The 10 best holiday rentals in Kissimmee, USA | Booking.com
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Holiday Rentals in Kissimmee

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The best holiday rentals in Kissimmee

Check out our pick of great holiday rentals in Kissimmee

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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 9.1
Superb - What previous guests thought, 23 reviews
Price from
US$165
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$172.80
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 9.6
Exceptional - What previous guests thought, 23 reviews
Price from
US$126
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 9.2
Superb - What previous guests thought, 43 reviews
Price from
US$132.45
1 night, 2 adults
Check availability

Magical Themed Home - Disney 15 min

Kissimmee

Featuring a spa bath, Magical Themed Home - Disney 15 min is set in Kissimmee. This holiday home has a private pool and a garden.

S
Sandris
From
Latvia
The house truly exceeded our expectations – very spacious, spotlessly clean, and although it is located in the city, it felt calm and almost like being in nature. Everything was simply perfect. Our children were so happy and full of positive energy after the stay, which made the experience even more special for us.
Scored out of 10, guest rating 9.9
Exceptional - What previous guests thought, 19 reviews
Price from
US$261.80
1 night, 2 adults
Check availability

Amazing 6BR Villa @ Storey Lake Resort Near Disney

Kissimmee

Featuring air-conditioned accommodation with a private pool, Amazing 6BR Villa @ Storey Lake Resort Near Disney is located in Kissimmee.

Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 8 reviews
Price from
US$287.20
1 night, 2 adults
Check availability

Luxury 9BR Villa @ Storey Lake Resort Near Disney

Kissimmee

Featuring a private pool and garden views, Luxury 9BR Villa @ Storey Lake Resort Near Disney is located in Kissimmee.

J
JOSEPH
From
United Kingdom
The villa as ideally positioned to access many local attractions, including Disney and Universal. The villa was very well equipped and comfortable, ideal for relaxing after a day of exploring. The host was easily contactable and very helpful. We had a great vacation using this villa as our base.
Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 11 reviews
Price from
US$720
1 night, 2 adults
Check availability

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

West Kissimmee, Kissimmee

Set in Kissimmee in the Florida region and Disney's Animal Kingdom reachable within 10 km, Veteran Owned 3bdr/3 bath Townhouse w/WiFi 3mi to Disney - Winter/Spring Specials offers accommodation with...

H
HerdísJ
From
Iceland
We were very happy with our stay. The neighborhood is friendly and the house is great for a family vacation.
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 5 reviews
Price from
US$117.86
1 night, 2 adults
Check availability

Beautiful Orlando Apt with Nemo Bedroom, 15 min to Disney!

West Kissimmee, Kissimmee

Set in the West Kissimmee district of Kissimmee, Beautiful Orlando Apt with Nemo Bedroom, 15 min to Disney! offers accommodation with a private pool, free WiFi and a lift.

F
Felicity
From
United Kingdom
Great location for Disney and there’s a supermarket really close by. Lovely having swimming pool on site as well. The apartment was a great size, clean and well equipped.
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 13 reviews
Price from
US$110.20
1 night, 2 adults
Check availability

Cozy Retreat - Close to Disney & Golf

Kissimmee

Set in Kissimmee in the Florida region, Cozy Retreat - Close to Disney & Golf features a patio. Guests can benefit from a balcony and a picnic area.

D
Darren
From
United Kingdom
Denise was extremely polite and helpful with accommodating us. The apartment was immaculate very welcoming and will definitely be staying here every time that I'm in Orlando. The perfect place to stay. Thankyou.
Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 5 reviews
Price from
US$224.10
1 night, 2 adults
Check availability
All holiday rentals in Kissimmee

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

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Enjoy breakfast in Kissimmee and nearby

  • Scored out of 10, guest rating 8.3
    Very good - What previous guests thought, 65 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.

    From US$713.92 per night

  • Royal 1

    Kissimmee
    Breakfast options
    Scored out of 10, guest rating 4.6
    Disappointing - What previous guests thought, 5 reviews

    Situated in Kissimmee in the Florida region, Royal 1 has a patio. This property offers access to a terrace and free private parking.

    From US$217.55 per night
  • Scored out of 10, guest rating 8.7
    Fabulous - What previous guests thought, 10 reviews

    Located 7.3 km from Gatorland and 18 km from Florida Mall in the centre of Kissimmee, 3120-206DR STOREY LAKE, CONDO 2/2 GARDEN VIEW provides accommodation with free WiFi and free private parking.

  • Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 2 reviews

    Situated in the centre of Kissimmee, 7.3 km from Gatorland and 18 km from SeaWorld Orlando, Newly Remodeled 1 story - 5 Bed 5 Bath with Pvt Pool Spa And Game Room offers free WiFi and air conditioning...

  • Scored out of 10, guest rating 9.2
    Superb - What previous guests thought, 7 reviews

    Situated 7.3 km from Gatorland and 18 km from SeaWorld Orlando in the centre of Kissimmee, Grand Home Near Disney With Private Pool, Air Hockey Table And Waterpark & Resort Access At Encore Resorts...

  • Scored out of 10, guest rating 9.2
    Superb - What previous guests thought, 8 reviews

    Set 7.3 km from Gatorland and 18 km from SeaWorld Orlando in the centre of Kissimmee, Magnificent Home Near Disney With Theater Room, Pool Table, Waterpark & Resort Access At Encore Resort Reunion -...

  • Scored out of 10, guest rating 9.6
    Exceptional - What previous guests thought, 7 reviews

    Situated 7.3 km from Gatorland and 18 km from SeaWorld Orlando in the centre of Kissimmee, Elegant Home Near Disney With Private Pool And Waterpark & Resort Access At Encore Resorts Reunion - 391Fl...

  • Scored out of 10, guest rating 9.4
    Superb - What previous guests thought, 7 reviews

    Situated 7.3 km from Gatorland and 18 km from SeaWorld Orlando in the centre of Kissimmee, Modern Home Near Disney With Private Pool, Media Room And Waterpark & Resort Access At Encore Resorts Reunion...

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

  • Heritage Park Inn

    Kissimmee
    Free cancellation options available
    Scored out of 10, guest rating 5.9
    Passable - 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.

    From US$76.94 per night

  • 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.

    From US$1,768.88 per night

  • 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.

  • Scored out of 10, guest rating 8.6
    Fabulous - What previous guests thought, 41 reviews

    A recently renovated apartment in Kissimmee, Ultimate Vacation Villa Near Disney Townhouse offers children's playground, parking on-site and sports facilities.

  • Terra Verde Vacation Rentals

    Kissimmee
    Free cancellation options available
    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.

    From US$541.30 per night

  • 4200 Paragraph Drive

    Kissimmee
    Free cancellation options available

    Located in Kissimmee, 4200 Paragraph Drive provides a private pool. The property is around 12 km from Gatorland, 13 km from ESPN Wide World of Sports and 13 km from Disney's Boardwalk.

  • VILLA wPrivate Pool & Game Room near Disney

    Kissimmee
    Free cancellation options available
    Scored out of 10, guest rating 8.0
    Very good - What previous guests thought, 15 reviews

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

  • Scored out of 10, guest rating 8.2
    Very good - What previous guests thought, 11 reviews

    Located in Kissimmee, 11 km from Disney Springs and 12 km from Gatorland, Stunning 3BD Condo 14 Mins to Disney World, Gated provides air-conditioned accommodation with a balcony and free WiFi.

    From US$262.03 per night

Holiday Rentals with swimming pools in Kissimmee and nearby

  • Scored out of 10, guest rating 8.0
    Very good - What previous guests thought, 1 review

    Four Bedroom Villa in Coral Cay, a property with a fitness centre and a garden, is set in Kissimmee, 12 km from Disney Springs, 13 km from ESPN Wide World of Sports, as well as 13 km from Disney's...

    From US$340.50 per night
  • Scored out of 10, guest rating 7.0
    Good - What previous guests thought, 1 review

    Set in Kissimmee, 12 km from Disney Springs and 12 km from Gatorland, 4321 QS - Magical Haven Townhome w Pool offers air-conditioned accommodation with a terrace and free WiFi.

  • Scored out of 10, guest rating 4.0
    Disappointing - What previous guests thought, 1 review

    Set in Kissimmee, 4520 Target Blvd offers a private pool. The property is located 12 km from Disney Springs, 12 km from ESPN Wide World of Sports and 12 km from Disney's Boardwalk.

    From US$1,522.40 per night
  • Scored out of 10, guest rating 8.3
    Very good - What previous guests thought, 18 reviews

    Set in Kissimmee, 13 km from Disney Springs and 13 km from Disney's Hollywood Studios, Grand Holiday 3BR Getaway Condo near Disney Parks offers air conditioning.

    From US$299.08 per night
  • Scored out of 10, guest rating 9.2
    Superb - What previous guests thought, 5 reviews

    Boasting air-conditioned accommodation with a private pool, Beautiful Modern Home wPrivate Pool Near WDW is situated in Kissimmee.

    From US$944.49 per night

  • Located in Kissimmee, 4801 ML - Ideal Retreat Townhome Oasis with Pool provides accommodation with a private pool.

  • Scored out of 10, guest rating 6.0
    Pleasant - What previous guests thought, 1 review

    Boasting air-conditioned accommodation with a private pool, Gorgeous, Modern Home wPrivate Pool is set in Kissimmee.

  • Scored out of 10, guest rating 8.2
    Very good - What previous guests thought, 7 reviews

    Featuring air-conditioned accommodation with a private pool, 2911 Fable Street is located in Kissimmee.

Highly rated holiday rentals in Kissimmee and nearby

  • Scored out of 10, guest rating 9.5
    Exceptional - What previous guests thought, 39 reviews

    Situated in Kissimmee, 9.3 km from Gatorland, Lakeview Villas in Storey Lake Resort by Diamond Vacation Homes features rooms with air conditioning and free WiFi.

    From US$817.76 per night
  • Scored out of 10, guest rating 9.4
    Superb - What previous guests thought, 10 reviews

    Featuring a private pool and lake views, Beautiful Home wPrivate Pool & Spa, near WDW is located in Kissimmee.

    From US$1,348.90 per night
  • Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 28 reviews

    Located only 9.4 km from Gatorland in Kissimmee, 3B2B-Beautiful Lake View-Baby Friendly-FREE WATER PARK!

  • Scored out of 10, guest rating 9.1
    Superb - What previous guests thought, 19 reviews

    3131 Paradox Cir Unit 203 is situated in Kissimmee, 10 km from Disney Springs, 10 km from ESPN Wide World of Sports, as well as 11 km from Disney's Hollywood Studios.

  • Scored out of 10, guest rating 9.3
    Superb - What previous guests thought, 20 reviews

    Updated Condo, 5 mi to Disney, On-site Water Park is located in Kissimmee, 10 km from Disney Springs, 10 km from ESPN Wide World of Sports, and 11 km from Disney's Hollywood Studios.

  • Scored out of 10, guest rating 8.8
    Fabulous - What previous guests thought, 5 reviews

    Boasting air-conditioned accommodation with a private pool, 4813 Crusoe Street is situated in Kissimmee. Both free WiFi and parking on-site are accessible at the holiday home free of charge.

    From US$786.33 per night
  • Scored out of 10, guest rating 8.3
    Very good - What previous guests thought, 19 reviews

    Gorgeous Fully Furnished 2-Bedroom Luxury Villa is a recently renovated villa in Kissimmee, where guests can make the most of its garden and barbecue facilities.

    From US$308.01 per night
  • Scored out of 10, guest rating 8.0
    Very good - What previous guests thought, 6 reviews

    Situated 7.3 km from Gatorland and 18 km from SeaWorld Orlando in the centre of Kissimmee, Charming Home With Private Pool Near Disney With Water Park & Resort Access At Encore Resort - 7489Mr...

FAQ about holiday rentals in Kissimmee

Holiday rentals that guests love in Kissimmee

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  • 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, 527 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 9.1
    Superb - What previous guests thought, 15 reviews
    Great location and a very nice holiday home!
    Guest review by
    Jay
    Family with young children

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