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Kissimmee Vacation Rentals

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Check prices for these dates

Tonight
Dec 28 - Dec 29
Tomorrow
Dec 29 - Dec 30
Next weekend
Jan 2 - Jan 4
In two weeks
Jan 9 - Jan 11

Our top choices for Kissimmee vacation rentals

Aerial view
Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration
3.0 star property
Kissimmee
8.6 out of 10, Excellent, (3133)
"Great place to stay"
United States
Jose
The price is ￥13,715
￥19,480 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Vacation Village Orlando, Celebration
Lobby
The Berkley, Orlando

The Berkley, Orlando

The Berkley, Orlando
4.0 star property
Kissimmee
9.6 out of 10, Exceptional, (2019)
"The location of the resort is great. The room was perfect for our group. Staff was great, pool, game room. We would stay again. "
United States
Sarha
The price is ￥23,822
￥28,577 total
includes taxes & fees
Jan 5 - Jan 6, 2026
The Berkley, Orlando
Dock
Barefoot Suites

Barefoot Suites

Barefoot Suites
3.0 star property
Kissimmee
9.0 out of 10, Wonderful, (1801)
"Clean room location "
United States
Bryan
Barefoot Suites
Exterior
voco Kissimmee Orlando by IHG

voco Kissimmee Orlando by IHG

voco Kissimmee Orlando by IHG
4.0 star property
Kissimmee
7.6 out of 10, Good, (1011)
"Place was clean, staff great, cozy very nice area swimming pool"
United States
KRYSTLE
The price is ￥9,707
￥14,571 total
includes taxes & fees
Jan 7 - Jan 8, 2026
voco Kissimmee Orlando by IHG
House | 5 bedrooms
Super Cool- Sleeps 17 Newly Built Near Parks

Super Cool- Sleeps 17 Newly Built Near Parks

Super Cool- Sleeps 17 Newly Built Near Parks
2.0 star property
Kissimmee
The price is ￥17,987
￥64,558 total
includes taxes & fees
Jan 16 - Jan 17, 2026
Super Cool- Sleeps 17 Newly Built Near Parks
Billiards
Regal Oaks Resort Vacation Townhomes by IDILIQ

Regal Oaks Resort Vacation Townhomes by IDILIQ

Regal Oaks Resort Vacation Townhomes by IDILIQ
4.0 star property
Kissimmee
8.4 out of 10, Very Good, (3037)
"Great accommodations, clean and very spacious. Highly recommend to others, especially families. Pool was lovely "
United States
Christopher
The price is ￥22,580
￥56,550 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Regal Oaks Resort Vacation Townhomes by IDILIQ
Interior
Modern 3 Bed Villa, Newly Renovated, Prime Location

Modern 3 Bed Villa, Newly Renovated, Prime Location

Modern 3 Bed Villa, Newly Renovated, Prime Location
3.0 star property
Kissimmee
The price is ￥19,102
￥46,732 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Modern 3 Bed Villa, Newly Renovated, Prime Location
House (3 Bedrooms) | Interior
Upstay: Bright Family-friendly Retreat With Patio

Upstay: Bright Family-friendly Retreat With Patio

Upstay: Bright Family-friendly Retreat With Patio
3.0 star property
Chatham Park
Upstay: Bright Family-friendly Retreat With Patio
2 outdoor pools
Storey Lake condos by UNE Homes

Storey Lake condos by UNE Homes

Storey Lake condos by UNE Homes
3.5 star property
Kissimmee
The price is ￥22,703
￥54,201 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Storey Lake condos by UNE Homes
Indoor pool, pool umbrellas, sun loungers
Pool •Spa •Game Rm •10 min Disney-Fun Disney Oasis

Pool •Spa •Game Rm •10 min Disney-Fun Disney Oasis

Pool •Spa •Game Rm •10 min Disney-Fun Disney Oasis
5.0 star property
Lindfields
The price is ￥28,965
￥60,275 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Pool •Spa •Game Rm •10 min Disney-Fun Disney Oasis
Lobby
Disney's Animal Kingdom Villas - Kidani Village

Disney's Animal Kingdom Villas - Kidani Village

Disney's Animal Kingdom Villas - Kidani Village
4.0 star property
Bay Lake
9.0 out of 10, Wonderful, (166)
"The animals are amazing and the location for Animal Kingdom was perfect! The room was clean and comfortable."
United States
Kelly
Disney's Animal Kingdom Villas - Kidani Village
Interior
Margaritaville Cottages Orlando by Rentyl

Margaritaville Cottages Orlando by Rentyl

Margaritaville Cottages Orlando by Rentyl
4.0 star property
Kissimmee
8.8 out of 10, Excellent, (1759)
"Great place "
United States
Lauren
The price is ￥31,157
￥66,701 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Margaritaville Cottages Orlando by Rentyl
2 outdoor pools, pool umbrellas, sun loungers
Encantada Resort Vacation Townhomes by IDILIQ

Encantada Resort Vacation Townhomes by IDILIQ

Encantada Resort Vacation Townhomes by IDILIQ
3.0 star property
Kissimmee
8.4 out of 10, Very Good, (1405)
"Good place to stay when visiting DisneyWorld for a decent price compared to hotels"
United States
Jessica
The price is ￥21,885
￥55,762 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Encantada Resort Vacation Townhomes by IDILIQ
Dock
Grand Lake Resort

Grand Lake Resort

Grand Lake Resort
3.0 star property
Kissimmee
9.2 out of 10, Wonderful, (156)
"Amber was great we had a ball definitely coming back resort was beautiful "
United States
TAIYLAR
The price is ￥24,660
￥29,398 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Grand Lake Resort
Villa (3 Bedrooms) | Interior
Lake Berkley Villas Swanky

Lake Berkley Villas Swanky

Lake Berkley Villas Swanky
4.0 star property
Lake Berkley
The price is ￥28,731
￥61,904 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Lake Berkley Villas Swanky
Design House, 6 Bedrooms, Private Pool | Private kitchen | Highchair
FL- 1844 GOBI DR

FL- 1844 GOBI DR

FL- 1844 GOBI DR
3.0 star property
Kissimmee
The price is ￥22,859
￥63,522 total
includes taxes & fees
Jan 9 - Jan 10, 2026
FL- 1844 GOBI DR
Interior
Enjoy Disney 3brs at Villas of Somerset

Enjoy Disney 3brs at Villas of Somerset

Enjoy Disney 3brs at Villas of Somerset
3.5 star property
Kissimmee
The price is ￥18,006
￥45,487 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Enjoy Disney 3brs at Villas of Somerset
Villa (4 Bedrooms) | Interior
Spacious 4BR Family Townhouseprivate Pool & BBQ

Spacious 4BR Family Townhouseprivate Pool & BBQ

Spacious 4BR Family Townhouseprivate Pool & BBQ
3.0 star property
Bellavida
The price is ￥18,788
￥54,912 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Spacious 4BR Family Townhouseprivate Pool & BBQ
Microwave, stovetop
Tiny house close to Disney KISSIMMEE

Tiny house close to Disney KISSIMMEE

Tiny house close to Disney KISSIMMEE
2.0 star property
Kissimmee
8.0 out of 10, Very Good, (3)
"The location was great. We really just needed somewhere to sleep because we spent the day at the Disney Parks. The place had enough beds and was a great price."
United States
Christine M.
The price is ￥12,995
￥29,432 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Tiny house close to Disney KISSIMMEE
Lake view
Lifetime of Vacations Resort

Lifetime of Vacations Resort

Lifetime of Vacations Resort
3.0 star property
Kissimmee
9.4 out of 10, Exceptional, (152)
"Very nice quiet place... very polite front desk personnel "
United States
Iliana
The price is ￥16,487
￥21,374 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Lifetime of Vacations Resort
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.
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Top Kissimmee Hotel Reviews

Ramada by Wyndham Kissimmee Gateway

Ramada by Wyndham Kissimmee Gateway

10/10 Excellent
"Great customer service "
pablo 1-night trip
Posted 11 hours ago
Ramada by Wyndham Kissimmee Gateway

Find out more about Kissimmee

Search for holiday rentals in Kissimmee on Expedia! You can easily find your home rentals, villas, holiday apartments in Kissimmee using one of the methods below:

  • View our selection of featured holiday rentals in Kissimmee
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  • Enter your travel dates to view the best deals on holiday rentals in Kissimmee while they last

Look no further and take a look at our great range of rental properties in Kissimmee!

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 lively festivals. The array of shops and entertainment choices 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 hot tub. Other favorite homes for rent in Kissimmee are Formosa Valley Resort by UNE Homes and Modern Luxury Villa with Everything.

How many vacation rentals are there in Kissimmee?

Choose from 1420 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 Medieval Times and Capone's Dinner Show. 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.