Kissimmee Vacation Rentals

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Vacation Rentals in Kissimmee

Exterior
Ramada by Wyndham Kissimmee Gateway
3.0 star property
7.2 out of 10, Good, (5967)
"I’ll come back! Thanks! My pet was happy! "
The price is CA $60
CA $90 total
includes taxes & fees
Jun 2 - Jun 3
Ramada by Wyndham Kissimmee Gateway
Water park
Flamingo Waterpark Resort
3.0 star property
6.6 out of 10, (1158)
"Good hotel, water park really fun, need a little work but is fun!!!"
The price is CA $103
CA $162 total
includes taxes & fees
Jun 16 - Jun 17
Flamingo Waterpark Resort
Property amenity
Holiday Inn & Suites Orlando SW - Celebration Area, an IHG Hotel
3.0 star property
7.8 out of 10, Good, (1446)
"The hotel was what I expected… the only thing I saw that could have been better is mold growing in the shower…. For the price I was satisfied "
The price is CA $83
CA $133 total
includes taxes & fees
Jun 10 - Jun 11
Holiday Inn & Suites Orlando SW - Celebration Area, an IHG Hotel
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2 outdoor pools, a heated pool, sun loungers
Seralago Hotel & Suites Main Gate East
3.0 star property
5.2 out of 10, (5281)
"This hotel is one my family and I would usually book, however it has absolutely gone down hill fast. There is absolutely NO dining area on premises, zero ice machines, rust and mold in the rooms, and no coffee makers in any rooms. We had to go off property just to even get a meal or snack. Oh and housekeeping is done ONLY after you check out. So needless to say, we WON'T be staying here again."
The price is CA $60
CA $93 total
includes taxes & fees
May 30 - May 31
Seralago Hotel & Suites Main Gate East
Interior
Margaritaville Resort Orlando Cottages by Rentyl
4.0 star property
8.8 out of 10, Excellent, (846)
"great stay"
Margaritaville Resort Orlando Cottages by Rentyl
Aerial view
Vacation Village at Parkway
3.0 star property
8.2 out of 10, Very good, (1264)
"This was a great place to stay, close to Disney, plenty of room for our family and a great price. We did not use any of the amenities like the workout room or the pool, we were in the parks most of the time during our stay. The only problem we had was one morning around 7:30 AM. Someone from the staff opened our door while we were still in bed which was a little frightening and put us on edge the rest of our visit. I called the front desk and they said they don’t have any record of anyone...
Vacation Village at Parkway
Lobby sitting area
The Berkley, Orlando
4.0 star property
9.4 out of 10, Exceptional, (1415)
"Nice and clean "
The Berkley, 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, (1714)
"Great Location and quiet "
The price is CA $196
CA $222 total
includes taxes & fees
Jun 16 - Jun 17
Embassy Suites by Hilton Orlando Lake Buena Vista South
Private pool
Club Wyndham Cypress Palms
3.5 star property
8.8 out of 10, Excellent, (1463)
"Very comfortable. Bathroom is very nice. Everything you would hope for in the kitchen."
Club Wyndham Cypress Palms
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, (2675)
"The rooms need to be updated. Carpet was very worn, bathroom door upstairs did not close all the way. Dishwater did not close properly. "
The price is CA $150
CA $389 total
includes taxes & fees
Jun 11 - Jun 12
Regal Oaks Resort Vacation Townhomes by IDILIQ
Outdoor pool, sun loungers, lifeguards on site
Spectrum Resort Orlando
4.0 star property
9.2 out of 10, Wonderful, (195)
"Loved the place. Wished the pool was open longer. "
Spectrum Resort Orlando
Waterslide
Reunion Resort & Golf Club
5.0 star property
8.6 out of 10, Excellent, (1124)
"Excellent service "
The price is CA $380
CA $486 total
includes taxes & fees
Jun 14 - Jun 15
Reunion Resort & Golf Club
Bar (on property)
Holiday Inn Express & Suites S Lake Buena Vista, an IHG Hotel
2.5 star property
8.6 out of 10, Excellent, (859)
"wonderful experience "
The price is CA $134
CA $188 total
includes taxes & fees
Jun 4 - Jun 5
Holiday Inn Express & Suites S Lake Buena Vista, an IHG Hotel
2 outdoor pools, pool umbrellas, sun loungers
Encantada Resort Vacation Townhomes by IDILIQ
3.0 star property
8.6 out of 10, Excellent, (1255)
"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 $139
CA $358 total
includes taxes & fees
Jun 12 - Jun 13
Encantada Resort Vacation Townhomes by IDILIQ
Pool
Modern Luxury Villa with Everything
9.8 out of 10, Exceptional, (297)
"This is a big home and was perfect for us. There were even some rooms that we didn't even use. Clean, great location, had everything we needed and wanted along with a pool! We couldn't have asked for more."
Modern Luxury Villa with Everything
Outdoor pool, pool umbrellas, sun loungers
Magic Village Yards, Trademark Collection by Wyndham
4.0 star property
9.2 out of 10, Wonderful, (1071)
"It was nice. Clean , professional customer service and great location. "
Magic Village Yards, Trademark Collection by Wyndham
Pool
Lakeview Luxury Villa with Everything
10.0 out of 10, Exceptional, (233)
"Booked this villa due to price, location, but primarily facilities in property, such as themed kids rooms, games room pool and cinema as we were a party if 11 wanting space and entertainment. A.phitos on booking site did not do the place justice - it was amazing and the resort facilities such as lazy river, slides and club house were an added bonus. Location was central to all attractions and check in was easy. Had a small maintenance problem which was dealt with immediately and the whole...
Lakeview Luxury Villa with Everything
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
Lake
Lifetime of Vacations Resort
3.0 star property
9.0 out of 10, Wonderful, (83)
"Place is good Its a older place but its safe and in a great location. Staff is very nice and area is a hub for Disneyland merchandise. "
Lifetime of Vacations Resort
Interior
Home w/ Pool, Hot Tub & Game Room, 6 Mi to Disney!
9.8 out of 10, Exceptional, (12)
"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
Next month
September
February
CA $162
Month
Price
January
CA $159
February
CA $198
March
CA $190
April
CA $136
May
CA $131
June
CA $162
July
CA $159
August
CA $138
September
CA $130
October
CA $136
November
CA $141
December
CA $165
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

In-room safe, laptop workspace, blackout drapes, iron/ironing board
Palazzo Lakeside Hotel
3.0 star property
8.0 out of 10, Very good, (4010)
"Staff were very friendly upon arrival and during check in. The room was very clean and spacious! "
The price is CA $57
CA $105 total
includes taxes & fees
Jun 24 - Jun 25
Palazzo Lakeside Hotel
4 outdoor pools, cabanas (surcharge), pool umbrellas
Hilton Vacation Club Mystic Dunes Orlando
3.5 star property
8.8 out of 10, Excellent, (3164)
"Great location. Found blood in one of the bed sheets"
The price is CA $119
CA $182 total
includes taxes & fees
Jun 4 - Jun 5
Hilton Vacation Club Mystic Dunes Orlando
Lobby
Margaritaville Resort Orlando
4.0 star property
8.8 out of 10, Excellent, (3034)
"Great time"
The price is CA $238
CA $332 total
includes taxes & fees
Jun 2 - Jun 3
Margaritaville Resort Orlando
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, cottages, cabins, villas... 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Kissimmee vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Kissimmee vacation rentals we have selected for you start as low as CA $60 per night. Entering your travel dates in the search wizard 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

Gaylord Palms Resort & Convention Center

Gaylord Palms Resort & Convention Center

5/5 Excellent
"Good "
A verified traveller stayed at Gaylord Palms Resort & Convention Center
Posted 15 hours ago
Gaylord Palms Resort & Convention Center