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Holiday rentals near Old Town
We found 29,579 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:1 Aug - 8 Aug
Image gallery for Super Fun House with Amazing Views
1010 out of 10 rating
Exceptional
(37 reviews)
Super Fun House with Amazing Views
Kissimmee, FL
8% off
Price is NZ$31,991
NZ$31,991
NZ$4,570 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
(115 reviews)
RATED#1 BEST HOME Near Disney! LUXURY 5BEDROOM 5Bath VILLA ,GATED RESORT ,POOL
Kissimmee, FL
7% off
Price is NZ$4,769
NZ$4,769
NZ$681 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
(149 reviews)
Big Pool&Spa/Themed rooms/Private yard/ CLOSE TO EVERYTHING, Lakeview,Playground
Kissimmee, FL
7% off
Price is NZ$4,814
NZ$4,814
NZ$688 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$2,564
NZ$2,564
NZ$366 per night
includes taxes & fees
Image gallery for Family Fun! ☀️ Private Heated Pool & Spa 4mi to Disney! 🦩
9.89.8 out of 10 rating
Exceptional
(15 reviews)
Family Fun! ☀️ Private Heated Pool & Spa 4mi to Disney! 🦩
Kissimmee, FL
8% off
Price is NZ$8,594
NZ$8,594
NZ$1,228 per night
includes taxes & fees
Image gallery for Reunion BRAND NEW Fancy Vacation Home
9.69.6 out of 10 rating
Exceptional
(14 reviews)
Reunion BRAND NEW Fancy Vacation Home
Kissimmee, FL
7% off
Price is NZ$5,866
NZ$5,866
NZ$838 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
(101 reviews)
Steps from clubhouse. "Be Our Guest" in Windsor Hills-Pool Heat
Kissimmee, FL
7% off
Price is NZ$3,053
NZ$3,053
NZ$436 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$6,131
NZ$6,131
NZ$876 per night
includes taxes & fees
Image gallery for *NEW* Windsor Hills - Ohana Oasis Pool Home Near Disney 4bd/4ba
9.69.6 out of 10 rating
Exceptional
(18 reviews)
*NEW* Windsor Hills - Ohana Oasis Pool Home Near Disney 4bd/4ba
Kissimmee, FL
8% off
Price is NZ$3,508
NZ$3,508
NZ$501 per night
includes taxes & fees
Image gallery for Prestige 2: Stunning Windsor at Westside, South Facing Pool/Spa, Game Rm
1010 out of 10 rating
Exceptional
(53 reviews)
Prestige 2: Stunning Windsor at Westside, South Facing Pool/Spa, Game Rm
Kissimmee, FL
5% off
Price is NZ$6,077
NZ$6,077
NZ$868 per night
includes taxes & fees
Image gallery for Orlando Disney World Inspired Five Bedroom Villa
1010 out of 10 rating
Exceptional
(39 reviews)
Orlando Disney World Inspired Five Bedroom Villa
Kissimmee, FL
7% off
Price is NZ$2,839
NZ$2,839
NZ$406 per night
includes taxes & fees
Image gallery for Family Friendly 4 Bd w Game Room Near Disney 5103
9.49.4 out of 10 rating
Exceptional
(20 reviews)
Family Friendly 4 Bd w Game Room Near Disney 5103
Kissimmee, Florida
7% off
Price is NZ$2,154
NZ$2,154
NZ$308 per night
includes taxes & fees
Image gallery for Stylish home, Themed Room with Private Pool
9.89.8 out of 10 rating
Exceptional
(25 reviews)
Stylish home, Themed Room with Private Pool
Davenport, FL
6% off
Price is NZ$3,615
NZ$3,615
NZ$516 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$2,153
NZ$2,153
NZ$308 per night
includes taxes & fees
Image gallery for Lake View and Top floor on Disney's doorstep - Great location
9.89.8 out of 10 rating
Exceptional
(46 reviews)
Lake View and Top floor on Disney's doorstep - Great location
Kissimmee, FL
7% off
Price is NZ$2,183
NZ$2,183
NZ$312 per night
includes taxes & fees
Image gallery for C4 Family Vacation close to Disney Theme Park
8.88.8 out of 10 rating
Excellent
(8 reviews)
C4 Family Vacation close to Disney Theme Park
Kissimmee, FL
7% off
Price is NZ$1,771
NZ$1,771
NZ$253 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
(29 reviews)
Unforgettable Escape: Private Pool, Smart TV, Dreamy Resort, Moments from Disney
Kissimmee, FL
6% off
Price is NZ$3,501
NZ$3,501
NZ$500 per night
includes taxes & fees
Image gallery for 5 Miles to Disney/Gorgeous Home/Wi-Fi/Parking/BBQ Grill/Family Friendly
9.69.6 out of 10 rating
Exceptional
(109 reviews)
5 Miles to Disney/Gorgeous Home/Wi-Fi/Parking/BBQ Grill/Family Friendly
Kissimmee, FL
7% off
Price is NZ$3,297
NZ$3,297
NZ$471 per night
includes taxes & fees
Image gallery for Resort Mansion w Pool, Hot Tub, Theatre, Games
8.48.4 out of 10 rating
Very good
(10 reviews)
Resort Mansion w Pool, Hot Tub, Theatre, Games
Kissimmee, Florida
8% off
Price is NZ$6,779
NZ$6,779
NZ$968 per night
includes taxes & fees
Image gallery for Corner House near Disney, 5BD Paradise, Gated Resort, Perfect Orlando Getaway!
9.69.6 out of 10 rating
Exceptional
(21 reviews)
Corner House near Disney, 5BD Paradise, Gated Resort, Perfect Orlando Getaway!
Kissimmee, FL
6% off
Price is NZ$3,055
NZ$3,055
NZ$436 per night
includes taxes & fees
Image gallery for 7 Bed, 5 Bath. 15 Mins From Closest Disney Attractions
8.88.8 out of 10 rating
Excellent
(30 reviews)
7 Bed, 5 Bath. 15 Mins From Closest Disney Attractions
Davenport, FL
7% off
Price is NZ$2,697
NZ$2,697
NZ$385 per night
includes taxes & fees
Image gallery for Upstay - Patio Paradise w Pool Spa Games & TikiBar
8.88.8 out of 10 rating
Excellent
(5 reviews)
Upstay - Patio Paradise w Pool Spa Games & TikiBar
Kissimmee, Florida
8% off
Price is NZ$17,394
NZ$17,394
NZ$2,485 per night
includes taxes & fees
Image gallery for Townhouse in Kissimmee Your perfect family getaway Fits up to 15 people! 4ba4be
8.08.0 out of 10 rating
Very good
(11 reviews)
Townhouse in Kissimmee Your perfect family getaway Fits up to 15 people! 4ba4be
Kissimmee, FL
11% off
Price is NZ$2,405
NZ$2,405
NZ$344 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
8% off
Price is NZ$3,990
NZ$3,990
NZ$570 per night
includes taxes & fees
Find spaces that suit your style
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Find properties near top attractions in Old Town
Map Attractions
Find the best place to stay - Old Town
Barefoot Suites
Sleeps 6 · 1 bedroom · 2 bathrooms
9.09.0 out of 10
Wonderfulwonderful
1,735 reviews(1,735 reviews)
Regal Oaks Resort Vacation Townhomes by IDILIQ
Sleeps 10 · 4 bedrooms
8.48.4 out of 10
Very goodvery good
2,885 reviews(2,885 reviews)
Barefoot'n Resort Kissimmee Orlando
Sleeps 4 · 1 bedroom
9.29.2 out of 10
Wonderfulwonderful
68 reviews(68 reviews)
Vacation Village at Parkway
Sleeps 8 · 2 bedrooms
8.48.4 out of 10
Very goodvery good
2,013 reviews(2,013 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
616 reviews(616 reviews)
Vacation USA LTD
Sleeps 7 · 3 bedrooms
6.86.8 out of 10
155 reviews(155 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