Vacation rentals near West Orange Trail
We found 25,666 vacation rentals — enter your dates for availability
Discover a selection of private vacation rentals within easy reach of West Orange Trail that can be your home away from home. Whether you're going on vacation with family or friends, vacation rentals have the amenities you need and want for your stay, which might include WiFi and a washer and dryer, No matter what you're looking for, you'll find a rental that has what everyone needs, including a place that is accessible or non-smoking.
Vacation rentals with weekly discounts - West Orange Trail
Showing deals for:Nov 14 - Nov 21
Image gallery for "THE FISHERMAN'S COTTAGE" # 1 DESTINATION Rental in Historic District~Mount Dora
1010 out of 10 rating
Exceptional
(111 reviews)
"THE FISHERMAN'S COTTAGE" # 1 DESTINATION Rental in Historic District~Mount Dora
Mount Dora, FL
5% off
Price is CA $306
CA $306
CA $2,779 total
CA $2,779 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 $1,114
CA $1,114
CA $10,686 total
CA $10,686 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 $538
CA $538
CA $4,902 total
CA $4,902 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 $94
CA $94
CA $862 total
CA $862 total
includes taxes & fees
Image gallery for Private 5 Bedroom Villa Near Disney, free WI-FI 10% OFF LONG TERM RENTALS
9.49.4 out of 10 rating
Exceptional
(129 reviews)
Private 5 Bedroom Villa Near Disney, free WI-FI 10% OFF LONG TERM RENTALS
Clermont, FL
10% off
Price is CA $204
CA $204
CA $1,759 total
CA $1,759 total
includes taxes & fees
Image gallery for Spacious upgraded 1st floor condo w/ Resort Amenities. Disney, less than 15 mins
9.69.6 out of 10 rating
Exceptional
(38 reviews)
Spacious upgraded 1st floor condo w/ Resort Amenities. Disney, less than 15 mins
Davenport, FL
10% off
Price is CA $167
CA $167
CA $1,642 total
CA $1,642 total
includes taxes & fees
Image gallery for Arcades, Bocce, Haunted Mansion Theater, Cabana, Enchanted Forest: Great Escape
1010 out of 10 rating
Exceptional
(6 reviews)
Arcades, Bocce, Haunted Mansion Theater, Cabana, Enchanted Forest: Great Escape
Kissimmee, FL
10% off
Price is CA $692
CA $692
CA $7,271 total
CA $7,271 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 $135
CA $135
CA $1,390 total
CA $1,390 total
includes taxes & fees
Image gallery for Waterfront-HUGE Pool-2.7 miles to Disney, w/ 4 Masters Suites, Arcades, Theater!
9.89.8 out of 10 rating
Exceptional
(122 reviews)
Waterfront-HUGE Pool-2.7 miles to Disney, w/ 4 Masters Suites, Arcades, Theater!
Kissimmee, FL
22% off
Price is CA $427
CA $427
CA $4,237 total
CA $4,237 total
includes taxes & fees
Image gallery for Emerald Island Resort Community,Gated 4 bedrooms 3 baths Heated Pool and Spa
9.49.4 out of 10 rating
Exceptional
(118 reviews)
Emerald Island Resort Community,Gated 4 bedrooms 3 baths Heated Pool and Spa
Kissimmee, FL
10% off
Price is CA $207
CA $207
CA $2,046 total
CA $2,046 total
includes taxes & fees
Image gallery for *Disney Pool Home-Heated Pool Included-Clermont FL
9.69.6 out of 10 rating
Exceptional
(67 reviews)
*Disney Pool Home-Heated Pool Included-Clermont FL
Clermont, FL
5% off
Price is CA $247
CA $247
CA $2,366 total
CA $2,366 total
includes taxes & fees
Image gallery for The Sunshine villa, 3 miles away from Disney, private pool and spa
9.29.2 out of 10 rating
Wonderful
(114 reviews)
The Sunshine villa, 3 miles away from Disney, private pool and spa
Kissimmee, FL
15% off
Price is CA $175
CA $175
CA $2,078 total
CA $2,078 total
includes taxes & fees
Image gallery for PRIVATE LUXURIOUS TOWNHOUSE IN RESORT JUST 2 MILES FROM DISNEY!
9.89.8 out of 10 rating
Exceptional
(54 reviews)
PRIVATE LUXURIOUS TOWNHOUSE IN RESORT JUST 2 MILES FROM DISNEY!
Kissimmee, FL
10% off
Price is CA $116
CA $116
CA $1,338 total
CA $1,338 total
includes taxes & fees
Image gallery for 1887 Royellou House 3BR 2BA
1010 out of 10 rating
Exceptional
(155 reviews)
1887 Royellou House 3BR 2BA
Mount Dora, FL
20% off
Price is CA $325
CA $325
CA $2,902 total
CA $2,902 total
includes taxes & fees
Image gallery for Zojo_ Lovely House Close TO Disney
1010 out of 10 rating
Exceptional
(13 reviews)
Zojo_ Lovely House Close TO Disney
Clermont, FL
10% off
Price is CA $186
CA $186
CA $1,852 total
CA $1,852 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 $260
CA $260
CA $2,223 total
CA $2,223 total
includes taxes & fees
Image gallery for The Adventure Villa - South Facing Pool with Jets - Min. to Disney - Game Room
9.89.8 out of 10 rating
Exceptional
(224 reviews)
The Adventure Villa - South Facing Pool with Jets - Min. to Disney - Game Room
Kissimmee, FL
19% off
Price is CA $206
CA $206
CA $2,237 total
CA $2,237 total
includes taxes & fees
Image gallery for Welcome to Hollywood Villa, 3 miles from Disney World, southfacing pool/spa
9.49.4 out of 10 rating
Exceptional
(229 reviews)
Welcome to Hollywood Villa, 3 miles from Disney World, southfacing pool/spa
Kissimmee, FL
15% off
Price is CA $199
CA $199
CA $2,281 total
CA $2,281 total
includes taxes & fees
Image gallery for Family Friendly Vacation Home - Private Pool - Minutes to Disney and Universal
9.89.8 out of 10 rating
Exceptional
(160 reviews)
Family Friendly Vacation Home - Private Pool - Minutes to Disney and Universal
Kissimmee, FL
10% off
Price is CA $235
CA $235
CA $2,381 total
CA $2,381 total
includes taxes & fees
Image gallery for Contemporary Villa with Private Heated Pool/Spa!
9.89.8 out of 10 rating
Exceptional
(86 reviews)
Contemporary Villa with Private Heated Pool/Spa!
Clermont, FL
15% off
Price is CA $226
CA $226
CA $2,231 total
CA $2,231 total
includes taxes & fees
Image gallery for Caribbean Breeze Villa
9.09.0 out of 10 rating
Wonderful
(94 reviews)
Caribbean Breeze Villa
Clermont, FL
5% off
Price is CA $182
CA $182
CA $1,967 total
CA $1,967 total
includes taxes & fees
Image gallery for Modern Luxury Villa with Everything
9.69.6 out of 10 rating
Exceptional
(239 reviews)
Modern Luxury Villa with Everything
Kissimmee, FL
10% off
Price is CA $367
CA $367
CA $3,965 total
CA $3,965 total
includes taxes & fees
Image gallery for Newly Updated, Large Pool, Spa, Game Room, Near Disney, No Rear Neighbor
8.68.6 out of 10 rating
Excellent
(27 reviews)
Newly Updated, Large Pool, Spa, Game Room, Near Disney, No Rear Neighbor
Orlando, FL
5% off
Price is CA $214
CA $214
CA $2,339 total
CA $2,339 total
includes taxes & fees
Image gallery for Luxury 10 Suite villa, man-guarded, at amazing Encore Resort at Reunion
9.49.4 out of 10 rating
Exceptional
(67 reviews)
Luxury 10 Suite villa, man-guarded, at amazing Encore Resort at Reunion
Kissimmee, FL
5% off
Price is CA $561
CA $561
CA $5,837 total
CA $5,837 total
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - West Orange Trail
Lake Front Suite -Close to all Attractions
Sleeps 4 · 1 bedroom · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
79 reviews(79 reviews)
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
692 reviews(692 reviews)
TR17406SB - New 3BR Villa w/ Pool | 17min Disney
Sleeps 8 · 3 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
Beautiful 4 Bedroom Pool Home Near Disney
Sleeps 10 · 4 bedrooms · 3 bathrooms
2 King 2 Twin 1 Queen Enormous Deck 3 BD Lakeview House at Waterfront Park
Sleeps 8 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
16 reviews(16 reviews)
FunTropicalTinyHomeGolfCartLake
Sleeps 5 · 7 bedrooms · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
Top rated rentals - West Orange Trail
Well equipped clean home
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Enjoyed our stay in winter garden, location was fantastic. Close walk to downtown and nice walk to lake apopka. We would definitely stay there again
Robin P.
Stayed May 2025
Best Place for A Family Stay
1010 out of 10
Exceptionalexceptional
145 reviews(145 reviews)
So fortunate to have found this property on VRBO. We spent 9 days with our family of 14. Everybody had tons of space. Accommodations were exceptionally clean. The decor is warm and welcoming. The outdoor set up was great for evening family meals and chats. Kitchen well stocked with pots and all dining essentials. The oversize washer is a bonus. The separate ice maker was such a bonus. Hosts were very quick to respond and kind. Definitely recommend!!
Lori B.
Stayed May 2025
Super great place
1010 out of 10
Exceptionalexceptional
184 reviews(184 reviews)
Eric is answering his message very fast and always available. The house was clean and perfect for our needs. The pool was great, the neighbours are nice. Close to Disney, grocery etc..it's a safe place for family!! 200% recommended this property
Karine S.
Stayed Apr 2025
Amazing
1010 out of 10
Exceptionalexceptional
239 reviews(239 reviews)
We had a lovely stay. Property was beautiful and clean
Shanna H.
Stayed Mar 2025
Amazing!!
1010 out of 10
Exceptionalexceptional
156 reviews(156 reviews)
Absolutely loved this place!!!
Michelle B.
Stayed Apr 2023
Great place
1010 out of 10
Exceptionalexceptional
168 reviews(168 reviews)
I stayed for 4 nights. This property is clean, comfortable and close to everything I needed. Jocelyn was very quick to respond to any questions. The yard is beautiful, with comfy patio loungers, pool, fireplace…. It really is all I needed and more. I’ll be back!!
Mike M.
Stayed Jan 2023
Great place
1010 out of 10
Exceptionalexceptional
385 reviews(385 reviews)
Great find love the place . Ron and Sherre are great hosts. Will be back again . Lovely town
tonia t.
Stayed Nov 2019
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