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Holiday rentals near Old Town
We found 29,653 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:19 Sept - 26 Sept
Image gallery for RATED#1 BEST HOME Near Disney! LUXURY 5BEDROOM 5Bath VILLA ,GATED RESORT ,POOL
9.49.4 out of 10 rating
Exceptional
(116 reviews)
RATED#1 BEST HOME Near Disney! LUXURY 5BEDROOM 5Bath VILLA ,GATED RESORT ,POOL
Kissimmee, FL
7% off
Price is NZ$3,464
NZ$3,464
NZ$495 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
(151 reviews)
Big Pool&Spa/Themed rooms/Private yard/ CLOSE TO EVERYTHING, Lakeview,Playground
Kissimmee, FL
7% off
Price is NZ$4,421
NZ$4,421
NZ$632 per night
includes taxes & fees
Image gallery for Really Fun House with tons of room, huge pool plenty to do and a terrific view
1010 out of 10 rating
Exceptional
(5 reviews)
Really Fun House with tons of room, huge pool plenty to do and a terrific view
Kissimmee, FL
22% off
Price is NZ$22,573
NZ$22,573
NZ$3,225 per night
includes taxes & fees
Image gallery for 3 Miles from Disney!!!!! 4 Bedroom Villa with Private Pool/Game Room
1010 out of 10 rating
Exceptional
(15 reviews)
3 Miles from Disney!!!!! 4 Bedroom Villa with Private Pool/Game Room
Kissimmee, FL
7% off
Price is NZ$3,127
NZ$3,127
NZ$447 per night
includes taxes & fees
Image gallery for Free Pool Heat and BBQ! No Rear Neighbors! South Facing Pool!-AC Game Room!
9.89.8 out of 10 rating
Exceptional
(91 reviews)
Free Pool Heat and BBQ! No Rear Neighbors! South Facing Pool!-AC Game Room!
Kissimmee, FL
9% off
Price is NZ$3,293
NZ$3,293
NZ$470 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$3,547
NZ$3,547
NZ$507 per night
includes taxes & fees
Image gallery for Sun filled south facing pool & spa with no rear neighbors! Game room!
1010 out of 10 rating
Exceptional
(60 reviews)
Sun filled south facing pool & spa with no rear neighbors! Game room!
Kissimmee, FL
7% off
Price is NZ$3,939
NZ$3,939
NZ$563 per night
includes taxes & fees
Image gallery for Villa with a pool/spa - close to Disney!
9.69.6 out of 10 rating
Exceptional
(95 reviews)
Villa with a pool/spa - close to Disney!
Davenport, FL
10% off
Price is NZ$3,544
NZ$3,544
NZ$506 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$2,839
NZ$2,839
NZ$406 per night
includes taxes & fees
Image gallery for Large Two Story Home with TWO Master Bedrooms with attached full baths.
1010 out of 10 rating
Exceptional
(55 reviews)
Large Two Story Home with TWO Master Bedrooms with attached full baths.
Kissimmee, FL
7% off
Price is NZ$4,012
NZ$4,012
NZ$573 per night
includes taxes & fees
Image gallery for Luxury resort mansion with swim up bar,pool slide,restaurants, golf, and Disney!
9.49.4 out of 10 rating
Exceptional
(34 reviews)
Luxury resort mansion with swim up bar,pool slide,restaurants, golf, and Disney!
Kissimmee, FL
7% off
Price is NZ$17,449
NZ$17,449
NZ$2,493 per night
includes taxes & fees
Image gallery for Reunion Resort -Free pool and spa heat - Designer home - - WHOLE HOUSE DVR -
9.49.4 out of 10 rating
Exceptional
(172 reviews)
Reunion Resort -Free pool and spa heat - Designer home - - WHOLE HOUSE DVR -
Kissimmee, FL
7% off
Price is NZ$3,680
NZ$3,680
NZ$526 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
(102 reviews)
Steps from clubhouse. "Be Our Guest" in Windsor Hills-Pool Heat
Kissimmee, FL
7% off
Price is NZ$2,108
NZ$2,108
NZ$301 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
(96 reviews)
SUNSHINE 🌞 and SMILES😎 - 5 mi to Disney, 4 bdrm / 3 bath, Private Pool
Kissimmee, FL
7% off
Price is NZ$2,535
NZ$2,535
NZ$362 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$2,934
NZ$2,934
NZ$419 per night
includes taxes & fees
Image gallery for Sleeps 26! Resort Home w/ On-Site Waterpark, Pool | Flamingo Grove by AvantStay
1010 out of 10 rating
Exceptional
(13 reviews)
Sleeps 26! Resort Home w/ On-Site Waterpark, Pool | Flamingo Grove by AvantStay
Davenport, Florida
6% off
Price is NZ$5,290
NZ$5,290
NZ$756 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
13% off
Price is NZ$3,200
NZ$3,200
NZ$457 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$2,186
NZ$2,186
NZ$312 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
(65 reviews)
😎RELAX at Windsor Hills🌴, minutes to Disney - 5 bed / 5 bath, Private Pool🌞
Kissimmee, FL
7% off
Price is NZ$3,621
NZ$3,621
NZ$517 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$2,437
NZ$2,437
NZ$348 per night
includes taxes & fees
Image gallery for Fun-Filled 5-Bedroom Home with Private Pool & Steps from Water Park!
1010 out of 10 rating
Exceptional
(10 reviews)
Fun-Filled 5-Bedroom Home with Private Pool & Steps from Water Park!
Davenport, FL
7% off
Price is NZ$2,394
NZ$2,394
NZ$342 per night
includes taxes & fees
Image gallery for Spacious condo close to Disney with heated pools, hot tubs, lots of amenities!
9.49.4 out of 10 rating
Exceptional
(15 reviews)
Spacious condo close to Disney with heated pools, hot tubs, lots of amenities!
Davenport, FL
7% off
Price is NZ$1,516
NZ$1,516
NZ$217 per night
includes taxes & fees
Image gallery for Welcome to Dream Weaver, 3/2 top floor condo with elevators, 3 miles from Disney
9.89.8 out of 10 rating
Exceptional
(81 reviews)
Welcome to Dream Weaver, 3/2 top floor condo with elevators, 3 miles from Disney
Kissimmee, FL
9% off
Price is NZ$1,783
NZ$1,783
NZ$255 per night
includes taxes & fees
Image gallery for Arcades, Mustang Pool Table, As Seen on TV, Massage Chair: The Adventurer
9.89.8 out of 10 rating
Exceptional
(47 reviews)
Arcades, Mustang Pool Table, As Seen on TV, Massage Chair: The Adventurer
Kissimmee, FL
6% off
Price is NZ$6,232
NZ$6,232
NZ$890 per night
includes taxes & fees
Find spaces that suit your style
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Find properties near top attractions in Old Town
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Find the best place to stay - Old Town
Showing deals for: 13 Sept - 16 Sept
Barefoot Suites
Sleeps 6 · 1 bedroom · 2 bathrooms
9.09.0 out of 10
Wonderfulwonderful
1,750 reviews(1,750 reviews)
The current price is NZ$670
NZ$670
for 3 nights, 1 room
NZ$223 per night
includes taxes & fees
Regal Oaks Resort Vacation Townhomes by IDILIQ
Sleeps 10 · 4 bedrooms
8.48.4 out of 10
Very goodvery good
2,915 reviews(2,915 reviews)
The current price is NZ$897
NZ$897
for 3 nights, 1 apartment
NZ$299 per night
includes taxes & fees
Barefoot'n Resort Kissimmee Orlando
Sleeps 4 · 1 bedroom
9.09.0 out of 10
Wonderfulwonderful
102 reviews(102 reviews)
The current price is NZ$569
NZ$569
for 3 nights, 1 room
NZ$190 per night
includes taxes & fees
Vacation USA LTD
Sleeps 7 · 3 bedrooms
6.66.6 out of 10
156 reviews(156 reviews)
The current price is NZ$1,253
NZ$1,253
for 3 nights, 1 home
NZ$418 per night
includes taxes & fees
Charming Home Perfect for Families! 3/3 with Pool
Sleeps 6 · 3 bedrooms · 3 bathrooms
9.29.2 out of 10
Wonderfulwonderful
125 reviews(125 reviews)
The current price is NZ$1,073
NZ$1,073
for 3 nights, 1 home
NZ$358 per night
includes taxes & fees
3 BR/2 Bath Luxury Condo- Minutes to Disney / Sea World. Lots of Fun at the Reso
Sleeps 8 · 3 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
136 reviews(136 reviews)
The current price is NZ$842
NZ$842
for 3 nights, 1 apartment
NZ$281 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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