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Holiday rentals near Old Town
We found holiday rentals — enter your dates for availability
Find the perfect holiday home within easy reach of Old Town. Holiday rentals provide the best amenities for you and your friends, family or even pets, such as parking and a fireplace. What you'll find is a property to rent that has what everyone needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Old Town
Showing deals for:18 Jul - 25 Jul
Image gallery for Super Fun House with Amazing Views
1010 out of 10 rating
Exceptional
(36 reviews)
Super Fun House with Amazing Views
Kissimmee, FL
8% off
Price is NZ$32,169
NZ$32,169
NZ$4,596 per night
includes taxes & fees
Image gallery for RATED#1 BEST HOME Near Disney! LUXURY 5BEDROOM 5Bath VILLA ,GATED RESORT ,POOL!
9.49.4 out of 10 rating
Exceptional
(114 reviews)
RATED#1 BEST HOME Near Disney! LUXURY 5BEDROOM 5Bath VILLA ,GATED RESORT ,POOL!
Kissimmee, FL
7% off
Price is NZ$4,796
NZ$4,796
NZ$685 per night
includes taxes & fees
Image gallery for Family Fun! ☀️ Private Heated Pool & Spa 4mi to Disney! 🦩
1010 out of 10 rating
Exceptional
(14 reviews)
Family Fun! ☀️ Private Heated Pool & Spa 4mi to Disney! 🦩
Kissimmee, FL
8% off
Price is NZ$10,306
NZ$10,306
NZ$1,472 per night
includes taxes & fees
Image gallery for SUMMER SALE! Hogwarts Haven - Universal Epic! Windsor Hills 3BR, near Disney!
1010 out of 10 rating
Exceptional
(42 reviews)
SUMMER SALE! Hogwarts Haven - Universal Epic! Windsor Hills 3BR, near Disney!
Kissimmee, FL
7% off
Price is NZ$2,944
NZ$2,944
NZ$421 per night
includes taxes & fees
Image gallery for Fun for kids and parents 6BR/4BA with private pool & hot tub in resort community
9.69.6 out of 10 rating
Exceptional
(62 reviews)
Fun for kids and parents 6BR/4BA with private pool & hot tub in resort community
Kissimmee, FL
7% off
Price is NZ$3,948
NZ$3,948
NZ$564 per night
includes taxes & fees
Image gallery for Steps from clubhouse. "Be Our Guest" in Windsor Hills-Pool Heat
1010 out of 10 rating
Exceptional
(99 reviews)
Steps from clubhouse. "Be Our Guest" in Windsor Hills-Pool Heat
Kissimmee, FL
8% off
Price is NZ$3,416
NZ$3,416
NZ$488 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
(61 reviews)
Villa 7748 - Arcade Rm Updated Mar 2025! 3 mi from Disney, Pool Heat, BBQ & PS5
Kissimmee, FL
8% off
Price is NZ$5,516
NZ$5,516
NZ$788 per night
includes taxes & fees
Image gallery for 5 Bd Disney Villa: Themed rooms, Pool, Spa, Close to Parks, king master suites
1010 out of 10 rating
Exceptional
(11 reviews)
5 Bd Disney Villa: Themed rooms, Pool, Spa, Close to Parks, king master suites
Davenport, FL
8% off
Price is NZ$5,546
NZ$5,546
NZ$792 per night
includes taxes & fees
Image gallery for Amazing 6-bedroom Villa with Private Pool Minutes from Disney! 5 Star Theming!
1010 out of 10 rating
Exceptional
(37 reviews)
Amazing 6-bedroom Villa with Private Pool Minutes from Disney! 5 Star Theming!
Kissimmee, FL
8% off
Price is NZ$5,998
NZ$5,998
NZ$857 per night
includes taxes & fees
Image gallery for 6/4 Home Pool/Spa Close to Disney, Free Water Park Use, Game RMThemed, WIFI BBQ
9.49.4 out of 10 rating
Exceptional
(221 reviews)
6/4 Home Pool/Spa Close to Disney, Free Water Park Use, Game RMThemed, WIFI BBQ
Kissimmee, FL
8% off
Price is NZ$3,885
NZ$3,885
NZ$555 per night
includes taxes & fees
Image gallery for Resort Style Living 2 miles from Disney World
9.29.2 out of 10 rating
Wonderful
(91 reviews)
Resort Style Living 2 miles from Disney World
Kissimmee, FL
8% off
Price is NZ$1,911
NZ$1,911
NZ$273 per night
includes taxes & fees
Image gallery for 3 br Disney area condo with a view & FREE resort!
1010 out of 10 rating
Exceptional
(6 reviews)
3 br Disney area condo with a view & FREE resort!
Kissimmee, FL
7% off
Price is NZ$2,404
NZ$2,404
NZ$343 per night
includes taxes & fees
Image gallery for Curated HIGH TECH Home Close to Disney 5 bedrooms, 4.5 bathrooms
9.29.2 out of 10 rating
Wonderful
(29 reviews)
Curated HIGH TECH Home Close to Disney 5 bedrooms, 4.5 bathrooms
Davenport, FL
6% off
Price is NZ$5,152
NZ$5,152
NZ$736 per night
includes taxes & fees
Image gallery for You can't get any closer to Disney!!
9.69.6 out of 10 rating
Exceptional
(57 reviews)
You can't get any closer to Disney!!
Kissimmee, FL
7% off
Price is NZ$2,574
NZ$2,574
NZ$368 per night
includes taxes & fees
Image gallery for 😎RELAX at Windsor Hills🌴, minutes to Disney - 5 bed / 5 bath, Private Pool🌞
9.89.8 out of 10 rating
Exceptional
(62 reviews)
😎RELAX at Windsor Hills🌴, minutes to Disney - 5 bed / 5 bath, Private Pool🌞
Kissimmee, FL
8% off
Price is NZ$4,041
NZ$4,041
NZ$577 per night
includes taxes & fees
Image gallery for Relaxing Lake Front House near the Mouse
9.69.6 out of 10 rating
Exceptional
(102 reviews)
Relaxing Lake Front House near the Mouse
Kissimmee, FL
6% off
Price is NZ$2,710
NZ$2,710
NZ$387 per night
includes taxes & fees
Image gallery for Reunion - Remodeled kitchen/master bathroom 2022! Golf /Water Park included
9.89.8 out of 10 rating
Exceptional
(92 reviews)
Reunion - Remodeled kitchen/master bathroom 2022! Golf /Water Park included
Kissimmee, FL
8% off
Price is NZ$6,613
NZ$6,613
NZ$945 per night
includes taxes & fees
Image gallery for Unforgettable Escape: Private Pool, Smart TV, Dreamy Resort, Moments from Disney
9.89.8 out of 10 rating
Exceptional
(27 reviews)
Unforgettable Escape: Private Pool, Smart TV, Dreamy Resort, Moments from Disney
Kissimmee, FL
6% off
Price is NZ$3,748
NZ$3,748
NZ$535 per night
includes taxes & fees
Image gallery for Villa 2655 - 3 mi from Disney, Free Heated Pool/Spa, BBQ, Game/Theater Rm, & PS5
9.89.8 out of 10 rating
Exceptional
(56 reviews)
Villa 2655 - 3 mi from Disney, Free Heated Pool/Spa, BBQ, Game/Theater Rm, & PS5
Kissimmee, FL
7% off
Price is NZ$5,056
NZ$5,056
NZ$722 per night
includes taxes & fees
Image gallery for Spacious condo close to Disney with heated pools, hot tubs, lots of amenities!
9.89.8 out of 10 rating
Exceptional
(12 reviews)
Spacious condo close to Disney with heated pools, hot tubs, lots of amenities!
Davenport, FL
7% off
Price is NZ$1,522
NZ$1,522
NZ$217 per night
includes taxes & fees
Image gallery for Discover magic just 7 mins away! Spacious 7-bedroom Kissimmee Villa
9.89.8 out of 10 rating
Exceptional
(113 reviews)
Discover magic just 7 mins away! Spacious 7-bedroom Kissimmee Villa
Kissimmee, FL
8% off
Price is NZ$4,608
NZ$4,608
NZ$658 per night
includes taxes & fees
Image gallery for Amazing vacation Townhome at Solterra Resort - 20min from Disney
9.89.8 out of 10 rating
Exceptional
(35 reviews)
Amazing vacation Townhome at Solterra Resort - 20min from Disney
Davenport, FL
8% off
Price is NZ$3,555
NZ$3,555
NZ$508 per night
includes taxes & fees
Image gallery for Harry Poter - 4BD Sleep 10 Pool + Spa + e-BBQ! Solara Resort
1010 out of 10 rating
Exceptional
(6 reviews)
Harry Poter - 4BD Sleep 10 Pool + Spa + e-BBQ! Solara Resort
Kissimmee, FL
7% off
Price is NZ$5,195
NZ$5,195
NZ$742 per night
includes taxes & fees
Image gallery for ***Big Disney Family Home!*** Sleeps 12! Private Pool, Spa and Game Room!
9.89.8 out of 10 rating
Exceptional
(50 reviews)
***Big Disney Family Home!*** Sleeps 12! Private Pool, Spa and Game Room!
Kissimmee, FL
8% off
Price is NZ$3,764
NZ$3,764
NZ$538 per night
includes taxes & fees
Find spaces that suit your style
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Cottage
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Chalet
Find properties near top attractions in Old Town
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Find the best place to stay - Old Town
Barefoot Suites
Sleeps 6 · 1 bedroom · 2 bathrooms
9.09.0 out of 10
Wonderfulwonderful
1,727 reviews(1,727 reviews)
Regal Oaks Resort Vacation Townhomes by IDILIQ
Sleeps 10 · 4 bedrooms
8.48.4 out of 10
Very goodvery good
2,880 reviews(2,880 reviews)
Vacation Village at Parkway
Sleeps 4 · 1 bedroom
8.48.4 out of 10
Very goodvery good
1,951 reviews(1,951 reviews)
Barefoot'n Resort Kissimmee Orlando
Sleeps 4 · 1 bedroom
9.29.2 out of 10
Wonderfulwonderful
60 reviews(60 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
609 reviews(609 reviews)
3 BR/2 Bath Luxury Condo- Minutes to Disney / Sea World. Lots of Fun at the Reso
Sleeps 8 · 3 bedrooms · 2 bathrooms
9.29.2 out of 10
Wonderfulwonderful
131 reviews(131 reviews)
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
More for lessMore space, more privacy, more amenities — more value