Kissimmee Vacation Rentals

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Check prices for these dates

In two weeks
May 29 - May 31
In two months
Jul 10 - Jul 12
In three months
Aug 7 - Aug 9
In four months
Sep 4 - Sep 6

Our top choices for Kissimmee vacation rentals

7 outdoor pools, pool umbrellas, sun loungers

Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration
3.0 star property
Kissimmee
8.6 out of 10, Excellent, (4,135 reviews)
"Fanily friendly, great value, great location!"
United States
Marivette
The price is ￥11,572
￥17,104 total
includes taxes & fees
May 30 - May 31
Vacation Village Orlando, Celebration
Outdoor pool

Affordable Stays Kissimmee

Affordable Stays Kissimmee
2.5 star property
Kissimmee
The price is ￥8,648
￥33,486 total
includes taxes & fees
May 24 - May 25
Affordable Stays Kissimmee
House | 2 bedrooms

Super Boho - At Lake Toho Fishing Vintage Vibes

Super Boho - At Lake Toho Fishing Vintage Vibes
2.0 star property
Historic Downtown Kissimmee
The price is ￥13,962
￥49,863 total
includes taxes & fees
May 17 - May 18
Super Boho - At Lake Toho Fishing Vintage Vibes
Lobby sitting area

The Berkley, Orlando

The Berkley, Orlando
4.0 star property
Kissimmee
9.6 out of 10, Exceptional, (2,220 reviews)
"Great place; great staff, easy check in"
United States
Jacquelynn
The price is ￥18,890
￥23,037 total
includes taxes & fees
May 31 - Jun 1
The Berkley, Orlando
Lounge

Adeline Apartments 15m to Parks, Pet Friendly, Free Parking by Heavenly Homes

Adeline Apartments 15m to Parks, Pet Friendly, Free Parking by Heavenly Homes
4.0 star property
Kissimmee
10.0 out of 10, Exceptional, (2 reviews)
"Would stay again and so should you! "
United States
katie
The price is ￥13,215
￥36,296 total
includes taxes & fees
May 18 - May 19
Adeline Apartments 15m to Parks, Pet Friendly, Free Parking by Heavenly Homes
Villa (3 Bedrooms) | Front of property

Upstay Modern 3BR Townhome With Pool Near Disney

Upstay Modern 3BR Townhome With Pool Near Disney
3.0 star property
Kissimmee
The price is ￥13,144
￥41,764 total
includes taxes & fees
May 19 - May 20
Upstay Modern 3BR Townhome With Pool Near Disney
Outdoor pool

Harmony Ensuite Room Shared Home No Car

Harmony Ensuite Room Shared Home No Car
2.5 star property
Kissimmee
The price is ￥6,671
￥31,296 total
includes taxes & fees
Jun 16 - Jun 17
Harmony Ensuite Room Shared Home No Car
Design House, 6 Bedrooms, Private Pool | Private kitchen | Highchair

FL- 1844 GOBI DR

FL- 1844 GOBI DR
3.0 star property
Kissimmee
10.0 out of 10, Exceptional, (1 review)
The price is ￥31,113
￥73,411 total
includes taxes & fees
May 17 - May 18
FL- 1844 GOBI DR
Outdoor pool, pool umbrellas, sun loungers

Barefoot Suites

Barefoot Suites
3.0 star property
Kissimmee
9.0 out of 10, Wonderful, (1,876 reviews)
"Great for families"
United States
Frank
The price is ￥15,227
￥20,420 total
includes taxes & fees
May 19 - May 20
Barefoot Suites
Outdoor pool

Aster Cove

Aster Cove
4.0 star property
Crescent Lakes
The price is ￥24,173
￥86,463 total
includes taxes & fees
May 17 - May 18
Aster Cove
Exterior

Modern Award Winning Newly Renovated, Gorgeous 2+2 Minutes Away From Disney

Modern Award Winning Newly Renovated, Gorgeous 2+2 Minutes Away From Disney
Kissimmee
9.2 out of 10, Wonderful, (164 reviews)
"Excellent accommodations."
United States
Raychelle
The price is ￥10,318
￥32,904 total
includes taxes & fees
May 20 - May 21
Modern Award Winning Newly Renovated, Gorgeous 2+2 Minutes Away From Disney
Outdoor pool

Maple Leaf Inn & Suites

Maple Leaf Inn & Suites
2.5 star property
Kissimmee
6.8 out of 10, (71 reviews)
"The room was clean and the staff was okay "
United States
Shaneka
The price is ￥9,523
￥10,809 total
includes taxes & fees
May 17 - May 18
Maple Leaf Inn & Suites
House | 3 bedrooms

Super YES - Many Amenities Relax GYM Courts

Super YES - Many Amenities Relax GYM Courts
2.0 star property
Kissimmee
The price is ￥15,758
￥56,153 total
includes taxes & fees
May 21 - May 22
Super YES - Many Amenities Relax GYM Courts
Exterior

Reunion Resort - Near Theme Parks & Airport

Reunion Resort - Near Theme Parks & Airport
Reunion
9.6 out of 10, Exceptional, (57 reviews)
"Had a as great stay at Reunion, fabulous facilities. "
United States
Helen H.
The price is ￥11,286
￥49,420 total
includes taxes & fees
May 23 - May 24
Reunion Resort - Near Theme Parks & Airport
Exterior

Barefoot'n Resort Kissimmee Orlando

Barefoot'n Resort Kissimmee Orlando
2.5 star property
Kissimmee
9.0 out of 10, Wonderful, (297 reviews)
"Very nice clean place to stay"
United States
THOMAS
The price is ￥13,488
￥17,290 total
includes taxes & fees
May 17 - May 18
Barefoot'n Resort Kissimmee Orlando
Apartment (2 Bedrooms) | Interior

Storey Lake Resort Condo w Patio5 Miles to Disney

Storey Lake Resort Condo w Patio5 Miles to Disney
3.0 star property
Kissimmee
The price is ￥16,668
￥42,160 total
includes taxes & fees
Jun 8 - Jun 9
Storey Lake Resort Condo w Patio5 Miles to Disney
Interior

Enjoy Disney 3brs at Villas of Somerset

Enjoy Disney 3brs at Villas of Somerset
3.5 star property
Kissimmee
8.0 out of 10, Very Good, (1 review)
"Nice home but bathroom are too old "
United States
Urvin
The price is ￥18,847
￥54,648 total
includes taxes & fees
May 18 - May 19
Enjoy Disney 3brs at Villas of Somerset
Exterior

Margaritaville Cottages Orlando by Rentyl with H2O Waterpark

Margaritaville Cottages Orlando by Rentyl with H2O Waterpark
4.0 star property
Kissimmee
8.8 out of 10, Excellent, (1,966 reviews)
"Great place for families "
United States
Luis
The price is ￥33,970
￥70,328 total
includes taxes & fees
May 19 - May 20
Margaritaville Cottages Orlando by Rentyl with H2O Waterpark
Family Apartment | Private kitchen | Full-size fridge, microwave, oven, dishwasher

LOVELY LUXURY APARTMENT CLOSE DISNEY

LOVELY LUXURY APARTMENT CLOSE DISNEY
3.5 star property
Kissimmee
8.4 out of 10, Very Good, (8 reviews)
"Nice appartment, everything you needed and clean and modern"
United Kingdom
Martyn
The price is ￥16,799
￥47,648 total
includes taxes & fees
May 27 - May 28
LOVELY LUXURY APARTMENT CLOSE DISNEY
Apartment (4 Bedrooms) | Interior

< 2 Mi to WDW Attractions: Luxe Family Getaway!

< 2 Mi to WDW Attractions: Luxe Family Getaway!
4.0 star property
Kissimmee
10.0 out of 10, Exceptional, (1 review)
"We really enjoyed our Disney trip! Very convenient location!"
United States
Zaily
The price is ￥14,763
￥56,389 total
includes taxes & fees
Jun 4 - Jun 5
< 2 Mi to WDW Attractions: Luxe Family Getaway!
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

Hilton Vacation Club Mystic Dunes Orlando

Hilton Vacation Club Mystic Dunes Orlando

10/10 Excellent
"Perfect for our stay. It was clean, comfortable, and had all the amenities we needed. Pricing was great and not too far from where we needed to be."
jenny 4-night trip
Posted 1 hour ago
Hilton Vacation Club Mystic Dunes Orlando

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 entertainment choices. 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 hot tub. Other favorite homes for rent in Kissimmee are Glam Villa Near the Parks w Gamer & Princess BRs, Huge Theater, Arcade, Spa Pool and Pool, Hot Tub+Game Rm, Mins to Disney & Universal | Sunshine Ridge by AvantStay.

How many vacation rentals are there in Kissimmee?

Choose from 1590 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 Osceola County Welcome Center and History Museum. 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.