Holiday rentals near Winter Park Playhouse
We found 8,800 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:14 Nov - 21 Nov
Image gallery for Escape to Paradise!Luxury Waterfront Heated Pool House in Tranquil Neighborhood.
9.89.8 out of 10 rating
Exceptional
(19 reviews)
Escape to Paradise!Luxury Waterfront Heated Pool House in Tranquil Neighborhood.
Kissimmee, FL
12% off
Price is S$2,341
S$2,341
S$334 per night
includes taxes & fees
Image gallery for Downtown Floating Bungalow Historic Sanford Lake Monroe Marina
1010 out of 10 rating
Exceptional
(57 reviews)
Downtown Floating Bungalow Historic Sanford Lake Monroe Marina
Sanford, FL
8% off
Price is S$1,759
S$1,759
S$251 per night
includes taxes & fees
Image gallery for 14 Bedroom mansion that sleeps 40 people. Host your wedding reception here
9.89.8 out of 10 rating
Exceptional
(27 reviews)
14 Bedroom mansion that sleeps 40 people. Host your wedding reception here
Kissimmee, FL
7% off
Price is S$10,446
S$10,446
S$1,492 per night
includes taxes & fees
Image gallery for Winter Park Citrus Escape; sleeps 8, relaxing pool, family & pet friendly
9.29.2 out of 10 rating
Wonderful
(21 reviews)
Winter Park Citrus Escape; sleeps 8, relaxing pool, family & pet friendly
Winter Park, FL
8% off
Price is S$4,303
S$4,303
S$615 per night
includes taxes & fees
Image gallery for Upstay - Patio Paradise w Pool Spa Games & TikiBar
8.88.8 out of 10 rating
Excellent
(8 reviews)
Upstay - Patio Paradise w Pool Spa Games & TikiBar
Kissimmee, FL
7% off
Price is S$11,768
S$11,768
S$1,681 per night
includes taxes & fees
Image gallery for Historic 1920 Farmhouse on 6 acres,Huge Pool, Chef’s Kitchen,minutes to Mt Dora!
1010 out of 10 rating
Exceptional
(28 reviews)
Historic 1920 Farmhouse on 6 acres,Huge Pool, Chef’s Kitchen,minutes to Mt Dora!
Sorrento, FL
7% off
Price is S$4,088
S$4,088
S$584 per night
includes taxes & fees
Image gallery for Stylish Boutique Guest house in Winter Park
1010 out of 10 rating
Exceptional
(87 reviews)
Stylish Boutique Guest house in Winter Park
Winter Park, FL
7% off
Price is S$1,689
S$1,689
S$241 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 S$1,601
S$1,601
S$229 per night
includes taxes & fees
Image gallery for Orlando 5 Star-Disney, By Convention Center-Penthouse, Excellent for Large Group
9.49.4 out of 10 rating
Exceptional
(33 reviews)
Orlando 5 Star-Disney, By Convention Center-Penthouse, Excellent for Large Group
Orlando, FL
7% off
Price is S$2,991
S$2,991
S$427 per night
includes taxes & fees
Image gallery for Spacious Vacation Home 20 min from Theme Parks!
9.29.2 out of 10 rating
Wonderful
(56 reviews)
Spacious Vacation Home 20 min from Theme Parks!
Kissimmee, FL
7% off
Price is S$2,143
S$2,143
S$306 per night
includes taxes & fees
Image gallery for Luxury Floating House - Boat Tree Marina on St. John’s River, Sanford
9.69.6 out of 10 rating
Exceptional
(23 reviews)
Luxury Floating House - Boat Tree Marina on St. John’s River, Sanford
Sanford, FL
8% off
Price is S$1,497
S$1,497
S$214 per night
includes taxes & fees
Image gallery for Near Disney and USTA tennis campus - Pool Villa on the Lake - Stunning Views!
9.89.8 out of 10 rating
Exceptional
(61 reviews)
Near Disney and USTA tennis campus - Pool Villa on the Lake - Stunning Views!
Kissimmee, FL
8% off
Price is S$3,113
S$3,113
S$445 per night
includes taxes & fees
Image gallery for Spacious Family Retreat w Pool, BBQ & Ping Pong
8.68.6 out of 10 rating
Excellent
(7 reviews)
Spacious Family Retreat w Pool, BBQ & Ping Pong
Kissimmee, FL
7% off
Price is S$3,227
S$3,227
S$461 per night
includes taxes & fees
Image gallery for Super fun spacious family home with top amenities | Pool/Spa | Sleeps 24
8.68.6 out of 10 rating
Excellent
(21 reviews)
Super fun spacious family home with top amenities | Pool/Spa | Sleeps 24
Kissimmee, FL
6% off
Price is S$4,277
S$4,277
S$611 per night
includes taxes & fees
Image gallery for SPACIOUS 1 BEDROOM LOFT GOLF CART IN DISNEY AREA 5 STAR RATED MILL CREEK RESORT
9.49.4 out of 10 rating
Exceptional
(25 reviews)
SPACIOUS 1 BEDROOM LOFT GOLF CART IN DISNEY AREA 5 STAR RATED MILL CREEK RESORT
Kissimmee, FL
13% off
Price is S$1,097
S$1,097
S$157 per night
includes taxes & fees
Image gallery for Spacious 2-Bedroom House + Golf Cart 5 Star Near Disney Mill Creek Resort 2748
9.89.8 out of 10 rating
Exceptional
(9 reviews)
Spacious 2-Bedroom House + Golf Cart 5 Star Near Disney Mill Creek Resort 2748
Kissimmee, FL
13% off
Price is S$1,007
S$1,007
S$144 per night
includes taxes & fees
Image gallery for The Coastal Cottage@park Place Inn
9.29.2 out of 10 rating
Wonderful
(27 reviews)
The Coastal Cottage@park Place Inn
Sanford, FL
8% off
Price is S$1,635
S$1,635
S$234 per night
includes taxes & fees
Image gallery for * Beautiful Lakehouse with Pool and Movie Theater*
9.69.6 out of 10 rating
Exceptional
(31 reviews)
* Beautiful Lakehouse with Pool and Movie Theater*
Casselberry, FL
8% off
Price is S$6,767
S$6,767
S$967 per night
includes taxes & fees
Image gallery for Once Upon A Time@Storey Lake-9 Bedroom Disney Haven w/ Game Room & Private Pool!
1010 out of 10 rating
Exceptional
(64 reviews)
Once Upon A Time@Storey Lake-9 Bedroom Disney Haven w/ Game Room & Private Pool!
Kissimmee, FL
7% off
Price is S$4,758
S$4,758
S$680 per night
includes taxes & fees
Image gallery for OASIS PALM HAVEN – 20 minutes to the Disney/Universal theme Parks
9.69.6 out of 10 rating
Exceptional
(79 reviews)
OASIS PALM HAVEN – 20 minutes to the Disney/Universal theme Parks
Kissimmee, FL
7% off
Price is S$1,692
S$1,692
S$242 per night
includes taxes & fees
Image gallery for Ultimate Lakeview Villa with Everything!
9.89.8 out of 10 rating
Exceptional
(370 reviews)
Ultimate Lakeview Villa with Everything!
Kissimmee, FL
7% off
Price is S$4,010
S$4,010
S$573 per night
includes taxes & fees
Image gallery for Spacious and Beautiful, South Facing Pool Spa, 3 miles to Disney, Key Less Entry
9.29.2 out of 10 rating
Wonderful
(80 reviews)
Spacious and Beautiful, South Facing Pool Spa, 3 miles to Disney, Key Less Entry
Orlando, FL
23% off
Price is S$2,202
S$2,202
S$315 per night
includes taxes & fees
Image gallery for Spacious & Private Guest Pool House Oasis
9.69.6 out of 10 rating
Exceptional
(14 reviews)
Spacious & Private Guest Pool House Oasis
Orlando, FL
8% off
Price is S$1,797
S$1,797
S$257 per night
includes taxes & fees
Image gallery for King bd / Charming 2 story cottage w/ Private Yard
1010 out of 10 rating
Exceptional
(16 reviews)
King bd / Charming 2 story cottage w/ Private Yard
Orlando, FL
11% off
Price is S$4,277
S$4,277
S$611 per night
includes taxes & fees
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Find the best place to stay - Winter Park Playhouse
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
686 reviews(686 reviews)
The Ultimate 10,350 sq ft Orlando Estate - Your Private Resort Near Disney
Sleeps 28 · 8 bedrooms · 9+ bathrooms
1010 out of 10
Exceptionalexceptional
22 reviews(22 reviews)
Vacation Village at Parkway
Sleeps 8 · 2 bedrooms · 2 bathrooms
8.68.6 out of 10
Excellentexcellent
2,724 reviews(2,724 reviews)
Spacious Bowling Villa, Lake Views, 14 Bdr/14bath, close to Disney, Sleeps 38
Sleeps 38 · 14 bedrooms · 14+ bathrooms
1010 out of 10
Exceptionalexceptional
24 reviews(24 reviews)
Lakeview Luxury Villa with Everything
Sleeps 19 · 8 bedrooms · 5 bathrooms
9.89.8 out of 10
Exceptionalexceptional
380 reviews(380 reviews)
Modern Luxury Villa with Everything
Sleeps 19 · 8 bedrooms · 5 bathrooms
9.89.8 out of 10
Exceptionalexceptional
432 reviews(432 reviews)
Top rated rentals - Winter Park Playhouse
Together with friends
1010 out of 10
Exceptionalexceptional
106 reviews(106 reviews)
Beautiful cottage, great location! The owner was so responsive to the one little issue we had. Will definitely stay again when we are back in the area.
Barbara W.
Stayed Jun 2022
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