

"Perfect location near attractions"

Loved our stay close to Disney and other attractions. Townhome was clean and had everything we needed for our stay. The owner was quick to respond to any questions. We would definitely stay here again.

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Kissimmee House
4 BR | 3 BA | Sleeps 9 | Quick View
Sleeps 9, 4 bedrooms, 3 bathrooms

$155

avg/night

$155
avg per night
View Details

Key Amenities

  • Air conditioning
  • WiFi

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

$246

avg/night

$246
avg per night
View Details

Key Amenities

  • Air conditioning
  • WiFi

About this property

When it comes to finding Orlando vacation rentals that are conveniently located and fully equipped, Terra Verde 137 is a great option. This 7-bed, 4-bath house is suited for up to 14 guests and is situated in one of the best locations in the incredible Terra Verde Resort community. This home offers all ...

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Property Type

Kissimmee House

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Kissimmee Villa
5 BR | 3 BA | Sleeps 11 | Quick View
Sleeps 11, 5 bedrooms, 3 bathrooms
2 reviews
last minute deal
LAST MINUTE DEAL 12/6 - 12/23: 20% off list price.

$259

avg/night

$259
avg per night
Offer for: Dec 6 - Dec 23:
20% off list price.

View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Last dates for 2024 are from December 6th until December 23rd (17 nights). Now taking bookings for 2025 and 2026. 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 ...

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Property Type

Kissimmee Villa

Featured review

"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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DEAL
Kissimmee Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
4 reviews

Distance to park: 5 miles to Disney World

$140

avg/night

$140
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

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

Featured review

"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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Kissimmee House
6 BR | 4.5 BA | Sleeps 14 | Quick View
Sleeps 14, 6 bedrooms, 4.5 bathrooms
3 reviews

$299

avg/night

$299
avg per night
View Details

Key Amenities

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

About this property

Welcome to your dream vacation home located in Windsor at Westside! This 6 bedroom, 4.5 bathroom sleeps 12 perfectly and is pure luxury. This home has 3 king bedrooms, 2 rooms with a twin and double and then one room with twin bunkbeds. The bedrooms are really fun for the kids with a Harry Potter theme ...

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Property Type

Kissimmee House

Featured review

"Disney vacay"

Mickeys mansion was wonderful. Very clean. Everything you may need in kitchen. We paid extra for heated pool and the adult kids and grandchildren loved it. We would definetly go back and rent this again.

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

$169

avg/night

$169
avg per night
View Details

Key Amenities

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

About this property

Private 2 story home with 4 Bedroom/3 Bathroom with private pool which has all of the spacious and convenient accommodations for your entire family vacation. Storey Lake is near to all of the major parks & attractions of Disney World, Epcot, Animal Kingdom, Disney Water Parks, Universal Studios and ...

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Property Type

Kissimmee Townhome

Featured review

"Great place"

We stayed here for a tournament at Orange County Convention and this was a perfect location and the amenities were amazing!! We loved this townhouse and would love to stay here again

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Kissimmee House
3 BR | 2 BA | Sleeps 7 | Quick View
Sleeps 7, 3 bedrooms, 2 bathrooms
12 reviews

Distance to park: 6 miles to Disney - Animal Kingdom

$118

avg/night

$118
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

This private, lakefront with nature reserve, pool home offers a fusion of luxury, comfort, and convenience. This spacious 3 bedroom and 2 bath home has cathedral ceilings and an open floorplan, with a living room, breakfast nook, and formal dining area. The kitchen is fully outfitted with all the appliances ...

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Property Type

Kissimmee House

Featured review

"Great Area"

Location was quiet. Home was beautiful and well maintained. My only comment would be to have a casserole dish to be able to bake something in the oven. Also a pizza pan. Besides these items it is well stocked. ...

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Kissimmee Villa
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

$160

avg/night

$160
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This newly remodeled pool Villa is the perfect getaway. From the new kitchen and bath to the newly resurfaced pool. Large pool deck with room to spread out. A covered area for dining and tons of pool deck for those who love the sun. The pool is south facing. Sunsets are spectacular. #3 bedrooms. ...

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Property Type

Kissimmee Villa

Featured review

"Awesome !!!"

Super Clean, Everything was excellent. Pool was amazing. Close enoogh tall many immendities for day trips. Had a very relaxing time very fun vacaton.

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

$249

avg/night

$249
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Name Of Home: Live Your Adventure Family Villa Location: Encore Resort (Gated community - Disney World only mins away!) Home Highlights: XBox, Private Pool, Marvel Themed Games Room Property 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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Kissimmee Townhome
3 BR | 2 BA | Sleeps 7 | Quick View
Sleeps 7, 3 bedrooms, 2 bathrooms

$120

avg/night

$120
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to our stunning townhouse located at 2600 Lodi Crescent in the charming city of Kissimmee, FL. This tastefully furnished property is the perfect choice for your next getaway. Whether you're visiting the magical Walt Disney World or exploring the vibrant attractions of Orlando, our townhouse ...

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Kissimmee Townhome

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

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

$122

avg/night

$122
avg per night
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Key Amenities

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

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

Featured review

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

$171

avg/night

$171
avg per night
View Details

Key Amenities

  • Air conditioning
  • WiFi

About this property

If you want to experience all the fun of Orlando while enjoying a bit of distance from the heart of the city, you might be interested in Kissimmee vacation rentals. This Amazing Vacation Home in Kissimmee, Florida, is one of the best! This home features 3 bedrooms and 2 bathrooms and is furnish with all ...

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Property Type

Kissimmee House

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Kissimmee House
3 BR | 2 BA | Sleeps 7 | Quick View
Sleeps 7, 3 bedrooms, 2 bathrooms
5 reviews

Distance to park: 6 miles to Disney - Animal Kingdom

$118

avg/night

$118
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

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

Featured review

"Very nice villa"

Had a 2 week stay at this very nice villa. Clean, comfortable and great pool area. Good locaction. We highly recommend.

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

$114

avg/night

$114
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Welcome to our charming condo in the heart of Kissimmee, Florida! Nestled in the sought-after Villa Island Club, our inviting three-bedroom, two-bathroom retreat is the perfect spot for your next vacation. Located just off HWY 192, you’ll be less than 15 minutes from the magical gates of Walt Disney ...

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Property Type

Kissimmee Condo

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Kissimmee House
6 BR | 3 BA | Sleeps 14 | Quick View
Sleeps 14, 6 bedrooms, 3 bathrooms
1 review

Distance to park: 5 miles to Disney World

$180

avg/night

$180
avg per night
View Details

Key Amenities

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

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

Featured review

"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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Kissimmee Villa
5 BR | 4 BA | Sleeps 11 | Quick View
Sleeps 11, 5 bedrooms, 4 bathrooms
4 reviews

$274

avg/night

$274
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

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

Featured review

"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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Kissimmee House
7 BR | 5.5 BA | Sleeps 16 | Quick View
Sleeps 16, 7 bedrooms, 5.5 bathrooms
5 reviews

Distance to park: 8 miles to Disney World

$389

avg/night

$389
avg per night
View Details

Key Amenities

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

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

$293

avg/night

$293
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Welcome to our charming townhome in Bella Vida Resort, just a short 8 mile drive from the entrance to Walt Disney World! Make your vacation truly magical with the comfort and convenience of our delightful home. Also, do add to the convenience there is a Walmart Superstore around the corner and many, many ...

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Property Type

Kissimmee House

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Kissimmee Condo
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom

$90

avg/night

$90
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

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

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Property Type

Kissimmee Condo

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Kissimmee Villa
9 BR | 5 BA | Sleeps 20 | Quick View
Sleeps 20, 9 bedrooms, 5 bathrooms
47 reviews

Distance to park: 7 miles to Disneyworld

$599

avg/night

$599
avg per night
View Details

Key Amenities

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

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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Kissimmee Condo
3 BR | 2 BA | Sleeps 7 | Quick View
Sleeps 7, 3 bedrooms, 2 bathrooms
1 review

$207

avg/night

$207
avg per night
View Details

Key Amenities

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

About this property

Welcome to your dream vacation stay! Nestled in a prime location, our 3-bedroom, 2-bathroom condo offers the ultimate blend of comfort and convenience, making it an ideal retreat for families and friends alike. Imagine starting your day in our fully equipped kitchen, brewing a fresh cup of coffee or whipping ...

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Property Type

Kissimmee Condo

Featured review

"Perfect Spot for a Peaceful Getaway"

I recently stayed at this rental and it was super relaxing. Every morning, I loved having my coffee on the balcony. It was a calm and quiet place, just perfect for starting the day. The rental is cozy and ...

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

$195

avg/night

$195
avg per night
View Details

Key Amenities

  • Air conditioning
  • WiFi

About this property

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

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Property Type

Kissimmee House

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Kissimmee Villa
6 BR | 5.5 BA | Sleeps 12 | Quick View
Sleeps 12, 6 bedrooms, 5.5 bathrooms

$243

avg/night

$243
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Welcome to Your Ultimate Vacation Haven at Bella Vida Resort! Escape to luxury and convenience with our stunning 6-bedroom home nestled in the heart of Bella Vida Resort. Perfect for families or groups of friends, this spacious retreat is designed to make your vacation unforgettable. Key Features: Bedroom ...

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Property Type

Kissimmee Villa

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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 260 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 $27 per night with an average price per night of $184.

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