Kissimmee Vacation Rentals

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May 15 - May 16
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May 16 - May 17
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May 17 - May 19
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May 24 - May 26

Vacation Rentals in Kissimmee

Pool
Lakeview Luxury Villa with Everything
10.0 out of 10, Exceptional, (230)
"The home was perfect for our group. The “Star Wars” room accommodated several of our girls And they loved the space. Each mom had a comfortable bed, plenty of space and great views! We lived the view from the back porch and were able To see several sunrises and sunsets as Well as some Resident wildlife! (Alligators, flamingos, etc). My only issue was that the TV’s in the theatre room need instructions as we are not techy and never got anything to work well. Lovely home, well appointed!"
Lakeview Luxury Villa with Everything
Interior
Home w/ Pool, Hot Tub & Game Room, 6 Mi to Disney!
10.0 out of 10, Exceptional, (11)
"The house was the perfect size and those beds. So comfy. The house is older but well maintained. Great communication with the host. We really felt safe and relaxed while we were there. Thank you again!!!"
Home w/ Pool, Hot Tub & Game Room, 6 Mi to Disney!
Fridge, microwave, oven, stovetop
⭐⭐⭐⭐⭐Expansive family-friendly vacation home, themed rooms, water park, fitness
10.0 out of 10, Exceptional, (1)
"The home is wonderfully and creatively decorated. The kitchen. dining. tv.pool table area is great fun for being together. We had rain on our visit but the home is conducive to handle all of that. Great visit, wonderfully responsive manager. Thank you"
⭐⭐⭐⭐⭐Expansive family-friendly vacation home, themed rooms, water park, fitness
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Pool
Modern Luxury Villa with Everything
9.8 out of 10, Exceptional, (291)
"The property was, as advertised!"
Modern Luxury Villa with Everything
Exterior
Caribbean Villa
9.8 out of 10, Exceptional, (12)
"Stay was nice, close to stores and easy drive to Disney. Would stay again."
The price is $85
$227 total
includes taxes & fees
May 20 - May 21
Caribbean Villa
Pool
Ultimate Lakeview Villa with Everything!
9.8 out of 10, Exceptional, (282)
"We loved the house. Plenty of space and lots to do between the pool, arcade room, and theater room. We also enjoyed the multiple clubhouse waterparks we had access to. We had a couple issues with the pool and a/c but property management resolved quickly. Highly recommend booking this house"
Ultimate Lakeview Villa with Everything!
Drive-In Theater, Forest Bedroom, Huge Pirate Ship, Lake Views, Pool Table, Grill: Movie Magic
9.8 out of 10, Exceptional, (12)
"Amazing place , very responsive Host Everything was perfect the place is beautiful!"
Drive-In Theater, Forest Bedroom, Huge Pirate Ship, Lake Views, Pool Table, Grill: Movie Magic
Lobby sitting area
The Berkley, Orlando
4.0 star property
9.4 out of 10, Exceptional, (1411)
"Close to Disney, nice small hotel. Rooms were exactly as described, super comfortable for a family of 5. Checkout is strict but we had a late flight and they were great about accommodating us after check out time with parking. "
The Berkley, Orlando
Outdoor pool, sun loungers, lifeguards on site
Spectrum Resort Orlando
4.0 star property
9.2 out of 10, Wonderful, (191)
"The Spectrum Resort townhome was excellent! We loved every minute of our stay there. We also had Mobile Spa come to the townhome while we were staying there. It was fabulous! We plan to return! One request is to stock extra blankets."
Spectrum Resort Orlando
2 restaurants, lunch, dinner served; American cuisine
Embassy Suites by Hilton Orlando Lake Buena Vista South
3.5 star property
9.2 out of 10, Wonderful, (1697)
"everything is excellent"
The price is $144
$163 total
includes taxes & fees
Jun 2 - Jun 3
Embassy Suites by Hilton Orlando Lake Buena Vista South
Outdoor pool, pool umbrellas, sun loungers
Magic Village Yards, Trademark Collection by Wyndham
4.0 star property
9.2 out of 10, Wonderful, (1066)
"We stayed here because it is close to all the parks. Pleasantly surprised with the unit too. All new!"
Magic Village Yards, Trademark Collection by Wyndham
Exterior
Stylish retreat with a private, heated pool, central AC, & garage game room
9.2 out of 10, Wonderful, (15)
"Very relaxing to have a home to go to after a busy day. Some minor things needed attention. Overall it was great. I would give it a 4.5 out of 5."
Stylish retreat with a private, heated pool, central AC, & garage game room
Lake
Lifetime of Vacations Resort
3.0 star property
9.0 out of 10, Wonderful, (82)
"Everything about the Property.is perfect nice and clean."
Lifetime of Vacations Resort
A heated pool
Luxury 4 bedroom 3 bath pool Home 283
9.0 out of 10, Wonderful, (12)
"Truly a Great Experience! Visited family In Kissimmee and our first time in an AirB&B. House was immaculate and furnished with everything we needed to enjoy ourselves. I had a question about the keypad code, I emailed at about 10:30 pm and the response was immediate. I really appreciated that. We will definitely return again."
Luxury 4 bedroom 3 bath pool Home 283
Outdoor pool, pool umbrellas, sun loungers
Grand Lake Resort
3.0 star property
9.0 out of 10, Wonderful, (84)
"nd quiet. Nobody bothering you the pool was amazing and heated the jacuzzi whew amazing lol. I will definitely book again when I visit. The view is also so nice in the backyard seeing the water. Option to even use the boat but I was scared of alligators lol so I stayed on shore. It’s an amazing quiet place. Even slept in a couple times due to the quietness and not knowing it was day time lol. Definitely an amazing birthday trip"
Grand Lake Resort
Interior
Margaritaville Resort Orlando Cottages by Rentyl
4.0 star property
8.8 out of 10, Excellent, (833)
"The property was very nice but we had no idea what layout we would be getting until we arrived which made it hard to plan. The villa did not come with the frozen drink machine it was supposed to have and had no extra blankets or pillows "
Margaritaville Resort Orlando Cottages by Rentyl
Private pool
Club Wyndham Cypress Palms
3.5 star property
8.8 out of 10, Excellent, (1450)
"Property was in excelent condition. Room was beautiful and nice. Front desk was very helpful. Self parking without problems. *****"
Club Wyndham Cypress Palms
Pool
Family Resort Home w Private Pool, BBQ, PingPong
8.8 out of 10, Excellent, (3)
"Overall, we made the best of the stay, there was so much space it's a pretty big house. I received a request for a deposit a day before check-in. That is not stated anywhere on the VRBO or Upstay site. I was disappointed that it wasn't included in the cost breakdown that it was separate. We almost lost our reservation because it came the day before. That should've been worked out the week the final payment was due. It was difficult to get in touch with the property manager up until the day of...
Family Resort Home w Private Pool, BBQ, PingPong
Waterslide
Reunion Resort & Golf Club
5.0 star property
8.6 out of 10, Excellent, (1119)
"Great hotel "
Reunion Resort & Golf Club
2 outdoor pools, pool umbrellas, sun loungers
Encantada Resort Vacation Townhomes by IDILIQ
3.0 star property
8.6 out of 10, Excellent, (1253)
"It was great besides no air conditioning upstairs where bedrooms are , even though they clean after you leave there should be a dust pan and mop to do cleaning while there "
The price is $112
$273 total
includes taxes & fees
May 19 - May 20
Encantada Resort Vacation Townhomes by IDILIQ
Don't see what you're looking for?
See all available properties in Kissimmee
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Kissimmee Vacation Rental Travel Info

Number of vacation rentals
2,837
Popular accommodation
Kissimmee private vacation homes
Known landmarks
Discovery Cove, Aquatica and Disney's Typhoon Lagoon Water Park
International airport
Orlando, FL (MCO-Orlando Intl.)

Price trends for vacation rentals in Kissimmee

Less expensive
More expensive
Next month
October
December
$139
Month
Price
January
$122
February
$139
March
$140
April
$111
May
$122
June
$139
July
$142
August
$115
September
$116
October
$108
November
$119
December
$150
Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed vacation rentals in Kissimmee. Select dates and complete search for nightly totals inclusive of taxes and fees.

Other types of properties in Kissimmee you may be interested in

4 outdoor pools, cabanas (surcharge), pool umbrellas
Hilton Vacation Club Mystic Dunes Orlando
3.5 star property
8.8 out of 10, Excellent, (3102)
"I loved the apartment/condo style of the rooms they have it’s very convenient and has plenty of space. "
The price is $87
$133 total
includes taxes & fees
May 21 - May 22
Hilton Vacation Club Mystic Dunes Orlando
Lobby
Margaritaville Resort Orlando
4.0 star property
8.8 out of 10, Excellent, (2992)
"It was great and very convenient that it had a strip of restaurants stores close where we could walk to do something different at night time"
The price is $136
$200 total
includes taxes & fees
May 21 - May 22
Margaritaville Resort Orlando
Water park
Red Lion Hotel Orlando Lake Buena Vista South
3.5 star property
8.6 out of 10, Excellent, (4318)
"room very clean and staff friendly "
The price is $60
$92 total
includes taxes & fees
May 22 - May 23
Red Lion Hotel Orlando Lake Buena Vista South
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Everything you need to know about Kissimmee vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Kissimmee vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Kissimmee vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Kissimmee vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Kissimmee. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Kissimmee in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $85 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Kissimmee rentals

At Expedia, we put the best Kissimmee vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Kissimmee rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Kissimmee vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Kissimmee. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find vacation rentals in Kissimmee?

Yes, we have vacation rentals in Kissimmee close to Disney's Animal Kingdom® Theme Park, or you can select a secluded option if you'd like a relaxing place to stay. Tourists who visit Kissimmee like the fun-filled theme parks and renowned opera. The array of shops and lively festivals are some other things you might want to check out while you're here.

What's the top vacation rental that Kissimmee has to offer?

The Berkley, Orlando: This Kissimmee vacation home rental offers a furnished patio, a terrace, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a microwave, and a coffee maker. You can relax into your vacation with an arcade game room and a spa tub. Another good choice for your trip to Kissimmee is Upstay - Theme Rooms|Movie Theatre|Pool|Sleeps 18.

How many vacation rentals are there in Kissimmee?

Choose from 19272 Expedia vacation rentals in Kissimmee for a memorable vacation.

What can I see and do in Kissimmee?

Disney's Animal Kingdom® Theme Park and Walt Disney World® Resort are a couple of family-friendly sights, whereas cultural attractions include Osceola Performing Arts Center and Medieval Times. Other popular places to visit in the area include Old Town and Disney Springs™.

What are vacation rentals like in Kissimmee?

Vacation rentals are privately owned properties you can book for several days or more in Kissimmee. Vacation rentals offer amenities like laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of privacy away from public hotel elevators and busy concierge desks while still allowing you to travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for a family trip.

Recent reviews of Kissimmee properties
Expedia verified reviews

Margaritaville Resort Orlando

Margaritaville Resort Orlando

5/5 Excellent
"It was great and very convenient that it had a strip of restaurants stores close where we could walk to do something different at night time"
A verified traveler stayed at Margaritaville Resort Orlando
Posted 12 hours ago
Margaritaville Resort Orlando