Kissimmee holiday homes
We found 35,296 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals near Kissimmee, FL (ISM-Kissimmee Gateway) that can be your home away from home. Whether you're travelling with your children and pets, with friends or just your children, holiday homes have the amenities that you expect for your stay, which might include a garden and pool. You'll be able to choose a property to rent that has what everyone needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Kissimmee, FL (ISM-Kissimmee Gateway)
Showing deals for:26 Sept - 3 Oct
Image gallery for 5 MINS to DISNEY! Themed! Costumes, Toys, HEATED POOL/SPA, PS4, Grill.
1010 out of 10 rating
Exceptional
(211 reviews)
5 MINS to DISNEY! Themed! Costumes, Toys, HEATED POOL/SPA, PS4, Grill.
Kissimmee, FL
5% off
Price is NZ$4,096
NZ$4,096
NZ$585 per night
includes taxes & fees
Image gallery for Big Pool&Spa/Themed rooms/Private yard/ CLOSE TO EVERYTHING, Lakeview,Playground
1010 out of 10 rating
Exceptional
(153 reviews)
Big Pool&Spa/Themed rooms/Private yard/ CLOSE TO EVERYTHING, Lakeview,Playground
Kissimmee, FL
7% off
Price is NZ$4,396
NZ$4,396
NZ$628 per night
includes taxes & fees
Image gallery for Luxurious 5 Bed/5 Bath 3500sf Villa With Private Pool In Highlands Reserve
1010 out of 10 rating
Exceptional
(148 reviews)
Luxurious 5 Bed/5 Bath 3500sf Villa With Private Pool In Highlands Reserve
Davenport, FL
8% off
Price is NZ$3,156
NZ$3,156
NZ$451 per night
includes taxes & fees
Image gallery for ✨Remodeled Luxury Retreat with Pool-Steps to Clubhouse! 🪄NEW Harry Potter Room!✨
1010 out of 10 rating
Exceptional
(72 reviews)
✨Remodeled Luxury Retreat with Pool-Steps to Clubhouse! 🪄NEW Harry Potter Room!✨
Kissimmee, FL
9% off
Price is NZ$2,881
NZ$2,881
NZ$412 per night
includes taxes & fees
Image gallery for 3 Miles from Disney!!!!! 4 Bedroom Villa with Private Pool/Game Room
9.89.8 out of 10 rating
Exceptional
(16 reviews)
3 Miles from Disney!!!!! 4 Bedroom Villa with Private Pool/Game Room
Kissimmee, FL
7% off
Price is NZ$3,111
NZ$3,111
NZ$444 per night
includes taxes & fees
Image gallery for Upscale WINDSOR HILLS Private Villa ♥ Pool/Spa, GAME ROOM ♥ 4 mi to DISNEY WORLD
1010 out of 10 rating
Exceptional
(44 reviews)
Upscale WINDSOR HILLS Private Villa ♥ Pool/Spa, GAME ROOM ♥ 4 mi to DISNEY WORLD
Kissimmee, FL
7% off
Price is NZ$3,442
NZ$3,442
NZ$492 per night
includes taxes & fees
Image gallery for Unforgettable Escape: Private Pool, Smart TV, Dreamy Resort, Moments from Disney
1010 out of 10 rating
Exceptional
(33 reviews)
Unforgettable Escape: Private Pool, Smart TV, Dreamy Resort, Moments from Disney
Kissimmee, FL
13% off
Price is NZ$2,367
NZ$2,367
NZ$338 per night
includes taxes & fees
Image gallery for 3BR/2B condo with views of Disney FIREWORKS!!!!
9.69.6 out of 10 rating
Exceptional
(33 reviews)
3BR/2B condo with views of Disney FIREWORKS!!!!
Kissimmee, FL
6% off
Price is NZ$1,471
NZ$1,471
NZ$210 per night
includes taxes & fees
Image gallery for Regal Palms Resort Dream Vacation-8 miles to Disney
1010 out of 10 rating
Exceptional
(11 reviews)
Regal Palms Resort Dream Vacation-8 miles to Disney
Davenport, FL
6% off
Price is NZ$2,202
NZ$2,202
NZ$315 per night
includes taxes & fees
Image gallery for Orlando Disney World Inspired Five Bedroom Villa
1010 out of 10 rating
Exceptional
(40 reviews)
Orlando Disney World Inspired Five Bedroom Villa
Kissimmee, FL
7% off
Price is NZ$2,822
NZ$2,822
NZ$403 per night
includes taxes & fees
Image gallery for 8 bdrms! Theatre! Game Room-4 Xboxes! Harry Potter, Toy Story, & Up Bedrooms!
1010 out of 10 rating
Exceptional
(22 reviews)
8 bdrms! Theatre! Game Room-4 Xboxes! Harry Potter, Toy Story, & Up Bedrooms!
Davenport, FL
7% off
Price is NZ$3,771
NZ$3,771
NZ$539 per night
includes taxes & fees
Image gallery for Villa 7748 - Arcade Rm Updated Mar 2025! 3 mi from Disney, Pool Heat, BBQ & PS5
1010 out of 10 rating
Exceptional
(65 reviews)
Villa 7748 - Arcade Rm Updated Mar 2025! 3 mi from Disney, Pool Heat, BBQ & PS5
Kissimmee, FL
7% off
Price is NZ$4,460
NZ$4,460
NZ$637 per night
includes taxes & fees
Image gallery for ChampionsGate, 9 Bed Luxury Spacious Villa, Sleeps 30+2, West Facing Pool & Spa
9.49.4 out of 10 rating
Exceptional
(142 reviews)
ChampionsGate, 9 Bed Luxury Spacious Villa, Sleeps 30+2, West Facing Pool & Spa
Davenport, FL
15% off
Price is NZ$4,699
NZ$4,699
NZ$671 per night
includes taxes & fees
Image gallery for Spectacular 5⭐Villa -⛳Golf Course View, Salt💧Pool/Spa, Game Room, BBQ & Theater
1010 out of 10 rating
Exceptional
(41 reviews)
Spectacular 5⭐Villa -⛳Golf Course View, Salt💧Pool/Spa, Game Room, BBQ & Theater
Davenport, FL
7% off
Price is NZ$5,935
NZ$5,935
NZ$848 per night
includes taxes & fees
Image gallery for Sleeps 18! Solterra Resort, Pool, GameRoom, Themed BDRs | Broad Oak by AvantStay
1010 out of 10 rating
Exceptional
(5 reviews)
Sleeps 18! Solterra Resort, Pool, GameRoom, Themed BDRs | Broad Oak by AvantStay
Davenport, Florida
6% off
Price is NZ$4,223
NZ$4,223
NZ$603 per night
includes taxes & fees
Image gallery for Shuffleboard, Arcades, Bubble Hockey, Pool Table, 15 Mins to Disney: Vacation Station
9.69.6 out of 10 rating
Exceptional
(28 reviews)
Shuffleboard, Arcades, Bubble Hockey, Pool Table, 15 Mins to Disney: Vacation Station
Kissimmee, Florida
7% off
Price is NZ$6,608
NZ$6,608
NZ$944 per night
includes taxes & fees
Image gallery for Getaway with Private Pool, Clubhouse, Lazy River - Family Home!
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Getaway with Private Pool, Clubhouse, Lazy River - Family Home!
Davenport, FL
14% off
Price is NZ$2,518
NZ$2,518
NZ$360 per night
includes taxes & fees
Image gallery for 5 Bedrooms with In-law suite REUNION RESORT Pool, Spa
9.29.2 out of 10 rating
Wonderful
(13 reviews)
5 Bedrooms with In-law suite REUNION RESORT Pool, Spa
Kissimmee, FL
6% off
Price is NZ$2,927
NZ$2,927
NZ$418 per night
includes taxes & fees
Image gallery for Quiet, Clean, Disney-3.5 miles, Well kept home! Free Pool/spa Heat!
1010 out of 10 rating
Exceptional
(255 reviews)
Quiet, Clean, Disney-3.5 miles, Well kept home! Free Pool/spa Heat!
Kissimmee, FL
7% off
Price is NZ$2,917
NZ$2,917
NZ$417 per night
includes taxes & fees
Image gallery for Top floor on Disney's doorstep - Great location
9.89.8 out of 10 rating
Exceptional
(183 reviews)
Top floor on Disney's doorstep - Great location
Kissimmee, FL
7% off
Price is NZ$2,170
NZ$2,170
NZ$310 per night
includes taxes & fees
Image gallery for A Blissful Stay near Disney World
1010 out of 10 rating
Exceptional
(11 reviews)
A Blissful Stay near Disney World
Kissimmee, FL
7% off
Price is NZ$3,466
NZ$3,466
NZ$495 per night
includes taxes & fees
Image gallery for 6 Bed, 5 Bath Villa with South Facing Pool, located close to Disney & Universal
9.69.6 out of 10 rating
Exceptional
(78 reviews)
6 Bed, 5 Bath Villa with South Facing Pool, located close to Disney & Universal
Davenport, FL
7% off
Price is NZ$3,320
NZ$3,320
NZ$474 per night
includes taxes & fees
Image gallery for Welcome to Star Wars Villa, 3 miles from Disney World, private pool/spa, wifi
9.29.2 out of 10 rating
Wonderful
(26 reviews)
Welcome to Star Wars Villa, 3 miles from Disney World, private pool/spa, wifi
Kissimmee, FL
9% off
Price is NZ$2,490
NZ$2,490
NZ$356 per night
includes taxes & fees
Image gallery for Sleeps 20! Resort Home Near Disney, Pool+Game Room | Twice-as-Nice by AvantStay
1010 out of 10 rating
Exceptional
(7 reviews)
Sleeps 20! Resort Home Near Disney, Pool+Game Room | Twice-as-Nice by AvantStay
Kissimmee, Florida
6% off
Price is NZ$4,901
NZ$4,901
NZ$700 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Kissimmee
Updated Villa by Disney Solara Resort w/Pool & Spa
Sleeps 24 · 9 bedrooms · 6+ bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Executive 5/6 Bed Villa with Private Pool, Games Room + Wifi, 12 miles to Disney
Sleeps 12 · 6 bedrooms · 4 bathrooms
1010 out of 10
Exceptionalexceptional
102 reviews(102 reviews)
Vacation USA LTD
Sleeps 7 · 3 bedrooms
6.86.8 out of 10
157 reviews(157 reviews)
Encore Resort
Sleeps 12 · 6 bedrooms
6.46.4 out of 10
117 reviews(117 reviews)
FLASH SALE! Lovely Condo Just 1 Mile From Disney w/ Resort Pool, WiFi & More
Sleeps 6 · 2 bedrooms · 2 bathrooms
9.29.2 out of 10
Wonderfulwonderful
635 reviews(635 reviews)
Luxurious, spacious house located close to Disney.
Sleeps 12 · 6 bedrooms · 5 bathrooms
9.29.2 out of 10
Wonderfulwonderful
117 reviews(117 reviews)