Kissimmee Vacation Rentals

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Vacation Rentals in Kissimmee

2 outdoor pools, a heated pool, sun loungers
Seralago Hotel & Suites Main Gate East
3.0 star property
5.2 out of 10, (5241)
"Excellent stay. Thank you"
The price is CA $53
CA $86 total
includes taxes & fees
May 20 - May 21
Seralago Hotel & Suites Main Gate East
Exterior
Ramada by Wyndham Kissimmee Gateway
3.0 star property
7.2 out of 10, Good, (5882)
"The front desk handed us the wrong keycards so we had to trek all the way back to the lobby to get the correct keycards. You’re also told that parking in the hotel’s own parking lot is: “Park at your own risk.” Other than that, it was decent for the price."
The price is CA $75
CA $107 total
includes taxes & fees
May 14 - May 15
Ramada by Wyndham Kissimmee Gateway
Water park
Flamingo Waterpark Resort
3.0 star property
6.6 out of 10, (1142)
"The only issue was that I called to service my room 2 days before my last day and for 12pm but nothing was done so I have to grab toilet paper and towels from lobby "
The price is CA $110
CA $169 total
includes taxes & fees
May 14 - May 15
Flamingo Waterpark Resort
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Interior
Margaritaville Resort Orlando Cottages by Rentyl
4.0 star property
8.8 out of 10, Excellent, (831)
"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
Aerial view
Vacation Village at Parkway
3.0 star property
8.2 out of 10, Very good, (1250)
"Wonderful place to stay. Clean and well maintained. Would recommend for stay."
Vacation Village at Parkway
Property amenity
Holiday Inn & Suites Orlando SW - Celebration Area, an IHG Hotel
3.0 star property
7.8 out of 10, Good, (1434)
"Property locale is the best for ESPN"
The price is CA $83
CA $133 total
includes taxes & fees
May 19 - May 20
Holiday Inn & Suites Orlando SW - Celebration Area, an IHG Hotel
Lobby sitting area
The Berkley, Orlando
4.0 star property
9.4 out of 10, Exceptional, (1409)
"Great resort very comfortable and loved the view of the lake we even saw a few alligators and fireworks from Disney "
The Berkley, Orlando
Outdoor pool, sun loungers, lifeguards on site
Spectrum Resort Orlando
4.0 star property
9.4 out of 10, Exceptional, (188)
"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
Exterior
Embassy Suites by Hilton Orlando Lake Buena Vista South
3.5 star property
9.2 out of 10, Wonderful, (1697)
"Check in friendliness "
The price is CA $196
CA $223 total
includes taxes & fees
Jun 2 - Jun 3
Embassy Suites by Hilton Orlando Lake Buena Vista South
2 outdoor pools, open 8:00 AM to 9:00 PM, cabanas (surcharge)
Regal Oaks Resort Vacation Townhomes by IDILIQ
4.0 star property
8.4 out of 10, Very good, (2663)
"I loved my stay at the regal oaks with my family perfect place for a family vacation. Food and drinks are great the customer service is excellent "
The price is CA $194
CA $440 total
includes taxes & fees
May 28 - May 29
Regal Oaks Resort Vacation Townhomes by IDILIQ
Private pool
Club Wyndham Cypress Palms
3.5 star property
8.8 out of 10, Excellent, (1443)
"Property was in excelent condition. Room was beautiful and nice. Front desk was very helpful. Self parking without problems. *****"
Club Wyndham Cypress Palms
Pool
Modern Luxury Villa with Everything
9.8 out of 10, Exceptional, (290)
"Overall very impressed with this property"
Modern Luxury Villa with Everything
Waterslide
Reunion Resort & Golf Club
5.0 star property
8.6 out of 10, Excellent, (1118)
"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 CA $140
CA $359 total
includes taxes & fees
Jun 12 - Jun 13
Encantada Resort Vacation Townhomes by IDILIQ
Bar (on property)
Holiday Inn Express & Suites S Lake Buena Vista, an IHG Hotel
2.5 star property
8.6 out of 10, Excellent, (854)
"The personal in the breakfast "
The price is CA $128
CA $181 total
includes taxes & fees
May 19 - May 20
Holiday Inn Express & Suites S Lake Buena Vista, an IHG Hotel
Outdoor pool, pool umbrellas, sun loungers
Magic Village Yards, Trademark Collection by Wyndham
4.0 star property
9.2 out of 10, Wonderful, (1065)
"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
House, Multiple Bedrooms | Pool
Storey Lake 9 Bed Game Room & Pool 9 Bedroom Home by Redawning
3.5 star property
Storey Lake 9 Bed Game Room & Pool 9 Bedroom Home by Redawning
Pool
Lakeview Luxury Villa with Everything
10.0 out of 10, Exceptional, (227)
"Love the place!"
Lakeview Luxury Villa with Everything
Lake
Lifetime of Vacations Resort
3.0 star property
9.0 out of 10, Wonderful, (79)
"Everything about the Property.is perfect nice and clean."
Lifetime of Vacations Resort
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!
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
This month
Next month
September
February
CA $139
CA $162
Month
Price
January
CA $165
February
CA $203
March
CA $185
April
CA $149
May
CA $139
June
CA $162
July
CA $162
August
CA $142
September
CA $127
October
CA $137
November
CA $146
December
CA $176
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)
"We arrived in Orlando at 11am. We took a chance and called to see if a room was ready. We were told our room was ready and we could come on over and check in. Check in was quick and easy. Our 2 bedroom suite was clean and nice. We loved the full kitchen. We went and bought groceries instead of eating out every day. The balcony is huge and screened in. The property is beautiful and always clean. The pools have plenty of chairs and umbrellas. We liked the text message communication with the front...
The price is CA $119
CA $182 total
includes taxes & fees
May 19 - May 20
Hilton Vacation Club Mystic Dunes Orlando
In-room safe, laptop workspace, blackout drapes, iron/ironing board
Palazzo Lakeside Hotel
3.0 star property
8.0 out of 10, Very good, (3952)
"This was my second time staying at this property. Every interaction with front desk was phenomenal. The functionality of the room was well thought out. The cleanliness was superior. Everything worked as it should. Loved the extra large Roku tv inside the room. Beds were nice and comfy. Super love that the deposit was only $50. Reasonable and realistic. My only suggestion would be to add an extra top lock for the doors that children can not reach. My daughter ran out the room while I was mid...
The price is CA $48
CA $93 total
includes taxes & fees
Jun 11 - Jun 12
Palazzo Lakeside Hotel
Water park
Red Lion Hotel Orlando Lake Buena Vista South
3.5 star property
8.6 out of 10, Excellent, (4353)
"Big room"
The price is CA $92
CA $136 total
includes taxes & fees
May 19 - May 20
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.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Kissimmee. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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