The 10 best holiday homes in Kissimmee, USA | Booking.com
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Holiday Homes in Kissimmee

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The best holiday homes in Kissimmee

Check out our pick of great holiday homes in Kissimmee

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Charming Family Friendly Home

Kissimmee

Featuring a hot tub, Charming Family Friendly Home is located in Kissimmee. This property offers access to a balcony, darts, free private parking and free WiFi.

Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 9 reviews
Price from
US$119.92
1 night, 2 adults
Check availability

Disney-Themed Townhome in ChampionsGate Resort 15 min from Disney World with 7 Pools, Gym, Golf, Lazy River, Water Park, Arcades, Theatre, and More!

Kissimmee

Featuring air-conditioned accommodation with a patio, Disney-Themed Townhome in ChampionsGate Resort 15 min from Disney World with 7 Pools, Gym, Golf, Lazy River, Water Park, Arcades, Theatre, and...

Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 13 reviews
Price from
US$158.40
1 night, 2 adults
Check availability

Wonderful Disney-Themed Home in ChampionsGate Resort 15 min from Disney World with 7 pools, Club houses, Water Park, Gym, Arcades, Lazy River, Golf, and More!

Kissimmee

Featuring air-conditioned accommodation with a patio, Wonderful Disney-Themed Home in ChampionsGate Resort 15 min from Disney World with 7 pools, Club houses, Water Park, Gym, Arcades, Lazy River,...

J
Joanna
From
United Kingdom
The property was modern, clean and had everything we needed as a family. We all loved the swimming pool complex
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 7 reviews
Price from
US$158.40
1 night, 2 adults
Check availability

Magical Home with private pool and close to parks

West Kissimmee, Kissimmee

Set in the Windsor Palms district of Kissimmee, Magical Home with private pool and close to parks offers accommodation with a private pool and a 24-hour front desk.

Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 7 reviews
Price from
US$297.50
1 night, 2 adults
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Trendy Retreat - Great Location - Fully Loaded

West Kissimmee, Kissimmee

Situated in Kissimmee in the Florida region, Trendy Retreat - Great Location - Fully Loaded features a patio. This property offers a private pool and free private parking.

m
mitchell
From
Netherlands
Very clean and spacious we had a perfect stay
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 21 reviews
Price from
US$162
1 night, 2 adults
Check availability

Disney Villa Magical Retreat Private Pool, LakeView & Game Room

West Kissimmee, Kissimmee

Featuring air-conditioned accommodation with a private pool, Disney Villa Magical Retreat Private Pool, LakeView & Game Room is set in Kissimmee.

J
Jansen
From
United Kingdom
Great pool, nice and quiet with good views.
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 7 reviews
Price from
US$234.90
1 night, 2 adults
Check availability

This Happy Place

West Kissimmee, Kissimmee

Featuring air-conditioned accommodation with a terrace, This Happy Place is set in Kissimmee. Including a private pool and a private beach area, this holiday home also features a restaurant.

K
Karen
From
United Kingdom
The property had all the amenities, very spacious and comfortable beds. Good location to all the parks.
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 5 reviews
Price from
US$137.70
1 night, 2 adults
Check availability

2440 One of a Kind 5b Villa-pool&game

West Kissimmee, Kissimmee

2440 One of a Kind 5b Villa-pool&game is located in the West Kissimmee district of Kissimmee, 14 km from Disney's Blizzard Beach Water Park, 17 km from Walt Disney World and 17 km from ESPN Wide World...

T
Terhi
From
Finland
Loved our stay in this beautiful house. 😊
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 8 reviews
Price from
US$352
1 night, 2 adults
Check availability

Family 4BR w Private Pool near Disney Parks

Kissimmee

Featuring air-conditioned accommodation with a private pool, Family 4BR w Private Pool near Disney Parks is set in Kissimmee.

ACK
From
Germany
We had a perfect stay, could not be better. Hosts Michelle and Allan are really awesome. The house was well equipped and very clean. We loved the splash pool, the gated community and the main pool area. We are looking forward to come back next year ;-))
Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 8 reviews
Price from
US$202
1 night, 2 adults
Check availability

Getaway Comfy House w Pool

Kissimmee

Situated in Kissimmee, Getaway Comfy House w Pool features accommodation with private pool, free WiFi and free private parking for guests who drive.

A
Ashli
From
Jamaica
It was hard to find things we didn't like about this property. The space was beautiful, clean and comfortable. They thought of everything, from dish washer pods to first aid kits and so much more. The host is also very responsive and polite. Just book it, you won't regret it!! 😁
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 6 reviews
Price from
US$232.20
1 night, 2 adults
Check availability
All holiday homes in Kissimmee

Looking for a holiday home?

Great for families or large parties, holiday homes are privately owned accommodation, available for long or short-term rental. These homes are furnished and equipped with kitchen facilities for self-catering, although breakfast may be offered as an add-on. These properties have their own independent front door, which makes them different to apartments.

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

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Save money on holiday homes in Kissimmee and nearby – budget options available

  • Set in Kissimmee, 12 km from Disney Springs and 12 km from Gatorland, 2604 - Luxury 4-BR Villa with Private Pool Retreat offers a spa and wellness centre and air conditioning.

  • Located in Kissimmee, 14 km from ESPN Wide World of Sports and 14 km from Disney Springs, SUPER YES - MANY AMENITIEs RELAX GYM COURTs offers air conditioning.

    From US$314.17 per night

  • 4337 QS - Charming Hideaway

    Kissimmee
    Budget options available

    Featuring air-conditioned accommodation with a rooftop pool, pool view and a balcony, 4337 QS - Charming Hideaway is located in Kissimmee.

  • 4562 YR Amazing

    Kissimmee
    Budget options available

    Set in Kissimmee, 11 km from Disney Springs and 12 km from Gatorland, 4562 YR Amazing offers a spa and wellness centre and air conditioning.

  • Scored out of 10, guest rating 7.0
    Good - What previous guests thought, 5 reviews

    Set in Kissimmee, 11 km from Disney Springs and 11 km from Gatorland, Relaxing 3BR Haven for 8 at Seven Dwarfs SD2610 offers air conditioning.

  • Set in Kissimmee, 9.3 km from Gatorland and 10 km from Disney Springs, Opulent 5 BR Villa Private Pool - 12 Guests - 3085 TS offers an outdoor swimming pool and air conditioning.

  • Scored out of 10, guest rating 6.0
    Pleasant - What previous guests thought, 7 reviews

    Located in Kissimmee, Magic Kingdom Getaway - DGM Resort provides accommodation with private pool, free WiFi and free private parking for guests who drive.

    From US$249.71 per night

  • Villa Hakuna Matata- Lucaya Village Resort is located in the Downtown Kissimmee district of Kissimmee, 18 km from SeaWorld Orlando, 18 km from Florida Mall and 19 km from Seaworld'S Discovery Cove.

Enjoy breakfast in Kissimmee and nearby

Great access to the city centre. Check these holiday homes in Kissimmee and nearby

  • Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 1 review

    Located in Kissimmee, 19 km from SeaWorld Orlando and 19 km from Seaworld'S Discovery Cove, SUPER BOHO - LAKE TOHO FISHiNG CIVIC CeNTER provides accommodation with amenities such as free WiFi and a TV...

    From US$266.98 per night
  • Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 1 review

    Located in the centre of Kissimmee, just 7.6 km from Gatorland and 19 km from SeaWorld Orlando, SUPER BOHO - LAKE TOHO FISHiNG WATER FRONTs provides accommodation with lake views and free WiFi.

    From US$278.96 per night

  • Located in the centre of Kissimmee, 7.6 km from Gatorland and 19 km from SeaWorld Orlando, SUPER BOHO - Lake Toho Timeless Charm offers free WiFi and air conditioning.

    From US$301.36 per night

  • Located in the centre of Kissimmee, 7.6 km from Gatorland and 19 km from SeaWorld Orlando, SUPER BOHO - At Lake Toho Fishing VINTaGE VIBEs offers free WiFi and air conditioning.

    From US$291.78 per night

  • Set in Kissimmee, 16 km from SeaWorld Orlando and 16 km from Seaworld'S Discovery Cove, SUPER FANCY- 15BDR 17BAs HUGE 7 000SQFT HOME offers air conditioning.

  • 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

  • Boasting air-conditioned accommodation with a private pool, SUPER SIZE - 11BDr SPACiOUS HOME w POOL & HOT TUB is situated in Kissimmee.

    From US$734.23 per night

  • 2605 Yountville Ave is located in Kissimmee, 15 km from SeaWorld Orlando, 16 km from Seaworld'S Discovery Cove, and 16 km from Disney Springs.

    From US$1,099.56 per night

FAQ about holiday homes in Kissimmee

Holiday homes that guests love in Kissimmee

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  • 4 Bedroom 3 Bathroom Villas At Seven Dwarfs 10-102

    Holiday Home in Kissimmee
    Scored out of 10, guest rating 9.5
    Exceptional - What previous guests thought, 4 reviews
    very clean everything I recommended
    Guest review by
    Florenta
    Group

  • Villas at Seven Dwarfs - Close to Disney

    Holiday Home in Kissimmee
    Scored out of 10, guest rating 7.9
    Good - What previous guests thought, 525 reviews
    The site was very clean, with many facilities.
    Guest review by
    Cristina
    People with friends

  • South Facing Pool, Close to Attractions, Remodeled

    Holiday Home in Kissimmee
    Scored out of 10, guest rating 8.0
    Very good - What previous guests thought, 3 reviews
    Very clean upon arrival Big spacious rooms Modern facilities
    Guest review by
    Julie
    Family with young children

  • Five Bedrooms TownHome with Pool 4849

    Holiday Home in Kissimmee
    Scored out of 10, guest rating 9.3
    Superb - What previous guests thought, 25 reviews
    The Hideaway Club which has a lazy river, pool and hottub was wonderful. On the nice days we got some sun and enjoyed the pools. On a few cool evenings we still walked over and hit the hot tub. The townhouse itself was spacious and had everything we needed. Wonder vacation Homes was very responsive to questions and resolving the one issue we had (1 of the toilets broke and they sent a handyman over who fixed it the next day), easy to reach them wth a question by text.
    Guest review by
    Lori
    Family with young children