
Vacation rentals near Theatre Downtown
We found 12,432 vacation rentals — enter your dates for availability
Discover a selection of private vacation rentals near Theatre Downtown that provide the perfect home base for your trip. Whether you're traveling with your kids or with friends, vacation rentals have the amenities you expect for your stay, which might include WiFi and a washer and dryer. You'll be able to choose a rental for everyone's needs, including options that are accessible or non-smoking.
Vacation rentals with weekly discounts - Theatre Downtown
Showing deals for:Nov 14 - Nov 21
Image gallery for Water Lovers Retreat

1010 out of 10 rating
Exceptional
(107 reviews)
Water Lovers Retreat
Sanford, FL
5% off
Price is CA $221
CA $221
CA $2,254 total
CA $2,254 total
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
10% off
Price is CA $1,118
CA $1,118
CA $10,726 total
CA $10,726 total
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
10% off
Price is CA $533
CA $533
CA $4,859 total
CA $4,859 total
includes taxes & fees
Image gallery for Relax by the pool at this retreat near parks, kayaking, and downtown.

1010 out of 10 rating
Exceptional
(168 reviews)
Relax by the pool at this retreat near parks, kayaking, and downtown.
Longwood, FL
5% off
Price is CA $95
CA $95
CA $865 total
CA $865 total
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
10% off
Price is CA $1,189
CA $1,189
CA $11,153 total
CA $11,153 total
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
10% off
Price is CA $237
CA $237
CA $2,298 total
CA $2,298 total
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
10% off
Price is CA $1,393
CA $1,393
CA $12,447 total
CA $12,447 total
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
10% off
Price is CA $187
CA $187
CA $1,809 total
CA $1,809 total
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
10% off
Price is CA $173
CA $173
CA $1,605 total
CA $1,605 total
includes taxes & fees
Image gallery for Tiny Farmhouse Haven!

9.69.6 out of 10 rating
Exceptional
(48 reviews)
Tiny Farmhouse Haven!
Apopka, FL
5% off
Price is CA $85
CA $85
CA $811 total
CA $811 total
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
10% off
Price is CA $359
CA $359
CA $3,341 total
CA $3,341 total
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
10% off
Price is CA $355
CA $355
CA $3,475 total
CA $3,475 total
includes taxes & fees
Image gallery for Alderwood lake house Sanford/Orlando near SFB

9.89.8 out of 10 rating
Exceptional
(109 reviews)
Alderwood lake house Sanford/Orlando near SFB
Sanford, FL
5% off
Price is CA $229
CA $229
CA $2,169 total
CA $2,169 total
includes taxes & fees
Image gallery for Rare Water Views in Vista Cay Resort | Corner Condo Boasting Stunning Lake Views |Near Epic Universe

9.69.6 out of 10 rating
Exceptional
(92 reviews)
Rare Water Views in Vista Cay Resort | Corner Condo Boasting Stunning Lake Views |Near Epic Universe
Orlando, FL
26% off
Price is CA $336
CA $336
CA $3,386 total
CA $3,386 total
includes taxes & fees
Image gallery for JUST REMODELED!! 3BR/2BR Chic Villa Near Disney UNIT A

9.69.6 out of 10 rating
Exceptional
(120 reviews)
JUST REMODELED!! 3BR/2BR Chic Villa Near Disney UNIT A
Kissimmee, FL
10% off
Price is CA $136
CA $136
CA $1,395 total
CA $1,395 total
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
10% off
Price is CA $301
CA $301
CA $2,951 total
CA $2,951 total
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
15% off
Price is CA $102
CA $102
CA $1,102 total
CA $1,102 total
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
10% off
Price is CA $850
CA $850
CA $7,168 total
CA $7,168 total
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
10% off
Price is CA $511
CA $511
CA $5,164 total
CA $5,164 total
includes taxes & fees
Image gallery for LUXURY 2 Bedroom Condo at Highrise Resort Walking distance to UNIVERSAL

9.49.4 out of 10 rating
Exceptional
(61 reviews)
LUXURY 2 Bedroom Condo at Highrise Resort Walking distance to UNIVERSAL
Orlando, FL
5% off
Price is CA $261
CA $261
CA $2,231 total
CA $2,231 total
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
10% off
Price is CA $407
CA $407
CA $4,318 total
CA $4,318 total
includes taxes & fees
Image gallery for Lakeview Condo minutes to Convention Center, Disney & Universal Studio

9.09.0 out of 10 rating
Wonderful
(31 reviews)
Lakeview Condo minutes to Convention Center, Disney & Universal Studio
Orlando, FL
5% off
Price is CA $355
CA $355
CA $2,929 total
CA $2,929 total
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
10% off
Price is CA $217
CA $217
CA $2,068 total
CA $2,068 total
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
10% off
Price is CA $210
CA $210
CA $1,978 total
CA $1,978 total
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Theatre Downtown
Vacation Village at Parkway
Sleeps 8 · 2 bedrooms · 2 bathrooms
8.68.6 out of 10
Excellentexcellent
2,756 reviews(2,756 reviews)
Floridays Resort Orlando
Sleeps 8 · 1 bedroom
8.68.6 out of 10
Excellentexcellent
11,470 reviews(11,470 reviews)
4-bedroom house in wonderful Orlando with WiFi, AC, and a large backyard.
Sleeps 10 · 4 bedrooms · 3 bathrooms
8.08.0 out of 10
Very goodvery good
1 review(1 review)
Marriott's Grande Vista | Two-Bedroom Villa
Sleeps 8 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
Luxury Family Retreat • Sleeps 8 • Near Disney World
Sleeps 8 · 3 bedrooms · 2 bathrooms
8.08.0 out of 10
Very goodvery good
4 reviews(4 reviews)
Full House with Big Fenced Backyard, Washer & Dryer and Pet-Friendly.
Sleeps 7 · 2 bedrooms · 1 bathroom
6.86.8 out of 10
3 reviews(3 reviews)
Top rated rentals - Theatre Downtown
Home away from home
1010 out of 10
Exceptionalexceptional
149 reviews(149 reviews)
Liz was an amazing host and very easy to communicate with. Quiet and safe neighborhood. Felt like being home while on vacation! Definitely our new go to place while in Florida!
Taylor N.
Stayed Jun 2025
Great property in Historic District of Sanford
1010 out of 10
Exceptionalexceptional
106 reviews(106 reviews)
A great mix of historic charm with modern conveniences. Very clean and comfortable. Close to restaurants and shops and Lake Munroe.Would definitely recommend and stay here again if possible.
Garry G.
Stayed May 2025
Family Disney vacation
1010 out of 10
Exceptionalexceptional
28 reviews(28 reviews)
What a fantastic home this is indeed. The host had everything ready, things I didn't know we wanted/needed what a nice touch. From reading all the reviews this place got about how great the host was .. I really wanted to try to pay it back and let him be for the week .. and manage on our own and yet they kindly checked in via verbo. They knew we were having a Disney trip and already had the Disney princess balloons .. kids absolutely loved everything about the house and the Disney parks. Everyone's favorite part of the trip was this beautiful home & our host who was always at the ready . Thank you so very much highly recommended! From a young family of four
Maureen B.
Stayed Feb 2025
Excellent Stay
1010 out of 10
Exceptionalexceptional
229 reviews(229 reviews)
We had a great time at this property. Beds were very comfortable. House was very clean. Had all the amenities we needed. Short drive to Disney. Lots of restaurants close by. Alfredo was a great host. Would stay again next time we are in Orlando.
Laszlo P.
Stayed Feb 2025
Family/Friends Vacation
1010 out of 10
Exceptionalexceptional
37 reviews(37 reviews)
The host was absolutely amazing to work with through the whole process. Location is amazing and the amenities included with staying here are absolutely fantastic! This house was the perfect home away from home for our family/friends vacation!
Leanne H.
Stayed Feb 2025
Mas de una casa regular- un lugar muy especial y muy maravilloso!
1010 out of 10
Exceptionalexceptional
87 reviews(87 reviews)
Heartfelt thanks Jose and Nuria for a beautiful stay in your magnificent and homey Casa Ordoñez. It was lovely to say the least and we had everything we could possibly need for a relaxed and comfortable stay. We appreciate how responsive you were to our questions about the property. It was an added advantage that your location is superb in its proximity to Winter Park Historical Downtown District.
We had a very enjoyable stay and would highly recommend your property to others.
Muchas gracias,
Denise and Jim, Canada
Denise D.
Stayed Aug 2024
It was a great stay.
1010 out of 10
Exceptionalexceptional
53 reviews(53 reviews)
We had a great stay here. House was well equipped. Great size and walking distance to the club house.
Heidi S.
Stayed Apr 2024
Wonderful Stay!
1010 out of 10
Exceptionalexceptional
175 reviews(175 reviews)
There were so many thoughtful touches that made a world of difference to our stay! From the picnic cooler to the basket of coffees (lasted us an entire week!) to the robes and lots of towels and extra blankets, we wanted for absolutely nothing. The cottage was spotless, super clean and very comfortable. There were books and games available, water sport items, even the ingredients for smores! Definitely would return and definitely do recommend!
Robert H.
Stayed Feb 2024
- 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, yards and more
- More for lessMore space, more privacy, more amenities — more value