Kissimmee Holiday Homes
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Orlando which includes a pond, a bridge and golf

Holiday Homes in Kissimmee

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Our top choices for Kissimmee holiday homes

Holiday Home in Kissimmee

Super Cool- Sleeps 17 Newly Built Near Parks

2.0 star property

The price is NZ$657

NZ$657

includes taxes & fees

25 Jan - 26 Jan 2026

Super Cool- Sleeps 17 Newly Built Near Parks

Condo, 4 Bedrooms (2 King, 1 Queen, & 2 Trundle Bed) | Balcony view

Holiday Home in Kissimmee

The Berkley, Orlando

4.0 star property

9.6 out of 10, Exceptional, (2019)

9.6/10

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. "

Sarha

The price is NZ$313

NZ$313

includes taxes & fees

4 Jan - 5 Jan 2026

The Berkley, Orlando

Indoor pool, pool umbrellas, pool loungers

House, Multiple Beds, Private Pool | Private kitchen

House, Multiple Beds, Private Pool | Living area

Holiday Home in Lindfields

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

5.0 star property

The price is NZ$660

NZ$660

includes taxes & fees

7 Jan - 8 Jan 2026

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

Design House, 6 Bedrooms, Private Pool | Private kitchen

Design House, 6 Bedrooms, Private Pool | Living area

Holiday Home in Kissimmee

FL- 1844 GOBI DR

3.0 star property

The price is NZ$697

NZ$697

includes taxes & fees

7 Jan - 8 Jan 2026

FL- 1844 GOBI DR

Holiday Home in Crescent Lakes

South Facing W/ Private Pool & Spa

4.0 star property

The price is NZ$1,094

NZ$1,094

includes taxes & fees

7 Jan - 8 Jan 2026

South Facing W/ Private Pool & Spa

Deluxe Condo, Garden View | Private kitchen

Holiday Home in Reunion

Heaven On Earth Private Home

4.0 star property

The price is NZ$682

NZ$682

includes taxes & fees

6 Jan - 7 Jan 2026

Heaven On Earth Private Home

Holiday Home in Kissimmee

4br Townhome Near Disney W/ Resort Amenities 4 Bedroom Townhouse

3.5 star property

The price is NZ$944

NZ$944

includes taxes & fees

2 Jan - 3 Jan 2026

4br Townhome Near Disney W/ Resort Amenities 4 Bedroom Townhouse

Comfort House, Multiple Bedrooms, Private Pool, Lakeside | Living area

Comfort House, Multiple Bedrooms, Private Pool, Lakeside | Private kitchen

Holiday Home in Kissimmee

FL- 1904 Nice Ct

3.0 star property

The price is NZ$808

NZ$808

includes taxes & fees

11 Jan - 12 Jan 2026

FL- 1904 Nice Ct

Deluxe Townhome, 4 Bedrooms, Private Pool | Living area

Deluxe Townhome, 5 Bedrooms, Private Pool | Private kitchen

Deluxe Townhome, 5 Bedrooms, Private Pool

Holiday Home in Kissimmee

Formosa Valley Resort by UNE Homes

4.0 star property

9.4 out of 10, Exceptional, (196)

9.4/10

Exceptional

(196)

"Loved our stay here. Would highly recommend "

Walter

The price is NZ$870

NZ$870

includes taxes & fees

5 Jan - 6 Jan 2026

Formosa Valley Resort by UNE Homes

Holiday Home in Kissimmee

Super Liked - 4BD 3 5b 6 Miles To Disney Springs

2.0 star property

The price is NZ$807

NZ$807

includes taxes & fees

16 Jan - 17 Jan 2026

Super Liked - 4BD 3 5b 6 Miles To Disney Springs

House, 2 Bedrooms, Lake View, Lakeside | Private kitchen

House, 2 Bedrooms, Lake View, Lakeside | Living room

House, 2 Bedrooms, Lake View, Lakeside | Dining room

Holiday Home in Historic Downtown Kissimmee

Super Boho - At Lake Toho's Water

2.0 star property

The price is NZ$427

NZ$427

includes taxes & fees

28 Jan - 29 Jan 2026

Super Boho - At Lake Toho's Water

Holiday Home in Kissimmee

Cozy 2-bedroom townhome in lovely gated community in Kissimmee- Close to Disney.

2.5 star property

10.0 out of 10, Exceptional, (1)

10/10

Exceptional

(1)

"We stayed for a month and very much enjoyed our stay. The home had just about everything we needed for a comfortable stay. The host and property manager were very attentive which made for a pleasant stay!"

Ralph P.

The price is NZ$498

NZ$498

includes taxes & fees

7 Jan - 8 Jan 2026

Cozy 2-bedroom townhome in lovely gated community in Kissimmee- Close to Disney.

TV, DVD player, ping pong, music library

Holiday Home in Kissimmee

Superb Townhouse Newly Renovated 1.5 miles to Disney

9.8 out of 10, Exceptional, (113)

9.8/10

Exceptional

(113)

"Great place to stay. Less than a15 minute drive to Disneyworld.Communication with owner was excellent. "

Kim M.

The price is NZ$361

NZ$361

includes taxes & fees

12 Jan - 13 Jan 2026

Superb Townhouse Newly Renovated 1.5 miles to Disney

Holiday Home in Kissimmee

5Br Kissimmee Home W/ Pool & Game Room Fun

4.0 star property

5Br Kissimmee Home W/ Pool & Game Room Fun

Holiday Home in Bellavida

Florida Breeze

4.0 star property

The price is NZ$1,190

NZ$1,190

includes taxes & fees

12 Jan - 13 Jan 2026

Florida Breeze

Holiday Home in Crescent Lakes

Aster Cove

4.0 star property

The price is NZ$988

NZ$988

includes taxes & fees

17 Jan - 18 Jan 2026

Aster Cove

3 bedrooms, laptop workspace, iron/ironing board, free WiFi

Holiday Home in Windsor Hills

Windsor Hills Getaway: 3br, Pool, Near Disney 3 Bedroom Townhouse

3.0 star property

The price is NZ$947

NZ$947

includes taxes & fees

2 Jan - 3 Jan 2026

Windsor Hills Getaway: 3br, Pool, Near Disney 3 Bedroom Townhouse

Holiday Home in Kissimmee

Relaxing Retreat with Pool and Movie Theater

2.0 star property

10.0 out of 10, Exceptional, (2)

10/10

Exceptional

(2)

"Our family was very happy with this property. It exceeded our expectations and was surprisingly close to Disney. We would stay again and our family already has friends asking about the property."

Joey

The price is NZ$784

NZ$784

includes taxes & fees

13 Jan - 14 Jan 2026

Relaxing Retreat with Pool and Movie Theater

Holiday Home in Reunion

Family fun or a company retreat - 8BR Luxury Home with Infinity Pool!

9.8 out of 10, Exceptional, (49)

9.8/10

Exceptional

(49)

"Great place, would definitely use again!"

Tony D.

The price is NZ$8,679

NZ$8,679

includes taxes & fees

11 Jan - 12 Jan 2026

Family fun or a company retreat - 8BR Luxury Home with Infinity Pool!

Holiday Home in Kissimmee

4BD/3BA Modern upgraded Townhome-private pool at Storey Lake

9.8 out of 10, Exceptional, (16)

9.8/10

Exceptional

(16)

"We really enjoyed our stay at this property. Having a private pool was an added bonus."

Arlene

The price is NZ$671

NZ$671

includes taxes & fees

7 Jan - 8 Jan 2026

4BD/3BA Modern upgraded Townhome-private pool at Storey Lake

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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