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Holiday Rentals in Kissimmee

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6539 rentals in Kissimmee.
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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, holiday rental in Kissimmee
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

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Sonshines Florida Villa, Peaceful Getaway  and Pool, holiday rental in Kissimmee
Sonshines Florida Villa, Peaceful Getaway  and Pool, holiday rental in Kissimmee
Sonshines Florida Villa, Peaceful Getaway  and Pool, holiday rental in Kissimmee

Sonshines Florida Villa, Peaceful Getaway and Pool

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Luxurious 5 Bedroom / 3 Bathroom Villa at Lake Berkley - Southern Exposure!, holiday rental in Kissimmee
Luxurious 5 Bedroom / 3 Bathroom Villa at Lake Berkley - Southern Exposure!, holiday rental in Kissimmee
Luxurious 5 Bedroom / 3 Bathroom Villa at Lake Berkley - Southern Exposure!, holiday rental in Kissimmee

Luxurious 5 Bedroom / 3 Bathroom Villa at Lake Berkley - Southern Exposure!

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Bella Vida New Phase 6 bedroom Modern Home, holiday rental in Kissimmee
Bella Vida New Phase 6 bedroom Modern Home, holiday rental in Kissimmee
Bella Vida New Phase 6 bedroom Modern Home, holiday rental in Kissimmee

Bella Vida New Phase 6 bedroom Modern Home

Holiday Rental House
6 bedrooms
7 bathrooms
Sleeps 12
Match: Sleeps
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Luxury Lakeside House with private solar heated pool & spa, holiday rental in Kissimmee
Luxury Lakeside House with private solar heated pool & spa, holiday rental in Kissimmee
Luxury Lakeside House with private solar heated pool & spa, holiday rental in Kissimmee

Luxury Lakeside House with private solar heated pool & spa

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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*CLEAN - Afforable Townhome - 5 Miles from Disney*, holiday rental in Kissimmee
*CLEAN - Afforable Townhome - 5 Miles from Disney*, holiday rental in Kissimmee
*CLEAN - Afforable Townhome - 5 Miles from Disney*, holiday rental in Kissimmee

*CLEAN - Afforable Townhome - 5 Miles from Disney*

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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5 Miles from Disney, Amazing Rental Home in Kissimmee  , holiday rental in Kissimmee
5 Miles from Disney, Amazing Rental Home in Kissimmee  , holiday rental in Kissimmee
5 Miles from Disney, Amazing Rental Home in Kissimmee  , holiday rental in Kissimmee

5 Miles from Disney, Amazing Rental Home in Kissimmee

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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villanirvana, holiday rental in Kissimmee
villanirvana, holiday rental in Kissimmee
villanirvana, holiday rental in Kissimmee

villanirvana

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Spacious 4-bed lakeside pool villa near Disney, holiday rental in Kissimmee
Spacious 4-bed lakeside pool villa near Disney, holiday rental in Kissimmee
Spacious 4-bed lakeside pool villa near Disney, holiday rental in Kissimmee

Spacious 4-bed lakeside pool villa near Disney

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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9 Br/6 Ba luxurious Pool House from $380/nt, Close To Disney, holiday rental in Kissimmee
9 Br/6 Ba luxurious Pool House from $380/nt, Close To Disney, holiday rental in Kissimmee
9 Br/6 Ba luxurious Pool House from $380/nt, Close To Disney, holiday rental in Kissimmee

9 Br/6 Ba luxurious Pool House from $380/nt, Close To Disney

Holiday Rental House
9 bedrooms
6 bathrooms
Sleeps 18
Match: Sleeps
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Private Villa with Security Gate, Sunset Lakes in Kissimmee, holiday rental in Kissimmee
Private Villa with Security Gate, Sunset Lakes in Kissimmee, holiday rental in Kissimmee
Private Villa with Security Gate, Sunset Lakes in Kissimmee, holiday rental in Kissimmee

Private Villa with Security Gate, Sunset Lakes in Kissimmee

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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A HOLIDAY HOME IN BEAUTIFUL LAKE MARION RESORT., holiday rental in Kissimmee
A HOLIDAY HOME IN BEAUTIFUL LAKE MARION RESORT., holiday rental in Kissimmee
A HOLIDAY HOME IN BEAUTIFUL LAKE MARION RESORT., holiday rental in Kissimmee

A HOLIDAY HOME IN BEAUTIFUL LAKE MARION RESORT.

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Lake Berkley Holiday Villa with FREE pool heating., holiday rental in Kissimmee
Lake Berkley Holiday Villa with FREE pool heating., holiday rental in Kissimmee
Lake Berkley Holiday Villa with FREE pool heating., holiday rental in Kissimmee

Lake Berkley Holiday Villa with FREE pool heating.

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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The Charming Mickey's Tree House,, holiday rental in Kissimmee
The Charming Mickey's Tree House,, holiday rental in Kissimmee
The Charming Mickey's Tree House,, holiday rental in Kissimmee

The Charming Mickey's Tree House,

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Debbie's Florida Retreat a Luxury Vacation Home, holiday rental in Kissimmee
Debbie's Florida Retreat a Luxury Vacation Home, holiday rental in Kissimmee
Debbie's Florida Retreat a Luxury Vacation Home, holiday rental in Kissimmee

Debbie's Florida Retreat a Luxury Vacation Home

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Lakeside Villa With Pool; WiFi, holiday rental in Kissimmee
Beautiful Lakeside Villa With Pool; WiFi, holiday rental in Kissimmee
Beautiful Lakeside Villa With Pool; WiFi, holiday rental in Kissimmee

Beautiful Lakeside Villa With Pool; WiFi

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Magical Memories, Pet-Friendly Home with WiFi, holiday rental in Kissimmee
Magical Memories, Pet-Friendly Home with WiFi, holiday rental in Kissimmee
Magical Memories, Pet-Friendly Home with WiFi, holiday rental in Kissimmee

Magical Memories, Pet-Friendly Home with WiFi

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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BRUSONS RETREAT, 5 Bed Villa, South Facing Pool & Terrace., holiday rental in Kissimmee
BRUSONS RETREAT, 5 Bed Villa, South Facing Pool & Terrace., holiday rental in Kissimmee
BRUSONS RETREAT, 5 Bed Villa, South Facing Pool & Terrace., holiday rental in Kissimmee

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

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Disney Vacation Villa with Lake View, holiday rental in Kissimmee
Disney Vacation Villa with Lake View, holiday rental in Kissimmee
Disney Vacation Villa with Lake View, holiday rental in Kissimmee

Disney Vacation Villa with Lake View

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Palm Tree Villa Florida, 5 Star Review Rating with Pool Lift & Wheel in Shower., holiday rental in Kissimmee
Palm Tree Villa Florida, 5 Star Review Rating with Pool Lift & Wheel in Shower., holiday rental in Kissimmee
Palm Tree Villa Florida, 5 Star Review Rating with Pool Lift & Wheel in Shower., holiday rental in Kissimmee

Palm Tree Villa Florida, 5 Star Review Rating with Pool Lift & Wheel in Shower.

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Amazing house with private pool near Disney, holiday rental in Kissimmee
Amazing house with private pool near Disney, holiday rental in Kissimmee
Amazing house with private pool near Disney, holiday rental in Kissimmee

Amazing house with private pool near Disney

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Secret Key Villa - villa rental in Kissimmee, Florida, holiday rental in Kissimmee
Secret Key Villa - villa rental in Kissimmee, Florida, holiday rental in Kissimmee
Secret Key Villa - villa rental in Kissimmee, Florida, holiday rental in Kissimmee

Secret Key Villa - villa rental in Kissimmee, Florida

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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The Retreat - Explore Disney & Florida in style, holiday rental in Kissimmee
The Retreat - Explore Disney & Florida in style, holiday rental in Kissimmee
The Retreat - Explore Disney & Florida in style, holiday rental in Kissimmee

The Retreat - Explore Disney & Florida in style

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Roomy and Comfy 3BR Villa Close to Disney Parks, holiday rental in Kissimmee
Roomy and Comfy 3BR Villa Close to Disney Parks, holiday rental in Kissimmee
Roomy and Comfy 3BR Villa Close to Disney Parks, holiday rental in Kissimmee

Roomy and Comfy 3BR Villa Close to Disney Parks

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lovely Affordable Ground Floor Condo at Cane Island Resort, holiday rental in Kissimmee
Lovely Affordable Ground Floor Condo at Cane Island Resort, holiday rental in Kissimmee
Lovely Affordable Ground Floor Condo at Cane Island Resort, holiday rental in Kissimmee

Lovely Affordable Ground Floor Condo at Cane Island Resort

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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4BR/3BA 1650 sqft Condo from $100/nt, 2 Miles to Disney, holiday rental in Kissimmee
4BR/3BA 1650 sqft Condo from $100/nt, 2 Miles to Disney, holiday rental in Kissimmee
4BR/3BA 1650 sqft Condo from $100/nt, 2 Miles to Disney, holiday rental in Kissimmee

4BR/3BA 1650 sqft Condo from $100/nt, 2 Miles to Disney

Condo/Apartment
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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1 bed/1 sofa With Kitchen, holiday rental in Kissimmee
1 bed/1 sofa With Kitchen, holiday rental in Kissimmee
1 bed/1 sofa With Kitchen, holiday rental in Kissimmee

1 bed/1 sofa With Kitchen

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Renovated Venetian Bay Townhome in Quiet Location, holiday rental in Kissimmee
Renovated Venetian Bay Townhome in Quiet Location, holiday rental in Kissimmee
Renovated Venetian Bay Townhome in Quiet Location, holiday rental in Kissimmee

Renovated Venetian Bay Townhome in Quiet Location

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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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, holiday rental in Kissimmee
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

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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⭐ Spacious and Comfortable Villa - Near Theme Parks ⭐, holiday rental in Kissimmee
⭐ Spacious and Comfortable Villa - Near Theme Parks ⭐, holiday rental in Kissimmee
⭐ Spacious and Comfortable Villa - Near Theme Parks ⭐, holiday rental in Kissimmee

⭐ Spacious and Comfortable Villa - Near Theme Parks ⭐

Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Palm Heaven Villa, Relaxing Family Getaway in Kissimmee, holiday rental in Kissimmee
Palm Heaven Villa, Relaxing Family Getaway in Kissimmee, holiday rental in Kissimmee
Palm Heaven Villa, Relaxing Family Getaway in Kissimmee, holiday rental in Kissimmee

Palm Heaven Villa, Relaxing Family Getaway in Kissimmee

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Veranda Palms Villa, holiday rental in Kissimmee
Veranda Palms Villa, holiday rental in Kissimmee
Veranda Palms Villa, holiday rental in Kissimmee

Veranda Palms Villa

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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♥ 70' 3-D LED TV - NEW GAME ROOM - 5 MIN TO DISNEY- POOL HEAT/BBQ ALL INCLUDED, holiday rental in Kissimmee
♥ 70' 3-D LED TV - NEW GAME ROOM - 5 MIN TO DISNEY- POOL HEAT/BBQ ALL INCLUDED, holiday rental in Kissimmee
♥ 70' 3-D LED TV - NEW GAME ROOM - 5 MIN TO DISNEY- POOL HEAT/BBQ ALL INCLUDED, holiday rental in Kissimmee

♥ 70' 3-D LED TV - NEW GAME ROOM - 5 MIN TO DISNEY- POOL HEAT/BBQ ALL INCLUDED

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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DISINFECTED! Wonderful 5 Bedroom w/ Pool Close to Disney 4801, holiday rental in Kissimmee
DISINFECTED! Wonderful 5 Bedroom w/ Pool Close to Disney 4801, holiday rental in Kissimmee
DISINFECTED! Wonderful 5 Bedroom w/ Pool Close to Disney 4801, holiday rental in Kissimmee

DISINFECTED! Wonderful 5 Bedroom w/ Pool Close to Disney 4801

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Buzz,Jake&Cinderella Rooms, Cars Movie Theater, Swingset, SplashPad (new4/2017), holiday rental in Kissimmee
Buzz,Jake&Cinderella Rooms, Cars Movie Theater, Swingset, SplashPad (new4/2017), holiday rental in Kissimmee
Buzz,Jake&Cinderella Rooms, Cars Movie Theater, Swingset, SplashPad (new4/2017), holiday rental in Kissimmee

Buzz,Jake&Cinderella Rooms, Cars Movie Theater, Swingset, SplashPad (new4/2017)

Holiday Rental House
7 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
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Family Friendly 4BR/4BA Pool Home in 5 Star Windsor Hills, holiday rental in Kissimmee
Family Friendly 4BR/4BA Pool Home in 5 Star Windsor Hills, holiday rental in Kissimmee
Family Friendly 4BR/4BA Pool Home in 5 Star Windsor Hills, holiday rental in Kissimmee

Family Friendly 4BR/4BA Pool Home in 5 Star Windsor Hills

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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VRBO STAYED!  6 Bedrms, Free Wifi,   2.5 Miles to Disney! Theater, Mickey Pool!, holiday rental in Kissimmee
VRBO STAYED!  6 Bedrms, Free Wifi,   2.5 Miles to Disney! Theater, Mickey Pool!, holiday rental in Kissimmee
VRBO STAYED!  6 Bedrms, Free Wifi,   2.5 Miles to Disney! Theater, Mickey Pool!, holiday rental in Kissimmee

VRBO STAYED! 6 Bedrms, Free Wifi, 2.5 Miles to Disney! Theater, Mickey Pool!

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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5 Stars House With WiFi, Game Room, Private Heated Spa & Pool In a Gated Area, holiday rental in Kissimmee
5 Stars House With WiFi, Game Room, Private Heated Spa & Pool In a Gated Area, holiday rental in Kissimmee
5 Stars House With WiFi, Game Room, Private Heated Spa & Pool In a Gated Area, holiday rental in Kissimmee

5 Stars House With WiFi, Game Room, Private Heated Spa & Pool In a Gated Area

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Alberto Circle, Fun Vacation House with Pool, holiday rental in Kissimmee
Alberto Circle, Fun Vacation House with Pool, holiday rental in Kissimmee
Alberto Circle, Fun Vacation House with Pool, holiday rental in Kissimmee

Alberto Circle, Fun Vacation House with Pool

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Special! Near Disney World: 4BR/2BA Pool Home + Free Internet, holiday rental in Kissimmee
Special! Near Disney World: 4BR/2BA Pool Home + Free Internet, holiday rental in Kissimmee
Special! Near Disney World: 4BR/2BA Pool Home + Free Internet, holiday rental in Kissimmee

Special! Near Disney World: 4BR/2BA Pool Home + Free Internet

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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'HARRY POTTER SLEPT HERE!' Incredible Home, Sleeps 8, Pool, Nesr Dis!, holiday rental in Kissimmee
'HARRY POTTER SLEPT HERE!' Incredible Home, Sleeps 8, Pool, Nesr Dis!, holiday rental in Kissimmee
'HARRY POTTER SLEPT HERE!' Incredible Home, Sleeps 8, Pool, Nesr Dis!, holiday rental in Kissimmee

'HARRY POTTER SLEPT HERE!' Incredible Home, Sleeps 8, Pool, Nesr Dis!

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Villa Sonrisa - 5 Bedroom/5 Bath Luxury, Minutes To Disney In Windsor Hills, holiday rental in Kissimmee
Villa Sonrisa - 5 Bedroom/5 Bath Luxury, Minutes To Disney In Windsor Hills, holiday rental in Kissimmee
Villa Sonrisa - 5 Bedroom/5 Bath Luxury, Minutes To Disney In Windsor Hills, holiday rental in Kissimmee

Villa Sonrisa - 5 Bedroom/5 Bath Luxury, Minutes To Disney In Windsor Hills

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Milazzo Florida Villa - 3 Miles from Disney / Orlando - Indian Creek / Kissimmee, holiday rental in Kissimmee
Milazzo Florida Villa - 3 Miles from Disney / Orlando - Indian Creek / Kissimmee, holiday rental in Kissimmee
Milazzo Florida Villa - 3 Miles from Disney / Orlando - Indian Creek / Kissimmee, holiday rental in Kissimmee

Milazzo Florida Villa - 3 Miles from Disney / Orlando - Indian Creek / Kissimmee

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Tropical Lakefront Villa, Gated, Pet-Friendly, less than 10 mins to Disney!, holiday rental in Kissimmee
Tropical Lakefront Villa, Gated, Pet-Friendly, less than 10 mins to Disney!, holiday rental in Kissimmee
Tropical Lakefront Villa, Gated, Pet-Friendly, less than 10 mins to Disney!, holiday rental in Kissimmee

Tropical Lakefront Villa, Gated, Pet-Friendly, less than 10 mins to Disney!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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SANITIZED  |  Storey Lake Luxury Resort |  Private Pool/Spa, holiday rental in Kissimmee
SANITIZED  |  Storey Lake Luxury Resort |  Private Pool/Spa, holiday rental in Kissimmee
SANITIZED  |  Storey Lake Luxury Resort |  Private Pool/Spa, holiday rental in Kissimmee

SANITIZED | Storey Lake Luxury Resort | Private Pool/Spa

Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 15
Match: Sleeps
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Fantasy Pool Home, holiday rental in Kissimmee
Fantasy Pool Home, holiday rental in Kissimmee
Fantasy Pool Home, holiday rental in Kissimmee

Fantasy Pool Home

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Disney, Minutes Away- With Comforts of Home, Free WiFi Gated Community, holiday rental in Kissimmee
Disney, Minutes Away- With Comforts of Home, Free WiFi Gated Community, holiday rental in Kissimmee
Disney, Minutes Away- With Comforts of Home, Free WiFi Gated Community, holiday rental in Kissimmee

Disney, Minutes Away- With Comforts of Home, Free WiFi Gated Community

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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New Water Park is Now OPEN!!! Spend the summer at Disney, holiday rental in Kissimmee
New Water Park is Now OPEN!!! Spend the summer at Disney, holiday rental in Kissimmee
New Water Park is Now OPEN!!! Spend the summer at Disney, holiday rental in Kissimmee

New Water Park is Now OPEN!!! Spend the summer at Disney

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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The Beautiful Life - Family Villa, 6 miles to Disney Pk, holiday rental in Kissimmee
The Beautiful Life - Family Villa, 6 miles to Disney Pk, holiday rental in Kissimmee
The Beautiful Life - Family Villa, 6 miles to Disney Pk, holiday rental in Kissimmee

The Beautiful Life - Family Villa, 6 miles to Disney Pk

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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DORAL WOODS SECLUDED VILLA, holiday rental in Kissimmee
DORAL WOODS SECLUDED VILLA, holiday rental in Kissimmee
DORAL WOODS SECLUDED VILLA, holiday rental in Kissimmee

DORAL WOODS SECLUDED VILLA

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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