Kissimmee Vacation Rentals

(233 rentals)
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Kissimmee Villa
4 BR | 4 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 4 bathrooms
2 reviews

$310

avg/night

$310
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
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms
13 reviews

Distance to park: 12 miles to All Disney Theme Park

$109

avg/night

$109
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

If you will be visiting Orlando Florida for all of the great attractions including Walt Disney World, Universal Studios, Sea World theme parks, and all of the other major attractions? You can stay in our beautifully decorated 3 bedroom private villa, which boasts it's own private pool for less than ...

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Property Type

Kissimmee Villa

Featured review

"New Years Getaway"

Stayed month of January..Villa was very well equipped and very comfortable.Location was fantastic being so close to all attractions. Would highly recommend for anybody to stay..

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

$139

avg/night

$139
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

"Florida Vacation! ️"

My family and I retuned back to Lisa’s beautiful home the week of Thanksgiving for a week long trip. This is our 2nd time staying in her house and we absolutely loved it! The house was so clean from top ...

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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: 6 miles to Disneyworld

$134

avg/night

$134
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 Villa
4 BR | 4.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4.5 bathrooms

Distance to park: 4 miles to Disney World

$223

avg/night

$223
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to Magic Village Views, part of Trademark Collection by Wyndham. With a stay in a luxury condominium in an ideally located community, you won’t run out of exciting things to do and thoughtful amenities to enjoy. The hotel’s ideal location is right next to Disney’s parks. You’ll ...

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Property Type

Kissimmee Villa

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

$530

avg/night

$530
avg per night
View Details

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 Condo
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms

Distance to park: 3 miles to Disney World

$159

avg/night

$159
avg per night
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Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Welcome to Surrounded in Magic! Kids of all ages will love this magical, bright and spacious Disney & Universal Studios themed (1400 sq ft), 3-bedroom, 2-bath, 1st floor condo. Set in a quiet location at the renowned Windsor Hills Resort within walking distance to the Clubhouse and pool area. ...

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Property Type

Kissimmee Condo

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

$237

avg/night

$237
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 Villa
5 BR | 3 BA | Sleeps 12 | Quick View
Sleeps 12, 5 bedrooms, 3 bathrooms
10 reviews

Distance to park: 3 miles to Disney

$182

avg/night

$182
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 Villa
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms
18 reviews

Distance to park: 3 miles to Mgm

$125

avg/night

$125
avg per night
View Details

Key Amenities

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

About this property

Beautiful 4 bedroom /3 bath private villa only 3 miles to Disney and other parks. Including heated pool/jacuzzi and game room. Free wifi and phone use in USA and Canada and PR. Fully furnished with all kitchen needs . Greatest location to shopping , all major restaurants and stores including supermarkets ...

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Property Type

Kissimmee Villa

Featured review

"Top class accommodation"

We couldn't fault our accommodation at all. Everything you needed was on hand. Lovely beds and a awesome view of the lakes in front of our pool.

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

$157

avg/night

$157
avg per night
View Details

Key Amenities

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

About this property

POOL SAFETY FENCE!!!! - Florida law requires that doors leading out to the pool have an alarm. THAT IS NOT ENOUGH!. If you are traveling with children please make sure the house you are renting has a pool safety fence. WE HAVE A NO PET POLICY FOR ALERGY REASONS This Beautiful home is well situated, ...

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Property Type

Kissimmee House

Featured review

"Fabulous home"

The home was comfortable for our big group. The kitchen was well stocked with utensils, cookie sheets, and bowls. We were able to make our Christmas brunch! The game room was fun for the teens. The location ...

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

$118

avg/night

$118
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
3 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3 bathrooms

Distance to park: 4 miles to Disney

$205

avg/night

$205
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
5 BR | 5 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 5 bathrooms

$205

avg/night

$205
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

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

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Property Type

Kissimmee Villa

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Kissimmee Condo
2 BR | 2 BA | Sleeps 40 | Quick View
Sleeps 40, 2 bedrooms, 2 bathrooms

$270

avg/night

$270
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This is a NON SMOKING condo * Community: Regal Palms Floors: Second Floor Condo Pets: Small Pets are ok, $150 pet fee Rooms: 2 Bed rooms, 2 Bath rooms. Bed Configuration: King Bed (1) Bunk Beds 1 Full 1 Twin Flooring: Hard wood throughout with tile in bath and kitchen. General: Wi-fi, ...

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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
3 reviews

$214

avg/night

$214
avg per night
View Details

Key Amenities

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

About this property

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

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Property Type

Kissimmee Villa

Featured review

"Awesome vacation"

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

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Kissimmee House
6 BR | 5.5 BA | Sleeps 18 | Quick View
Sleeps 18, 6 bedrooms, 5.5 bathrooms
58 reviews

Distance to park: 4 miles to Animal Kingdom

$158

avg/night

$158
avg per night
View Details

Key Amenities

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

About this property

Some of the best features of this house from Guest Reviews • Beautiful Vinyl Plank Flooring in all bedrooms, halls and on the steps • Less than a 4-mile drive to Disney World’s Animal Kingdom Theme Park • Two leather couches and a recliner with a total of 5 power reclining seats • ...

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Property Type

Kissimmee House

Featured review

"Spacious, well-appointed house in a great location close to the Disney Parks."

The owner provided very detailed and helpful information regarding the house, the Orlando area and the Disney parks before we arrived. The house was very clean and tidy and all the rooms were as described. ...

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Kissimmee House
3 BR | 2 BA | Sleeps 10 | Quick View
Sleeps 10, 3 bedrooms, 2 bathrooms
20 reviews

$180

avg/night

$180
avg per night
View Details

Key Amenities

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

About this property

Sunset Lakes is ideally situated, just 4 miles from Disney World and a short drive from other popular attractions like Universal Studios, Sea World, and more. The proximity to Orlando and other destinations makes it a prime choice for travelers. The gated community offers various amenities such as a community ...

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Property Type

Kissimmee House

Featured review

"Vacation retreat/$15 Uber to Disney/ HGTV looking retreat"

We are completing our stay in the morning at this beautiful vacation retreat! We brought the family all seven of us ranging from age in two years old to 60 years old. The pool and patio is incredibly maintained, ...

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

$344

avg/night

$344
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
7 BR | 4.5 BA | Sleeps 14 | Quick View
Sleeps 14, 7 bedrooms, 4.5 bathrooms
1 review

$431

avg/night

$431
avg per night
View Details

Key Amenities

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

About this property

5 star property! Reviews say it all! You will be delighted by the great combination of lux comfort and Disney theming for the whole family! Located in the upscale Emerald Island Resort gated community, our newly remodeled home is a welcome oasis to return to after a long day enjoying the parks. Relax ...

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Property Type

Kissimmee House

Featured review

"Where to even start!!!"

Whenever we travel, I read reviews. Some reviews you wonder about because no two people seem to see it the same way. However with this house everyone seemed to love it and after staying there I can see ...

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

Distance to park: 3 miles to Disney

$175

avg/night

$175
avg per night
View Details

Key Amenities

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

About this property

The Magic Emerald Island Villa invites you to experience an elegant escape near Disney World and Universal Studios. Our 4-bedroom, 3-bathroom villa accommodates up to 9 guests in comfort and style: • The main master bedroom features a king-size bed, a private en suite bathroom with a garden tub, ...

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Property Type

Kissimmee House

Featured review

"5*+ Magic Emerald Island Villa"

Excellent villa wonderful host. From the very first enquiry about renting Yelena’s Magic Emerald Island villa she was fantastic, guiding me through the booking and rental period until we left. Yelena ...

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

$250

avg/night

$250
avg per night
View Details

Key Amenities

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

About this property

Enjoy a whimsical getaway when you book a stay at this sleek, refreshing, 8-bedroom, 6-bathroom vacation rental home. Take a dip in the private pool, fix up something tasty in the fully equipped kitchen, play a game of pool in the game room, or head to the community fitness center for a quick workout. ...

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Property Type

Kissimmee House

Featured review

"Kissimmee Home/Windsor"

My family & I enjoyed our stay at this lovely home during the summer time. This house gave us an enjoyable experience that we will all remember. We didnt have any problems with the house and we hope to ...

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

$332

avg/night

$332
avg per night
View Details

Key Amenities

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

About this property

Welcome to your ultimate themed vacation experience in the heart of Kissimmee, Florida! Prepare to embark on an extraordinary journey as you step into this spectacular 6-bedroom, 4-bathroom house in the prestigious Windsor Hills community. This newly listed paradise has been meticulously designed to immerse ...

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Property Type

Kissimmee House

Featured review

"Amazing"

This was an amazing experience for my kids and I. I would definitely choose again!!!!!!!!!!!!!!!!!!!

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

Welcome to Magic Village Views, part of Trademark Collection by Wyndham. "Boutique style 3BDR 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, ...

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Property Type

Kissimmee Villa

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Kissimmee Villa
6 BR | 4.5 BA | Sleeps 12 | Quick View
Sleeps 12, 6 bedrooms, 4.5 bathrooms
9 reviews

$193

avg/night

$193
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

The Villa is fully air conditioned, pool has solar heating, all rooms have cable tv, Free WIFI, local calls are free, Safe and baby equipment also available for use at no extra cost. The villa has a 30ft South West facing solar heated Pool/Spa with a large patio area with table chairs and sun loungers, Also ...

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Property Type

Kissimmee Villa

Featured review

"Extremely Satisfied"

My family and I enjoyed our stay at Brendas home. It was clean and very comfortable. It felt just like “home”. Though it was too cold that week in Florida, we weren’t able to enjoy the pool and jacuzzi ...

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Kissimmee House
5 BR | 4 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 4 bathrooms
8 reviews
owner special
Owner special: 10% Discount for 7 night booking between Feb 26th - March 7th.

$240

avg/night

$240
avg per night
Owner special:
10% Discount for 7 night booking between Feb 26th - March 7th.

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

$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

Featured review

"Great time with Family"

The house had tons of space and was exactly what we needed to have a great time. We were there for the Citrus Bowl!! Go Cocks!!

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

$356

avg/night

$356
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Forget your worries in this spacious and serene space. Plenty of room for all your traveling members! Disney getaway? Or just want a fun in the sun getaway? Then this is the house! Beautiful lake views while relaxing in the pool and spa! Discover your perfect getaway in this stunning 6-bedroom, 4-bathroom ...

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Property Type

Kissimmee Villa

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

$140

avg/night

$140
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Luxury villa right on lake edge. Free fishing on 3 lakes. Gated 5 Star Resort. FREE Gas BBQ. Hi speed WiFi and air con throughout the villa. Our 4 Bed, 2 Bath villa is furnished to a very high standard and benefits from a perfect lake view position. Free fishing on 3 well stocked lakes. The ...

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Property Type

Kissimmee Villa

Featured review

"Great Stay"

My family and I chose to do Disney for the holiday. We stayed at one of your florida rentals. I must say that we had a pleasant stay. Very nice and quiet community. I would definitely return as a frequent ...

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

Distance to park: 4 miles to Disney World

$150

avg/night

$150
avg per night
View Details

Key Amenities

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

About this property

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

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Property Type

Kissimmee House

Featured review

"Great Villa"

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

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

Distance to park: 5 miles to Animal Kingdom Lodge

$158

avg/night

$158
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
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms
16 reviews

Distance to park: 4 miles to Disney

$150

avg/night

$150
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 House
5 BR | 4 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 4 bathrooms
2 reviews

Distance to park: 7 miles to Disney Hollywood Studio

$143

avg/night

$143
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

"Great Location!"

We had a great stay. The house is located in a close proximity to many places we visited. Would stay again.

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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 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 | 3 BA | Sleeps 11 | Quick View
Sleeps 11, 5 bedrooms, 3 bathrooms
2 reviews
last minute deal
LAST MINUTE DEAL 2/21 - 2/28: Free pool and spa heat

$264

avg/night

$264
avg per night
Offer for: Feb 21 - Feb 28:
Free pool and spa heat

View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

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 birds on Lake Berkley resort in Kissimmee. Being one of only seven villas ...

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

$201

avg/night

$201
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 Bungalow
4 BR | 3 BA | Sleeps 9 | Quick View
Sleeps 9, 4 bedrooms, 3 bathrooms
6 reviews

$120

avg/night

$120
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Luxury Villa near Universal Studios and 15 Minutes from Disney with Large Private Pool, Game Room and Free Wifi. LCD TVs and Game Room in the villa complement the upscale furnishings and large pool included in the villa. There is plenty of space to spread out with 4 bedrooms and 3 bathrooms. Welcome ...

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Property Type

Kissimmee Bungalow

Featured review

"The house was fantastic and a great location."

The house was very easy to find, quiet neighborhood and Walmart was 2 minutes away. The was neat and tidy with all kitchen amenities needed to prepare a home cook meal. The Air conditioner was the best, ...

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

$129

avg/night

$129
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 Villa
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms
1 review

$169

avg/night

$169
avg per night
View Details

Key Amenities

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

About this property

More info can be found at property website www. dolphinvillas-orlando dot com or directly click the links at end of this page. For over 15 years, Dolphin Villa - Doral Woods has been listed with Holiday Lettings/Trip Advisor, receiving 5-star reviews. If you're interested, we can provide you ...

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Property Type

Kissimmee Villa

Featured review

"Recommend!!"

Great experience during our recent stay at Dolphin House! Clean, spacious and everything you need to have a relaxing time. The welcome gift basket was such a thoughtful and helpful idea. Much appreciated! ...

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Kissimmee House
6 BR | 3.5 BA | Sleeps 12 | Quick View
Sleeps 12, 6 bedrooms, 3.5 bathrooms
1 review

$266

avg/night

$266
avg per night
View Details

Key Amenities

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

About this property

Step into sheer Luxury and experience gated resort style vacationing at its finest. at our Windsor Palms, 6 bedroom pool home, the special touches will leave every family member with a smile. This gorgeous home has two king bedrooms, two queen bedrooms and two rooms with 2 twin beds. With 4 bathrooms ...

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Property Type

Kissimmee House

Featured review

"Caaa vacasional"

Hola estoy muy interesado en rentar su casa de vacaciones la fecha es junio 26a julio 10 con mi familia somos 12

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

$338

avg/night

$338
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
4 BR | 3 BA | Sleeps 11 | Quick View
Sleeps 11, 4 bedrooms, 3 bathrooms

$250

avg/night

$250
avg per night
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
4 BR | 3 BA | Sleeps 9 | Quick View
Sleeps 9, 4 bedrooms, 3 bathrooms

$173

avg/night

$173
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
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 Condo
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
3 reviews

Distance to park: 1 miles to Disney Animal Kingdom

$97

avg/night

$97
avg per night
View Details

Key Amenities

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

About this property

Come and enjoy your vacation in this comfortable condo, right by Disney. Yes Enjoy Three large screen TV's, DVD and free Wi-FI. Yes Beautiful/alluring condo, 1 mile from Disney world and minutes from other attractions, Such as sea world and Universal studio. In Celebration area Florida. Walking ...

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Property Type

Kissimmee Condo

Featured review

"Great location, clean and comfortable."

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

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

$516

avg/night

$516
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 Villa
6 BR | 4 BA | Sleeps 14 | Quick View
Sleeps 14, 6 bedrooms, 4 bathrooms
2 reviews

Inquire for rates

Inquire for rates

View Details

Key Amenities

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

About this property

Just 2 miles to Disney, in Orlando's favorite resort community, Windsor Hills. When only the best will do, our luxurious 6 bed/4 bath sleeps up to 14 and covers more than 3500 sq ft with every comfort that you would expect from a 5* resort. Check out our south-facing private pool with spillover ...

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Property Type

Kissimmee Villa

Featured review

"Clean and Spacious Family Home"

The property was clean and spacious! The location offered privacy and comfort. King, 2 queen, 4 twin beds offered plenty of comfort. Well kept with attentive management.

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

Distance to park: 3 miles to Disney Animal Kingdom

$681

avg/night

$681
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
4 BR | 3 BA | Sleeps 9 | Quick View
Sleeps 9, 4 bedrooms, 3 bathrooms

$185

avg/night

$185
avg per night
View Details

Key Amenities

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

About this property

Immerse yourself in luxury at our Kissimmee villa, perfectly located minutes from Disney and Universal. Nestled in a secure gated community, our home boasts a private pool and spa, a fully-equipped modern kitchen, and comfortable bedrooms including a master suite with a king bed. Exclusive amenities include ...

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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 233 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 $180.

Can I rent a house in Kissimmee?

Yes, you can find house rentals in Kissimmee close to Lakefront Park, Monument of States, and Old Town. Don't forget to stop in to Shingle Creek Park or the nearby theme parks!

Do any vacation rentals in Kissimmee have a pool?

Yes, there are 178 vacation rentals in Kissimmee with a pool on FloridaRentals.com. Search using our filters and book one for your next vacation!