Holiday rentals near Winter Park Village
We found 922 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:14 Nov - 21 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 NZ$6,570
NZ$6,570
NZ$939 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
(48 reviews)
Magnificent Lakefront House • Swim/Boat/Relax • EV Charger • Long term stays OK
Apopka, FL
16% off
Price is NZ$7,849
NZ$7,849
NZ$1,121 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
(21 reviews)
Winter Park Citrus Escape; sleeps 8, relaxing pool, family & pet friendly
Winter Park, FL
8% off
Price is NZ$5,907
NZ$5,907
NZ$844 per night
includes taxes & fees
Image gallery for Spacious and relaxing Home - North Of Orlando In Longwood, Florida
9.49.4 out of 10 rating
Exceptional
(32 reviews)
Spacious and relaxing Home - North Of Orlando In Longwood, Florida
Longwood, FL
8% off
Price is NZ$4,420
NZ$4,420
NZ$631 per night
includes taxes & fees
Image gallery for Orlando Area 5BR/2BA Home w/ Jacuzzi!
9.49.4 out of 10 rating
Exceptional
(41 reviews)
Orlando Area 5BR/2BA Home w/ Jacuzzi!
Altamonte Springs, FL
16% off
Price is NZ$3,387
NZ$3,387
NZ$484 per night
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
9% off
Price is NZ$7,405
NZ$7,405
NZ$1,058 per night
includes taxes & fees
Image gallery for The Bedford House Countryside
9.89.8 out of 10 rating
Exceptional
(21 reviews)
The Bedford House Countryside
Sanford, FL
7% off
Price is NZ$4,456
NZ$4,456
NZ$637 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$3,238
NZ$3,238
NZ$463 per night
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 NZ$1,562
NZ$1,562
NZ$223 per night
includes taxes & fees
Image gallery for Mid-Century Modern Gem Near Downtown/Winter Park/Baldwin Park
1010 out of 10 rating
Exceptional
(43 reviews)
Mid-Century Modern Gem Near Downtown/Winter Park/Baldwin Park
Orlando, FL
8% off
Price is NZ$3,622
NZ$3,622
NZ$517 per night
includes taxes & fees
Image gallery for Incredible Private Lakefront Cottage Retreat
1010 out of 10 rating
Exceptional
(27 reviews)
Incredible Private Lakefront Cottage Retreat
Altamonte Springs, FL
14% off
Price is NZ$2,424
NZ$2,424
NZ$346 per night
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 NZ$3,282
NZ$3,282
NZ$469 per night
includes taxes & fees
Image gallery for Stylish Boutique Guest house in Winter Park
1010 out of 10 rating
Exceptional
(87 reviews)
Stylish Boutique Guest house in Winter Park
Winter Park, FL
7% off
Price is NZ$2,210
NZ$2,210
NZ$316 per night
includes taxes & fees
Image gallery for *Travel Themed Property with Backyard Oasis*
9.89.8 out of 10 rating
Exceptional
(26 reviews)
*Travel Themed Property with Backyard Oasis*
Maitland, FL
13% off
Price is NZ$9,393
NZ$9,393
NZ$1,342 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$3,089
NZ$3,089
NZ$441 per night
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 NZ$2,309
NZ$2,309
NZ$330 per night
includes taxes & fees
Image gallery for Spacious Family House with Private Pool in Central Florida
1010 out of 10 rating
Exceptional
(30 reviews)
Spacious Family House with Private Pool in Central Florida
Longwood, FL
11% off
Price is NZ$3,583
NZ$3,583
NZ$512 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$3,445
NZ$3,445
NZ$492 per night
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 NZ$9,185
NZ$9,185
NZ$1,312 per night
includes taxes & fees
Image gallery for King bd / Charming 2 story cottage w/ Private Yard
1010 out of 10 rating
Exceptional
(16 reviews)
King bd / Charming 2 story cottage w/ Private Yard
Orlando, FL
11% off
Price is NZ$5,725
NZ$5,725
NZ$818 per night
includes taxes & fees
Image gallery for Recharge @ Timberland Lodge: Pool Hottub Sauna
1010 out of 10 rating
Exceptional
(11 reviews)
Recharge @ Timberland Lodge: Pool Hottub Sauna
Longwood, FL
8% off
Price is NZ$9,209
NZ$9,209
NZ$1,316 per night
includes taxes & fees
Image gallery for Retreat | Lake Hot Tub Paddle Boards Speakeasy
1010 out of 10 rating
Exceptional
(15 reviews)
Retreat | Lake Hot Tub Paddle Boards Speakeasy
Orlando, FL
8% off
Price is NZ$10,186
NZ$10,186
NZ$1,455 per night
includes taxes & fees
Image gallery for Spacious & Private Guest Pool House Oasis
9.69.6 out of 10 rating
Exceptional
(14 reviews)
Spacious & Private Guest Pool House Oasis
Orlando, FL
8% off
Price is NZ$2,362
NZ$2,362
NZ$337 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$5,459
NZ$5,459
NZ$780 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Winter Park Village
Prvt Home w/large pool/4Beds/3Baths
Sleeps 8 · 4 bedrooms · 3 bathrooms
7.47.4 out of 10
Goodgood
3 reviews(3 reviews)
Charming Winter Park Fully Furnished & Pet Friendly Farmhouse Bungalow
Sleeps 6 · 3 bedrooms · 2 bathrooms
9.29.2 out of 10
Wonderfulwonderful
92 reviews(92 reviews)
Botanical Garden Home-20 min to Disney, 10 Min to Downtown & 40 Min to the beach
Sleeps 6 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
THE CHLOE by EVRH
Sleeps 16 · 3 bedrooms · 2 bathrooms
9.09.0 out of 10
Wonderfulwonderful
65 reviews(65 reviews)
🧡 Unique 6/3, Pool, Pergola, 🎥 Movie/Game Room, UCF, Disney, Beaches, 5⭐!
Sleeps 20 · 6 bedrooms · 3 bathrooms
9.89.8 out of 10
Exceptionalexceptional
74 reviews(74 reviews)
Walk into Tropical Paradise - POOL - GYM - HOT TUB
Sleeps 9 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
5 reviews(5 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