
Holiday rentals near Orlando Shakespeare Theater
We found 12,289 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 AU$11,923
AU$11,923
AU$1,703 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 AU$5,396
AU$5,396
AU$771 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$12,437
AU$12,437
AU$1,777 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 AU$13,916
AU$13,916
AU$1,988 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 AU$2,145
AU$2,145
AU$306 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 AU$6,779
AU$6,779
AU$968 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 AU$2,548
AU$2,548
AU$364 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 AU$1,781
AU$1,781
AU$254 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 AU$2,007
AU$2,007
AU$287 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$3,705
AU$3,705
AU$529 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 AU$3,877
AU$3,877
AU$554 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 AU$2,145
AU$2,145
AU$306 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 AU$1,222
AU$1,222
AU$175 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 AU$4,771
AU$4,771
AU$682 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 AU$5,671
AU$5,671
AU$810 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 AU$2,013
AU$2,013
AU$288 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 AU$6,656
AU$6,656
AU$951 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 AU$1,946
AU$1,946
AU$278 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
(65 reviews)
Modern Vista Cay Condo |Across from Epic Universe |Great Resort Amenities |Pet-Friendly |Sleeps 6
Orlando, FL
18% off
Price is AU$3,458
AU$3,458
AU$494 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 AU$1,189
AU$1,189
AU$170 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 AU$5,071
AU$5,071
AU$724 per night
includes taxes & fees
Image gallery for Location! Lakefront, Pool/Spa, Arcade, Themed KidsRooms, Porch, Grill, LazyRiver

1010 out of 10 rating
Exceptional
(61 reviews)
Location! Lakefront, Pool/Spa, Arcade, Themed KidsRooms, Porch, Grill, LazyRiver
Kissimmee, FL
7% off
Price is AU$8,040
AU$8,040
AU$1,149 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 AU$2,070
AU$2,070
AU$296 per night
includes taxes & fees
Image gallery for 3min Walk To Water Park, Game Rm, Fun For All Ages, Traveling Around the World

1010 out of 10 rating
Exceptional
(48 reviews)
3min Walk To Water Park, Game Rm, Fun For All Ages, Traveling Around the World
Kissimmee, FL
10% off
Price is AU$6,624
AU$6,624
AU$946 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