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Holiday rentals near Old Town
We found 29,615 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:12 Sept - 19 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 AU$3,157
AU$3,157
AU$451 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 AU$4,030
AU$4,030
AU$576 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
23% off
Price is AU$19,513
AU$19,513
AU$2,788 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 AU$3,045
AU$3,045
AU$435 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 AU$2,850
AU$2,850
AU$407 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 AU$3,590
AU$3,590
AU$513 per night
includes taxes & fees
Image gallery for 3BR/2B condo with views of Disney FIREWORKS!!!!
9.89.8 out of 10 rating
Exceptional
(32 reviews)
3BR/2B condo with views of Disney FIREWORKS!!!!
Kissimmee, FL
8% off
Price is AU$1,314
AU$1,314
AU$188 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 AU$3,228
AU$3,228
AU$461 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 AU$2,614
AU$2,614
AU$373 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
8% off
Price is AU$3,658
AU$3,658
AU$523 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 AU$3,393
AU$3,393
AU$485 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
8% off
Price is AU$14,868
AU$14,868
AU$2,124 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 AU$1,937
AU$1,937
AU$277 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 AU$2,334
AU$2,334
AU$333 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 AU$4,844
AU$4,844
AU$692 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 AU$2,672
AU$2,672
AU$382 per night
includes taxes & fees
Image gallery for Windsor Hills Condo - Closest to the pool! - 10 minutes from Disney
9.89.8 out of 10 rating
Exceptional
(74 reviews)
Windsor Hills Condo - Closest to the pool! - 10 minutes from Disney
Kissimmee, FL
7% off
Price is AU$1,750
AU$1,750
AU$250 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 AU$2,916
AU$2,916
AU$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 AU$2,023
AU$2,023
AU$289 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
8% off
Price is AU$3,300
AU$3,300
AU$471 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
(36 reviews)
Amazing vacation Townhome at Solterra Resort - 20min from Disney
Davenport, FL
7% off
Price is AU$2,009
AU$2,009
AU$287 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 AU$2,245
AU$2,245
AU$321 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 AU$2,203
AU$2,203
AU$315 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 AU$1,404
AU$1,404
AU$201 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
Barefoot Suites
Sleeps 6 · 1 bedroom · 2 bathrooms
9.09.0 out of 10
Wonderfulwonderful
1,750 reviews(1,750 reviews)
Regal Oaks Resort Vacation Townhomes by IDILIQ
Sleeps 10 · 4 bedrooms
8.48.4 out of 10
Very goodvery good
2,914 reviews(2,914 reviews)
Barefoot'n Resort Kissimmee Orlando
Sleeps 4 · 1 bedroom
9.09.0 out of 10
Wonderfulwonderful
102 reviews(102 reviews)
3 BR/2 Bath Luxury Condo- Minutes to Disney / Sea World. Lots of Fun at the Reso
Sleeps 8 · 3 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
136 reviews(136 reviews)
Vacation USA LTD
Sleeps 7 · 3 bedrooms
6.66.6 out of 10
156 reviews(156 reviews)
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)
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