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Holiday Rentals in Kissimmee

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3258 rentals in Kissimmee.
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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
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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
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Villa Linton - Beautiful Florida Home with Themed Bedrooms, holiday rental in Kissimmee

Villa Linton - Beautiful Florida Home with Themed Bedrooms

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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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
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Fantasy Pool Home, holiday rental in Kissimmee

Fantasy Pool Home

4 bedrooms
2 bathrooms
Sleeps 8
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villanirvana, holiday rental in Kissimmee

villanirvana

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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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
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Debbie's Florida Retreat a Luxury Vacation Home, holiday rental in Kissimmee

Debbie's Florida Retreat a Luxury Vacation Home

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

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Colonial type Villa in a beautiful setting., holiday rental in Kissimmee

Colonial type Villa in a beautiful setting.

6 bedrooms
6 bathrooms
Sleeps 14
Match: Sleeps
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The Emerald Dolphin, Kissimmee Rental with WiFi, Hot Tub and Pool, holiday rental in Kissimmee

The Emerald Dolphin, Kissimmee Rental with WiFi, Hot Tub and Pool

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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DISNEY WORLD! LOW $'S!  ENTIRE NEW Home! Harry Potter Theme, Sleeps 8!, holiday rental in Kissimmee

DISNEY WORLD! LOW $'S! ENTIRE NEW Home! Harry Potter Theme, Sleeps 8!

3 bedrooms
2 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,

4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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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
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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.

5 bedrooms
4 bathrooms
Sleeps 10
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Disney Vacation Villa with Lake View, holiday rental in Kissimmee

Disney Vacation Villa with Lake View

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Kissimmee Disney Villa with Wireless Internet, holiday rental in Kissimmee

Kissimmee Disney Villa with Wireless Internet

3 bedrooms
2 bathrooms
Sleeps 8
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Executive Villa with Stunning Lakeviews & South Facing Pool and Spa / Jacuzzi - a dream vacation home, holiday rental in Kissimmee

Executive Villa with Stunning Lakeviews & South Facing Pool and Spa / Jacuzzi - a dream vacation home

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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New Opening 9 Br/6 Ba luxurious Pool House from $300/nt, Close To Disney, holiday rental in Kissimmee

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

9 bedrooms
6 bathrooms
Sleeps 18
Match: Sleeps
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Roughtallys Villa, holiday rental in Kissimmee

Roughtallys Villa

7 bedrooms
4 bathrooms
Sleeps 14
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Some 2021 openings available, holiday rental in Kissimmee

Some 2021 openings available

3 bedrooms
3 bathrooms
Sleeps 8
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.

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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2675CA - Sonoma Resort, holiday rental in Kissimmee

2675CA - Sonoma Resort

6 bedrooms
6 bathrooms
Sleeps 14
Match: Sleeps
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A stunning pool home in Kissimmee, Disney Paradi, holiday rental in Kissimmee

A stunning pool home in Kissimmee, Disney Paradi

4 bedrooms
3 bathrooms
Sleeps 9
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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
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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

5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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DORAL WOODS SECLUDED VILLA, holiday rental in Kissimmee

DORAL WOODS SECLUDED VILLA

4 bedrooms
4 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.

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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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
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⭐Spacious 7 Bedrooms w/ Private Pool - Great Location!⭐, holiday rental in Kissimmee

⭐Spacious 7 Bedrooms w/ Private Pool - Great Location!⭐

7 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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Disney Dream Villa At CLC Encantada Resort, holiday rental in Kissimmee

Disney Dream Villa At CLC Encantada Resort

3 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.

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Large Condo close to Disney World & all of the other Orlando theme parks, holiday rental in Kissimmee

Large Condo close to Disney World & all of the other Orlando theme parks

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Superior Home with Private Pool, 4307, holiday rental in Kissimmee

Superior Home with Private Pool, 4307

6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Veranda Palms Villa, holiday rental in Kissimmee

Veranda Palms Villa

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful 5 bed/3.5 bath-2 En-suites, Free SPA Heat, WiFi, Disney/Universal., holiday rental in Kissimmee

Beautiful 5 bed/3.5 bath-2 En-suites, Free SPA Heat, WiFi, Disney/Universal.

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Bass Lake Beauty with a Pool, WiFi and Air Conditioning, holiday rental in Kissimmee

Bass Lake Beauty with a Pool, WiFi and Air Conditioning

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Stunning 5 Bd w/ Pool Close to Disney * Storey Lake 2767, holiday rental in Kissimmee

Stunning 5 Bd w/ Pool Close to Disney * Storey Lake 2767

5 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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Ultimate luxury 15 bedroom suites for 30 guests, holiday rental in Kissimmee

Ultimate luxury 15 bedroom suites for 30 guests

15 bedrooms
15 bathrooms
Sleeps 30
Match: Sleeps
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Magical Pool Villa - 4 Miles to Disney!, holiday rental in Kissimmee

Magical Pool Villa - 4 Miles to Disney!

7 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
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Mickeys Clubhouse Windsor Palm Frozen & New Minion themed rooms, holiday rental in Kissimmee

Mickeys Clubhouse Windsor Palm Frozen & New Minion themed rooms

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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9 Bedroom Home w-Pool Storey Lake -1672, holiday rental in Kissimmee

9 Bedroom Home w-Pool Storey Lake -1672

9 bedrooms
5 bathrooms
Sleeps 26
Match: Sleeps
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⭐⭐⭐Disney Contemporary 3 ⭐⭐⭐, holiday rental in Kissimmee

⭐⭐⭐Disney Contemporary 3 ⭐⭐⭐

4 bedrooms
3 bathrooms
Sleeps 15
Match: Sleeps
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*****..'Emerald Hunny Pot Villa'..*****, holiday rental in Kissimmee

*****..'Emerald Hunny Pot Villa'..*****

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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4BR-2 King-Large Pool/Spa-GamesRm-ROKU-WiFi, holiday rental in Kissimmee

4BR-2 King-Large Pool/Spa-GamesRm-ROKU-WiFi

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Pet Friendly Home with Private Pool, 4405, holiday rental in Kissimmee

Pet Friendly Home with Private Pool, 4405

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Chris and Sue's Disney Condo at Windsor Palms Resort, holiday rental in Kissimmee

Chris and Sue's Disney Condo at Windsor Palms Resort

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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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
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Grandmas's Ami (4907TV) - Trafalgar Village, holiday rental in Kissimmee

Grandmas's Ami (4907TV) - Trafalgar Village

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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