Holiday rentals near Winter Park Village
We found 933 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:8 Aug - 15 Aug
Image gallery for King bd / Charming 2 story cottage w/ Private Yard
1010 out of 10 rating
Exceptional
(14 reviews)
King bd / Charming 2 story cottage w/ Private Yard
Orlando, FL
11% off
Price is NZ$4,731
NZ$4,731
NZ$676 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
(114 reviews)
Resort Like Private Pool Waterfront Retreat 4/2 Home in Orlando Weekly discounts
Orlando, FL
7% off
Price is NZ$3,015
NZ$3,015
NZ$431 per night
includes taxes & fees
Image gallery for Luxury, Lakeview away from it all...
9.89.8 out of 10 rating
Exceptional
(100 reviews)
Luxury, Lakeview away from it all...
Orlando, FL
8% off
Price is NZ$1,710
NZ$1,710
NZ$244 per night
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 NZ$3,114
NZ$3,114
NZ$445 per night
includes taxes & fees
Image gallery for #LakeBeachKayaksHotTub
1010 out of 10 rating
Exceptional
(11 reviews)
#LakeBeachKayaksHotTub
Orlando, FL
8% off
Price is NZ$5,632
NZ$5,632
NZ$805 per night
includes taxes & fees
Image gallery for *Travel Themed Property with Backyard Oasis*
9.89.8 out of 10 rating
Exceptional
(24 reviews)
*Travel Themed Property with Backyard Oasis*
Maitland, Florida
12% off
Price is NZ$5,351
NZ$5,351
NZ$764 per night
includes taxes & fees
Image gallery for This Charming House with an outdoor pool, 3 bedrooms, 2 full baths.
1010 out of 10 rating
Exceptional
(5 reviews)
This Charming House with an outdoor pool, 3 bedrooms, 2 full baths.
Longwood, FL
8% off
Price is NZ$3,320
NZ$3,320
NZ$474 per night
includes taxes & fees
Image gallery for Tropical Oasis - Heated Luxury Pool - Game Room
1010 out of 10 rating
Exceptional
(15 reviews)
Tropical Oasis - Heated Luxury Pool - Game Room
Longwood, FL
8% off
Price is NZ$5,057
NZ$5,057
NZ$722 per night
includes taxes & fees
Image gallery for Luxurious resort-style home with a Heated Pool on .34 acres!
9.49.4 out of 10 rating
Exceptional
(6 reviews)
Luxurious resort-style home with a Heated Pool on .34 acres!
Apopka, FL
5% off
Price is NZ$5,104
NZ$5,104
NZ$729 per night
includes taxes & fees
Image gallery for 5BDR Villa Pet Friendly Fenced in Backyard Walking Distance to Restaurants
9.49.4 out of 10 rating
Exceptional
(7 reviews)
5BDR Villa Pet Friendly Fenced in Backyard Walking Distance to Restaurants
Orlando, FL
12% off
Price is NZ$5,919
NZ$5,919
NZ$846 per night
includes taxes & fees
Image gallery for Lake Getaway to Orlando Magic!
1010 out of 10 rating
Exceptional
(7 reviews)
Lake Getaway to Orlando Magic!
Apopka, FL
16% off
Price is NZ$5,272
NZ$5,272
NZ$753 per night
includes taxes & fees
Image gallery for Lakefront Artist's Studio- Isolate in Luxury!
9.69.6 out of 10 rating
Exceptional
(56 reviews)
Lakefront Artist's Studio- Isolate in Luxury!
Orlando, FL
8% off
Price is NZ$2,161
NZ$2,161
NZ$309 per night
includes taxes & fees
Image gallery for Cottage Retreat in the City
1010 out of 10 rating
Exceptional
(28 reviews)
Cottage Retreat in the City
Orlando, FL
7% off
Price is NZ$1,710
NZ$1,710
NZ$244 per night
includes taxes & fees
Image gallery for Cozy 4/2, Centrally Located, King Beds, Pergola, Hot Tub & Pool!
1010 out of 10 rating
Exceptional
(12 reviews)
Cozy 4/2, Centrally Located, King Beds, Pergola, Hot Tub & Pool!
Casselberry, FL
8% off
Price is NZ$3,915
NZ$3,915
NZ$559 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
(139 reviews)
Temporary living that feels like home where you can relax and be yourself.
Maitland, FL
8% off
Price is NZ$2,307
NZ$2,307
NZ$330 per night
includes taxes & fees
Image gallery for Peaceful Guest Unit
9.69.6 out of 10 rating
Exceptional
(46 reviews)
Peaceful Guest Unit
Orlando, FL
11% off
Price is NZ$1,225
NZ$1,225
NZ$175 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$2,994
NZ$2,994
NZ$428 per night
includes taxes & fees
Image gallery for Hidden Garden Cottage-Sleeps 6, Ctrl Orlando Disney Universal SeaWorld Beaches,
8.68.6 out of 10 rating
Excellent
(10 reviews)
Hidden Garden Cottage-Sleeps 6, Ctrl Orlando Disney Universal SeaWorld Beaches,
Altamonte Springs, FL
5% off
Price is NZ$2,222
NZ$2,222
NZ$317 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
(76 reviews)
Salt Pool, cozy House near Downtown and International Airport
Orlando, FL
8% off
Price is NZ$2,668
NZ$2,668
NZ$381 per night
includes taxes & fees
Image gallery for Tiny remodel mobile home close to Orlando and Sanford Airport.
9.29.2 out of 10 rating
Wonderful
(15 reviews)
Tiny remodel mobile home close to Orlando and Sanford Airport.
Casselberry, FL
8% off
Price is NZ$1,699
NZ$1,699
NZ$243 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
13% off
Price is NZ$4,031
NZ$4,031
NZ$576 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$2,138
NZ$2,138
NZ$305 per night
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
(14 reviews)
Winter Park Citrus Escape; sleeps 8, relaxing pool, family & pet friendly
Winter Park, FL
8% off
Price is NZ$3,756
NZ$3,756
NZ$537 per night
includes taxes & fees
Image gallery for CountryClub Lakeview Home Away from Home
9.29.2 out of 10 rating
Wonderful
(59 reviews)
CountryClub Lakeview Home Away from Home
Orlando, FL
8% off
Price is NZ$1,710
NZ$1,710
NZ$244 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Winter Park Village
Casa Feliz
Sleeps 8 · 3 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
36 reviews(36 reviews)
Casa Winter Park
Sleeps 8 · 4 bedrooms · 4 bathrooms
9.89.8 out of 10
Exceptionalexceptional
109 reviews(109 reviews)
Charming Winter Park Fully Furnished & Pet Friendly Farmhouse Bungalow
Sleeps 6 · 3 bedrooms · 2 bathrooms
9.29.2 out of 10
Wonderfulwonderful
87 reviews(87 reviews)
Relax in Style at a Lovely Apartment with 3 Pools: Ideal Vacation Destination!
Sleeps 6 · 2 bedrooms · 2 bathrooms
6.06.0 out of 10
4 reviews(4 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
43 reviews(43 reviews)
"Orlando Magic at 3697 Vacation Apartment: Your Getaway!"
Sleeps 5 · 2 bedrooms · 2 bathrooms
9.29.2 out of 10
Wonderfulwonderful
26 reviews(26 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