
Holiday rentals near Orlando Shakespeare Theater
We found 12,253 holiday rentals — enter your dates for availability
Scroll through and discover holiday rentals within easy reach of Orlando Shakespeare Theater that can be your home away from home. Whether you're travelling with a group or just with your pet, holiday homes have the best amenities for hanging out with the people that matter most, such as Wi-Fi and cable TV. At the end of the day, you'll find a property to rent that has what everyone needs, including accessible or non-smoking choices.
Holiday rentals with weekly discounts - Orlando Shakespeare Theater
Showing deals for:14 Nov - 21 Nov
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 NZ$13,342
NZ$13,342
NZ$1,906 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 NZ$5,907
NZ$5,907
NZ$844 per night
includes taxes & fees
Image gallery for LAKEFRONT - kayak, fish, paddleboard, canoe, HOT TUB, golf -near Orlando

1010 out of 10 rating
Exceptional
(175 reviews)
LAKEFRONT - kayak, fish, paddleboard, canoe, HOT TUB, golf -near Orlando
Montverde, FL
6% off
Price is NZ$2,363
NZ$2,363
NZ$338 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 NZ$2,805
NZ$2,805
NZ$401 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 NZ$1,960
NZ$1,960
NZ$280 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
9% off
Price is NZ$7,405
NZ$7,405
NZ$1,058 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 NZ$13,912
NZ$13,912
NZ$1,987 per night
includes taxes & fees
Image gallery for Upstay Luxury Mansion w Pool, Hot tub and BBQ area

9.69.6 out of 10 rating
Exceptional
(8 reviews)
Upstay Luxury Mansion w Pool, Hot tub and BBQ area
Kissimmee, FL
8% off
Price is NZ$15,628
NZ$15,628
NZ$2,233 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 NZ$4,076
NZ$4,076
NZ$582 per night
includes taxes & fees
Image gallery for Our Retro Mod Pod-Disney & Old Town Minutes Away!

9.49.4 out of 10 rating
Exceptional
(8 reviews)
Our Retro Mod Pod-Disney & Old Town Minutes Away!
Kissimmee, FL
10% off
Price is NZ$1,356
NZ$1,356
NZ$194 per night
includes taxes & fees
Image gallery for SPACIOUS 1 BEDROOM LOFT IN DISNEY AREA 5 STAR RATED MILL CREEK RESORT 2767

9.49.4 out of 10 rating
Exceptional
(25 reviews)
SPACIOUS 1 BEDROOM LOFT IN DISNEY AREA 5 STAR RATED MILL CREEK RESORT 2767
Kissimmee, FL
13% off
Price is NZ$1,318
NZ$1,318
NZ$188 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 NZ$2,362
NZ$2,362
NZ$337 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 NZ$4,264
NZ$4,264
NZ$609 per night
includes taxes & fees
Image gallery for Spacious 2-Bedroom House 5 Star Near Disney Mill Creek Resort 2748

9.89.8 out of 10 rating
Exceptional
(9 reviews)
Spacious 2-Bedroom House 5 Star Near Disney Mill Creek Resort 2748
Kissimmee, FL
13% off
Price is NZ$1,318
NZ$1,318
NZ$188 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 NZ$2,217
NZ$2,217
NZ$317 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 NZ$2,141
NZ$2,141
NZ$306 per night
includes taxes & fees
Image gallery for Ultimate Lakeview Villa with Everything!

9.89.8 out of 10 rating
Exceptional
(372 reviews)
Ultimate Lakeview Villa with Everything!
Kissimmee, FL
7% off
Price is NZ$5,246
NZ$5,246
NZ$749 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 NZ$6,205
NZ$6,205
NZ$886 per night
includes taxes & fees
Image gallery for Modern Vista Cay Condo |Across from Epic Universe |Great Resort Amenities |Pet-Friendly |Sleeps 6

9.49.4 out of 10 rating
Exceptional
(66 reviews)
Modern Vista Cay Condo |Across from Epic Universe |Great Resort Amenities |Pet-Friendly |Sleeps 6
Orlando, FL
18% off
Price is NZ$3,808
NZ$3,808
NZ$544 per night
includes taxes & fees
Image gallery for Minutes to Disney ~ Private End Unit in Regal Oaks "Little Oasis" ~ Resort Pool

9.89.8 out of 10 rating
Exceptional
(70 reviews)
Minutes to Disney ~ Private End Unit in Regal Oaks "Little Oasis" ~ Resort Pool
Kissimmee, FL
7% off
Price is NZ$2,281
NZ$2,281
NZ$326 per night
includes taxes & fees
Image gallery for Minutes from Disney! Lake Buena Vista Resort 3 bed 2 bath. full kitchen/laundry

9.49.4 out of 10 rating
Exceptional
(100 reviews)
Minutes from Disney! Lake Buena Vista Resort 3 bed 2 bath. full kitchen/laundry
Orlando, FL
7% off
Price is NZ$2,386
NZ$2,386
NZ$341 per night
includes taxes & fees
Image gallery for Lakeview Luxury Villa with Everything

9.89.8 out of 10 rating
Exceptional
(102 reviews)
Lakeview Luxury Villa with Everything
Kissimmee, FL
7% off
Price is NZ$5,578
NZ$5,578
NZ$797 per night
includes taxes & fees
Image gallery for Lakeview Storey Lake 10BR/5BA-Pool/Spa/Rec-Close to Disney/Universal Studios

9.89.8 out of 10 rating
Exceptional
(46 reviews)
Lakeview Storey Lake 10BR/5BA-Pool/Spa/Rec-Close to Disney/Universal Studios
Kissimmee, FL
7% off
Price is NZ$7,275
NZ$7,275
NZ$1,039 per night
includes taxes & fees
Image gallery for Clear Lake Front home near Orlando / Sanford SFB Boombah

9.89.8 out of 10 rating
Exceptional
(39 reviews)
Clear Lake Front home near Orlando / Sanford SFB Boombah
Sanford, FL
8% off
Price is NZ$2,525
NZ$2,525
NZ$361 per night
includes taxes & fees
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Find the best place to stay - Orlando Shakespeare Theater
⚡️Summer Special! Bliss Pool Villa Close to Disney & Universal; Great Clubhouse🏝️
Sleeps 13 · 6 bedrooms · 5 bathrooms
1010 out of 10
Exceptionalexceptional
43 reviews(43 reviews)
Beautiful Summer Home
Sleeps 12 · 4 bedrooms · 3 bathrooms
9.89.8 out of 10
Exceptionalexceptional
236 reviews(236 reviews)
Chic Luxury Haven - Unforgettable Retreat
Sleeps 13 · 6 bedrooms · 5 bathrooms
9.09.0 out of 10
Wonderfulwonderful
15 reviews(15 reviews)
🧡 Unique 6/3, Pool, Pergola, 🎥 Movie/Game Room, UCF, Disney, Beaches, 5⭐!
Sleeps 20 · 6 bedrooms · 3 bathrooms
9.89.8 out of 10
Exceptionalexceptional
74 reviews(74 reviews)
“5BR/5BA Townhome w/ Screened Pool & Aquarius Club – Near SeaWorld”
Sleeps 14 · 5 bedrooms · 5 bathrooms
7.27.2 out of 10
Goodgood
5 reviews(5 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