We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Homes in Kissimmee

List your property
Owner log in
Check-in
— / — / —
Check-out
— / — / —
Guests
0+ rooms, 2+ guests
Distance from
1 km
Price per night
$0
$1,000+
Suitability
Show more
Bathrooms
Any
Amenities
Show more
Property type
Show more
Distinctive Features
Show more
Neighbourhood
Show more
4050 rentals in Kissimmee.
Sort by:
Tripadvisor Sort
Belle's Cove, Family-Friendly Villa with Gameroom and Hot Tub, holiday rental in Kissimmee

Belle's Cove, Family-Friendly Villa with Gameroom and Hot Tub

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Family-Friendly Large Villa with a Pool, Jacuzzi,, holiday rental in Kissimmee

Family-Friendly Large Villa with a Pool, Jacuzzi,

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Disney 5 Star Vacations / The Osprey Villa, holiday rental in Kissimmee

Disney 5 Star Vacations / The Osprey Villa

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
BRUSONS RETREAT, 5 Bed Villa, South Facing Pool & Terrace., holiday rental in Kissimmee

BRUSONS RETREAT, 5 Bed Villa, South Facing Pool & Terrace.

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
villanirvana, holiday rental in Kissimmee

villanirvana

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Oakhill Disney Villa, holiday rental in Kissimmee

Oakhill Disney Villa

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Plenty of 2021 openings, holiday rental in Kissimmee

Plenty of 2021 openings

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Disney Family Villa pool/spa/games room, 5 bds 4 bathrooms, 15 Mins to Disney, holiday rental in Kissimmee

Disney Family Villa pool/spa/games room, 5 bds 4 bathrooms, 15 Mins to Disney

5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Superb 4 Bedroom Home, just 3 minutes from Disney, holiday rental in Kissimmee

Superb 4 Bedroom Home, just 3 minutes from Disney

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Seasons Villa,5 Bedrooms, Pool with Spa, Gameroom Sleeps 10, holiday rental in Kissimmee

Seasons Villa,5 Bedrooms, Pool with Spa, Gameroom Sleeps 10

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Save time - get the best Kissimmee rentals sent straight to your email!
Disney Vacation Villa with Lake View, holiday rental in Kissimmee

Disney Vacation Villa with Lake View

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
New 9br/6ba pool villa from $280/nt,Close to Disney, holiday rental in Kissimmee

New 9br/6ba pool villa from $280/nt,Close to Disney

9 bedrooms
6 bathrooms
Sleeps 20
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
New 9Br/6Ba luxurious Pool House from $300/nt, Close To Disney, holiday rental in Kissimmee

New 9Br/6Ba luxurious Pool House from $300/nt, Close To Disney

9 bedrooms
6 bathrooms
Sleeps 18
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
SUPER Close To Disney, Gameroom, Private Backyard, Lake, Free WiFi, Pool, Spa, holiday rental in Kissimmee

SUPER Close To Disney, Gameroom, Private Backyard, Lake, Free WiFi, Pool, Spa

7 bedrooms
5 bathrooms
Sleeps 17
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Sonshines Florida Villa, Peaceful Getaway  and Pool, holiday rental in Kissimmee

Sonshines Florida Villa, Peaceful Getaway and Pool

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
New 8br/6ba pool villa from $260/nt , Close to Disney, holiday rental in Kissimmee

New 8br/6ba pool villa from $260/nt , Close to Disney

8 bedrooms
6 bathrooms
Sleeps 18
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Roughtallys Villa, holiday rental in Kissimmee

Roughtallys Villa

7 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Located in Emerald Island Resort  Beautiful 7 Bed 4.5 Bath Villa Close 2  Disney, holiday rental in Kissimmee

Located in Emerald Island Resort Beautiful 7 Bed 4.5 Bath Villa Close 2 Disney

7 bedrooms
7 bathrooms
Sleeps 16
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
New 6 Bedrooms, Special lighting ,4 miles - Disneys, CHECK THIS OUT!!, holiday rental in Kissimmee

New 6 Bedrooms, Special lighting ,4 miles - Disneys, CHECK THIS OUT!!

6 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Bella Vida New Phase 6 bedroom Modern Home, holiday rental in Kissimmee

Bella Vida New Phase 6 bedroom Modern Home

6 bedrooms
7 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Luxury 6 bedroom villa ✦ 3 Miles or 5 min to Disney ✦ South pool ✦Movie Room, holiday rental in Kissimmee

Luxury 6 bedroom villa ✦ 3 Miles or 5 min to Disney ✦ South pool ✦Movie Room

6 bedrooms
6 bathrooms
Sleeps 14
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Star Lake Villa, close to Disney with pool, holiday rental in Kissimmee

Star Lake Villa, close to Disney with pool

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Hideaway Villa,Terra Verde Resort - Xbox,PS2,Games Room, Pool, holiday rental in Kissimmee

Hideaway Villa,Terra Verde Resort - Xbox,PS2,Games Room, Pool

5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Luxury 4 Bedroom Villa with Private Pool, 2 Miles from Disney, holiday rental in Kissimmee

Luxury 4 Bedroom Villa with Private Pool, 2 Miles from Disney

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Family Resort - 14BR Mansion - Private Pool and BBQ!, holiday rental in Kissimmee

Family Resort - 14BR Mansion - Private Pool and BBQ!

14 bedrooms
11 bathrooms
Sleeps 31
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
6 Bdr Vacation Home in Beautiful Resort, holiday rental in Kissimmee

6 Bdr Vacation Home in Beautiful Resort

6 bedrooms
7 bathrooms
Sleeps 17
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Luxury Lakeside House with private solar heated pool & spa, holiday rental in Kissimmee

Luxury Lakeside House with private solar heated pool & spa

5 bedrooms
4 bathrooms
Sleeps 13
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
The Retreat - Explore Disney & Florida in style, holiday rental in Kissimmee

The Retreat - Explore Disney & Florida in style

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
6-bedroom house w/ private pool 10 min from Disney, holiday rental in Kissimmee

6-bedroom house w/ private pool 10 min from Disney

6 bedrooms
6 bathrooms
Sleeps 14
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Wow! 7 Bed Lakeside Villa Pool/Spa Nr Disney Fast Wifi, Gamerm. Guarded Resort!, holiday rental in Kissimmee

Wow! 7 Bed Lakeside Villa Pool/Spa Nr Disney Fast Wifi, Gamerm. Guarded Resort!

7 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
The Seasons Villa, lake view and 4 master bedrooms, holiday rental in Kissimmee

The Seasons Villa, lake view and 4 master bedrooms

6 bedrooms
6 bathrooms
Sleeps 13
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Family Friendly Four Bedroom w/ Pool 4896, holiday rental in Kissimmee

Family Friendly Four Bedroom w/ Pool 4896

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Tranquil Holiday Home-Games Room, Private Pool, WiFi, Disney/Orlando, holiday rental in Kissimmee

Tranquil Holiday Home-Games Room, Private Pool, WiFi, Disney/Orlando

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Pat and Ron's Holiday Home, Relaxing Retreat, holiday rental in Kissimmee

Pat and Ron's Holiday Home, Relaxing Retreat

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Executive 4 Bedroom / 3 Bathroom Lake View Home in Gated Resort Community, holiday rental in Kissimmee

Executive 4 Bedroom / 3 Bathroom Lake View Home in Gated Resort Community

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
SPECIAL OFFER! - AMAZING NEW HOUSE with Lake View in Orlando, 5 MIN DISNEY, holiday rental in Kissimmee

SPECIAL OFFER! - AMAZING NEW HOUSE with Lake View in Orlando, 5 MIN DISNEY

6 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Amazing Disney Condo, Pool & Hot tub Onsite, holiday rental in Kissimmee

Amazing Disney Condo, Pool & Hot tub Onsite

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Disney Orlando House w/Private Pool, holiday rental in Kissimmee

Disney Orlando House w/Private Pool

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Completely remodelled 2020. Luxury 4 Bed 3 Bath Villa with own pool. Near Disney, holiday rental in Kissimmee

Completely remodelled 2020. Luxury 4 Bed 3 Bath Villa with own pool. Near Disney

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Florida Villa Dreams Come True, holiday rental in Kissimmee

Florida Villa Dreams Come True

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Alberto Circle, Fun Vacation House with Pool, holiday rental in Kissimmee

Alberto Circle, Fun Vacation House with Pool

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Spacious 4-bed lakeside pool villa near Disney, holiday rental in Kissimmee

Spacious 4-bed lakeside pool villa near Disney

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
M8631 Pondview Luxury 8 Bedroom Villa, New Remodel, holiday rental in Kissimmee

M8631 Pondview Luxury 8 Bedroom Villa, New Remodel

8 bedrooms
5 bathrooms
Sleeps 20
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
4BR Private Pool/Spa, WiFi, ROKU TVs, BBQ-Pets Considered-Clean and Spacious, holiday rental in Kissimmee

4BR Private Pool/Spa, WiFi, ROKU TVs, BBQ-Pets Considered-Clean and Spacious

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Villa di Lusso, holiday rental in Kissimmee

Villa di Lusso

6 bedrooms
10 bathrooms
Sleeps 14
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Only 5 miles to Disney, Dog Friendly,  New Car Game, All Desinfected, holiday rental in Kissimmee

Only 5 miles to Disney, Dog Friendly, New Car Game, All Desinfected

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Family Golf Resort 'Villa Bonita' Southern Dunes, holiday rental in Kissimmee

Family Golf Resort 'Villa Bonita' Southern Dunes

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
4 br, Very close to Disney. Luxury furnished, Gated Resort,  Private Pool. WIFI, holiday rental in Kissimmee

4 br, Very close to Disney. Luxury furnished, Gated Resort, Private Pool. WIFI

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Cottage near Disney at the New Margaritaville Resort Orlando, holiday rental in Kissimmee

Cottage near Disney at the New Margaritaville Resort Orlando

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
CW2- 1 mile from Disney, nice town home in Gated Community, holiday rental in Kissimmee

CW2- 1 mile from Disney, nice town home in Gated Community

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Previous