Holiday rentals near Old Town
We found 29,329 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:10 Jul - 17 Jul
Image gallery for Emerald Pleasure Villa - Private Pool, Resort Community, Near Disney
8.48.4 out of 10, Very good, (23 reviews)
Very good
(23 reviews)
Emerald Pleasure Villa - Private Pool, Resort Community, Near Disney
Kissimmee
7% off
Price is NZ$3,386
NZ$3,386
for 7 nights, 1 villa
NZ$484 per night
includes taxes & fees
Image gallery for Private Pool Villa Near Disney – Kissimmee 3 Bed 2 Bath Emerald Island
9.29.2 out of 10, Wonderful, (42 reviews)
Wonderful
(42 reviews)
Private Pool Villa Near Disney – Kissimmee 3 Bed 2 Bath Emerald Island
Kissimmee
7% off
Price is NZ$2,486
NZ$2,486
for 7 nights, 1 home
NZ$355 per night
includes taxes & fees
Image gallery for "Escape to Paradise: Luxurious Vacation Home in Davenport, Florida"
1010 out of 10, Exceptional, (12 reviews)
Exceptional
(12 reviews)
"Escape to Paradise: Luxurious Vacation Home in Davenport, Florida"
Davenport
7% off
Price is NZ$4,204
NZ$4,204
for 7 nights, 1 villa
NZ$601 per night
includes taxes & fees
Image gallery for 4 Bed/3+ Bath Home w/ Screened Pool + Spa --
9.49.4 out of 10, Exceptional, (87 reviews)
Exceptional
(87 reviews)
4 Bed/3+ Bath Home w/ Screened Pool + Spa --
Davenport
7% off
Price is NZ$2,532
NZ$2,532
for 7 nights, 1 villa
NZ$362 per night
includes taxes & fees
Image gallery for Stylish and Cozy Pool Home near Disney in a Gated Community
9.69.6 out of 10, Exceptional, (24 reviews)
Exceptional
(24 reviews)
Stylish and Cozy Pool Home near Disney in a Gated Community
Kissimmee
7% off
Price is NZ$5,060
NZ$5,060
for 7 nights, 1 villa
NZ$723 per night
includes taxes & fees
Image gallery for Wonderful house! Grill, Heating pool and Jacuzzi included.
1010 out of 10, Exceptional, (32 reviews)
Exceptional
(32 reviews)
Wonderful house! Grill, Heating pool and Jacuzzi included.
Davenport
6% off
Price is NZ$4,894
NZ$4,894
for 7 nights, 1 villa
NZ$699 per night
includes taxes & fees
Image gallery for Sabal Palm House - Modern 7 BR Resort Home w/ Private Pool
1010 out of 10, Exceptional, (19 reviews)
Exceptional
(19 reviews)
Sabal Palm House - Modern 7 BR Resort Home w/ Private Pool
Kissimmee
7% off
Price is NZ$5,148
NZ$5,148
for 7 nights, 1 home
NZ$735 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, Exceptional, (18 reviews)
Exceptional
(18 reviews)
Really Fun House with tons of room, huge pool plenty to do and a terrific view
Kissimmee
8% off
Price is NZ$28,514
NZ$28,514
for 7 nights, 1 villa
NZ$4,073 per night
includes taxes & fees
Image gallery for Waterfront-HUGE Pool-2.7 miles to Disney, w/ 4 Masters Suites, Arcades, Theater!
9.69.6 out of 10, Exceptional, (133 reviews)
Exceptional
(133 reviews)
Waterfront-HUGE Pool-2.7 miles to Disney, w/ 4 Masters Suites, Arcades, Theater!
Kissimmee
8% off
Price is NZ$10,126
NZ$10,126
for 7 nights, 1 home
NZ$1,447 per night
includes taxes & fees
Image gallery for Villa Stella, 6 bedroom house in golf community near Disney World
9.49.4 out of 10, Exceptional, (42 reviews)
Exceptional
(42 reviews)
Villa Stella, 6 bedroom house in golf community near Disney World
Kissimmee
7% off
Price is NZ$5,136
NZ$5,136
for 7 nights, 1 home
NZ$734 per night
includes taxes & fees
Image gallery for ⭐⭐NEW!!!⭐⭐ Private Pool! In a Gated Resort Minutes from Disney! FREE Pool Heat!
8.48.4 out of 10, Very good, (32 reviews)
Very good
(32 reviews)
⭐⭐NEW!!!⭐⭐ Private Pool! In a Gated Resort Minutes from Disney! FREE Pool Heat!
Davenport
5% off
Price is NZ$5,078
NZ$5,078
for 7 nights, 1 home
NZ$725 per night
includes taxes & fees
Image gallery for Lakefront Sunsets, Private Pool, Lazy River, Clubhouse & 24~7 Owner Support
1010 out of 10, Exceptional, (75 reviews)
Exceptional
(75 reviews)
Lakefront Sunsets, Private Pool, Lazy River, Clubhouse & 24~7 Owner Support
Davenport
8% off
Price is NZ$4,280
NZ$4,280
for 7 nights, 1 home
NZ$611 per night
includes taxes & fees
Image gallery for Upstay: Stunning Resort Home w Hot Tub-Pool-Cinema
9.89.8 out of 10, Exceptional, (8 reviews)
Exceptional
(8 reviews)
Upstay: Stunning Resort Home w Hot Tub-Pool-Cinema
Davenport
7% off
Price is NZ$7,339
NZ$7,339
for 7 nights, 1 home
NZ$1,048 per night
includes taxes & fees
Image gallery for 5 MINS to DISNEY! Themed! Costumes, Toys, HEATED POOL/SPA, PS4, Grill.
1010 out of 10, Exceptional, (223 reviews)
Exceptional
(223 reviews)
5 MINS to DISNEY! Themed! Costumes, Toys, HEATED POOL/SPA, PS4, Grill.
Kissimmee
7% off
Price is NZ$5,239
NZ$5,239
for 7 nights, 1 home
NZ$748 per night
includes taxes & fees
Image gallery for AMZNG Townhome with Heated Pool - 5B 4.5B - Windsor Island Resort near Disney
9.49.4 out of 10, Exceptional, (46 reviews)
Exceptional
(46 reviews)
AMZNG Townhome with Heated Pool - 5B 4.5B - Windsor Island Resort near Disney
Davenport
7% off
Price is NZ$3,257
NZ$3,257
for 7 nights, 1 home
NZ$465 per night
includes taxes & fees
Image gallery for Villa 7757 - 3 mi from Disney, Free Heated Pool/Spa, BBQ, Game/Theater Rm, & PS5
9.89.8 out of 10, Exceptional, (108 reviews)
Exceptional
(108 reviews)
Villa 7757 - 3 mi from Disney, Free Heated Pool/Spa, BBQ, Game/Theater Rm, & PS5
Kissimmee
8% off
Price is NZ$6,131
NZ$6,131
for 7 nights, 1 home
NZ$876 per night
includes taxes & fees
Image gallery for 3076- Great Family Home near Disney, private pool, Storey Lake Resort
9.69.6 out of 10, Exceptional, (81 reviews)
Exceptional
(81 reviews)
3076- Great Family Home near Disney, private pool, Storey Lake Resort
Kissimmee
5% off
Price is NZ$3,737
NZ$3,737
for 7 nights, 1 home
NZ$534 per night
includes taxes & fees
Image gallery for 900- Great Family Home near Disney, private pool. Bellavida Resort.
9.69.6 out of 10, Exceptional, (55 reviews)
Exceptional
(55 reviews)
900- Great Family Home near Disney, private pool. Bellavida Resort.
Kissimmee
5% off
Price is NZ$3,662
NZ$3,662
for 7 nights, 1 home
NZ$523 per night
includes taxes & fees
Image gallery for Themed rooms - Near attractions - Private patio with BBQ grill and fire pit!
9.89.8 out of 10, Exceptional, (17 reviews)
Exceptional
(17 reviews)
Themed rooms - Near attractions - Private patio with BBQ grill and fire pit!
Davenport
5% off
Price is NZ$2,934
NZ$2,934
for 7 nights, 1 home
NZ$419 per night
includes taxes & fees
Image gallery for Upstay: 15BR Villa w Games Room, Pool & Cinema
9.29.2 out of 10, Wonderful, (18 reviews)
Wonderful
(18 reviews)
Upstay: 15BR Villa w Games Room, Pool & Cinema
Kissimmee
8% off
Price is NZ$23,367
NZ$23,367
for 7 nights, 1 home
NZ$3,338 per night
includes taxes & fees
Image gallery for Blue Villa Beauty- 3bed/3bath Margaritaville Resort
1010 out of 10, Exceptional, (68 reviews)
Exceptional
(68 reviews)
Blue Villa Beauty- 3bed/3bath Margaritaville Resort
Kissimmee
7% off
Price is NZ$2,791
NZ$2,791
for 7 nights, 1 home
NZ$399 per night
includes taxes & fees
Image gallery for Bahama Bay Highest Rated, best Location 3BR/2Bath, Recently Renovated 3rd Floor
9.69.6 out of 10, Exceptional, (175 reviews)
Exceptional
(175 reviews)
Bahama Bay Highest Rated, best Location 3BR/2Bath, Recently Renovated 3rd Floor
Davenport
8% off
Price is NZ$3,638
NZ$3,638
for 7 nights, 1 apartment
NZ$520 per night
includes taxes & fees
Image gallery for 588 - Great Family Home near Disney, private pool - Bellavida Resort
9.29.2 out of 10, Wonderful, (22 reviews)
Wonderful
(22 reviews)
588 - Great Family Home near Disney, private pool - Bellavida Resort
Kissimmee
5% off
Price is NZ$5,371
NZ$5,371
for 7 nights, 1 home
NZ$767 per night
includes taxes & fees
Image gallery for CLEAN! Themed rooms, HUGE pool,private yard, GREAT reviews, Game room, FreeGrill
1010 out of 10, Exceptional, (184 reviews)
Exceptional
(184 reviews)
CLEAN! Themed rooms, HUGE pool,private yard, GREAT reviews, Game room, FreeGrill
Kissimmee
8% off
Price is NZ$6,936
NZ$6,936
for 7 nights, 1 home
NZ$991 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'n Resort Kissimmee Orlando
Sleeps 4 · 1 bedroom
9.29.2 out of 10
Wonderful
wonderful
261 reviews
(261 reviews)
Regal Oaks Resort Vacation Townhomes by IDILIQ
8.48.4 out of 10
Very good
very good
3,099 reviews
(3,099 reviews)
2BR Family Suite With Waterpark Access | Orlando | Near Theme Parks
Sleeps 6 · 2 bedrooms · 1 bathroom
7.87.8 out of 10
Good
good
60 reviews
(60 reviews)
Barefoot Suites
Sleeps 6
9.09.0 out of 10
Wonderful
wonderful
1,854 reviews
(1,854 reviews)
Vacation Village Orlando, Celebration
Sleeps 2 · 1 bedroom
8.68.6 out of 10
Excellent
excellent
3,831 reviews
(3,831 reviews)
Popular 4 Bed Resort home, w/resort pool, & water slides. Disney 4 miles
Sleeps 8 · 4 bedrooms · 3+ bathrooms
8.88.8 out of 10
Excellent
excellent
18 reviews
(18 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