Holiday rentals near Winter Park Playhouse
We found 8,668 holiday rentals — enter your dates for availability
Select the perfect private holiday rental that's near Winter Park Playhouse. Holiday rentals provide the best amenities for you and your friends, family or even pets, such as parking and a washer and dryer. You'll be sure to find a property to rent to meet everyone's needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Winter Park Playhouse
Showing deals for:26 Sept - 3 Oct
Image gallery for DISNEY LUXURIOUS /5BD/ POLL SONOMA WHITEROSE VILLA LUXURY MEETS AFFORDABILITY
9.09.0 out of 10 rating
Wonderful
(7 reviews)
DISNEY LUXURIOUS /5BD/ POLL SONOMA WHITEROSE VILLA LUXURY MEETS AFFORDABILITY
Kissimmee, FL
10% off
Price is NZ$3,990
NZ$3,990
NZ$570 per night
includes taxes & fees
Image gallery for Escape to Paradise! Luxury Waterfront Heated Pool House in Tranquil Neighborhood
9.89.8 out of 10 rating
Exceptional
(16 reviews)
Escape to Paradise! Luxury Waterfront Heated Pool House in Tranquil Neighborhood
Kissimmee, FL
12% off
Price is NZ$3,052
NZ$3,052
NZ$436 per night
includes taxes & fees
Image gallery for THE CHLOE by EVRH
9.09.0 out of 10 rating
Wonderful
(60 reviews)
THE CHLOE by EVRH
Altamonte Springs, FL
7% off
Price is NZ$3,158
NZ$3,158
NZ$451 per night
includes taxes & fees
Image gallery for Cozy Suite in the Heart of Orlando near Universal Hot Tub Spa
9.29.2 out of 10 rating
Wonderful
(16 reviews)
Cozy Suite in the Heart of Orlando near Universal Hot Tub Spa
Orlando, FL
15% off
Price is NZ$1,085
NZ$1,085
NZ$155 per night
includes taxes & fees
Image gallery for Winter Park Citrus Escape; sleeps 8, relaxing pool, family & pet friendly
9.49.4 out of 10 rating
Exceptional
(17 reviews)
Winter Park Citrus Escape; sleeps 8, relaxing pool, family & pet friendly
Winter Park, FL
8% off
Price is NZ$3,568
NZ$3,568
NZ$510 per night
includes taxes & fees
Image gallery for Resort Like Private Pool Waterfront Retreat 4/2 Home in Orlando Weekly discounts
1010 out of 10 rating
Exceptional
(116 reviews)
Resort Like Private Pool Waterfront Retreat 4/2 Home in Orlando Weekly discounts
Orlando, FL
7% off
Price is NZ$2,969
NZ$2,969
NZ$424 per night
includes taxes & fees
Image gallery for Temporary living that feels like home where you can relax and be yourself.
1010 out of 10 rating
Exceptional
(142 reviews)
Temporary living that feels like home where you can relax and be yourself.
Maitland, FL
8% off
Price is NZ$2,276
NZ$2,276
NZ$325 per night
includes taxes & fees
Image gallery for Salt Pool, cozy House near Downtown and International Airport
9.89.8 out of 10 rating
Exceptional
(77 reviews)
Salt Pool, cozy House near Downtown and International Airport
Orlando, FL
7% off
Price is NZ$2,543
NZ$2,543
NZ$363 per night
includes taxes & fees
Image gallery for Lakeside and Beautiful
1010 out of 10 rating
Exceptional
(27 reviews)
Lakeside and Beautiful
Sanford, FL
7% off
Price is NZ$2,593
NZ$2,593
NZ$370 per night
includes taxes & fees
Image gallery for Luxury, Lakeview away from it all...
9.89.8 out of 10 rating
Exceptional
(102 reviews)
Luxury, Lakeview away from it all...
Orlando, FL
7% off
Price is NZ$1,712
NZ$1,712
NZ$245 per night
includes taxes & fees
Image gallery for PentHouse Suite with 2X View
1010 out of 10 rating
Exceptional
(28 reviews)
PentHouse Suite with 2X View
Orlando, FL
8% off
Price is NZ$3,281
NZ$3,281
NZ$469 per night
includes taxes & fees
Image gallery for 🧡 Unique 6/3, Pool, Pergola, 🎥 Movie/Game Room, UCF, Disney, Beaches, 5⭐!
9.89.8 out of 10 rating
Exceptional
(74 reviews)
🧡 Unique 6/3, Pool, Pergola, 🎥 Movie/Game Room, UCF, Disney, Beaches, 5⭐!
Oviedo, FL
8% off
Price is NZ$4,353
NZ$4,353
NZ$622 per night
includes taxes & fees
Image gallery for Floating Cottage Summer and Fall Rates Reduced
1010 out of 10 rating
Exceptional
(157 reviews)
Floating Cottage Summer and Fall Rates Reduced
Sanford, FL
11% off
Price is NZ$2,084
NZ$2,084
NZ$298 per night
includes taxes & fees
Image gallery for Spacious Vacation Home 20 min from Theme Parks!
9.49.4 out of 10 rating
Exceptional
(51 reviews)
Spacious Vacation Home 20 min from Theme Parks!
Kissimmee, FL
7% off
Price is NZ$2,790
NZ$2,790
NZ$399 per night
includes taxes & fees
Image gallery for Lakefront Artist's Loft - Isolate in Luxury!
9.69.6 out of 10 rating
Exceptional
(55 reviews)
Lakefront Artist's Loft - Isolate in Luxury!
Orlando, FL
7% off
Price is NZ$1,867
NZ$1,867
NZ$267 per night
includes taxes & fees
Image gallery for Charming 1920's House - pet friendly, 45 minutes from beach & attractions!
1010 out of 10 rating
Exceptional
(12 reviews)
Charming 1920's House - pet friendly, 45 minutes from beach & attractions!
Sanford, FL
16% off
Price is NZ$2,859
NZ$2,859
NZ$408 per night
includes taxes & fees
Image gallery for CountryClub Lakeview Home Away from Home
9.29.2 out of 10 rating
Wonderful
(61 reviews)
CountryClub Lakeview Home Away from Home
Orlando, FL
7% off
Price is NZ$1,712
NZ$1,712
NZ$245 per night
includes taxes & fees
Image gallery for Home away from Home Luxury 2 bed/2bath Country Club Condo
9.69.6 out of 10 rating
Exceptional
(56 reviews)
Home away from Home Luxury 2 bed/2bath Country Club Condo
Orlando, FL
7% off
Price is NZ$1,712
NZ$1,712
NZ$245 per night
includes taxes & fees
Image gallery for NOT YOUR TYPICAL HOUSEBOAT: 60 FEET OF FUN!
9.89.8 out of 10 rating
Exceptional
(95 reviews)
NOT YOUR TYPICAL HOUSEBOAT: 60 FEET OF FUN!
Sanford, FL
8% off
Price is NZ$2,708
NZ$2,708
NZ$387 per night
includes taxes & fees
Image gallery for THE OLIVIA by EVRH
8.68.6 out of 10 rating
Excellent
(31 reviews)
THE OLIVIA by EVRH
Altamonte Springs, FL
7% off
Price is NZ$2,858
NZ$2,858
NZ$408 per night
includes taxes & fees
Image gallery for Spacious & Private Guest Pool House Oasis
9.69.6 out of 10 rating
Exceptional
(13 reviews)
Spacious & Private Guest Pool House Oasis
Orlando, FL
7% off
Price is NZ$1,690
NZ$1,690
NZ$241 per night
includes taxes & fees
Image gallery for The Launch Pad with a pool! King bed and private backyard
9.29.2 out of 10 rating
Wonderful
(45 reviews)
The Launch Pad with a pool! King bed and private backyard
Orlando, FL
7% off
Price is NZ$2,452
NZ$2,452
NZ$350 per night
includes taxes & fees
Image gallery for Lake Front Suite -Close to all Attractions
9.49.4 out of 10 rating
Exceptional
(73 reviews)
Lake Front Suite -Close to all Attractions
Apopka, FL
8% off
Price is NZ$1,112
NZ$1,112
NZ$159 per night
includes taxes & fees
Image gallery for Orlando Happy Guest House by Universal Studios
1010 out of 10 rating
Exceptional
(10 reviews)
Orlando Happy Guest House by Universal Studios
Orlando, FL
8% off
Price is NZ$2,023
NZ$2,023
NZ$289 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Winter Park Playhouse
Showing deals for: 22 Sept - 25 Sept
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
639 reviews(639 reviews)
The current price is NZ$748
NZ$748
for 3 nights, 1 apartment
NZ$249 per night
includes taxes & fees
Vacation Village at Parkway
Sleeps 8 · 2 bedrooms · 2 bathrooms
8.68.6 out of 10
Excellentexcellent
2,280 reviews(2,280 reviews)
The current price is NZ$410
NZ$410
for 3 nights, 1 apartment
NZ$137 per night
includes taxes & fees
Lakeview Luxury Villa with Everything
Sleeps 19 · 8 bedrooms · 5 bathrooms
9.89.8 out of 10
Exceptionalexceptional
362 reviews(362 reviews)
The current price is NZ$2,527
NZ$2,527
for 3 nights, 1 villa
NZ$842 per night
includes taxes & fees
Lake Buena Vista Resort Village & Spa
Sleeps 8 · 1 bedroom
8.48.4 out of 10
Very goodvery good
8,871 reviews(8,871 reviews)
The current price is NZ$884
NZ$884
for 3 nights, 1 apartment
NZ$295 per night
includes taxes & fees
Margaritaville Cottages Orlando with H2O Waterpark by Rentyl
Sleeps 12
8.88.8 out of 10
Excellentexcellent
1,439 reviews(1,439 reviews)
The current price is NZ$1,161
NZ$1,161
for 3 nights, 1 room
NZ$387 per night
includes taxes & fees
Modern Luxury Villa with Everything
Sleeps 19 · 8 bedrooms · 5 bathrooms
9.89.8 out of 10
Exceptionalexceptional
421 reviews(421 reviews)
The current price is NZ$2,527
NZ$2,527
for 3 nights, 1 villa
NZ$842 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
More for lessMore space, more privacy, more amenities — more value