Kissimmee Vacation Rentals

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Vacation Rentals in Kissimmee

Ramada by Wyndham Kissimmee Gateway
Exterior
Ramada by Wyndham Kissimmee Gateway
3.0 star property
7.2 out of 10, Good, (5993)
"Like that it had 2 different areas to accommodate people for the swimming pools and the outdoor games, the movie, loved that...my room was nice except that there's hardly any pressure in the shower head and there was a small leak under the sink. "
The price is $44
$66 total
includes taxes & fees
Jun 4 - Jun 5
Ramada by Wyndham Kissimmee Gateway
Flamingo Waterpark Resort
Water park
Flamingo Waterpark Resort
3.0 star property
6.8 out of 10, (1167)
"Una estadía amena, el personal muy atento y cerca de muchas cosas. El parque de aguas excelente para las atracciones que tiene."
The price is $76
$119 total
includes taxes & fees
Jun 18 - Jun 19
Flamingo Waterpark Resort
Seralago Hotel & Suites Main Gate East
2 outdoor pools, a heated pool, sun loungers
Seralago Hotel & Suites Main Gate East
3.0 star property
5.2 out of 10, (5293)
"Very basic nothing to brag about "
The price is $42
$65 total
includes taxes & fees
Jun 4 - Jun 5
Seralago Hotel & Suites Main Gate East
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Holiday Inn & Suites Orlando SW - Celebration Area, an IHG Hotel
Property amenity
Holiday Inn & Suites Orlando SW - Celebration Area, an IHG Hotel
3.0 star property
7.8 out of 10, Good, (1454)
"I enjoyed my stay at the hotel on my girls trip memorial weekend.. The room was nice and roomy enough for 4.. My issue with this whole booking is the fact that Expedia states there is a car charger on site but there isn’t one.. That issue needs to be rectified as this is false advertisement to anyone like myself who rented a electric car and chose this hotel for that specific reason.."
The price is $61
$98 total
includes taxes & fees
Jun 10 - Jun 11
Holiday Inn & Suites Orlando SW - Celebration Area, an IHG Hotel
Margaritaville Resort Orlando Cottages by Rentyl
Interior
Margaritaville Resort Orlando Cottages by Rentyl
4.0 star property
8.8 out of 10, Excellent, (849)
"Property was absolutely beautiful! The cottages were amazing! We got to use the amenities after checking out. I would highly recommend this place with families with children. If you want to go to a resort to relax by the pool, this isn’t it, this is more for people with families. The cottages are well equipped for families. Overall his beautiful !!"
Margaritaville Resort Orlando Cottages by Rentyl
Vacation Village at Parkway
Aerial view
Vacation Village at Parkway
3.0 star property
8.2 out of 10, Very Good, (1269)
"Rooms and facilities need updating"
Vacation Village at Parkway
The Berkley, Orlando
Lobby sitting area
The Berkley, Orlando
4.0 star property
9.4 out of 10, Exceptional, (1418)
"The unit is very spacious, full kitchen and full size washer and dryer. Nice pool area, not crowded "
The Berkley, Orlando
Embassy Suites by Hilton Orlando Lake Buena Vista South
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, (1719)
"Loved the property, we had an amazing time without even leaving the property!! Free adult beverages, great dining options, and great customer service!! "
The price is $140
$159 total
includes taxes & fees
Jun 9 - Jun 10
Embassy Suites by Hilton Orlando Lake Buena Vista South
Spectrum Resort Orlando
Outdoor pool, sun loungers, lifeguards on site
Spectrum Resort Orlando
4.0 star property
9.2 out of 10, Wonderful, (197)
"Loved our stay. Great for families. We will be back again! "
Spectrum Resort Orlando
Club Wyndham Cypress Palms
Private pool
Club Wyndham Cypress Palms
3.5 star property
8.8 out of 10, Excellent, (1466)
"Friendly staff, nice room and pleasant pool view. "
Club Wyndham Cypress Palms
Regal Oaks Resort Vacation Townhomes by IDILIQ
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, (2681)
"The property was very clean and our townhome felt like home. "
The price is $110
$285 total
includes taxes & fees
Jun 11 - Jun 12
Regal Oaks Resort Vacation Townhomes by IDILIQ
Reunion Resort & Golf Club
Waterslide
Reunion Resort & Golf Club
5.0 star property
8.6 out of 10, Excellent, (1126)
"Excellent service "
The price is $251
$325 total
includes taxes & fees
Jun 14 - Jun 15
Reunion Resort & Golf Club
Modern Luxury Villa with Everything
Pool
Modern Luxury Villa with Everything
9.8 out of 10, Exceptional, (300)
"Amazing staying"
Modern Luxury Villa with Everything
Encantada Resort Vacation Townhomes by IDILIQ
2 outdoor pools, pool umbrellas, sun loungers
Encantada Resort Vacation Townhomes by IDILIQ
3.0 star property
8.6 out of 10, Excellent, (1255)
"The breaker flipped and the power went out in the middle of me cooking. But maintenance was there pretty swiftly to get the power restored."
The price is $119
$282 total
includes taxes & fees
Jun 9 - Jun 10
Encantada Resort Vacation Townhomes by IDILIQ
Holiday Inn Express & Suites S Lake Buena Vista, an IHG Hotel
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 $98
$138 total
includes taxes & fees
Jun 10 - Jun 11
Holiday Inn Express & Suites S Lake Buena Vista, an IHG Hotel
Lakeview Luxury Villa with Everything
Pool
Lakeview Luxury Villa with Everything
10.0 out of 10, Exceptional, (234)
"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
Storey Lake 9 Bed Game Room & Pool 9 Bedroom Home by RedAwning
Pool | A heated 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
Magic Village Yards, Trademark Collection by Wyndham
Outdoor pool, pool umbrellas, sun loungers
Magic Village Yards, Trademark Collection by Wyndham
4.0 star property
9.2 out of 10, Wonderful, (1071)
"The location of this property and convenience is amazing "
The price is $326
$621 total
includes taxes & fees
Jul 1 - Jul 2
Magic Village Yards, Trademark Collection by Wyndham
Lifetime of Vacations Resort
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
Home w/ Pool, Hot Tub & Game Room, 6 Mi to Disney!
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
This month
Next month
May
March
$134
$146
Month
Price
January
$129
February
$153
March
$159
April
$110
May
$104
June
$134
July
$146
August
$123
September
$116
October
$107
November
$116
December
$125
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

Palazzo Lakeside Hotel
In-room safe, laptop workspace, blackout drapes, iron/ironing board
Palazzo Lakeside Hotel
3.0 star property
8.0 out of 10, Very Good, (4051)
"Siempre excelente servicio."
The price is $57
$95 total
includes taxes & fees
Jun 4 - Jun 5
Palazzo Lakeside Hotel
Hilton Vacation Club Mystic Dunes Orlando
4 outdoor pools, cabanas (surcharge), pool umbrellas
Hilton Vacation Club Mystic Dunes Orlando
3.5 star property
8.8 out of 10, Excellent, (3198)
"Very clean."
The price is $87
$133 total
includes taxes & fees
Jun 10 - Jun 11
Hilton Vacation Club Mystic Dunes Orlando
Margaritaville Resort Orlando
Lobby
Margaritaville Resort Orlando
4.0 star property
8.8 out of 10, Excellent, (3052)
"It’s beautiful and there are great activities to do. "
The price is $155
$222 total
includes taxes & fees
Jun 4 - Jun 5
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, 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 $42 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

Ramada by Wyndham Kissimmee Gateway

Ramada by Wyndham Kissimmee Gateway

5/5 Excellent
"Have a really good time"
A verified traveler stayed at Ramada by Wyndham Kissimmee Gateway
Posted 14 hours ago
Ramada by Wyndham Kissimmee Gateway