Holiday rentals near Winter Park Village
We found 974 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 NZ$2,993
NZ$2,993
NZ$428 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 NZ$1,973
NZ$1,973
NZ$282 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 NZ$3,869
NZ$3,869
NZ$553 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 NZ$2,109
NZ$2,109
NZ$301 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 NZ$3,158
NZ$3,158
NZ$451 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 NZ$3,474
NZ$3,474
NZ$496 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 NZ$3,568
NZ$3,568
NZ$510 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 NZ$2,969
NZ$2,969
NZ$424 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 NZ$2,543
NZ$2,543
NZ$363 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 NZ$2,276
NZ$2,276
NZ$325 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 NZ$3,493
NZ$3,493
NZ$499 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 NZ$3,098
NZ$3,098
NZ$443 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 NZ$1,712
NZ$1,712
NZ$245 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 NZ$2,516
NZ$2,516
NZ$359 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
7% off
Price is NZ$1,867
NZ$1,867
NZ$267 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 NZ$4,353
NZ$4,353
NZ$622 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 NZ$2,454
NZ$2,454
NZ$351 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 NZ$1,712
NZ$1,712
NZ$245 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 NZ$1,712
NZ$1,712
NZ$245 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 NZ$1,712
NZ$1,712
NZ$245 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 NZ$1,690
NZ$1,690
NZ$241 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 NZ$2,513
NZ$2,513
NZ$359 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 NZ$1,112
NZ$1,112
NZ$159 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 NZ$3,012
NZ$3,012
NZ$430 per night
includes taxes & fees
Find spaces that suit your style
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Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Winter Park Village
Showing deals for: 22 Sept - 25 Sept
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)
The current price is NZ$812
NZ$812
for 3 nights, 1 home
NZ$271 per night
includes taxes & fees
Casa Winter Park
Sleeps 8 · 4 bedrooms · 4 bathrooms
9.89.8 out of 10
Exceptionalexceptional
112 reviews(112 reviews)
The current price is NZ$1,954
NZ$1,954
for 3 nights, 1 home
NZ$651 per night
includes taxes & fees
Casa Feliz
Sleeps 8 · 3 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
39 reviews(39 reviews)
The current price is NZ$1,999
NZ$1,999
for 3 nights, 1 home
NZ$666 per night
includes taxes & fees
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)
The current price is NZ$1,098
NZ$1,098
for 3 nights, 1 home
NZ$366 per night
includes taxes & fees
Orlando Lakefront Tiny House Community
Sleeps 4 · 2 bedrooms
9.49.4 out of 10
Exceptionalexceptional
317 reviews(317 reviews)
The current price is NZ$1,067
NZ$1,067
for 3 nights, 1 cottage
NZ$356 per night
includes taxes & fees
Spacious & Private Guest Pool House Oasis
Sleeps 2 · 1 bedroom · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
13 reviews(13 reviews)
The current price is NZ$881
NZ$881
for 3 nights, 1 home
NZ$294 per night
includes taxes & fees
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