Holiday rentals near Winter Park Village
We found 978 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:25 Jul - 1 Aug
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$3,456
NZ$3,456
NZ$494 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$3,139
NZ$3,139
NZ$448 per night
includes taxes & fees
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$5,393
NZ$5,393
NZ$770 per night
includes taxes & fees
Image gallery for Relaxing four bed room getaway built for long stays
9.49.4 out of 10 rating
Exceptional
(12 reviews)
Relaxing four bed room getaway built for long stays
Orlando, FL
7% off
Price is NZ$2,933
NZ$2,933
NZ$419 per night
includes taxes & fees
Image gallery for Weekly discounts! Resort Like Private Pool Waterfront Retreat 4/2 Home Orlando
1010 out of 10 rating
Exceptional
(112 reviews)
Weekly discounts! Resort Like Private Pool Waterfront Retreat 4/2 Home Orlando
Orlando, FL
7% off
Price is NZ$3,422
NZ$3,422
NZ$489 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$5,494
NZ$5,494
NZ$785 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$5,152
NZ$5,152
NZ$736 per night
includes taxes & fees
Image gallery for Historic downtown bungalow
1010 out of 10 rating
Exceptional
(9 reviews)
Historic downtown bungalow
Orlando, FL
7% off
Price is NZ$2,767
NZ$2,767
NZ$395 per night
includes taxes & fees
Image gallery for Tropical Oasis - Heated Luxury Pool - Game Room
1010 out of 10 rating
Exceptional
(14 reviews)
Tropical Oasis - Heated Luxury Pool - Game Room
Longwood, FL
8% off
Price is NZ$5,219
NZ$5,219
NZ$746 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$2,150
NZ$2,150
NZ$307 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
(72 reviews)
🧡 Unique 6/3, Pool, Pergola, 🎥 Movie/Game Room, UCF, Disney, Beaches, 5⭐!
Oviedo, FL
8% off
Price is NZ$4,827
NZ$4,827
NZ$690 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$4,611
NZ$4,611
NZ$659 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$5,551
NZ$5,551
NZ$793 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$1,767
NZ$1,767
NZ$252 per night
includes taxes & fees
Image gallery for Charming Winter Park 3 Bedroom Villa with Pool
1010 out of 10 rating
Exceptional
(8 reviews)
Charming Winter Park 3 Bedroom Villa with Pool
Winter Park, FL
7% off
Price is NZ$2,317
NZ$2,317
NZ$331 per night
includes taxes & fees
Image gallery for Orlando Poolside Oasis
1010 out of 10 rating
Exceptional
(5 reviews)
Orlando Poolside Oasis
Altamonte Springs, FL
11% off
Price is NZ$3,605
NZ$3,605
NZ$515 per night
includes taxes & fees
Image gallery for Country Club Home away from Home
9.49.4 out of 10 rating
Exceptional
(41 reviews)
Country Club Home away from Home
Orlando, FL
8% off
Price is NZ$1,702
NZ$1,702
NZ$243 per night
includes taxes & fees
Image gallery for Pet-Friendly Cozy 5-Bed Home
9.89.8 out of 10 rating
Exceptional
(9 reviews)
Pet-Friendly Cozy 5-Bed Home
Orlando, FL
11% off
Price is NZ$3,475
NZ$3,475
NZ$496 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$1,219
NZ$1,219
NZ$174 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$2,668
NZ$2,668
NZ$381 per night
includes taxes & fees
Image gallery for Magnificent Lakefront House • Swim/Boat/Relax • EV Charger • Long term stays OK
1010 out of 10 rating
Exceptional
(45 reviews)
Magnificent Lakefront House • Swim/Boat/Relax • EV Charger • Long term stays OK
Apopka, FL
16% off
Price is NZ$7,482
NZ$7,482
NZ$1,069 per night
includes taxes & fees
Image gallery for Designer Furnished HOME In the Heart of Orlando!
9.29.2 out of 10 rating
Wonderful
(10 reviews)
Designer Furnished HOME In the Heart of Orlando!
Orlando, FL
7% off
Price is NZ$2,244
NZ$2,244
NZ$321 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$1,690
NZ$1,690
NZ$241 per night
includes taxes & fees
Image gallery for Salt Pool, cozy House near Downtown and International Airport
9.69.6 out of 10 rating
Exceptional
(74 reviews)
Salt Pool, cozy House near Downtown and International Airport
Orlando, FL
8% off
Price is NZ$2,655
NZ$2,655
NZ$379 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)
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)
Upscale 3/2 Townhome | King Bed | Patio | Wifi
Sleeps 6 · 3 bedrooms · 2+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
Casa Winter Park
Sleeps 8 · 4 bedrooms · 4 bathrooms
9.89.8 out of 10
Exceptionalexceptional
107 reviews(107 reviews)
Spectacular and Modern Villa with Pool/ near Parks
Sleeps 8 · 3 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
25 Minutes to Universal Studios 3/2 Home
Sleeps 11 · 3 bedrooms · 2 bathrooms
7.07.0 out of 10
Goodgood
10 reviews(10 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