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Osceola County long stay rentals
Stay a week, a month or longer in a comfortable place all your own
Featured long stay living spaces - Osceola County
Properties highly-rated for stays of 28 nights or longer, with space to feel right at home
Showing deals for:18 Aug - 15 Sept
Image gallery for 3BR/2B condo with views of Disney FIREWORKS!!!!
9.89.8 out of 10 rating
Exceptional
(29 reviews)
3BR/2B condo with views of Disney FIREWORKS!!!!
Kissimmee, FL
6% off
Price is NZ$6,473
NZ$6,473
NZ$231 per night
includes taxes & fees
Image gallery for Beautiful 3 bedroom/2 bath condo, balcony, resort, pools, Disney just 9 miles!
1010 out of 10 rating
Exceptional
(35 reviews)
Beautiful 3 bedroom/2 bath condo, balcony, resort, pools, Disney just 9 miles!
Kissimmee, FL
7% off
Price is NZ$6,420
NZ$6,420
NZ$229 per night
includes taxes & fees
Image gallery for Reunion Resort | Family and a Golf Course Paradise
1010 out of 10 rating
Exceptional
(1 review)
Reunion Resort | Family and a Golf Course Paradise
Kissimmee, FL
8% off
Price is NZ$6,308
NZ$6,308
NZ$225 per night
includes taxes & fees
Image gallery for Resort Style Living 2 miles from Disney World
9.29.2 out of 10 rating
Wonderful
(93 reviews)
Resort Style Living 2 miles from Disney World
Kissimmee, FL
13% off
Price is NZ$6,584
NZ$6,584
NZ$235 per night
includes taxes & fees
Image gallery for 4 Bed 3 Bath Town home close to Disney, Private pool!!!
9.89.8 out of 10 rating
Exceptional
(94 reviews)
4 Bed 3 Bath Town home close to Disney, Private pool!!!
Kissimmee, FL
11% off
Price is NZ$7,226
NZ$7,226
NZ$258 per night
includes taxes & fees
Image gallery for Quiet and beautiful place
1010 out of 10 rating
Exceptional
(78 reviews)
Quiet and beautiful place
Kissimmee, FL
8% off
Price is NZ$7,993
NZ$7,993
NZ$285 per night
includes taxes & fees
Image gallery for 5 MINS to DISNEY! Themed! Costumes, Toys, HEATED POOL/SPA, PS4, Grill.
1010 out of 10 rating
Exceptional
(209 reviews)
5 MINS to DISNEY! Themed! Costumes, Toys, HEATED POOL/SPA, PS4, Grill.
Kissimmee, FL
17% off
Price is NZ$13,609
NZ$13,609
NZ$486 per night
includes taxes & fees
Image gallery for SOLO! Tiny house cozy retreat
1010 out of 10 rating
Exceptional
(45 reviews)
SOLO! Tiny house cozy retreat
Kissimmee, FL
13% off
Price is NZ$3,730
NZ$3,730
NZ$133 per night
includes taxes & fees
Image gallery for Top floor on Disney's doorstep - Great location
9.89.8 out of 10 rating
Exceptional
(180 reviews)
Top floor on Disney's doorstep - Great location
Kissimmee, FL
8% off
Price is NZ$7,504
NZ$7,504
NZ$268 per night
includes taxes & fees
Image gallery for Luxurious 4BR/3BA Home with Private Pool & Hot Tub near Disney & Universal
1010 out of 10 rating
Exceptional
(62 reviews)
Luxurious 4BR/3BA Home with Private Pool & Hot Tub near Disney & Universal
Kissimmee, FL
8% off
Price is NZ$10,817
NZ$10,817
NZ$386 per night
includes taxes & fees
Image gallery for Colorful 7BR Villa in Windsor Hills Themed Bedrooms Pool and Waterpark Access
1010 out of 10 rating
Exceptional
(2 reviews)
Colorful 7BR Villa in Windsor Hills Themed Bedrooms Pool and Waterpark Access
Kissimmee, FL
17% off
Price is NZ$17,106
NZ$17,106
NZ$611 per night
includes taxes & fees
Image gallery for Luxury Villa Close to Disney 5br Private Pool
9.89.8 out of 10 rating
Exceptional
(55 reviews)
Luxury Villa Close to Disney 5br Private Pool
Davenport, FL
16% off
Price is NZ$7,880
NZ$7,880
NZ$281 per night
includes taxes & fees
Image gallery for Oak Island Harbor- 4/2+2- Southfacing, near Disney, Lake view,Pool/Spa
1010 out of 10 rating
Exceptional
(166 reviews)
Oak Island Harbor- 4/2+2- Southfacing, near Disney, Lake view,Pool/Spa
Kissimmee, FL
6% off
Price is NZ$12,830
NZ$12,830
NZ$458 per night
includes taxes & fees
Image gallery for Luxury Home in Champions' Gate with Private Pool & Game Room!
9.29.2 out of 10 rating
Wonderful
(17 reviews)
Luxury Home in Champions' Gate with Private Pool & Game Room!
Davenport, FL
17% off
Price is NZ$7,955
NZ$7,955
NZ$284 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
8% off
Price is NZ$10,314
NZ$10,314
NZ$368 per night
includes taxes & fees
Image gallery for Our Retro Mod Pod-Disney & Old Town Minutes Away!
9.69.6 out of 10 rating
Exceptional
(7 reviews)
Our Retro Mod Pod-Disney & Old Town Minutes Away!
Kissimmee, FL
8% off
Price is NZ$4,761
NZ$4,761
NZ$170 per night
includes taxes & fees
Image gallery for Minutes from Disney! Lakefront villa with south facing pool and jacuzzi!
1010 out of 10 rating
Exceptional
(103 reviews)
Minutes from Disney! Lakefront villa with south facing pool and jacuzzi!
Kissimmee, FL
6% off
Price is NZ$12,924
NZ$12,924
NZ$462 per night
includes taxes & fees
Image gallery for Luxury Home inside Champions Gate, private pool + hot tub + No Extra Fees
9.89.8 out of 10 rating
Exceptional
(20 reviews)
Luxury Home inside Champions Gate, private pool + hot tub + No Extra Fees
Davenport, FL
12% off
Price is NZ$15,504
NZ$15,504
NZ$554 per night
includes taxes & fees
Image gallery for Margaritaville Resort Cottage - 4 BR - Minutes from Disney
9.89.8 out of 10 rating
Exceptional
(45 reviews)
Margaritaville Resort Cottage - 4 BR - Minutes from Disney
Kissimmee, FL
8% off
Price is NZ$15,528
NZ$15,528
NZ$555 per night
includes taxes & fees
Image gallery for SUNSHINE 🌞 and SMILES😎 - 5 mi to Disney, 4 bdrm / 3 bath, Private Pool
9.69.6 out of 10 rating
Exceptional
(95 reviews)
SUNSHINE 🌞 and SMILES😎 - 5 mi to Disney, 4 bdrm / 3 bath, Private Pool
Kissimmee, FL
8% off
Price is NZ$9,246
NZ$9,246
NZ$330 per night
includes taxes & fees
Image gallery for Disney World 2 Miles! Family condo
8.88.8 out of 10 rating
Excellent
(31 reviews)
Disney World 2 Miles! Family condo
Kissimmee, FL
12% off
Price is NZ$5,632
NZ$5,632
NZ$201 per night
includes taxes & fees
Image gallery for Solara 7BR/6.5BA Villa w/Pool/Spa, 3544 sqft, Sleeps 18, Lake and green view.
9.69.6 out of 10 rating
Exceptional
(37 reviews)
Solara 7BR/6.5BA Villa w/Pool/Spa, 3544 sqft, Sleeps 18, Lake and green view.
Kissimmee, FL
8% off
Price is NZ$12,726
NZ$12,726
NZ$454 per night
includes taxes & fees
Image gallery for CINDERELLA'S CASTLE Close to Disney, ONE story Home_5 bedrooms 4 baths_Pool/Spa
9.89.8 out of 10 rating
Exceptional
(25 reviews)
CINDERELLA'S CASTLE Close to Disney, ONE story Home_5 bedrooms 4 baths_Pool/Spa
Kissimmee, FL
8% off
Price is NZ$13,401
NZ$13,401
NZ$479 per night
includes taxes & fees
Image gallery for NEW OPENING! 5b4b Disney Themed Vacation Home w/Pool & BBQ ~12 min from Disney~
1010 out of 10 rating
Exceptional
(4 reviews)
NEW OPENING! 5b4b Disney Themed Vacation Home w/Pool & BBQ ~12 min from Disney~
Kissimmee, FL
27% off
Price is NZ$7,224
NZ$7,224
NZ$258 per night
includes taxes & fees
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
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