Holiday rentals near Winter Park Village
We found 935 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:21 Nov - 28 Nov
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$6,241
AU$6,241
AU$892 nightly
Includes taxes & fees
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$3,402
AU$3,402
AU$486 nightly
Includes taxes & fees
Image gallery for Magnificent Lakefront House • Swim/Boat/Relax • EV Charger • Long term stays OK
1010 out of 10 rating
Exceptional
(49 reviews)
Magnificent Lakefront House • Swim/Boat/Relax • EV Charger • Long term stays OK
Apopka, FL
16% off
Price is AU$6,219
AU$6,219
AU$888 nightly
Includes taxes & fees
Image gallery for 4 Bedroom 2 Bath Pet-Friendly Pool Home Orlando Airport
9.89.8 out of 10 rating
Exceptional
(10 reviews)
4 Bedroom 2 Bath Pet-Friendly Pool Home Orlando Airport
Orlando, FL
11% off
Price is AU$3,185
AU$3,185
AU$455 nightly
Includes taxes & fees
Image gallery for Winter Park Citrus Escape; sleeps 8, relaxing pool, family & pet friendly
9.09.0 out of 10 rating
Wonderful
(22 reviews)
Winter Park Citrus Escape; sleeps 8, relaxing pool, family & pet friendly
Winter Park, FL
8% off
Price is AU$4,758
AU$4,758
AU$680 nightly
Includes taxes & fees
Image gallery for Alluring 2bd/2ba in East Orlando.
1010 out of 10 rating
Exceptional
(9 reviews)
Alluring 2bd/2ba in East Orlando.
Orlando, FL
7% off
Price is AU$1,812
AU$1,812
AU$259 nightly
Includes taxes & fees
Image gallery for Pool+Grill+Huge yard+outdoor movies+Plenty parking space
9.29.2 out of 10 rating
Wonderful
(9 reviews)
Pool+Grill+Huge yard+outdoor movies+Plenty parking space
Apopka, FL
5% off
Price is AU$4,655
AU$4,655
AU$665 nightly
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
8% off
Price is AU$6,577
AU$6,577
AU$940 nightly
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
13% off
Price is AU$3,669
AU$3,669
AU$524 nightly
Includes taxes & fees
Image gallery for Salt Pool, cozy House near Downtown and International Airport
9.69.6 out of 10 rating
Exceptional
(80 reviews)
Salt Pool, cozy House near Downtown and International Airport
Orlando, FL
7% off
Price is AU$2,477
AU$2,477
AU$354 nightly
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$2,563
AU$2,563
AU$366 nightly
Includes taxes & fees
Image gallery for A Delightful Retreat 3/2 1/2 bath Countryside
9.89.8 out of 10 rating
Exceptional
(21 reviews)
A Delightful Retreat 3/2 1/2 bath Countryside
Sanford, FL
7% off
Price is AU$3,508
AU$3,508
AU$501 nightly
Includes taxes & fees
Image gallery for Weekday Special Orlando Cozy Cottage with queen bed & nearby pickleball courts
1010 out of 10 rating
Exceptional
(15 reviews)
Weekday Special Orlando Cozy Cottage with queen bed & nearby pickleball courts
Lake Mary, FL
7% off
Price is AU$1,451
AU$1,451
AU$207 nightly
Includes taxes & fees
Image gallery for Downtown Orlando Creative Oasis- Hand Painted Murals & Free Parking.
9.69.6 out of 10 rating
Exceptional
(16 reviews)
Downtown Orlando Creative Oasis- Hand Painted Murals & Free Parking.
Orlando, FL
8% off
Price is AU$3,323
AU$3,323
AU$475 nightly
Includes taxes & fees
Image gallery for Lakefront Home Where You Can Retreat And Relax
9.89.8 out of 10 rating
Exceptional
(18 reviews)
Lakefront Home Where You Can Retreat And Relax
Longwood, FL
7% off
Price is AU$2,838
AU$2,838
AU$405 nightly
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$2,501
AU$2,501
AU$357 nightly
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
8% off
Price is AU$8,730
AU$8,730
AU$1,247 nightly
Includes taxes & fees
Image gallery for Modern Garden Suite!
9.69.6 out of 10 rating
Exceptional
(25 reviews)
Modern Garden Suite!
Orlando, FL
8% off
Price is AU$2,170
AU$2,170
AU$310 nightly
Includes taxes & fees
Image gallery for Charming Winter Park 3 Bedroom Villa with Pool
9.89.8 out of 10 rating
Exceptional
(9 reviews)
Charming Winter Park 3 Bedroom Villa with Pool
Winter Park, FL
7% off
Price is AU$2,179
AU$2,179
AU$311 nightly
Includes taxes & fees
Image gallery for Luxury Golf Country Club Condo 2 Bedroom 2 Bathroom
9.69.6 out of 10 rating
Exceptional
(54 reviews)
Luxury Golf Country Club Condo 2 Bedroom 2 Bathroom
Orlando, FL
8% off
Price is AU$1,575
AU$1,575
AU$225 nightly
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
(58 reviews)
Home away from Home Luxury 2 bed/2bath Country Club Condo
Orlando, FL
8% off
Price is AU$1,575
AU$1,575
AU$225 nightly
Includes taxes & fees
Image gallery for CountryClub 2/2 Home Away from Home
9.49.4 out of 10 rating
Exceptional
(63 reviews)
CountryClub 2/2 Home Away from Home
Orlando, FL
8% off
Price is AU$1,575
AU$1,575
AU$225 nightly
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$3,168
AU$3,168
AU$453 nightly
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$1,716
AU$1,716
AU$245 nightly
Includes taxes & fees
Find spaces that suit your style
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Chalet
Find the best place to stay - Winter Park Village
Charming 3-bedroom house with WiFi, AC in Winter Park
Sleeps 8 · 3 bedrooms · 2 bathrooms
Temporary living that feels like home where you can relax and be yourself.
Sleeps 6 · 4 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
144 reviews(144 reviews)
THE CHLOE by EVRH
Sleeps 16 · 3 bedrooms · 2 bathrooms
9.09.0 out of 10
Wonderfulwonderful
65 reviews(65 reviews)
Walk into Tropical Paradise - POOL - GYM - HOT TUB
Sleeps 9 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
5 reviews(5 reviews)
Prvt Home w/large pool/4Beds/3Baths
Sleeps 8 · 4 bedrooms · 3 bathrooms
7.47.4 out of 10
Goodgood
3 reviews(3 reviews)
Casa Jardin
Sleeps 6 · 3 bedrooms · 3+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
22 reviews(22 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