Holiday rentals near Winter Park Village
We found 976 holiday rentals — enter your dates for availability
Take a look at holiday rentals close to Winter Park Village that can be your home away from home. Whether you're travelling with family, friends or just your furry companion, holiday homes have the amenities that you expect for your stay, which might include a garden and hot tub. Whatever you're looking for, you'll find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.
Holiday rentals with weekly discounts - Winter Park Village
Showing deals for:26 Sept - 3 Oct
Image gallery for ORL Modern Zen Vibe Brand new 2/2 construction in the Heart of Downtown Orlando
1010 out of 10 rating
Exceptional
(8 reviews)
ORL Modern Zen Vibe Brand new 2/2 construction in the Heart of Downtown Orlando
Orlando, FL
8% off
Price is AU$2,755
AU$2,755
AU$394 per night
includes taxes & fees
Image gallery for Alluring 2bd/2ba in East Orlando.
1010 out of 10 rating
Exceptional
(8 reviews)
Alluring 2bd/2ba in East Orlando.
Orlando, FL
7% off
Price is AU$1,815
AU$1,815
AU$259 per night
includes taxes & fees
Image gallery for Cozy 4/2, on ⭐ Beautiful Lake, 🧡 Hot Tub, 😎 Chill Patio & 🎮 Game/Bunk Room!
1010 out of 10 rating
Exceptional
(8 reviews)
Cozy 4/2, on ⭐ Beautiful Lake, 🧡 Hot Tub, 😎 Chill Patio & 🎮 Game/Bunk Room!
Oviedo, FL
8% off
Price is AU$3,559
AU$3,559
AU$508 per night
includes taxes & fees
Image gallery for Florida Vacation with pool fun for families
9.69.6 out of 10 rating
Exceptional
(28 reviews)
Florida Vacation with pool fun for families
Casselberry, FL
7% off
Price is AU$1,978
AU$1,978
AU$283 per night
includes taxes & fees
Image gallery for THE CHLOE by EVRH
9.09.0 out of 10 rating
Wonderful
(60 reviews)
THE CHLOE by EVRH
Altamonte Springs, FL
7% off
Price is AU$2,909
AU$2,909
AU$416 per night
includes taxes & fees
Image gallery for Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool and Patio
9.69.6 out of 10 rating
Exceptional
(15 reviews)
Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool and Patio
Orlando, FL
8% off
Price is AU$3,201
AU$3,201
AU$457 per night
includes taxes & fees
Image gallery for Winter Park Citrus Escape; sleeps 8, relaxing pool, family & pet friendly
9.49.4 out of 10 rating
Exceptional
(17 reviews)
Winter Park Citrus Escape; sleeps 8, relaxing pool, family & pet friendly
Winter Park, FL
8% off
Price is AU$3,282
AU$3,282
AU$469 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
(9 reviews)
4 Bedroom 2 Bath Pet-Friendly Pool Home Orlando Airport
Orlando, FL
11% off
Price is AU$3,218
AU$3,218
AU$460 per night
includes taxes & fees
Image gallery for Resort Like Private Pool Waterfront Retreat 4/2 Home in Orlando Weekly discounts
1010 out of 10 rating
Exceptional
(116 reviews)
Resort Like Private Pool Waterfront Retreat 4/2 Home in Orlando Weekly discounts
Orlando, FL
7% off
Price is AU$2,735
AU$2,735
AU$391 per night
includes taxes & fees
Image gallery for Salt Pool, cozy House near Downtown and International Airport
9.89.8 out of 10 rating
Exceptional
(77 reviews)
Salt Pool, cozy House near Downtown and International Airport
Orlando, FL
7% off
Price is AU$2,340
AU$2,340
AU$334 per night
includes taxes & fees
Image gallery for Temporary living that feels like home where you can relax and be yourself.
1010 out of 10 rating
Exceptional
(142 reviews)
Temporary living that feels like home where you can relax and be yourself.
Maitland, FL
8% off
Price is AU$2,121
AU$2,121
AU$303 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
12% off
Price is AU$2,854
AU$2,854
AU$408 per night
includes taxes & fees
Image gallery for Luxury, Lakeview away from it all...
9.89.8 out of 10 rating
Exceptional
(102 reviews)
Luxury, Lakeview away from it all...
Orlando, FL
7% off
Price is AU$1,577
AU$1,577
AU$225 per night
includes taxes & fees
Image gallery for Private Studio in the heart of downtown Orlando. Modern Zen Vibe
1010 out of 10 rating
Exceptional
(22 reviews)
Private Studio in the heart of downtown Orlando. Modern Zen Vibe
Orlando, FL
8% off
Price is AU$2,316
AU$2,316
AU$331 per night
includes taxes & fees
Image gallery for CHARMING - Cozy Retreat Near Lake Killarney in Winter Park
9.69.6 out of 10 rating
Exceptional
(21 reviews)
CHARMING - Cozy Retreat Near Lake Killarney in Winter Park
Winter Park, FL
7% off
Price is AU$2,287
AU$2,287
AU$327 per night
includes taxes & fees
Image gallery for Lakefront Artist's Loft - Isolate in Luxury!
9.69.6 out of 10 rating
Exceptional
(55 reviews)
Lakefront Artist's Loft - Isolate in Luxury!
Orlando, FL
8% off
Price is AU$1,720
AU$1,720
AU$246 per night
includes taxes & fees
Image gallery for 🧡 Unique 6/3, Pool, Pergola, 🎥 Movie/Game Room, UCF, Disney, Beaches, 5⭐!
9.89.8 out of 10 rating
Exceptional
(74 reviews)
🧡 Unique 6/3, Pool, Pergola, 🎥 Movie/Game Room, UCF, Disney, Beaches, 5⭐!
Oviedo, FL
8% off
Price is AU$4,012
AU$4,012
AU$573 per night
includes taxes & fees
Image gallery for CountryClub Lakeview Home Away from Home
9.29.2 out of 10 rating
Wonderful
(61 reviews)
CountryClub Lakeview Home Away from Home
Orlando, FL
7% off
Price is AU$1,577
AU$1,577
AU$225 per night
includes taxes & fees
Image gallery for Luxury Golf Country Club Condo 2 Bedroom 2 Bathroom
9.69.6 out of 10 rating
Exceptional
(53 reviews)
Luxury Golf Country Club Condo 2 Bedroom 2 Bathroom
Orlando, FL
7% off
Price is AU$1,577
AU$1,577
AU$225 per night
includes taxes & fees
Image gallery for Home away from Home Luxury 2 bed/2bath Country Club Condo
9.69.6 out of 10 rating
Exceptional
(56 reviews)
Home away from Home Luxury 2 bed/2bath Country Club Condo
Orlando, FL
7% off
Price is AU$1,577
AU$1,577
AU$225 per night
includes taxes & fees
Image gallery for Spacious & Private Guest Pool House Oasis
9.69.6 out of 10 rating
Exceptional
(13 reviews)
Spacious & Private Guest Pool House Oasis
Orlando, FL
7% off
Price is AU$1,556
AU$1,556
AU$222 per night
includes taxes & fees
Image gallery for Modern Oasis in Downtown Orlando! 2-bedroom oasis! 5 minutes from downtown!
9.89.8 out of 10 rating
Exceptional
(17 reviews)
Modern Oasis in Downtown Orlando! 2-bedroom oasis! 5 minutes from downtown!
Orlando, FL
11% off
Price is AU$2,313
AU$2,313
AU$330 per night
includes taxes & fees
Image gallery for Lake Front Suite -Close to all Attractions
9.49.4 out of 10 rating
Exceptional
(73 reviews)
Lake Front Suite -Close to all Attractions
Apopka, FL
8% off
Price is AU$1,017
AU$1,017
AU$145 per night
includes taxes & fees
Image gallery for Indulge at “Da Comfy House”
9.49.4 out of 10 rating
Exceptional
(10 reviews)
Indulge at “Da Comfy House”
Orlando, FL
6% off
Price is AU$2,773
AU$2,773
AU$396 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Winter Park Village
Charming Winter Park Fully Furnished & Pet Friendly Farmhouse Bungalow
Sleeps 6 · 3 bedrooms · 2 bathrooms
9.29.2 out of 10
Wonderfulwonderful
90 reviews(90 reviews)
Casa Winter Park
Sleeps 8 · 4 bedrooms · 4 bathrooms
9.89.8 out of 10
Exceptionalexceptional
112 reviews(112 reviews)
Casa Feliz
Sleeps 8 · 3 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
39 reviews(39 reviews)
Quiet Oasis in Lovely Neighborhood
Sleeps 3 · 1 bedroom
9.89.8 out of 10
Exceptionalexceptional
138 reviews(138 reviews)
The Launch Pad with a pool! King bed and private backyard
Sleeps 6 · 3 bedrooms · 2 bathrooms
9.29.2 out of 10
Wonderfulwonderful
45 reviews(45 reviews)
Orlando Lakefront Tiny House Community
Sleeps 4 · 2 bedrooms
9.49.4 out of 10
Exceptionalexceptional
317 reviews(317 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