Kissimmee Holiday Rentals

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Holiday 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, (293)
"Great location and clean premises."
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 NZ$371
per night
20 May - 21 May
Caribbean Villa
Pool
Ultimate Lakeview Villa with Everything!
9.8 out of 10, Exceptional, (283)
"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!
A heated pool
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, (1412)
"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, pool loungers, lifeguards on site
Spectrum Resort Orlando
4.0 star property
9.2 out of 10, Wonderful, (191)
"Loved the place. Wished the pool was open longer. "
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 NZ$266
per night
2 Jun - 3 Jun
Embassy Suites by Hilton Orlando Lake Buena Vista South
Outdoor pool, pool umbrellas, pool 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
Fridge, microwave, oven, stovetop
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)
"I have stayed here multiple times. Hotel staff are always friendly and helpful rooms are always clean have a jet tub and full kitchen. hotel also has pool,tiki area, paddle boats on the lake, bbq areas w. Picnic tables , kids playset and more to makevthe stay a little more enjoyable . "
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, pool 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, (836)
"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, (1452)
"Great place to stay!"
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)
"Perfect for the family. "
The price is NZ$465
per night
1 Jun - 2 Jun
Reunion Resort & Golf Club
2 outdoor pools, pool umbrellas, pool 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 NZ$192
per night
12 Jun - 13 Jun
Encantada Resort Vacation Townhomes by IDILIQ
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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.

Other types of properties in Kissimmee you may be interested in

4 outdoor pools, pool cabanas (surcharge), pool umbrellas
Hilton Vacation Club Mystic Dunes Orlando
3.5 star property
8.8 out of 10, Excellent, (3113)
"The rooms where clean, spacious and up to date. The staff was very friendly. The customer assistance through text message was very helpful and responded quickly. It’s conveniently close to stores and restaurants and only 15-20 minutes away from all the Disney parks. Will definitely be returning. "
The price is NZ$162
per night
29 May - 30 May
Hilton Vacation Club Mystic Dunes Orlando
Lobby
Margaritaville Resort Orlando
4.0 star property
8.8 out of 10, Excellent, (2993)
"Love Margaritaville! The best food and atmosphere. "
The price is NZ$239
per night
27 May - 28 May
Margaritaville Resort Orlando
Water park
Red Lion Hotel Orlando Lake Buena Vista South
3.5 star property
8.6 out of 10, Excellent, (4323)
"Wonderful stay"
The price is NZ$114
per night
22 May - 23 May
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 holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Kissimmee holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Kissimmee. 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 Kissimmee. 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 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 holiday 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 Kissimmee short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Kissimmee?

Yes, there are holiday rentals in Kissimmee close to Disney's Animal Kingdom® Theme Park, or you can select a more secluded option if you're looking for a relaxing 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 are some of the best holiday rentals that Kissimmee has to offer?

The Berkley, Orlando: This highly rated holiday home rental in Kissimmee offers a furnished patio, a terrace and a BBQ 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 holiday with an arcade/games room and 1 hot tub. Another good choice for your trip to Kissimmee is Upstay - Theme Rooms|Movie Theatre|Pool|Sleeps 18.

How many holiday rentals are there in Kissimmee?

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

What can I see and do in Kissimmee?

Disney's Animal Kingdom® Theme Park and Walt Disney World® Resort are a couple of the 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 holiday rentals like in Kissimmee?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Kissimmee. Holiday rentals feature amenities like laundry facilities and kitchens so you'll have everything you want. If you're concerned about a sanitised environment, a holiday rental can offer a sense of seclusion away from public hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great choice for a small group gathering.

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