The 10 best holiday rentals in Kissimmee, USA | Booking.com
Skip to main content

Holiday Rentals in Kissimmee

Find the holiday rentals that appeal to you the most

Holiday Rentals for every style

Find the right holiday rental for you in Kissimmee

The best holiday rentals in Kissimmee

Check out our pick of great holiday rentals in Kissimmee

Show hotels on map

Filter by:

Review score

Amazing 3bd/2ba Condo with water view @ Disney

West Kissimmee, Kissimmee

Situated in Kissimmee, Amazing 3bd/2ba Condo with water view @ Disney offers a patio with pool and river views, as well as a year-round outdoor pool, sauna and hot tub.

c
clare
From
United Kingdom
Some parts were a bit dated but it was comfortable , close to all Disney parks , quiet would highly recommend
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 6 reviews
Price from
US$308.12
1 night, 2 adults
Check availability

Great 6bedrooms home in Kissimmee w Private Pool 8426

West Kissimmee, Kissimmee

Featuring air-conditioned accommodation with a terrace, Great 6bedrooms home in Kissimmee w Private Pool 8426 is located in Kissimmee. Guests can go for a swim in the private pool.

K
Kerry
From
United Kingdom
Comfortable. Clean. Plenty of space. Excellent location.
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 22 reviews
Price from
US$410.62
1 night, 2 adults
Check availability

Windsor Palms, next to clubhouse

West Kissimmee, Kissimmee

Located in the Windsor Palms district of Kissimmee, Windsor Palms, next to clubhouse features accommodation with a private pool and bicycle parking. Guests can benefit from a balcony and a picnic...

A
Andrew
From
United Kingdom
Location to the pool etc and very comfortable
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 10 reviews
Price from
US$284.58
1 night, 2 adults
Check availability

Chic 5Bed Home close to Disney parks

Kissimmee

Featuring air-conditioned accommodation with a private pool, Chic 5Bed Home close to Disney parks is set in Kissimmee. Guests staying at this holiday home have access to a patio.

J
Jay
From
United Kingdom
Great location and a very nice holiday home!
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 14 reviews
Price from
US$593.10
1 night, 2 adults
Check availability

Stay at Hogwarts Harry Potter's Home, Free Parking, Pets Allowed

Kissimmee

Featuring air-conditioned accommodation with a patio, Stay at Hogwarts Harry Potter's Home, Free Parking, Pets Allowed is located in Kissimmee.

R
Rachel
From
United Kingdom
The themed rooms are great, and the kids loved our stay at 'Hogwarts'. The area felt safe and location was good for us to explore the areas of Orlando we wanted to. Andrea was very responsive to my queries and all in all a great host.
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 29 reviews
Price from
US$280.46
1 night, 2 adults
Check availability

Exquisite 2 Br Storey Lake, 7 Min To Disney

Kissimmee

Boasting air-conditioned accommodation with a terrace, Exquisite 2 Br Storey Lake, 7 Min To Disney is situated in Kissimmee. Guests staying at this apartment have access to a balcony.

J
Jemma
From
United Kingdom
Had everything we needed great for families, around 11-15 bucks to Disney in an Uber. Uber eats was also helpful. A car is usually. There is a pool just outside that is less busy, the lazy river pool was packed you can’t bring in snacks to this pool and we found it expensive, it’s busy on the weekends. The washing machine is very useful, beds comfy.
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 6 reviews
Price from
US$257.65
1 night, 2 adults
Check availability

Nice & Cozy - Vacation Home

Kissimmee

Situated in Kissimmee, 10 km from ESPN Wide World of Sports, Nice & Cozy - Vacation Home features accommodation with a hot tub. This property offers a private pool and free private parking.

N
Nicola
From
United Kingdom
Very spacious on a safe complex with excellent facilities.
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 22 reviews
Price from
US$256.48
1 night, 2 adults
Check availability

Luxury 5Bed Home with Pool and Game Room

Kissimmee

Featuring air-conditioned accommodation with a private pool, Luxury 5Bed Home with Pool and Game Room is set in Kissimmee. This holiday home offers accommodation with a patio.

A
Andrew
From
United Kingdom
High quality house, loads of space, great finish and lovely to stay in, great location for disney parks, nice pool, very very helpful hosts who helped us when we messed up our check out dates!
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 17 reviews
Price from
US$575.32
1 night, 2 adults
Check availability

Amazing 4 Bed home w private Pool close to Disney 1180KING

Kissimmee

Featuring air-conditioned accommodation with a private pool, Amazing 4 Bed home w private Pool close to Disney 1180KING is set in Kissimmee. Guests staying at this holiday home have access to a patio....

S
Shatanna
From
United States
The home was beautiful and very well organized I love the decorations throughout the home this is must stay whenever my family visit Again
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 15 reviews
Price from
US$446.08
1 night, 2 adults
Check availability

Luxury Champions Gate Condo, Resort-Style Retreat

Kissimmee

Set just 21 km from Disney's Boardwalk, Luxury Champions Gate Condo, Resort-Style Retreat offers accommodation in Kissimmee with access to a fitness centre, a bar, as well as private check-in and...

W
William
From
United States
The place was clean and comfortable
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 40 reviews
Price from
US$372.06
1 night, 2 adults
Check availability
All holiday rentals in Kissimmee

Most booked holiday rentals in Kissimmee and surroundings in the past month

See all

Highly rated holiday rentals in Kissimmee and nearby

  • Scored out of 10, guest rating 8.0
    Very good - What previous guests thought, 62 reviews

    Encore Resort and Water Park at Reunion by Rentyl offers accommodation within 700 metres of the centre of Kissimmee, with free WiFi, and a kitchen with a dishwasher, an oven and a microwave.

  • Island 1

    Kissimmee
    8.0+ review score
    Scored out of 10, guest rating 8.4
    Very good - What previous guests thought, 22 reviews

    Set in Kissimmee, Island 1 offers accommodation with private pool, free WiFi and free private parking for guests who drive. This holiday home features air-conditioned accommodation with a patio.

  • Scored out of 10, guest rating 8.9
    Fabulous - What previous guests thought, 9 reviews

    Situated in Kissimmee, Remarkable Cozy 4Bed-3Ba Townhouse features accommodation with private pool, free WiFi and free private parking for guests who drive.

  • Scored out of 10, guest rating 8.8
    Fabulous - What previous guests thought, 25 reviews

    Featuring air-conditioned accommodation with a balcony, Great Lovely Family Apartment close Disney is located in Kissimmee. With garden views, this accommodation provides a patio and a swimming pool.

  • JC DISNEY House

    Kissimmee
    8.0+ review score
    Scored out of 10, guest rating 9.6
    Exceptional - What previous guests thought, 14 reviews

    Boasting garden views, JC DISNEY House provides accommodation with a fitness centre and a patio, around 12 km from Gatorland.

  • Scored out of 10, guest rating 8.7
    Fabulous - What previous guests thought, 16 reviews

    Set in Kissimmee, 13 km from Gatorland and 16 km from Disney Springs, Terra Verde Vacation Rentals offers air-conditioned accommodation with a terrace and free WiFi.

  • Scored out of 10, guest rating 8.7
    Fabulous - What previous guests thought, 13 reviews

    Set in Kissimmee, 14 km from ESPN Wide World of Sports and 14 km from Disney Springs, 4 BR No carpet Just Remodeled Unit SR1205 offers air conditioning.

  • Scored out of 10, guest rating 9.2
    Superb - What previous guests thought, 10 reviews

    Boasting air-conditioned accommodation with a private pool, Ground floor spacious house 4BR VP2512 is situated in Kissimmee.

Enjoy breakfast in Kissimmee and nearby

These holiday rentals in Kissimmee and nearby have options with free cancellation

  • Scored out of 10, guest rating 5.4
    Passable - What previous guests thought, 7 reviews

    Featuring air-conditioned accommodation with a patio, Hidden City Riverfront Apt Near Lakes Golf & Disney is located in Kissimmee.

  • Scored out of 10, guest rating 6.8
    Pleasant - What previous guests thought, 17 reviews

    Boasting a garden, pool with a view and lake views, 2222 Venettian Bay retreat- 3 bedroom full of amenities is set in Kissimmee.

  • Heritage Park Inn

    Kissimmee
    Free cancellation options available
    Scored out of 10, guest rating 6.0
    Pleasant - What previous guests thought, 222 reviews

    Heritage Park Inn, a property with a garden, is set in Kissimmee, 11 km from Gatorland, 22 km from Florida Mall, as well as 23 km from Seaworld'S Discovery Cove.

  • Serene Sunsets Villa - E04

    Kissimmee
    Free cancellation options available

    Boasting air-conditioned accommodation with a private pool, Serene Sunsets Villa - E04 is set in Kissimmee. Guests staying at this holiday home have access to a patio.

  • 4423 Scene Lane

    Kissimmee
    Free cancellation options available

    Boasting air-conditioned accommodation with a private pool, 4423 Scene Lane is set in Kissimmee. Both free WiFi and parking on-site are accessible at the holiday home free of charge.

  • Featuring air-conditioned accommodation with a private pool, South Facing Pool with Stunning Lake View - Family Friendly Home - Nr Disney is located in Kissimmee.

  • Scored out of 10, guest rating 8.9
    Fabulous - What previous guests thought, 27 reviews

    Set in Kissimmee in the Florida region and Disney Springs reachable within 12 km, Cozy Oasis near Disney! 4 bedroom 3 bath Townhouse!

  • VILLA wPrivate Pool & Game Room near Disney

    Kissimmee
    Free cancellation options available
    Scored out of 10, guest rating 8.6
    Fabulous - What previous guests thought, 14 reviews

    Boasting air-conditioned accommodation with a private pool, VILLA wPrivate Pool & Game Room near Disney is situated in Kissimmee.

FAQ about holiday rentals in Kissimmee

Holiday rentals that guests love in Kissimmee

See all

  • Veteran Owned 3bdr/3 bath Townhouse w/WiFi 3mi to Disney - Fall/Winter Specials

    Holiday Rental in Kissimmee
    Scored out of 10, guest rating 9.4
    Superb - What previous guests thought, 29 reviews
    Our recent stay at this villa was an amazing experience. We spent three weeks in Florida as a family—two adults and three kids. The villa is much larger than it looks in the pictures, and the communication with the owners is spot-on. I would happily stay here again on future trips. The location is perfect for Disney and Universal.
    Guest review by
    David
    Family with young children

  • Disney-Themed Villa with Heated Pool, 10 Mi to Parks

    Holiday Rental in Kissimmee
    Scored out of 10, guest rating 9.5
    Exceptional - What previous guests thought, 2 reviews
    Lovely villa, so many little extra Disney themed touches. Local contact was very responsive when I couldn't find a couple of things. Really comfortable beds and lovely pool, we had a great time!
    Guest review by
    Helen
    Family with young children

  • Villas at Seven Dwarfs - Close to Disney

    Holiday Rental in Kissimmee
    Scored out of 10, guest rating 7.8
    Good - What previous guests thought, 518 reviews
    Our Villa was amazing! Location was perfect! Staff was nice and very helpful!
    Guest review by
    Chameka
    Family with young children

  • Chic 5Bed Home close to Disney parks

    Holiday Rental in Kissimmee
    Scored out of 10, guest rating 9.2
    Superb - What previous guests thought, 14 reviews
    Great location and a very nice holiday home!
    Guest review by
    Jay
    Family with young children

Research, refine and make plans for your whole trip

Holiday Rentals in New York

Take a look at holiday rentals in New York and explore more of the United States.

Holiday Rentals in Las Vegas

Discover another destination in the United States.

Hotels near Walt Disney World

Hotels close to a popular local landmark.

Hotels near Universal Studios Orlando

Hotels close to a popular local landmark.

Holiday Rentals in Disney World Area

Extend your search and explore the surrounding area.

Holiday Rentals in Florida

Extend your search and explore the surrounding area.

Holiday Rentals in Davie

Want to extend your trip or still just browsing? Try Davie, also popular with our guests!

Cheap holidays in Kissimmee

Book the best flights, stays and more – all in one place

Hotels near Give Kids The World Village

Places to stay near one of the top places to see.

Hotels near Orlando International Airport

Perfect for a late arrival or early departure.

Hotels near Orlando Sanford International Airport

Perfect for a late arrival or early departure.

Holiday Rentals in the United States

Pack a bigger bag and see more of the country.

When to visit the United States

Events, prices, the weather – everything you need to know about the best time to visit the United States.

Hotels in Kissimmee

More great accommodation options for your trip.

Holiday Homes in Kissimmee

More great accommodation options for your trip.

Cheap hotels in Kissimmee

More great accommodation options for your trip.

Motels in Kissimmee

More great accommodation options for your trip.

Villas in Kissimmee

More great accommodation options for your trip.

Things to do in Kissimmee

Attractions, tours and more – how will you spend your time in Kissimmee?

Holiday Rentals in Davenport

Find more hotels in a city close to Davenport.

Holiday Rentals in Orlando

Find more hotels in a city close to Orlando.

Hotels in Downtown Kissimmee

Get to know one of the city's most popular neighbourhoods.

Car hire in Kissimmee

Hire a car and hit the road.