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Vacation rentals in Kissimmee, Florida, United States

7BR 4.5BA Pool Home in gated Vacation Resort TERRA VERDE

large open Kitchen, Granite Counters

large open Kitchen, Granite Counters

Family Room with large Sofa

7-Bedroom Terra Verde Resort Pool Home in Kissimmee – Sleeps 15

7 bedrooms·4½ baths

Kissimmee • Florida

$ 910,47 USD $ 885,74 USD totaal voor 3 nachten

8–11 nov 2026

Wonder World Bowling Villa, 14 bedrooms/14.5 baths

Wonder World Bowling Villa, 14 bedrooms/14.5 baths

Wonder World Bowling Villa, 14 bedrooms/14.5 baths

wall-to-wall TV in living room

Wonder World Bowling Villa, 14 bedrooms/14.5 baths

Wonder World Bowling Villa, 14 bedrooms/14.5 baths

10 bedrooms·10 baths

Kissimmee • Florida

4.86(7 reviews)

$ 6.110,84 USD totaal voor 3 nachten

15–18 nov 2026

LAKE BERKLEY (975PT) - 4BR 3.5BA Townhome

LAKE BERKLEY (975PT) - 4BR 3.5BA Townhome

Resort Kids Splash Pool Area

bright, open Living Area, high ceilings

LAKE BERKLEY (975PT) - 4BR 3.5BA Townhome

4 bedrooms·3½ baths

Kissimmee • Florida

5(3 reviews)

$ 603,27 USD $ 588,40 USD totaal voor 3 nachten

8–11 nov 2026

*NEW* King Bed | Glow In The Dark Kid Cave

*NEW* King Bed | Glow In The Dark Kid Cave

*NEW* King Bed | Glow In The Dark Kid Cave

*NEW* King Bed | Glow In The Dark Kid Cave

*NEW* King Bed | Glow In The Dark Kid Cave

NEW King Bed | Glow In The Dark Kid Cave

4 bedrooms·3 baths

Kissimmee • Florida

5(7 reviews)

$ 726,39 USD totaal voor 3 nachten

28 nov – 1 dec 2026

Villa mit 6 Schlafzimmern und atemberaubendem Seeblick

Kitchen / Dining Room

Kitchen / Dining Room

Kitchen / Dining Room

Villa mit 6 Schlafzimmern und atemberaubendem Seeblick

6 bedrooms·4 baths

Kissimmee • Florida

A Magical Villa Getaway-20 Min from Disney World!

A Magical Villa Getaway-20 Min from Disney World!

A Magical Villa Getaway-20 Min from Disney World!

A Magical Villa Getaway-20 Min from Disney World!

A Magical Villa Getaway-20 Min from Disney World!

A Magical Villa Getaway-20 Min from Disney World!

5 bedrooms·1 bath

Kissimmee • Florida

4.83(6 reviews)

$185/ nacht(excl. kosten & belastingen)

Lake Berkley Villa

Lake Berkley Villa

Lake Berkley Villa

Lake Berkley Villa

Lake Berkley Villa

Lake Berkley Villa

5 bedrooms·3 baths

Kissimmee • Florida

4.93(58 reviews)

$ 1.163,38 USD totaal voor 5 nachten

25–30 nov 2026

Moderne Villa mit Seeblick nur wenige Minuten von Disney entfernt

Moderne Villa mit Seeblick nur wenige Minuten von Disney entfernt

4 bedrooms·2 baths

Kissimmee • Florida

$233/ nacht(excl. kosten & belastingen)

Cozy 4 Bed 3 Bath Pool Hm with Game Room-4450NP

Cozy 4 Bed 3 Bath Pool Hm with Game Room-4450NP

Cozy 4 Bed 3 Bath Pool Hm with Game Room-4450NP

Cozy 4 Bed 3 Bath Pool Hm with Game Room-4450NP

Cozy 4 Bed 3 Bath Pool Hm with Game Room-4450NP

Cozy 4 Bed 3 Bath Pool Hm with Game Room-4450NP

4 bedrooms·3 baths

Kissimmee • Florida

Come into Beyond Imagination game room and enjoy our homes' commercial arcade games, foosball, Xbox & Play Station

Bedroom 8 - Spaceship Queen Bed

Bedroom 5 - Princess Themed Room with two twin beds, Princess play castle, & dress up clothes

Bedroom 6 - Superhero King Size Bed

Private Pool with Spa

Themed Villa w Arcade & Pool/Spa 1 Block to Resort

9 bedrooms·5 baths

Kissimmee • Florida

$ 1.491,33 USD totaal voor 3 nachten

15–18 nov 2026

Seasons Retreat mit privatem Pool in der Nähe von Disney

Aerial photography

Aerial photography

Seasons Retreat mit privatem Pool in der Nähe von Disney

5 bedrooms·4 baths

Kissimmee • Florida

$262/ nacht(excl. kosten & belastingen)

4-Schlafzimmer-Ferienhaus mit Whirlpool

Kitchen / Dining Room

4-Schlafzimmer-Ferienhaus mit Whirlpool

4 bedrooms·3 baths

Kissimmee • Florida

$235/ nacht(excl. kosten & belastingen)

Poolside paradise awaits under a twinkling canopy of garden lights! Dive into relaxation and let the evening ambiance enchant you in our serene oasis. Welcome to your own private slice of paradise.

Gather 'round! Our Airbnb dining room sets the stage for memorable meals with loved ones. With a spacious 8-seater table and beautiful lighting, every dinner becomes an occasion to cherish.

Welcome home! Step into our inviting entrance and feel the warmth of hospitality embrace you. From the moment you arrive, you're part of our family.

Experience luxury and convenience on the main floor! Our elegant bedroom offers a king bed, stylish furniture, and ample closet space, ensuring a comfortable and accessible stay. Welcome to your perfect retreat!

Our kitchen is fully equipped with all the essentials for crafting delicious home-cooked meals. From utensils to cozy counter chairs, every detail is designed to make your cooking experience as enjoyable as possible.

Beauty 6BR Vacation Home w/ South Pool, Spa & more

6 bedrooms·5 baths

Kissimmee • Florida

4.81(31 reviews)

$ 5.186,95 USD totaal voor 5 nachten

8–13 nov 2026

4BR Pool Home in Gated Lake Berkley Resort Near Disney, Wifi

Private Pool, Conservation View for added Privacy

4BR Pool Home in Gated Lake Berkley Resort Near Disney, Wifi

Family Room, Smart TV

4BR Pool Home in Gated Lake Berkley Resort Near Disney, Wifi

4 bedrooms·3 baths

Kissimmee • Florida

$ 916,56 USD $ 889,16 USD totaal voor 4 nachten

8–12 nov 2026

Wunderschönes Haus mit 4 Schlafzimmern und privatem Pool

Wunderschönes Haus mit 4 Schlafzimmern und privatem Pool

Wunderschönes Haus mit 4 Schlafzimmern und privatem Pool

4 bedrooms·3 baths

Kissimmee • Florida

RESORT PROPERTY *20 MINS TO DISNEY*

RESORT PROPERTY *20 MINS TO DISNEY*

RESORT PROPERTY *20 MINS TO DISNEY*

RESORT PROPERTY *20 MINS TO DISNEY*

RESORT PROPERTY *20 MINS TO DISNEY*

RESORT PROPERTY 20 MINS TO DISNEY

3 bedrooms·2½ baths

Kissimmee • Florida

4.94(16 reviews)

$ 682,56 USD totaal voor 5 nachten

28 nov – 3 dec 2026

Luxurious 6Bd Pool Haven Refreshing and Chic-4464N

Luxurious 6Bd Pool Haven Refreshing and Chic-4464N

Luxurious 6Bd Pool Haven Refreshing and Chic-4464N

Luxurious 6Bd Pool Haven Refreshing and Chic-4464N

Luxurious 6Bd Pool Haven Refreshing and Chic-4464N

Luxurious 6Bd Pool Haven Refreshing and Chic-4464N

6 bedrooms·4 baths

Kissimmee • Florida

$ 1.084,96 USD totaal voor 3 nachten

8–11 nov 2026

Disney Area 3BR Townhome Resort Pool, Patio

Disney Area 3BR Townhome Resort Pool, Patio

Disney Area 3BR Townhome Resort Pool, Patio

Disney Area 3BR Townhome Resort Pool, Patio

3 bedrooms·2½ baths

Kissimmee • Florida

$ 569,14 USD $ 554,65 USD totaal voor 3 nachten

8–11 nov 2026

3 Bed Pool Escape & Gameroom Close to Disney image 1

3 Bed Pool Escape & Gameroom Close to Disney image 2

3 Bed Pool Escape & Gameroom Close to Disney image 3

3 Bed Pool Escape & Gameroom Close to Disney image 4

3 Bed Pool Escape & Gameroom Close to Disney image 5

3 Bed Pool Escape & Gameroom Close to Disney

3 bedrooms·2 baths

Kissimmee • Florida

4.78(108 reviews)

$ 685,00 USD totaal voor 3 nachten

28 nov – 1 dec 2026

Your little ones can dress as princess; play with princess toys; read books in Minion theme room; play arcade games, air hockey, foosball, or board games in our game room, or enjoy the pirate ship playscape only a few blocks away at the resort.

Enjoy our private full size amazing pool and/or spa (hot tub) with water views and views of the conservation area. Our south facing pool gets sun all day!

Enjoy hot tub after a day back from the parks!

Primary 50's theme bedroom with King bed and workstation desk and chair.

Come sleep in our Super Hero bedroom with a king size bed on the second floor and entrance to Jack n Jill bathroom!

NEW 9Bdrm S. Facing Pool on Preserve near Dis/Univ

9 bedrooms·5 baths

Kissimmee • Florida

$ 1.211,17 USD totaal voor 3 nachten

17–20 nov 2026

Dream Vacation Home with Lake View, Pool & more

Dream Vacation Home with Lake View, Pool & more

Dream Vacation Home with Lake View, Pool & more

Dream Vacation Home with Lake View, Pool & more

Dream Vacation Home with Lake View, Pool & more

Dream Vacation Home with Lake View, Pool & more

9 bedrooms·5 baths

Kissimmee • Florida

4.88(40 reviews)

$ 4.159,78 USD totaal voor 5 nachten

15–20 nov 2026

Disney Villa w/ Themed Rooms, Pool, Hot Tub, PS5

Disney Villa w/ Themed Rooms, Pool, Hot Tub, PS5

Disney Villa w/ Themed Rooms, Pool, Hot Tub, PS5

Disney Villa w/ Themed Rooms, Pool, Hot Tub, PS5

Disney Villa w/ Themed Rooms, Pool, Hot Tub, PS5

Disney Villa w/ Themed Rooms, Pool, Hot Tub, PS5

4 bedrooms·3 baths

Kissimmee • Florida

$ 862,27 USD totaal voor 3 nachten

17–20 nov 2026

Elegant Luxury Villa Movie Game Room Private Pool

Elegant Dining Room. Seats 10 comfortably. (Nearby Breakfast bar seats 5. Outside Patio Seats an additional 8).

Back yard overlooks a peaceful forest conservation preserve. (Does not backup to another house like many listings).

Elegant Luxury Villa Movie Game Room Private Pool

Elegant Luxury Villa Movie Game Room Private Pool

Elegant Luxury Villa Movie Game Room Private Pool

9 bedrooms·5 baths

Kissimmee • Florida

4.93(15 reviews)

$ 4.155,20 USD totaal voor 4 nachten

23–27 nov 2026

Welcome to Joy House One - your dream vacation house in Kissimmee

Nemo Room w/ Double & Twin Beds

Storey Lake Clubhouse & pools

Brand-new Storey Lake 9-bedroom villa w/ lake view

9 bedrooms·5 baths

Kissimmee • Florida

5(43 reviews)

$ 5.885,49 USD totaal voor 3 nachten

16–19 nov 2026