Holiday rentals near Winter Park Playhouse
We found 8,671 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:21 Nov - 28 Nov
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 AU$2,155
AU$2,155
AU$308 per night
includes taxes & fees
Image gallery for 4 Bedroom 2 Bath Pet-Friendly Pool Home Orlando Airport
9.89.8 out of 10 rating
Exceptional
(10 reviews)
4 Bedroom 2 Bath Pet-Friendly Pool Home Orlando Airport
Orlando, FL
11% off
Price is AU$3,185
AU$3,185
AU$455 per night
includes taxes & fees
Image gallery for Winter Park Citrus Escape; sleeps 8, relaxing pool, family & pet friendly
9.09.0 out of 10 rating
Wonderful
(22 reviews)
Winter Park Citrus Escape; sleeps 8, relaxing pool, family & pet friendly
Winter Park, FL
8% off
Price is AU$4,758
AU$4,758
AU$680 per night
includes taxes & fees
Image gallery for Salt Pool, cozy House near Downtown and International Airport
9.69.6 out of 10 rating
Exceptional
(80 reviews)
Salt Pool, cozy House near Downtown and International Airport
Orlando, FL
7% off
Price is AU$2,477
AU$2,477
AU$354 per night
includes taxes & fees
Image gallery for Cozy Suite in the Heart of Orlando near Universal Hot Tub Spa
9.09.0 out of 10 rating
Wonderful
(18 reviews)
Cozy Suite in the Heart of Orlando near Universal Hot Tub Spa
Orlando, FL
16% off
Price is AU$986
AU$986
AU$141 per night
includes taxes & fees
Image gallery for Beautiful 3 Bedroom 2 full bath 2 car 🚗 garage.
1010 out of 10 rating
Exceptional
(17 reviews)
Beautiful 3 Bedroom 2 full bath 2 car 🚗 garage.
Oviedo, FL
13% off
Price is AU$3,669
AU$3,669
AU$524 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
8% off
Price is AU$23,018
AU$23,018
AU$3,288 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
(24 reviews)
Luxury Floating House - Boat Tree Marina on St. John’s River, Sanford
Sanford, FL
8% off
Price is AU$1,818
AU$1,818
AU$260 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 AU$1,943
AU$1,943
AU$278 per night
includes taxes & fees
Image gallery for Walk into Tropical Paradise - POOL - GYM - HOT TUB
1010 out of 10 rating
Exceptional
(5 reviews)
Walk into Tropical Paradise - POOL - GYM - HOT TUB
Altamonte Springs, FL
8% off
Price is AU$6,577
AU$6,577
AU$940 per night
includes taxes & fees
Image gallery for THE OLIVIA by EVRH
8.88.8 out of 10 rating
Excellent
(34 reviews)
THE OLIVIA by EVRH
Altamonte Springs, FL
7% off
Price is AU$2,664
AU$2,664
AU$381 per night
includes taxes & fees
Image gallery for CountryClub 2/2 Home Away from Home
9.49.4 out of 10 rating
Exceptional
(63 reviews)
CountryClub 2/2 Home Away from Home
Orlando, FL
8% off
Price is AU$1,575
AU$1,575
AU$225 per night
includes taxes & fees
Image gallery for Pool+Grill+Huge yard+outdoor movies+Plenty parking space
9.29.2 out of 10 rating
Wonderful
(9 reviews)
Pool+Grill+Huge yard+outdoor movies+Plenty parking space
Apopka, FL
5% off
Price is AU$4,655
AU$4,655
AU$665 per night
includes taxes & fees
Image gallery for The Launch Pad with a pool! King bed and private backyard
9.09.0 out of 10 rating
Wonderful
(50 reviews)
The Launch Pad with a pool! King bed and private backyard
Orlando, FL
7% off
Price is AU$2,283
AU$2,283
AU$326 per night
includes taxes & fees
Image gallery for Orlando Happy Guest House by Universal Studios
1010 out of 10 rating
Exceptional
(12 reviews)
Orlando Happy Guest House by Universal Studios
Orlando, FL
8% off
Price is AU$2,221
AU$2,221
AU$317 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
(62 reviews)
Near Disney and USTA tennis campus - Pool Villa on the Lake - Stunning Views!
Kissimmee, FL
8% off
Price is AU$3,918
AU$3,918
AU$560 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
8% off
Price is AU$5,254
AU$5,254
AU$751 per night
includes taxes & fees
Image gallery for Family Retreat w/ Pool, Lake View & Disney Nearby – 5BR Storey Lake Getaway
1010 out of 10 rating
Exceptional
(13 reviews)
Family Retreat w/ Pool, Lake View & Disney Nearby – 5BR Storey Lake Getaway
Kissimmee, FL
7% off
Price is AU$3,779
AU$3,779
AU$540 per night
includes taxes & fees
Image gallery for Upstay Luxury Resort Mansion w Pool—Near Disney
9.49.4 out of 10 rating
Exceptional
(6 reviews)
Upstay Luxury Resort Mansion w Pool—Near Disney
Kissimmee, FL
8% off
Price is AU$5,721
AU$5,721
AU$817 per night
includes taxes & fees
Image gallery for Pool, Jacuzzi, Cabana Oh My!! Welcome to Paradise
9.49.4 out of 10 rating
Exceptional
(34 reviews)
Pool, Jacuzzi, Cabana Oh My!! Welcome to Paradise
Orlando, FL
12% off
Price is AU$2,559
AU$2,559
AU$366 per night
includes taxes & fees
Image gallery for Orlando 20 Guest Villa Centrally Located with Game Room
1010 out of 10 rating
Exceptional
(6 reviews)
Orlando 20 Guest Villa Centrally Located with Game Room
Windermere, FL
16% off
Price is AU$3,936
AU$3,936
AU$562 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
7% off
Price is AU$1,742
AU$1,742
AU$249 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 AU$8,730
AU$8,730
AU$1,247 per night
includes taxes & fees
Image gallery for The Cozy Crash Pad: Tiny House Experience
9.29.2 out of 10 rating
Wonderful
(19 reviews)
The Cozy Crash Pad: Tiny House Experience
Orlando, FL
8% off
Price is AU$990
AU$990
AU$141 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Winter Park Playhouse
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
2,775 reviews(2,775 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
26 reviews(26 reviews)
Lakeview Luxury Villa with Everything
Sleeps 19 · 8 bedrooms · 5 bathrooms
9.89.8 out of 10
Exceptionalexceptional
382 reviews(382 reviews)
Modern Luxury Villa with Everything
Sleeps 19 · 8 bedrooms · 5 bathrooms
9.89.8 out of 10
Exceptionalexceptional
433 reviews(433 reviews)
Close to Attractions! Comfy Unit, Pool, Shuttle to Parks, Parking, Breakfast
Sleeps 4 · 1 bedroom · 1 bathroom
6.86.8 out of 10
196 reviews(196 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